United States v. Amirnazmi

PRECEDENTIAL

UNITED STATES COURT OF APPEALS

FOR THE THIRD CIRCUIT

___________

No. 10-1198

___________

UNITED STATES OF AMERICA

v.

ALI AMIRNAZMI,

Appellant

_______________________

On Appeal from the United States District Court

for the Eastern District of Pennsylvania

D.C. Criminal No. 2-08-cr-00429-001

(Honorable Cynthia M. Rufe)

______________

Argued January 11, 2011

Before: SCIRICA, BARRY and VANASKIE, Circuit Judges.

(Filed: May 13, 2011)

ELIZABETH K. AINSLIE, ESQUIRE (ARGUED)

VINCENT A. LaMONACA, ESQUIRE

Schnader Harrison Segal & Lewis

1600 Market Street, Suite 3600

Philadelphia, Pennsylvania 19103

Attorneys for Appellant

BERNADETTE A. McKEON, ESQUIRE (ARGUED)

STEPHEN A. MILLER, ESQUIRE

Office of United States Attorney

615 Chestnut Street, Suite 1250

Philadelphia, Pennsylvania 19106

Attorney for Appellee

_________________

OPINION OF THE COURT

_________________

SCIRICA, Circuit Judge.

In pursuit of his stated goal of transforming the Islamic

Republic of Iran into a global chemical powerhouse, Ali

Amirnazmi, a chemical engineer, marketed a dynamic

software program to Iranian actors and entered into

agreements with various Iranian entities in which he pledged

to provide technology to facilitate the construction of multiple

chemical plants. Following a jury trial, Amirnazmi was

convicted on ten charges—four counts stemming from

violations of the International Emergency Economic Powers

Act (IEEPA), three counts of making false statements, and

three counts of bank fraud. Amirnazmi moved both for a

2

judgment of acquittal and for a new trial. The District Court

denied both motions and sentenced him to a four-year prison

term. We will affirm.

I.

Amirnazmi, a dual citizen of the United States and

Iran, founded a company called TranTech Consultants, Inc.,

in 1981. Billed as a business geared toward providing “an

innovative approach to strategic decision making for the

Chemical Process Industries,” TranTech marketed its primary

product—a computer software program called ChemPlan—as

an “exclusive, fully integrated, worldwide database” designed

to allow chemical companies to assess product viability and

cost based on a number of variables. ChemPlan had two

principal functions. As a database that illuminated how

chemical reactions could be disaggregated into their

component parts, it included both public information and

proprietary data derived from Amirnazmi’s expert analysis of

the various processes. 1 And as a dynamic planning tool,

ChemPlan enabled end users to determine individualized

production costs and the feasibility of embarking on

prospective projects by allowing them to change the input

1

ChemPlan’s licensing agreement alerted software

purchasers to the proprietary nature of the database,

indicating it contained “valuable TRADE SECRET and

confidential, unpublished information developed or acquired

by TranTech at great expense, including data, data structure,

data processing algorithms, innovations and concepts.”

3

variables in order to generate “what if” scenarios accounting

for market fluctuations. These features made ChemPlan

attractive to major manufacturers such as the Dow Chemical

Company, LyondellBasell Industries, and Rohm and Haas

Company.

Aiming to facilitate Iran’s transformation into “an

independent chemical powerhouse,” 2 and seeking to spur “a

flow of Iranian[ ] [scientists] back to Iran” where he would

ultimately join them to impart his expertise, 3 Amirnazmi

began, in the mid-1990s, to explore business partnerships

with Iranian entities. First, he initiated efforts to sell

ChemPlan to the state-owned National Petrochemical

Company of Iran (NPC). In August 1997, TranTech and NPC

executed a Software/Data License Agreement whereby NPC

agreed to purchase a subscription to ChemPlan for $64,000.

Amirnazmi directed NPC to wire payment to a European

bank account, and he traveled to Iran to demonstrate the

product’s functionality to NPC officials. In 1998, NPC

purchased a software update for $18,000. In 2000, NPC

enlisted Amirnazmi’s assistance in its quest to obtain an off-

the-shelf software package called BoxScore, a suite of

programs manufactured in the United States and consequently

unavailable to Iranian entities affected by U.S. trade

2

Letter from Ali Amirnazmi to Mrs. F. Parvaresh, Manager,

National Petrochemical Company of Iran (April 30, 1998).

3

Email from Amirnazmi to Mr. Robert G. Williamson,

Attorney at Law (undated).

4

sanctions. Amirnazmi procured the software, sent it to an

intermediary in Germany, and charged NPC $667.85 for his

efforts.

Amirnazmi met in person with NPC personnel at a

2000 international petrochemical conference held in Iran.

Thereafter, he sent NPC’s Director of Planning and

Development a letter in which he encouraged NPC to renew

its ChemPlan subscription and proposed three options—

including the formation of a joint venture—for tailoring

ChemPlan to NPC’s unique needs. Amirnazmi attended the

same conference in 2001 and again attempted to solicit NPC

interest in a customized ChemPlan package by sending an

NPC contact several renewed proposals along with

subscription order forms.

In 2002, Amirnazmi endeavored to engage an Iranian

company to handle its advertising and promotional efforts. In

connection with this deal, Amirnazmi attempted to transfer

$250 to an Iranian bank account. The U.S. bank declined to

complete the transaction, and the Treasury Department’s

Office of Foreign Assets Control (OFAC) requested from

Amirnazmi a detailed explanation for this attempted transfer.

Amirnazmi responded that he had not known such a

transaction was prohibited by the sanctions then in place

against Iran. 4

4

OFAC, the arm of the U.S. Treasury Department

responsible for administering the regulations implementing

the embargo against Iran, had previously flagged

5

After indicating he was willing to conduct business

with Iran, Amirnazmi was granted a private audience with

Iranian President Mahmoud Ahmadinejad at an event in New

York City in September 2006. At this meeting and in

subsequent correspondence, Amirnazmi expressed his desire

to transfer ChemPlan’s technical and economic knowledge to

Iran and sought President Ahmadinejad’s assistance in

helping him return to Iran so that he might serve the country

in his “field of expertise.” 5 In a January 2007 letter,

Amirnazmi beseeched President Ahmadinejad to arrange an

in-person meeting in Tehran so that he might unveil his

“plan” to help Iran, and he decried the United States’ “cruel

and tyran[nical]” treatment of the Iranian people. 6

Having brought himself to President Ahmadinejad’s

attention, Amirnazmi’s efforts to improve Iran’s chemical

Amirnazmi’s attempt to wire the registration fee for the 2000

petrochemical conference to an Iranian bank. After

Amirnazmi’s local bank informed him it could not forward

funds to a bank owned or controlled by Iranian authorities,

the conference organizers waived Amirnazmi’s attendance

fee.

5

Letter from Amirnazmi to Mahmoud Ahmadinejad,

President of the Islamic Republic of Iran (Nov. 7, 2006).

6

Fax from Amirnazmi to Ahmadinejad (Jan. 24, 2007) (as

read from the witness stand by Special Agent Eugene Robert

Lanzillo, Jr.).

6

capacities began to show results. In December 2007,

Amirnazmi (on behalf of TranTech) signed a Memorandum

of Understanding with the Institute for Business Analysis and

Consultancy (IBACO), an Iranian company, regarding the

provision of technology for a proposed polyvinyl butyral

chemical plant to be constructed in Iran. In May 2008,

Amirnazmi entered into a separate confidentiality agreement

with IBACO in which he agreed to have TranTech provide

software licensing, equipment and chemicals in connection

with the construction of a glacial acrylic acid and super

absorbent polymer plant in Iran.

Amirnazmi and NPC rekindled their working

partnership in 2008, entering into a new licensing agreement

for the ChemPlan software. During the negotiations leading

up to this agreement, Amirnazmi represented that the 1997

ChemPlan licensing agreement was “still valid.” 7 And in June

2008, Amirnazmi entered into a Memorandum of

Understanding with the Nokhbegan Institute of Technology

Development (NITD), an Iranian company, to create a joint

venture to provide software, database and technology transfer

services to clients in the chemical process industry. Under the

agreement, Amirnazmi pledged to have TranTech transfer the

ChemPlan system to a newly-formed company in Iran in

which TranTech would have been the majority shareholder.

The Memorandum of Understanding with NITD

expired by its own terms after two months. The 2008

7

Fax from Amirnazmi to Mr. Gorbanpour, NPC official (Feb.

26, 2008).

7

licensing agreement with NPC, which was signed by the

counterparties and which fixed the subscription fee at

$270,000, was to become effective upon installation of

ChemPlan on NPC hardware. Amirnazmi twice met with

IBACO officials in 2008 to negotiate the terms of a formal

contract covering the polyvinyl butyral plant, but the resulting

Technology Transfer and Construction Agreement was never

signed by the parties. And the IBACO confidentiality

agreement concerning the super absorbent polymer plant

contemplated further elucidation within the framework of a

formal contract drafted upon “finalizing negotiation[s] with

investors.”

Amirnazmi drew the attention of U.S. Customs and

Border Protection by traveling to Iran in 2007 and twice more

in 2008. Customs agents interviewed Amirnazmi upon his

return to the United States in both April and June of 2008.

Upon questioning, he claimed both trips were to visit his

elderly mother and that the latter trip also permitted him to

attend a petroleum conference. Although Amirnazmi

repeatedly disavowed any commercial purpose for his travels,

the presence of ostensibly business-related possessions cast

doubt on the credibility of his responses. In April he claimed

the sundry business cards and documents found in his

briefcase were personal effects he had not made use of on his

trip. In June 2008, confronted by Customs officials with

computer files and hard copy documents detailing plans to

build chemical plants in Iran, he declined to offer an

explanation.

8

On June 4, 2008, the day after his second encounter

with Customs officials, Amirnazmi contacted the OFAC

compliance hotline to inquire in general about U.S.

restrictions on commercial activity with Iran. Without either

delving into the specifics of how ChemPlan operated or

mentioning his prior business dealings with Iranian

companies, he asked whether making public documents

available on a website would fall within the informational-

materials exemption to IEEPA and whether exporting an

unidentified “good” would theoretically require dispensation

in the form of a license issued by OFAC.

Two days after this telephone conversation,

Amirnazmi was questioned by agents from the Internal

Revenue Service and the Federal Bureau of Investigation. He

acknowledged meeting President Ahmadinejad but denied

having conducted business on either of his 2008 trips to Iran,

and he claimed his only two financial transactions with Iran

had been the disallowed wire transfers much earlier in the

decade. The agents subsequently obtained a search warrant

for Amirnazmi’s business. Despite Amirnazmi’s protestations

that none of the documents named in the warrant were located

on the premises, the authorities seized numerous physical

documents and the hard drive from his computer, which also

contained pertinent documents. Upon further interrogation,

Amirnazmi conceded he had business relations with NPC

both in 1997 and in the more recent past, and he

acknowledged having met with Iranian state officials during

his trips abroad.

II.

9

On July 24, 2008, the government filed a ten-count

indictment against Amirnazmi in the Eastern District of

Pennsylvania charging him with (1) one count of conspiracy

to violate IEEPA, in violation of 18 U.S.C. § 371; (2) four

substantive counts of violating IEEPA, in violation of 50

U.S.C. § 1705, and of aiding and abetting the same, in

violation of 18 U.S.C. § 2; (3) one count of conspiracy to act

as an illegal agent of a foreign government, in violation of the

Foreign Agents Registration Act (FARA) and in violation of

18 U.S.C. § 371; (4) one substantive count of acting as an

illegal agent of a foreign government, in violation of 18

U.S.C. § 951, and of aiding and abetting the same, in

violation of 18 U.S.C. § 2; and (5) three counts of making

false statements to government officials, in violation of 18

U.S.C. § 1001. On October 2, the government filed a

superseding indictment, charging Amirnazmi with three

additional counts of bank fraud, in violation of 18 U.S.C. §

1344, and supplementing the original indictment with further

factual allegations.

Prior to trial, Amirnazmi filed a motion to dismiss in

which he alleged (1) IEEPA regulations are the product of an

unconstitutional delegation of legislative authority to the

Executive; and (2) portions of the superseding indictment

referencing conduct that occurred more than five years prior

to the indictment should be barred by the statute of

limitations. The court denied the motion, concluding IEEPA

does not violate the nondelegation doctrine and that

Amirnazmi’s actions prior to 2003 were part of a continuing

course of conduct that extended into the limitations period

and contributed to the charged conspiracy. See United States

10

v. Amirnazmi, No. 08-CR-0429-01, 2009 U.S. Dist. LEXIS

624 (E.D. Pa. Jan. 5, 2009). 8

The jury convicted Amirnazmi on all but one of the

IEEPA counts and on all of the false statement and bank fraud

counts. 9 Amirnazmi was acquitted of the FARA violations

charged in Counts Six and Seven. Amirnazmi moved for a

judgment of acquittal under Fed. R. Crim. P. 29 on the IEEPA

counts, the false statement counts and one of the bank fraud

counts. He reiterated his argument that IEEPA

8

Also prior to trial, the government moved to admit audio

recordings and transcripts of certain conversations in which

Amirnazmi had participated while in pretrial custody.

Amirnazmi moved to suppress, arguing the government had

used trial subpoenas to conduct further investigation after the

indictment had been returned in violation of Fed. R. Crim. P.

17(c). The court determined the subpoenas properly directed

the custodian of records to appear with the documents on

dates that corresponded with scheduled proceedings in the

case and consequently allowed the government to admit the

evidence.

9

Amirnazmi was found not guilty on Count Three of the

superseding indictment, which charged him with violating

IEEPA by entering into an agreement with the Research

Institute of Petroleum Industry, a division of Iran’s Ministry

of Petroleum, in which he agreed to conduct negotiations with

a Danish chemical company for the purpose of establishing a

joint venture in Iran.

11

unconstitutionally delegates to the Executive authority to

criminalize commercial conduct, and he added an argument

that the accompanying OFAC regulations under which he was

convicted are unconstitutionally vague. He also argued the

evidence was insufficient to prove his conduct did not fall

within IEEPA’s informational-materials exemption and that

the government failed to prove IEEPA required him to obtain

a license to engage in his activities. The court denied

Amirnazmi’s motion in its entirety. It rested on its previous

ruling concerning the nondelegation doctrine, concluded that

the IEEPA regulations are not unconstitutionally vague, and

determined the government had produced sufficient evidence

to sustain each conviction. See United States v. Amirnazmi,

No. 08-CR-0429-01, 2009 U.S. Dist. LEXIS 74833 (E.D. Pa.

Aug. 21, 2009).

Amirnazmi also moved for a new trial under Fed. R.

Crim. P. 33. Amirnazmi reiterated his claims that the prison

tapes were improperly obtained and should not have been

admitted and that evidence of his conduct prior to 2003

should have been barred by the statute of limitations. The

court denied this motion, resting on its previous ruling with

respect to the tapes and concluding Amirnazmi’s pre-2003

actions fell within the scope of his conspiracy “to bring his

technical wherewithal, especially the ChemPlan system, back

to Iran for the benefit of that country.” See United States v.

Amirnazmi, 648 F. Supp. 2d 718, 723 (E.D. Pa. 2009).

12

As noted, the District Court sentenced Amirnazmi to a

48-month term of imprisonment followed by five years’

supervised release. Amirnazmi timely appealed. 10

III.

On appeal, Amirnazmi principally challenges the

constitutionality of IEEPA and the accompanying OFAC

regulations. We will first address the constitutionality of the

statute itself, which Amirnazmi challenges on two fronts.

First, he argues that Congress—when delegating the authority

to create criminal offenses—must articulate the standards by

which executive conduct will be governed with greater

precision than is required in the context of delegations of civil

authority. IEEPA, Amirnazmi contends, lacks the requisite

specificity. Second, he claims Congress’s failure to comply

with its statutory responsibility to oversee the implementation

of the Iranian sanctions regime left the Executive’s discretion

wholly unchecked. Because IEEPA reserves for Congress the

final word in determining trade policy during peacetime

emergencies, Amirnazmi alleges, Congress’s abdication of its

oversight role rendered the delegation unconstitutional. 11

10

The District Court had jurisdiction under 18 U.S.C. § 3231.

We have jurisdiction under 28 U.S.C. § 1291.

11

We review challenges to the constitutionality of a statute de

novo. United States v. Fullmer, 584 F.3d 132, 151 (3d Cir.

2009).

13

A.

As the source of statutory authority for the Executive’s

exercise of emergency economic powers in response to

peacetime crises, IEEPA traces its provenance to § 5(b) of the

Trading with the Enemy Act of 1917, Pub. L. No. 65-91, § 5,

40 Stat. 411, 415 (1917), as amended, 12 U.S.C. § 95a

(TWEA). Dames & Moore v. Regan, 453 U.S. 654, 671

(1981). TWEA endowed the President with sweeping powers

to regulate international trade in times of war or “national

emergency,” but it lacked a countervailing mechanism to

divest the President of such authority once the emergency had

ebbed. Because Presidents had displayed a tendency to allow

“emergency” declarations to linger “even after the

circumstances or tensions that had led to the declaration could

no longer be said to pose a threat of emergency proportion to

the Nation,” some expressed concern that TWEA effectively

served as a “one-way ratchet to enhance greatly the

President’s discretionary authority over foreign policy.”

Regan v. Wald, 468 U.S. 222, 245 (1984) (Blackmun, J.,

dissenting).

In an effort to address TWEA’s evolution into a

“flexible instrument of foreign policy in nonemergency

situations,” id. at 246, Congress amended § 5(b) in 1977,

restricting the Executive’s ability to act under that statute

strictly to times of war, Pub. L. No. 95-223, Tit. I, § 101, 91

Stat. 1625, 1625 (1977) (striking “or during any other period

of national emergency declared by the President” from the

text of § 5(b)). Contemporaneously, Congress enacted the

International Emergency Economic Powers Act to serve as

14

the locus of executive economic authority during national-

emergency situations. See id. at Tit. II, 91 Stat. at 1626

(codified at 50 U.S.C. § 1701 et seq.). Although the powers

conferred in IEEPA closely mirror those granted in its

progenitor, IEEPA removed certain tools from the President’s

peacetime kit. 12 And, significantly for our purposes, IEEPA

subjected the President’s authority to a host of procedural

limitations designed to ensure Congress would retain its

essential legislative superiority in the formulation of sanctions

regimes erected under the Act’s delegation of emergency

power. 13

The predicate for an exercise of executive authority

under IEEPA is the declaration of a national emergency under

the National Emergencies Act (NEA). See 50 U.S.C. §§ 1621,

1701(b). Under IEEPA, the emergency must stem from an

“unusual and extraordinary threat, which has its source in

whole or substantial part outside the United States, to the

national security, foreign policy, or economy of the United

States.” Id. § 1701(a). After declaring such an emergency, the

12

Unlike TWEA, IEEPA does not authorize the Executive to

take title to foreign assets, to regulate purely domestic

transactions, to regulate gold or bullion, or to seize records.

See Regan, 468 U.S. at 228 n.8.

13

As explained at greater length in Section III.C.2 infra,

Congress’s reservation of a stricter oversight role in IEEPA is

relevant to Amirnazmi’s separation-of-powers argument.

15

President may, through “regulations . . . instructions, licenses,

or otherwise,”

(A) investigate, regulate, or prohibit —

(i) any transactions in foreign exchange,

(ii) transfers of credit or payments

between, by, through, or to any banking

institution, to the extent that such

transfers or payments involve any

interest of any foreign country or a

national thereof,

(iii) the importing or exporting of

currency or securities,

by any person, or with respect to any property,

subject to the jurisdiction of the United States;

(B) investigate, block during the pendency of an

investigation, regulate, direct and compel,

nullify, void, prevent or prohibit, any

acquisition, holding, withholding, use, transfer,

withdrawal, transportation, importation or

exportation of, or dealing in, or exercising any

right, power, or privilege with respect to, or

transactions involving, any property in which

any foreign country or a national thereof has

any interest by any person, or with respect to

any property, subject to the jurisdiction of the

United States . . . .

16

Id. § 1702(a)(1).

In tandem, IEEPA and NEA subject the President’s

exercise of emergency economic powers to an assortment of

procedural requirements. The President must consult with

Congress before exercising any of his powers under IEEPA

“in every possible instance,” and he “shall consult regularly

with the Congress so long as such authorities are exercised.”

Id. § 1703(a); see also id. § 1703(c) (stipulating that the

President must report to Congress “[a]t least once during each

succeeding six-month period after” the initial exercise of any

authority granted by the IEEPA). Whenever the President acts

pursuant to IEEPA, he must provide Congress with a report

detailing:

(1) the circumstances which necessitate such

exercise of authority;

(2) why the President believes those

circumstances constitute an unusual and

extraordinary threat, which has its source in

whole or substantial part outside the United

States, to the national security, foreign policy,

or economy of the United States;

(3) the authorities to be exercised and the

actions to be taken in the exercise of those

authorities to deal with those circumstances;

(4) why the President believes such actions are

necessary to deal with those circumstances; and

17

(5) any foreign countries with respect to which

such actions are to be taken and why such

actions are to be taken with respect to those

countries.

Id. § 1703(b). After each six-month interval, Congress “shall

meet to consider a vote on a joint resolution to determine

whether that emergency shall be terminated.” Id. § 1622(b);

id. § 1706(b) (providing for the cessation of presidential

authority under IEEPA upon congressional termination of an

emergency declared under NEA).

Substantively, the regulations contain several

exemptions and constraints. That is, regulations promulgated

under IEEPA may not impinge upon transactions incident to

travel or curtail the free exchange of personal

communications, humanitarian aid, or “information or

informational materials.” Id. § 1702(b). Moreover, criminal

penalties under IEEPA are reserved exclusively for those who

“willfully commit[ ], willfully attempt[ ] to commit, or

willfully conspire[ ] to commit” a violation of any license,

order or regulation issued pursuant to IEEPA. Id. § 1705(c).

And the Act exempts those who act in “good faith” reliance

on IEEPA, or on “any regulation, instruction, or direction”

issued under IEEPA, from both civil and criminal liability. Id.

§ 1702(a)(3).

On March 15, 1995, President Bill Clinton issued

Executive Order 12957, which declared a national emergency

to deal with the “unusual and extraordinary threat” posed to

the national security, foreign policy and economy of the

18

United States by “the actions and policies of the Government

of Iran,” and which prohibited United States involvement

with petroleum development in Iran. 60 Fed. Reg. 14615

(Mar. 17, 1995). 14 On May 6, 1995, President Clinton signed

Executive Order 12959, which fortified the sanctions regime

by banning U.S. firms from exporting to Iran, importing from

Iran, or investing in Iran, subject to the exemptions provided

in IEEPA. See 60 Fed. Reg. 24757 (May 9, 1995); see also

Exec. Order No. 13059, 62 Fed. Reg. 44531 (Aug. 21, 1997)

(clarifying the preceding Orders). The Executive Orders

authorized the Secretary of the Treasury, in consultation with

the Secretary of State, “to take such actions, including the

promulgation of rules and regulations . . . as may be

necessary to carry out the purposes” of the Orders. See, e.g.,

60 Fed. Reg. 14615 at § 3. The Treasury Department

subsequently issued the Iranian Transactions Regulations

(ITR). See generally 31 C.F.R. Part 560.

Subject to limited exemptions and to licenses issued by

OFAC, the ITR prohibits, in part, the “exportation,

reexportation, sale, or supply, directly or indirectly, from the

United States, or by a United States person, wherever located,

of any goods, technology, or services to Iran or the

Government of Iran,” 31 C.F.R. § 560.204, and “any new

investment by a United States person in Iran or in property

14

The national emergency with respect to Iran has been

extended annually through presidential notices. See Executive

Documents summarized in the annotations to 50 U.S.C. §

1701.

19

(including entities) owned or controlled by the Government

of Iran,” id. § 560.207; see also id. § 560.206(a) (generally

prohibiting “any transaction or dealing in or related to . . .

[g]oods, technology, or services for exportation,

reexportation, sale or supply, directly or indirectly, to Iran or

the Government of Iran”). 15 The regulations also incorporate

the statutory exemption permitting the exportation of

“informational materials.” Id. § 560.210(c). Critically, this

exemption does not apply to informational materials “not

fully created and in existence at the date of the transactions,

or to the substantive or artistic alteration or enhancement of

informational materials.” Id.

B.

15

OFAC authorizes otherwise proscribed transactions

through general licenses set forth in the ITR and through

specific licenses issued pursuant to the procedures outlined in

31 C.F.R. Part 560, Subpart E. Whereas a general license

categorically authorizes “a particular type of transaction for a

class of persons without the need to apply for a license,” a

specific license is a “written document issued by OFAC to a

particular person or entity, authorizing a particular transaction

in response to a written license application.” OFAC,

Frequently Asked Questions and Answers,

http://www.treasury.gov/resource-

center/faqs/Sanctions/Pages/answer.aspx (last visited April

29, 2011).

20

The maxim that Congress may not delegate legislative

power to the President is “universally recognized as vital to

the integrity and maintenance of the system of government

ordained by the Constitution.” Field v. Clark, 143 U.S. 649,

692 (1892). Nevertheless, the Supreme Court has invoked the

unconstitutional delegation doctrine—which derives its

constitutional underpinning from Article I’s vesting of “all

legislative powers” with Congress 16—to strike down a law

only twice in its history. See Panama Ref. Co. v. Ryan, 293

U.S. 388 (1935) (invalidating delegation under section 9(c) of

the National Industrial Recovery Act permitting the President

to prohibit the interstate transportation of petroleum goods);

A.L.A. Schechter Poultry Corp. v. United States, 295 U.S. 495

(1935) (striking down section 3 of the same Act, which

authorized trade and industrial associations to propose “codes

of fair competition” that would become legally binding if

approved by the President). The Court’s jurisprudence has

been animated by a “practical understanding that in our

increasingly complex society, replete with ever changing and

more technical problems, Congress simply cannot do its job

absent an ability to delegate power under broad general

directives.” Mistretta v. United States, 488 U.S. 361, 372

(1989). Accordingly, in assessing a permissible delegation,

the Court has decreed it will be “‘constitutionally sufficient if

Congress clearly delineates the general policy, the public

agency which is to apply it, and the boundaries of this

delegated authority.’” Id. at 372-73 (quoting Am. Power &

Light Co. v. SEC, 329 U.S. 90, 105 (1946)).

16

U.S. Const. art. I, § 1.

21

Congress’s ability to endow a coordinate branch of

government with a measure of discretion is circumscribed by

the requirement that it must “lay down by legislative act an

intelligible principle to which the person or body authorized

to [exercise the delegated authority] is directed to conform.”

J.W. Hampton, Jr. & Co. v. United States, 276 U.S. 394, 409

(1928). Whereas Congress must itself elucidate “the standards

of legal obligation” in order to fulfill its “essential legislative

function,” it may devolve to “selected instrumentalities

[responsibility for] the making of subordinate rules within

prescribed limits and the determination of facts to which the

policy as declared by the legislature is to apply.” Schechter

Poultry, 295 U.S. at 530. Because no one standard can

account for the range of contexts in which Congress

legislates, “the degree of agency discretion that is acceptable

varies according to the scope of the power congressionally

conferred.” Whitman v. Am. Trucking Ass’ns, Inc., 531 U.S.

457, 475 (2001).

The Supreme Court has upheld Congress’s delegation

to the President of civil authority to nullify certain

attachments and transfers of assets under IEEPA. Dames &

Moore, 453 U.S. at 675. But Amirnazmi contends IEEPA’s

delegation of authority to define criminal conduct is

inherently more suspect and that, consequently, only a lesser

degree of executive discretion is constitutionally permissible

in this context. The Court has expressly refrained from

deciding whether Congress must provide stricter guidance

than a mere “intelligible principle” when authorizing the

Executive “to promulgate regulations that contemplate

criminal sanctions.” Touby v. United States, 500 U.S. 160,

22

165-66 (1991). After concluding the contested delegation

would pass constitutional muster even under a heightened

standard, the Court refrained from resolving the petitioner’s

argument that criminal regulations promulgated under

congressional delegations of authority should be subject to

more searching scrutiny on account of the “heightened risk to

individual liberty” they pose. Id. at 166. 17

C.

17

In Touby, the Court held section 201(h) of the Controlled

Substances Act, which delegated to the Attorney General the

authority to temporarily designate a substance as “controlled”

without submitting to the full complement of procedural

requirements for permanent scheduling, “meaningfully

constrain[ed] the Attorney General’s discretion to define

criminal conduct.” Id. at 166. The Court pointed to “multiple

specific restrictions on the Attorney General’s discretion”

that, together, satisfied the nondelegation doctrine. Id. at 167.

To schedule a drug temporarily, the Attorney General was

required to find that doing so would be “necessary to avoid an

imminent hazard to the public safety.” Id. at 166 (citing 21

U.S.C. § 811(h)(1)). In rendering this determination, the

Attorney General was “required to consider” three specific

factors, ordered to publish 30-day notice of the proposed

scheduling in the Federal Register and to transmit notice to

the Secretary of Health and Human Services, and bound by

several of the strictures for permanent scheduling (“high

potential for abuse,” “no currently accepted medical use”). Id.

at 166-67.

23

1.

Two of our sister circuits have analyzed IEEPA’s

delegation of authority to criminalize conduct in light of

Touby and have concluded the Act withstands constitutional

scrutiny. In United States v. Arch Trading Co., 987 F.2d

1087, 1092-94 (4th Cir. 1993), the Fourth Circuit discerned

“constraining factors” in IEEPA comparable to those found

sufficient in Touby and concluded the President’s powers are

“explicitly defined and circumscribed.” And in United States

v. Dhafir, 461 F.3d 211, 217 (2d Cir. 2006), the Second

Circuit adopted the Fourth Circuit’s logic, concluding IEEPA

would satisfy even a heightened standard because “the

authorities delegated are defined and limited.” 18

We too conclude that IEEPA “meaningfully

constrains” the President’s discretion. See Touby, 500 U.S. at

166. Under the Controlled Substance Act provision examined

in Touby, the Attorney General could not temporarily

schedule a drug without first finding that doing so would be

“necessary to avoid an imminent hazard to the public safety.”

Id. Similarly, to activate IEEPA, the President must find that

an “unusual and extraordinary threat . . . to the national

18

District Courts have followed suit. See United States v.

Mirza, No. H-06-421, 2010 U.S. Dist. LEXIS 34556, at *3-4

(S.D. Tex. Apr. 7, 2010); United States v. Esfahani, No. 05-

CR-0255, 2006 U.S. Dist. LEXIS 1839, at *11-12 (N.D. Ill.

Jan. 17, 2006); United States v. Anvari-Hamedani, 378 F.

Supp. 2d 821, 829-30 (N.D. Ohio 2005).

24

security, foreign policy, or economy of the United States”

originating on foreign soil has reached “national emergency”

proportions. See 50 U.S.C. § 1701. In Touby, the Court found

the Attorney General was constrained by the requirement that

he abide by several of the more rigorous features of the

permanent scheduling process designating illegal drugs. 500

U.S. at 166-67. Likewise, IEEPA prohibits the President from

regulating certain exempt transactions, 50 U.S.C. § 1702(b),

from prosecuting unwitting violators or holding liable those

who act in good faith reliance on the statute and regulations,

id. §§ 1705(c), 1702(a)(3), and from obviating Congress’s

role as ultimate arbiter of emergency trade policy, see id. §§

1622(b), 1703, 1706; 19 see also Mistretta, 488 U.S. at 372-73

(explaining Congress must “clearly delineate[ ] the general

policy . . . and the boundaries of this delegated authority”).

In effecting the shift of peacetime authority from

TWEA to IEEPA, Congress “placed several procedural

restrictions on the President’s exercise of the national-

emergency powers, including congressional consultation,

review, and termination.” Regan, 468 U.S. at 249 (Blackmun,

J., dissenting). In so doing, Congress reaffirmed its “essential

legislative function,” see Schechter Poultry, 295 U.S. at 530,

and struck a careful balance between affording the President a

degree of authority to address the exigencies of national

emergencies and restraining his ability to perpetuate

19

The Constitution vests the power to regulate commerce

with foreign nations in the hands of Congress. U.S. Const. art.

I, § 8.

25

emergency situations indefinitely by creating more

opportunities for congressional input, cf. Panama Ref. Co.,

293 U.S. at 430 (“Congress has declared no policy, has

established no standard, has laid down no rule”). 20 Therefore,

IEEPA meets the same standard of constraint outlined in

Touby; that is, IEEPA meaningfully constrains the

Executive’s discretion. Accordingly, it is unnecessary for us

to address the unsettled question of whether something more

demanding than an “intelligible principle” is necessitated

within the context of delegating authority to define criminal

conduct.

2.

Second, Amirnazmi claims Congress has violated

fundamental separation-of-powers precepts by neglecting its

statutory responsibility to monitor the implementation of the

20

Amirnazmi unconvincingly attempts to distinguish Touby

by arguing the power to classify newly designed drugs is “far

narrower” than the powers conferred by the IEEPA. The

petitioner in Dhafir raised a similar argument, contending the

Touby court upheld a “temporary power” to schedule

controlled substances whereas IEEPA confers authority that

can persist indefinitely. 461 F.3d at 217. The Second Circuit

rejected this position, pointing to the need for the President to

reaffirm the national emergency at regular intervals and

Congress’s ability to terminate the declaration as indicia of

proper limitation. Id. We find no material durational

difference between the delegations at issue here and in Touby.

26

Iranian sanctions regime established under IEEPA. In so

doing, Amirnazmi claims, the legislature has allowed the

President to arrogate “virtually unlimited power over foreign

trade,” thereby fomenting a “serious threat to public liberty

[that] necessitates judicial intervention.” This allegation

implicates interrelated issues of foreign policy, congressional

authorization, and statutorily mandated oversight. Because

these considerations are intertwined, we consider them in

concert.

The linchpin of Amirnazmi’s claim is 50 U.S.C. §

1622(b), which reads: “Not later than six months after a

national emergency is declared, and not later than the end of

each six-month period thereafter that such emergency

continues, each House of Congress shall meet to consider a

vote on a joint resolution to determine whether that

emergency shall be terminated.” In Dhafir, the Second Circuit

noted in passing that Congress’s failure to fulfill its oversight

responsibilities might conceivably raise “complicated and

sensitive issues concerning separation of powers” but

declined to expound in light of an inadequate factual record.

461 F.3d at 217 n.3. Given the conventional wisdom that the

shift in authority from TWEA to IEEPA was inspired in part

by a prevailing sentiment that Congress’s role in devising

emergency trade policy warranted strengthening, see supra

27

Section III.A, its failure to police executive conduct would

appear counterintuitive. 21

As a threshold matter, we must determine whether a

national emergency properly declared under NEA terminates

automatically when Congress fails to meet in conformance

with the language of § 1622(b). In Beacon Products Corp. v.

Reagan, 814 F.2d 1, 4 (1st Cir. 1987), the First Circuit

answered that question in the negative. The court reasoned

that the disparity between § 1622(d), which explicitly

provides for the automatic termination of a national

emergency should the President fail to extend it, and §

1622(b), which is devoid of a parallel congressional

provision, suggests Congress deliberately withheld automatic

termination as a remedy for violation of the “periodic

meeting” clause. Id. at 4. Next, the court noted Congress

eliminated a sunset provision from an earlier draft of NEA,

reserving for itself “the burden of acting affirmatively” by

substituting in that provision’s place the requirement that it

pass a resolution to end an emergency. Id. (referencing 50

U.S.C. § 1622(a)). The court then concluded Congress likely

intended “to give those who want to end the emergency the

chance to force a vote on the issue, rather than to require

those who do not want to end the emergency to force

congressional action to prevent automatic termination.” Id. at

5. We agree that Congress did not effectively terminate the

21

The parties agree that Congress has not met regularly to

consider terminating the national emergency with respect to

Iran.

28

emergency against Iran simply by virtue of its failure to hold

the periodic meetings addressed in § 1622(b).

Amirnazmi contends Beacon Products should not

control our analysis because the issue here is not merely one

of statutory interpretation but instead one that requires us to

consider whether Congress’s failure to regularly convene to

evaluate the desirability of a continued emergency trade

regime violates the power-sharing program contemplated by

IEEPA. That is, Amirnazmi would have us hold that

Congress’s assumption of a silent partner role transforms a

limited delegation into a blank check that confers upon the

Executive unbridled power to create trade policy. In Dames v.

Moore, the Court wrote that IEEPA “constitutes specific

congressional authorization to the President” to take certain

emergency measures. 453 U.S. at 675. Following

Amirnazmi’s logic, the issue would then become whether

protracted inaction vitiates this authorization. If this were the

case, we would likely consider whether, after express

authorization has ostensibly lapsed, the President’s continued

criminalization of certain commercial conduct has either been

implicitly countenanced or whether he is in fact acting

pursuant to some form of inherent authority.

The constitutionality of IEEPA’s delegation of

criminal authority does not rest on Congress affirmatively

renewing its approval of each ongoing emergency at regular

six-month intervals. Equating inaction with a withdrawal of

authorization would be particularly improper with a statute

that concerns foreign affairs, “a sphere in which delegation is

afforded even broader deference.” Dhafir, 461 F.3d at 215.

29

“Congress—in giving the Executive authority over matters of

foreign affairs—must of necessity paint with a brush broader

than that it customarily wields in domestic areas.” Zemel v.

Rusk, 381 U.S. 1, 17 (1965); see also Veterans & Reservists

for Peace in Vietnam v. Reg. Comm’r of Customs, 459 F.2d

676, 679 (3d Cir. 1972) (“Ordinarily, when dealing with

matters of foreign relations, Congress may lawfully delegate

to the President broader discretion than would be permissible

with regard to domestic affairs.”); United States v. Curtiss-

Wright Exp. Corp., 299 U.S. 304, 319-20 (1936) (upholding

Congress’s ability to delegate the power to prohibit the sale of

arms to certain countries designated by the President and

explaining that it was “important to bear in mind that we are

here dealing not alone with an authority vested in the

President by an exertion of legislative power, but with such

an authority plus the very delicate, plenary and exclusive

power of the President as the sole organ of the federal

government in the field of international relations”). Mindful

of the heightened deference accorded the Executive in this

field, we decline to interpret the legislative grant of authority

parsimoniously. Congress may act to terminate the national

emergency; NEA does not necessarily compel Congress to

take affirmative steps to prolong the President’s charted

course. See Beacon Prods., 814 F.2d at 4; 50 U.S.C. § 1622.

Congress’s failure to satisfy the periodic meeting

requirements of § 1622(b) does not ineluctably lead to a

conclusion that the President’s continued prosecution of trade

sanctions under IEEPA has ceased to be “pursuant to an

express or implied authorization.” See Youngstown Sheet &

Tube Co. v. Sawyer, 343 U.S. 579, 635 (1952) (Jackson, J.,

30

concurring) (setting forth the familiar tripartite framework for

evaluating executive action and explaining the President’s

power is “at its maximum” when he acts according to

congressional directive). In Haig v. Agee, 453 U.S. 280, 300-

01 (1981), the Court inferred congressional approval of a

“longstanding and officially promulgated” executive policy

from both inaction and statutory developments that “‘left

completely untouched the broad rule-making authority

granted in the earlier Act.’” Id. (quoting Zemel, 381 U.S. at

12). Under Agee, we must generally defer to a consistent

administrative construction of a statute. Id. at 291. “This is

especially so in the areas of foreign policy and national

security, where congressional silence is not to be equated

with congressional disapproval.” Id. The Court’s analysis in

Agee was buttressed by its determination that Congress had

“endorsed not only the underlying premise of Executive

authority in the areas of foreign policy and national security,

but also its specific application” to the subject matter at issue.

Id. at 294.

Similarly, this regulatory embargo against Iran has

been in place since 1995. Far from sitting by as successive

Presidents maintained a sweeping sanctions regime, Congress

has expanded, deepened and formalized the sanctions in a

comprehensive legislative effort to target Iran through

economic measures. In 1996, Congress passed the Iran

Sanctions Act, Pub. L. No. 104-172, 110 Stat. 1541 (1996)

(codified in part at 50 U.S.C. § 1701 (note)), which mandated

the imposition of specified sanctions against foreign firms

that reached threshold levels of involvement with Iran’s

31

energy sector. 22 Subsequently, in 2006, Congress passed the

Iran Freedom Support Act. Pub L. No. 109-293, 120 Stat.

1344 (2006) (codified in part at 50 U.S.C. § 1701 (note)). In

addition to appropriating funds earmarked for the support of

persons and organizations “working for the purpose of

supporting and promoting democracy for Iran,” id. § 302, the

Act placed Congress’s imprimatur on executive sanctions

against Iran. Under the heading “Codification of Sanctions,”

Congress wrote:

United States sanctions with respect to Iran

imposed pursuant to sections 1 and 3 of

Executive Order No. 12957, sections 1(e),

(1)(g) and (3) of Executive Order No. 12959,

22

See id. at § 3 (“The Congress declares that it is the policy of

the United States to deny Iran the ability to support acts of

international terrorism and to fund the development and

acquisition of weapons of mass destruction and the means to

deliver them by limiting the development of Iran’s ability to

explore for, extract, refine, or transport by pipeline petroleum

resources of Iran.”). Iran has been designated a state sponsor

of terrorism continuously since January 19, 1984. Prevatt v.

Islamic Republic of Iran, 421 F. Supp. 2d 152, 156 (D.D.C.

2006). This classification has restricted the flow of goods into

Iran under section 6(j) of the Export Administration Act of

1979 (codified at 50 U.S.C. App’x § 2405(j)), section 620A

of the Foreign Assistance Act of 1961 (codified at 22 U.S.C.

§ 2371), and sections 38 and 40 of the Arms Export Control

Act (codified at 22 U.S.C. § 2780).

32

and sections 2, 3, and 5 of Executive Order No.

13059 (relating to exports and certain other

transactions with Iran) as in effect on January 1,

2006, shall remain in effect. The President may

terminate such sanctions, in whole or in part, if

the President notifies Congress at least 15 days

in advance of such termination.

Id. at § 101(a). Notably, one of the provisions incorporated by

reference (section 2 of Executive Order 13059) specifically

prohibited “the exportation, reexportation, sale, or supply,

directly or indirectly, from the United States, or by a United

States person, wherever located, of any goods, technology, or

services to Iran or the Government of Iran.” 62 Fed. Reg.

44531.

And in 2010, Congress passed the Comprehensive Iran

Sanctions, Accountability, and Divestment Act of 2010. Pub.

L. No. 111-195, 124 Stat. 1312 (2010) (codified in part at 50

U.S.C § 1701 (note)). CISADA expanded the Iran Sanctions

Act by targeting Iran’s ability to make or import gasoline and

placing new restrictions on financial institutions. Id. Most

significantly for our purposes, however, is § 103(b)(2), in

which Congress codified the prohibitions on the exportation

of goods, services and technology of United States origin to

Iran that were then in effect under executive orders

promulgated pursuant to IEEPA. Id. at Tit. I, § 103, 124 Stat.

at 1328-31. 23 Therefore, when Amirnazmi was tried and

23

CISADA incorporated the exemptions provided in 50

U.S.C. § 1702(b), including the informational-materials

33

convicted, Congress had already ratified the OFAC

regulations under which he was charged. And, in the

aftermath of his conviction, Congress once more manifested

its approval of executive conduct by again codifying the

extant prohibitions on exports issued pursuant to IEEPA.

These measures demonstrate Congress’s approval of the

emergency measures undertaken against Iran notwithstanding

its failure to adhere to the meeting requirements of §

1622(b). 24

Far from being unaware or indifferent, in the case of

Iran, Congress has clearly and consistently demonstrated its

support of the Executive’s agenda. This is not a scenario in

which we are compelled to divine the significance—if any—

of congressional silence. Nevertheless, given the number of

countries against which trade sanctions have been leveled

exemption, into this blanket codification. Pub. L. No. 111-195

at Tit. I, § 103(b)(2)(B)(i), 124 Stat. at 1328-29.

24

Unsurprisingly, Congress’s enactment of legislative

sanctions against Iran coincided with its eschewing of

periodic meetings to review the Executive’s IEEPA-based

sanctions. This reality corroborates the First Circuit’s

supposition in Beacon Products that “[f]ailure to vote likely

means that few legislators wish to end the emergency. It

would be odd to think that Congress would make it easier to

terminate a popular emergency than an unpopular one.” 814

F.2d at 4-5.

34

pursuant to IEEPA, 25 it is not difficult to envisage a situation

in which Congress’s position is less robustly documented.

Although Congress’s failure to periodically meet neither

automatically terminates an emergency nor bespeaks its

dissatisfaction with the President’s policies, § 1622(b)

provides a regularized mechanism for disquieted

representatives to initiate a dialogue about or even contest the

wisdom of continuing on with the President’s strategy. Once

the President has invoked his power to criminalize certain

conduct under IEEPA, Congress retains an ongoing part in

ensuring the Executive’s actions remain “meaningfully

constrained” so as to satisfy the requirements of Touby. 26

25

Since the statute’s inception, Presidents have found

“unusual and extraordinary” threats emanating from

Afghanistan, Angola, Belarus, Burma, Colombia, Cote

d’Ivoire, the Democratic Republic of the Congo, Haiti, Iran,

Iraq, Liberia, Libya, Nicaragua, North Korea, Panama, Sierra

Leone, South Africa, Sudan, Syria, the Western Balkans, and

Zimbabwe. See Executive Documents summarized in the

annotations to 50 U.S.C. § 1701.

26

Originally, NEA provided for termination of an emergency

state by “concurrent resolution” of Congress. See Beacon

Products v. Reagan, 633 F. Supp. 1191, 1194 (D. Mass.

1986) (citing the first iteration of 50 U.S.C. § 1622(a)).

However, in INS v. Chadha, 462 U.S. 919, 959 (1983), the

Supreme Court invalidated a similar provision as an

unconstitutional “legislative veto” insofar as it allowed

Congress to act without obtaining the President’s signature.

35

The Supreme Court has held that “[m]atters intimately

related to foreign policy and national security are rarely

proper subjects for judicial intervention,” Agee, 453 U.S. at

292, and federal courts have historically declined to review

“the essentially political questions surrounding the

declaration or continuance of a national emergency,” United

States v. Spawr Optical Research, Inc., 685 F.2d 1076, 1080

(9th Cir. 1982) (internal quotation marks omitted). Although

such considerations do not preclude enforcing compliance

with statutory dictates, NEA places the onus on Congress to

ensure emergency situations remain anomalous and do not

quietly evolve into default norms. See Youngstown, 343 U.S.

at 654 (Jackson, J., concurring) (“[P]ower to legislate for

emergencies belongs in the hands of Congress, but only

Subsequently, Congress amended NEA and the

unconstitutional clause with one that called for termination of

an emergency by “joint resolution.” Pub. L. No. 99-93, Tit.

VIII, § 801, 99 Stat. 405, 448 (1985) (amending 50 U.S.C. §

1622 by striking each use of the word “concurrent” and

inserting in its place the word “joint”). IEEPA, on its face,

permits a national emergency to be “terminated by the

Congress by concurrent resolution pursuant to section 202 of

the National Emergencies Act [50 U.S.C. § 1622].” See 50

U.S.C. § 1706(b) (2011). Chadha and the amendment to the

cross-referenced section in NEA would appear to have

rendered the words “by concurrent resolution” in § 1706(b)

ineffective. “[P]ursuant to section 202 of the National

Emergencies Act,” Congress may only terminate an

emergency via joint resolution.

36

Congress itself can prevent power from slipping through its

fingers.”).

IV.

Next, Amirnazmi argues the government failed to

prove beyond a reasonable doubt that ChemPlan does not fall

within the scope of IEEPA’s informational-materials

exemption. He contends that Congress intended to insulate

transactions incident to the free flow of information from

regulation and that the sale of ChemPlan, which conveys

pricing information and scientific information, falls within

this category of presumptively exempt activity. He urges us to

vacate his convictions on Counts Two and Five of the

superseding indictment, which charged him with ChemPlan-

related IEEPA violations, because, he argues, OFAC’s

interpretation of this exemption both flouts congressional

intent and is unconstitutionally vague.

Congress proscribes the Executive from regulating,

pursuant to IEEPA,

the importation from any country, or the

exportation to any country, whether commercial

or otherwise, regardless of format or medium of

transmission, of any information or

informational materials, including but not

limited to, publications, films, posters,

phonograph records, photographs, microfilms,

microfiche, tapes, compact disks, CD ROMs,

artworks, and news wire feeds . . . .

37

50 U.S.C. § 1702(b)(3). OFAC has incorporated the statutory

exemption into the ITR; the regulations provide a general

license authorizing transactions involving “information and

informational materials.” See 31 C.F.R. § 560.210(c)(1).

Although not enumerated in the statute, technology and

software are capable of qualifying as “informational

materials” under the regulations. See id. § 560.418 (“The

release of technology or software in the United States . . . to

any person violates the [ITR] if made with knowledge or

reason to know the technology is intended for Iran or the

Government of Iran, unless that technology or software meets

the definition of information and informational materials in §

560.315.”). However, under OFAC’s interpretation, the

general license is not applicable to “transactions related to

information and informational materials not fully created and

in existence at the date of the transactions, or to the

substantive or artistic alteration or enhancement of

informational materials, or to the provision of marketing and

business consulting services.” Id. § 560.210(c)(2) (emphasis

added).

At trial, the parties agreed to submit the issue of

whether ChemPlan fell within the exemption to the jury as a

factual matter, and the jury was instructed that the

government had the burden of proving beyond a reasonable

doubt the exemption did not apply. In his Rule 29 motion,

Amirnazmi appeared to challenge the sufficiency of the

evidence supporting his conviction on the IEEPA counts. The

District Court, viewing the evidence in the light most

favorable to the government, concluded a reasonable

factfinder could have found the government had proven

38

beyond a reasonable doubt that ChemPlan was “not fully

created and in existence at the date of the [relevant]

transactions” and thus could have found the informational-

materials exemption inapplicable. Amirnazmi, 2009 U.S. Dist.

LEXIS 74833, at *18. In reaching this conclusion, the District

Court cited Amirnazmi’s description of ChemPlan as a

“dynamic tool, which allows the user to generate ‘what if’

scenarios,” as well as testimony indicating that ChemPlan

packages were specifically tailored to end users and that the

program allowed users to enter their own data in order to

generate customized reports.

Ordinarily, our review of whether a jury verdict rests

on legally sufficient evidence is “particularly deferential.”

United States v. Dent, 149 F.3d 180, 187 (3d Cir. 1998). We

must “view the evidence in the light most favorable to the

Government . . . and will sustain the verdict if any rational

trier of fact could have found the essential elements of the

crime beyond a reasonable doubt.” Id. (internal quotation

marks omitted). The government argues Amirnazmi has

waived any claim that the exemption applies as a matter of

law by accepting the proposed jury instruction. See United

States ex rel. O’Connor v. New Jersey, 405 F.2d 632, 634 n.2

(3d Cir. 1969) (quoting Johnson v. Zerbst, 304 U.S. 458, 464

(1938) (defining a waiver as “an intentional relinquishment or

abandonment of a known right or privilege”)).

But because the jury returned a guilty verdict without

specific interrogatories, we cannot say with any certainty

whether it concluded ChemPlan simply did not qualify as

“informational materials” or whether, as the District Court

39

surmised, it concluded the exemption was inapplicable on

account of the regulatory carve-out. In federal criminal cases,

a general verdict will be upheld if the government has

adduced sufficient evidence in support of at least one of the

alternative theories on which the jury was charged. Griffin v.

United States, 502 U.S. 46, 49 (1991). 27 We agree with the

District Court that a reasonable factfinder could have found

the government proved beyond a reasonable doubt that

ChemPlan was “not fully created and in existence at the date

of the transactions,” and was therefore subject to OFAC

regulation under the ITR. 28

27

In its jury charge, the District Court quoted both IEEPA’s

informational-materials exemption and the regulatory carve-

out within the ITR. It then stressed that “the defendant has

raised this [informational-materials] exemption as an issue

during trial. The government has the burden to prove beyond

a reasonable doubt that the exemption does not apply.”

28

We will thus assume without deciding that the ChemPlan

software could conceivably satisfy the definition of

“information and informational materials” in 31 C.F.R. §

560.315. See 31 C.F.R. § 560.418. Nevertheless, it bears

noting that OFAC has consistently treated software as

conceptually distinct from other forms of informational

materials. See id. § 560.210(c)(3) (“This section does not

exempt from regulation or authorize transactions incident to

the exportation of software subject to the Export

Administration Regulations (15 CFR parts 730-774).”); id. §

560.210(c)(4) (“This section does not exempt from regulation

40

Amirnazmi argues reliance on this regulatory language

is fatally misplaced for two reasons. First, he claims OFAC’s

interpretation of the informational-materials exemption is

ultra vires. As Congress has structured IEEPA to disempower

the Executive from imposing trade sanctions that impinge

upon certain conduct, he argues, a regulation that undercuts

this legislative charge by purporting to criminalize such

conduct would be unenforceable. Second, he argues this

regulation fails to inform those potentially affected by IEEPA

that certain conduct is proscribed. Because the regulation did

not announce with unmistakable clarity that a product of

ChemPlan’s nature would not fall within the general license

for “informational materials,” he contends, it is

unconstitutionally vague.

A.

First, Amirnazmi contends OFAC’s regulation

removing informational materials “not fully created and in

existence at the date of the transactions” from the scope of the

statutory exemption reflects an impermissible agency

interpretation that should be struck down under the principles

enunciated in Chevron U.S.A. v. Natural Resources Defense

Council, Inc., 467 U.S. 837, 842-43 (1984). We disagree.

or authorize the exportation of goods (including software) . . .

where such exportation . . . is for use in the transmission of

any data.”).

41

Prior to 1988, trade sanctions that hampered the

exchange of informational materials were routinely justified

under TWEA and IEEPA as incidental to the broader

commercial purpose of these trade measures. See, e.g.,

Teague v. Regional Comm’r of Customs, 404 F.2d 441, 445

(2d Cir. 1968) (upholding TWEA regulations that effected a

categorical prohibition on importation of informational

materials from China, North Korea and North Vietnam

because the limitation was “incidental to the proper general

purpose of the regulations: restricting the dollar flow to

hostile nations”). In Veterans & Reservists for Peace in

Vietnam, we wrote:

[A] statute is not overly broad and thus

violative of the First Amendment merely

because it regulates incident to its scheme

protected activities or property. It is only where

the statute directly regulates speech or

expression arguably protected by the First

Amendment, or where as its mechanism the

statute has granted discretion to a delegatee to

determine whether particular items of

expression may be prohibited on the basis of

their content, that the question of overbreadth

arises. [TWEA] Section 5(b) does not directly

regulate First Amendment protected material,

rather it controls transactions concerning

property in which an enemy has an economic

interest. The purport of the statute is clear on its

face, and therefore provides guidance to the

42

delegatee with regard to the exercise of his

functions.

459 F.2d at 681. Until 1988, this line of reasoning held sway.

The regulations “nominally allowed the importation of

informational materials . . . but in reality banned it by

requiring that the importers make payment into blocked U.S.

accounts.” Walsh v. Brady, 927 F.2d 1229, 1230 (D.C. Cir.

1991) (citing 31 C.F.R. § 515.545 (1987)).

Congress amended section 5 of TWEA and section

203(b) of IEEPA in 1988 to exempt the regulation of

informational materials from the Executive’s congeries of

powers. See Omnibus Trade and Competitiveness Act of

1988, Pub. L. No. 100-418, § 2502, 102 Stat. 1107, 1371

(1988) (codified at 50 U.S.C. app. § 5(b), 50 U.S.C. §

1072(b)). 29 The amendment specifically removed from the

29

The amendment restricted the Executive from regulating or

prohibiting, directly or indirectly,

the importation from any country, or the

exportation to any country, whether commercial

or otherwise, of publications, films, posters,

phonograph records, photographs, microfilms,

microfiche, tapes, or other informational

materials, which are not otherwise controlled

for export under section 5 of the Export

Administration Act of 1979 or with respect to

which no acts are prohibited by chapter 37 of

title 18, United States Code.

43

Executive’s purview the authority to regulate or prohibit such

transactions “directly or indirectly.” Id. This Berman

Amendment was considered “a reaction to several seizures by

the United States of shipments of magazines and books from

embargoed countries and to the Treasury Department’s

restrictions on the permissible forms of payment for

informational materials purchased from Cuba.” Kalantari v.

NITV, Inc., 352 F.3d 1202, 1205 (9th Cir. 2003) (footnotes

omitted).

In the wake of the Berman Amendment, OFAC

amended its regulations to conform with the new statutory

language. See Foreign Assets Control Regulations and Cuban

Assets Control Regulations, 54 Fed. Reg. 5229 (Feb. 2, 1989)

(codified at 31 C.F.R. §§ 500.206, 500.332). Paralleling the

statute, the new regulations exempted informational

materials, “whether commercial or otherwise,” from

prohibition or regulation. Id. Notably, however, OFAC took a

narrow view of what constituted “informational materials.”

From the outset, OFAC reserved the right to regulate

transactions related to “informational materials not fully

created and in existence at the date of the transaction” and

those concerning “the substantive or artistic alteration or

enhancement of informational materials.” Id. OFAC also

excluded “intangible items, such as telecommunications

transmissions,” from the definition of “informational

materials.” Id.

Pub. L. No. 100-418, § 2502(b)(1)(C).

44

A divergence in views soon developed with regard to

how expansively OFAC was required to interpret the Berman

Amendment. In Cernuda v. Heavey, 720 F. Supp. 1544, 1549-

51 (S.D. Fla. 1989), the District Court for the Southern

District of Florida discerned from the legislative history of the

Berman Amendment an “obvious First Amendment

orientation.” In holding OFAC’s exclusion of original

artwork from the definition of “informational materials”

unreasonable, the court determined Congress had amended

TWEA and IEEPA “to prevent the statute from running afoul

of the First Amendment.” Id. at 1551-53. Because original

artwork merits First Amendment protection, the court

concluded, OFAC could not exclude it from the sweep of

“informational materials.” In dictum, the court theorized that

the Berman Amendment “totally exempts from prohibition or

regulation the import of ideas and information protected by

the First Amendment.” Id. at 1550 n.10.

By contrast, in Capital Cities/ABC, Inc. v. Brady, 740

F. Supp. 1007, 1011-13 (S.D.N.Y. 1990), the District Court

for the Southern District of New York concluded OFAC’s

exclusion of intangibles was consistent with the amendment’s

“other informational materials” language. Capital Cities had

purchased the exclusive rights to televise the 1991 Pan

American Games from Havana, Cuba for $ 8.7 million and

agreed to remit seventy-five percent of this sum to the host

organizer of the games. Id. at 1009-10. OFAC informed

Capital Cities the proposed transaction would not fall within a

general license provision and that it would not issue a specific

license so long as the transaction would result in a substantial

sum being transferred to Cuba. Id. The court found the

45

Berman Amendment was susceptible of multiple reasonable

interpretations and found the agency’s interpretation that

excluded intangibles such as telecommunications worthy of

deference under Chevron. Id. at 1011. In contrast to the

Cernuda court, the Capital Cities court found “the legislative

history reflects, at best, a general purpose to foster the

exchange of ideas across national borders.” Id. 30

In 1994, Congress expanded this limitation on

executive authority by enacting the Free Trade in Ideas Act.

Pub. L. No. 103-236, § 525, 108 Stat. 382, 474 (1994)

(codified as amended at 12 U.S.C. § 95a, 50 U.S.C. §

1702(b)). In part, Congress responded to OFAC’s exclusion

of intangible materials from the definition of “informational

materials” by amending IEEPA’s exemption to restrict the

Executive from regulating transactions concerning

informational materials “regardless of format or medium of

transmission.” Id. § 525(c)(1) (amending 50 U.S.C.

§1702(b)(3)). Congress also added “compact disks, CD

ROMS, artworks, and news wire feeds” to the nonexclusive

30

In analyzing Capital Cities’ First Amendment arguments,

the court noted that “the Berman Amendment is in derogation

of the Executive’s constitutional authority to conduct foreign

affairs by the use of embargoes on trade with hostile nations.”

Id. at 1013. Balancing this constitutional prerogative with the

First Amendment issues implicated by deference to OFAC’s

interpretation, the court found OFAC’s narrowing

interpretation prudentially avoided a separation-of-powers

problem. Id.

46

litany of enumerated media that could qualify as

“informational materials.” Id. The House Conference Report

stated:

[N]o embargo may prohibit or restrict directly

or indirectly the import or export of information

that is protected under the First Amendment to

the U.S. Constitution. The language was

explicitly intended, by including the words

“directly or indirectly,” to have a broad scope.

However, the Treasury Department has

narrowly and restrictively interpreted the

language in ways not originally intended. The

present amendment is only intended to address

some of those restrictive interpretations, for

example limits on the type of information that is

protected or on the medium or method of

transmitting the information.

H.R. Conf. Rep. No. 103-482, at 239 (1994), reprinted in

1994 U.S.C.C.A.N. 398, 483. Significantly, although

Congress overrode OFAC’s interpretation to the extent that it

excluded intangible materials from the definition of

“informational materials,” it did not disabuse OFAC of its

belief that it could permissibly regulate “informational

materials not fully created and in existence at the date of the

transaction.” That carve-out remained in place and, to date,

has not been challenged as ultra vires.

Before this Court, Amirnazmi relies on Cernuda to

argue that, because ChemPlan is a product that would merit

47

First Amendment protection, it necessarily falls outside the

scope of OFAC’s regulatory capabilities. Although it suffused

its opinion with constitutional considerations, the Cernuda

court refrained from reaching the merits of the petitioner’s

First Amendment challenge to the regulations, opting instead

to rest on “statutory construction and the legislative history of

the [Berman] [A]mendment.” 720 F. Supp. at 1553.

Similarly, Amirnazmi stresses he “is not challenging his

conviction under the IEEPA on First Amendment grounds.”

Consequently, whether ChemPlan theoretically could qualify

for First Amendment protection is not the dispositive

inquiry. 31 Instead, we must determine whether OFAC’s

31

Amirnazmi endeavors to bring ChemPlan within the ambit

of First Amendment protection by analogy to two categories

of speech. First, he argues ChemPlan functionally resembles

the prescription drug pricing information classified as

protected by Virginia State Bd. of Pharmacy v. Virginia

Citizens Consumer Council, 425 U.S. 748, 770 (1976), in that

it enables consumers to make more educated decisions and

thus serves the free market system by steering resources to

their most productive ends. Second, he characterizes

ChemPlan as “scientific expression” protected under Miller v.

California, 413 U.S. 15, 34 (1973); see also Universal City

Studios, Inc. v. Corley, 273 F.3d 429, 454 (2d Cir. 2001)

(computer code capable of meriting First Amendment

protection). Because Amirnazmi has not pursued a First

Amendment challenge at any stage in this litigation, we need

not determine whether OFAC’s regulation would pass

constitutional muster.

48

interpretation of the “informational materials” exemption

comports with congressional intent. See Chevron, 467 U.S. at

843 n.9 (“The judiciary is the final authority on issues of

statutory construction and must reject administrative

constructions which are contrary to clear congressional

intent.”).

We are satisfied that OFAC’s interpretation of

IEEPA’s informational-materials exemption is “based on a

permissible construction of the statute.” Chevron, 467 U.S. at

843. With the Berman Amendment and the Free Trade in

Ideas Act, Congress sought to ensure the robust exchange of

informational materials would not be unduly inhibited by

OFAC. When OFAC enacted regulations that Congress

considered at odds with this overarching purpose, the

legislature intervened and modified the statutory language to

rectify OFAC’s perceived missteps. Critically, although

Congress addressed one facet of OFAC’s 1989 interpretation

of the informational-materials exemption by stressing in 1994

that the Executive may not regulate informational materials

“regardless of format or medium of transmission,” it did not

counteract the component of that interpretation at issue here.

Presumably cognizant of OFAC’s narrowing interpretations,

Congress could have inserted text stipulating that the

Executive may not regulate informational materials regardless

of whether fully created and in existence at the date of the

transactions. Although the legislative history obliquely

alludes to other ways in which OFAC had interpreted the

exemption in an unforeseen manner, it chose to “only . . .

address some of those restrictive interpretations.” See H.R.

Conf. Rep. No. 103-482, at 239. “[W]hen Congress is aware

49

of an agency’s interpretation of a statute and takes no action

to correct it while amending other portions of the statute, it

may be inferred that the agency’s interpretation is consistent

with congressional intent.” Barrera-Echavarria v. Rison, 44

F.3d 1441, 1444-45 (9th Cir. 1995) (en banc) (citing North

Haven Bd. of Educ. v. Bell, 456 U.S. 512, 535 (1982)),

superseded by statute on other grounds as stated in Kwai Fun

Wong v. United States INS, 373 F.3d 952, 972 n.26 (9th Cir.

2004).

Moreover, there is ample evidence to suggest Congress

has accepted OFAC’s decision to permit the circulation of

informational materials already in existence while

concomitantly regulating transactions that contemplate the

creation of new materials. In the ITR, OFAC has fleshed out

the scope of the regulatory carve-out by explaining:

Transactions that are prohibited notwithstanding

this section include, but are not limited to,

payment of advances for information and

informational materials not yet created and

completed (with the exception of prepaid

subscriptions for widely circulated magazines

and other periodical publications), and

provision of services to market, produce or co-

produce, create or assist in the creation of

information and informational materials.

50

31 C.F.R. § 560.210(c)(2). 32 OFAC has made a reasoned

determination that Congress’s paramount concern for

facilitating transactions and activities incident to the flow of

informational materials in-being does not reach goods and

events that would not be produced but for financing from the

United States (in the case of imports) or financing from

purchasers in embargoed countries (in the case of exports). In

the case of commercial goods, the key distinction rests

between informational materials that are widely circulated in

a standardized format and those that are bespoke. Whereas

OFAC may not regulate the sale or transfer of prefabricated

32

OFAC’s general interpretation of the informational-

materials exemption, in place when Congress amended the

informational-materials exemption in 1994, reads:

[P]rohibited transactions include, without

limitation, payment of advances for

informational materials not yet created and

completed, provision of services to market,

produce or co-produce, create or assist in the

creation of informational materials, and

payment or royalties to a designated national

with respect to income received for

enhancements or alterations made by persons

subject to the jurisdiction of the United States to

informational materials imported from a

designated national.

54 Fed. Reg. 5229 (codified at 31 C.F.R. § 500.206(c)).

51

or mass-produced informational materials, custom-made

materials crafted to suit the unique specifications of a

particular purchaser are not sacrosanct. This distinction is

sensible, and it reflects a permissible implementation of the

statutory exemption in light of IEEPA’s competing

imperatives (i.e. restricting material support for hostile

regimes while encouraging the robust interchange of

information).

At trial, the government adduced sufficient evidence to

convince a reasonable factfinder beyond a reasonable doubt

that ChemPlan was not “fully created and in existence” at the

date of the relevant transactions. Amirnazmi trumpeted the

software’s dynamism. Joseph Mehl, a computer network

support technician who provided services to TranTech,

testified to his belief that each ChemPlan package was

“specifically tailored to the end user, depending on what

industry they worked in.” In aggressively pursuing

commercial ties with NPC, Amirnazmi attempted to stoke his

counterparty’s interest by proposing several options for

calibrating the software to NPC’s unique needs. As explained

below, the sale of ChemPlan to NPC was the cornerstone of

Amirnazmi’s conspiracy to bring his technical expertise to

Iran for that country’s aggrandizement. Consequently, the

transfer of ChemPlan to Iranian purchasers does not fit neatly

into the paradigm of informational exchange envisioned by

Congress. Quite clearly, Amirnazmi envisioned ChemPlan as

being of singular functional utility to Iranian users. Since the

inception of the informational-materials exemption, OFAC

has excepted such transactions from the scope of the general

license.

52

Accordingly, we conclude that 31 C.F.R. §

560.210(c)(2) is a permissible construction of IEEPA’s

informational-materials exemption and is worthy of deference

under Chevron. See 467 U.S. at 843. Therefore, a reasonable

factfinder could have found the government proved beyond a

reasonable doubt that the sale of ChemPlan to Iranian

purchasers did not qualify for exemption from IEEPA as a

matter of law.

B.

Next, Amirnazmi contends OFAC’s regulations are

imprecisely drafted and consequently void for vagueness. His

core argument is that the carve-outs to the informational-

materials exemption fail to provide “clear principles.”

According to him, it is impossible to determine whether a

work is “fully created and in existence” without necessarily

invoking “an untethered subjective judgment.” Again, we find

Amirnazmi’s argument unconvincing. 33

33

Amirnazmi has challenged all four of his IEEPA

convictions on the theory that OFAC’s regulations are

unconstitutionally vague. He argues that the alleged

vagueness of the informational-materials exemption is

“exacerbated by the vagueness of other provisions in the

regulations.” Specifically, he argues that the amorphousness

of 31 C.F.R. § 560.206(a) allowed the government to convict

him for engaging “solely in preliminary negotiations with

Iranian entities.” However, that regulation prohibits “any

transaction or dealing.” Id. This language flatly proscribes the

53

“A statute is void on vagueness grounds if it: (1) ‘fails

to provide people of ordinary intelligence a reasonable

opportunity to understand what conduct it prohibits’; or (2)

‘authorizes or even encourages arbitrary and discriminatory

enforcement.’” United States v. Stevens, 533 F.3d 218, 249

(3d Cir. 2008) (quoting Hill v. Colorado, 530 U.S. 703, 732

(2000)). In the criminal context, “since vagueness attacks are

based on lack of notice, ‘they may be overcome in any

specific case where reasonable persons would know their

conduct puts [them] at risk’ of punishment under the statute.”

San Filippo v. Bongiovanni, 961 F.2d 1125, 1138 (3d Cir.

1992) (quoting Maynard v. Cartwright, 486 U.S, 356, 361

(1988) (alteration in original)). Criminal statutes need only

give “fair warning that certain conduct is prohibited” to

survive constitutional challenges. Id. (internal quotation

marks omitted).

Furthermore, the Supreme Court has stated that:

[E]conomic regulation is subject to a less strict

vagueness test because its subject matter is

conduct for which Amirnazmi was convicted. See United

States v. Parise, 159 F.3d 790, 797 (3d Cir. 1998)

(concluding that the “plain meaning” of the term “dealings”

encompassed “all interactions or contacts” that a jury could

have considered as “proof of the requisite association”

between a RICO defendant and an illicit enterprise).

Therefore, we will confine our analysis to the regulatory

carve-out and Amirnazmi’s ChemPlan-related IEEPA

convictions.

54

often more narrow, and because businesses,

which face economic demands to plan behavior

carefully, can be expected to consult relevant

legislation in advance of action [and may]

clarify the meaning of the regulation by [their]

own inquiry, or by resort to an administrative

process.

Village of Hoffman Estates v. Flipside, Hoffman Estates, Inc.,

455 U.S. 489, 498 (1982). And, significantly, “the Court has

recognized that a scienter requirement may mitigate a law’s

vagueness, especially with respect to the adequacy of notice

to the complainant that his conduct is proscribed.” Id. at 499;

see also United States v. Hescorp, Heavy Equip. Sales Corp.,

801 F.2d 70, 77 (2d Cir. 1986) (“[A] requirement of

willfulness makes a vagueness challenge especially difficult

to sustain. . . . ‘A mind intent upon willful evasion is

inconsistent with surprised innocence.’” (quoting United

States v. Ragen, 314 U.S. 513, 524 (1942))).

The District Court rested its conclusion that the

regulation is not unconstitutionally vague on two grounds.

First, it reasoned that the sophisticated nature of those

required to consult the IEEPA regulations coupled with the

availability of guidance from OFAC officials on electronic

and telephone hotlines negated any notice concerns. And

second, it noted that IEEPA’s scienter requirement counseled

55

against a vagueness finding. See Amirnazmi, 2009 U.S. Dist.

LEXIS 74833, at *4-8. 34

As to the latter point, the government had to prove

beyond a reasonable doubt that Amirnazmi willfully violated

the trade restrictions. See 50 U.S.C. § 1705(c) (restricting

IEEPA convictions to those who “willfully commit[ ],

willfully attempt[ ] to commit, or willfully conspire[ ] to

commit” a violation of any license, order or regulation issued

pursuant to IEEPA); see also id. § 1702(a)(3) (“No person

shall be held liable in any court for or with respect to

anything done or omitted in good faith in connection with the

administration of, or pursuant to and in reliance on, this title,

or any regulation, instruction, or direction issued under this

title.”). As the District Court noted, “this is a case where

34

Without explicitly pronouncing on the constitutionality of

the informational-materials exemption, federal courts have

uniformly upheld the regulations in the face of vagueness

challenges. See, e.g., United States v. Soussi, 316 F.3d 1095,

1101-03 (10th Cir. 2002); United States v. Quinn, 401 F.

Supp. 2d 80, 100 (D.D.C. 2005) (“[T]he Iran trade embargo

laws . . . are not apt to sweep within their coverage the

everyday acts of average citizens. Rather, they govern the

activities of relatively sophisticated individuals who are

deliberately engaged in international commerce and,

therefore, must be familiar with (if not expert in) various legal

regimes . . . in multiple countries.”); Anvari-Hamedani, 378

F. Supp. 2d at 830-31; United States v. Lindh, 212 F. Supp.

2d 541, 573-74 (E.D. Va. 2002); United States v. Geissler,

731 F. Supp. 93, 100-01 (E.D.N.Y. 1990).

56

ignorance of the law is a defense; the inability to appreciate

the meaning of the law negatives the mens rea required for

conviction, and Defendant was free to, and did, argue this to

the jury.” Amirnazmi, 2009 U.S. Dist. LEXIS 74833, at *7

(internal quotation marks omitted). The jury unanimously

concluded Amirnazmi knew his conduct was unlawful.

And, as to the former point, the record reveals

Amirnazmi only halfheartedly availed himself of the

opportunity to receive definitive guidance from OFAC.

Amirnazmi first contacted OFAC upon his return from Iran

on June 3, 2008. He indicated he was curious as to whether

consolidating publicly available documents in a single

location to increase the ease of access for individuals in Iran

would fall within the informational-materials exemption, and

he alluded to the possibility of exporting a good to Iran. He

did not mention the computations that could be done with the

data, nor did he ask if confidential trade secrets were exempt.

On June 10, after FBI and IRS officials had executed the

search warrant for TranTech, Amirnazmi again contacted the

OFAC hotline, this time to complain his office had been

searched, but without making any inquiries about the

interplay between ChemPlan and the Iranian sanctions. On

June 11, he sent a letter to OFAC confirming his unsupported

understanding that ChemPlan fell within the exemption but

again failed to disclose how ChemPlan functioned as a

dynamic planning tool. Amirnazmi once more contacted

OFAC on June 17 and was told to submit a “detailed

explanation of the transactions he wanted to carry out” if he

wanted authoritative guidance. One month later, he was

indicted. The District Court concluded Amirnazmi did not

57

contact OFAC “in good faith or with the intention of actually

procuring guidance in complying with the OFAC

regulations.” Amirnazmi, 2009 U.S. Dist. LEXIS 74833, at *6

n.17. Amirnazmi’s refusal to provide OFAC with the detailed

information that might have allowed the agency to offer

reasoned guidance supports the District Court’s conclusion.

Moreover, OFAC’s interpretive rulings do not cast

doubt on the ability of reasonable persons to appreciate

whether their conduct was prohibited. Amirnazmi points to a

sequence of rulings in which OFAC attempted to demarcate

the scope of permissible editing of Iranian-authored works to

be published in the United States. After OFAC ruled on

September 30, 2003, that “collaboration on and editing of

manuscripts submitted by persons in Iran, including activities

such as the reordering of paragraphs or sentences, correction

of syntax, grammar, and replacement of inappropriate words

by U.S. persons, prior to publication, may result in a

substantively altered or enhanced product,” it revisited this

broad statement after meeting with publishing representatives,

concluding on April 2, 2004, that “style and copy editing,”

such as correcting grammar and spelling and reformatting the

document for publication, was exempt activity. On July 19,

2004, OFAC addressed how these prior rulings would apply

to U.S. newspapers seeking to publish Iranian-authored

articles. It wrote that “substantive edits to the work’s content

to make the work more cohesive, efficient, argumentative or

effective . . . and to make the work conform to the

newspaper’s editorial standards would not constitute

58

substantive or artistic alteration or enhancement of the article

or commentary.” 35

Although Amirnazmi would read this publishing

trilogy as indicating the regulations are so convoluted as to

render them incomprehensible even to those charged with

administering the sanctions, the salient lesson is that

representatives of the publishing entities actually met with

OFAC officials to proactively and candidly discuss how the

regulations should apply to their line of work. 36 OFAC, for its

35

On the heels of this series of interpretive rulings, OFAC

created a general license for transactions “necessary and

ordinarily incident to publishing.” See 69 Fed. Reg. 75468,

75471 (Dec. 17, 2004) (codified at 31 C.F.R. § 560.538).

36

Amirnazmi fails to grapple with other OFAC rulings that

are arguably more germane to ChemPlan’s status as

informational material. A February 3, 2003, ruling specified

that, with respect to the “provision of access to a database, the

inclusion of an electric [sic] search function that does no

more than search and sort the exempt information in the

database is . . . exempt from the prohibitions of the ITR.” It

further noted that such guidance did “not address any

additional product that may be offered in connection with the

use of the database; nor does it apply to technical support,

customer support, or any other services that might be

provided.” On December 11, 2003, OFAC distinguished

between the provision of basic information and the provision

of services “beyond the mere dissemination of information in-

being.” As explained above in Section IV.A, this line of

59

part, demonstrated its willingness to partake in productive

consultations with businesses that approached it. If

Amirnazmi had been perplexed by the applicability of the

regulations, he had abundant opportunity to obtain

clarification. See Village of Hoffman Estates, 455 U.S. at 498

(noting that the ability of sophisticated businesses to obtain

clarification “by resort to an administrative process” provides

one of the rationales for according economic regulations

greater latitude upon a review for vagueness).

In sum, we agree with the District Court’s conclusion

that, in light of the “narrow subject matter and reach of the

IEEPA regulations, as well as the sophisticated nature of the

persons they affect and the ability of such persons to obtain

guidance from OFAC itself, the IEEPA regulations are not

unconstitutionally vague.” Amirnazmi, 2009 U.S. Dist.

LEXIS 74833, at *6. 37 Because OFAC’s regulations are

demarcation encourages the inference that products falling

within this latter category, such as ChemPlan, would fail to

find refuge in the exemption.

37

Amirnazmi’s challenge to the constitutionality of the

regulations takes the form of a facial challenge. However, the

Supreme Court has written that a petitioner “who engages in

some conduct that is clearly proscribed cannot complain of

the vagueness of the law as applied to the conduct of others.

A court should therefore examine the complainant’s conduct

before analyzing other hypothetical applications of the law.”

Village of Hoffman Estates, 455 U.S. at 495 (footnote

omitted). Because Amirnazmi had ample notice that his

60

neither ultra vires nor unconstitutionally vague, we will deny

Amirnazmi’s request to vacate his IEEPA convictions on

these grounds.

V.

Finally, Amirnazmi’s appeal requires us to address two

further issues: (1) whether there was a variance between the

indictment, which charged Amirnazmi with one continuous

conspiracy, and the facts established at trial; and (2) whether

the District Court abused its discretion in admitting tape

recordings of Amirnazmi’s prison telephone calls. We

conclude Amirnazmi is not entitled to relief on either of these

grounds.

A.

Amirnazmi contends there was a variance between the

indictment and the facts established at trial, and that this

variance caused evidence to be admitted that would otherwise

have been barred by the statute of limitations. 38 Namely,

conduct was captured by the regulations, his facial vagueness

challenge, which would be upheld “only if the enactment is

impermissibly vague in all of its applications,” must fail. See

id.

38

We exercise plenary review over claims of variance. United

States v. Daraio, 445 F.3d 253, 259 (3d Cir. 2006). When,

however, the petitioner does not raise a claim in a timely

fashion, our review is for plain error. United States v.

Williams, 464 F.3d 443, 445 (3d Cir. 2006). In the District

61

Court, Amirnazmi moved for a new trial on the ground that

the court erroneously admitted evidence of conduct that fell

outside the statute of limitations period on the faulty premise

that he had engaged in one continuous course of conduct. On

appeal, he has converted this argument into a claim of

prejudicial variance. Although both require us to determine

whether Amirnazmi’s pre-2003 conduct was part of the same

continuing course of action that precipitated the 2008

conspiracy charge, the variance claim would allow us to

undertake a plenary review of the District Court’s decision

whereas resubmitting the evidentiary claim would constrain

our review by limiting us to the deferential abuse of

discretion standard. Whether or not we review Amirnazmi’s

variance claim de novo or for plain error, he must

demonstrate that the District Court prejudiced a substantial

right. See United States v. Kemp, 500 F.3d 257, 287 (3d Cir.

2007) (“A conviction must be vacated when (1) there is a

variance between the indictment and the proof presented at

trial and (2) the variance prejudices a substantial right of the

defendant.”) (internal quotation marks omitted) (emphases

added); Williams, 464 F.3d at 445 (“Under the plain error

standard, before an appellate court can correct an error not

raised at trial, there must be (1) error, (2) that is plain, and (3)

that affect[s] substantial rights.”) (internal quotation marks

omitted) (alteration in original) (emphases added). Because

Amirnazmi cannot prove a substantial right was unfairly

prejudiced, the dispute over the appropriate standard is

immaterial.

62

Amirnazmi alleges the evidence, “if anything,” proved he

engaged in two separate conspiracies, one of which

terminated before the limitations period. The statute of

limitations for violations of IEEPA is five years. See 18

U.S.C. § 3282(a) (setting the default statute of limitations for

non-capital federal offenses). But, because the District Court

concluded Amirnazmi’s actions dating back to 1997 were part

of a single, continuous conspiracy, it admitted evidence of

acts occurring prior to 2003. Amirnazmi contends, as he did

in his Rule 33 motion, that the introduction of evidence

relating to his activities outside the limitations period tainted

his trial.

“There is a variance if the indictment charges a single

conspiracy while the evidence presented at trial proves only

the existence of multiple conspiracies.” United States v.

Kemp, 500 F.3d 257, 287 (3d Cir. 2007). The rule against

variance “protects the defendant’s right to an indictment

sufficiently inform[ing] [him] of the charges against him so

that he may prepare his defense and not be misled or

surprised at trial.” United States v. Schurr, 775 F.2d 549, 553-

54 (3d Cir. 1985) (internal quotation marks omitted)

(alterations in original). Conspiracy “is a continuing offense

and a jury may consider each and all of a defendant’s actions

in furtherance of the conspiracy so long as the indictment is

brought within five years of the last overt act.” United States

v. Jake, 281 F.3d 123, 130 n.6 (3d Cir. 2002). “[T]he crucial

question in determining whether the statute of limitations has

run is the scope of the conspiratorial agreement, for it is that

which determines both the duration of the conspiracy, and

whether the act relied on as an overt act may properly be

63

regarded as in furtherance of the conspiracy.” Grunewald v.

United States, 353 U.S. 391, 397 (1957).

The government’s superseding indictment charged

Amirnazmi with conspiring to violate IEEPA from 1996

through July 2008 by engaging in transactions with

companies located in Iran despite knowing such conduct was

prohibited. When the District Court analyzed Amirnazmi’s

claim within the statute of limitations context, it defined

Amirnazmi’s conspiracy as a plot “to bring his technical

wherewithal, especially the ChemPlan system, back to Iran

for the benefit of that country.” Amirnazmi, 648 F. Supp. 2d

at 723. The superseding indictment set forth six pre-2003

overt acts that allegedly contributed to the advancement of

this conspiracy, and the court concluded that the evidence

adduced by the government at trial demonstrated this conduct

was “closely tied” to his “continuing efforts to sell his

ChemPlan software to the [NPC].” 39

39

Specifically, the court cited evidence that Amirnazmi (1)

signed a 1997 agreement with NPC to sell the ChemPlan

software and traveled to Iran to conduct demonstrations and

training; (2) sold NPC a ChemPlan update in 1998; (3) helped

secure the BoxScore software for NPC in 2000; (4) met with

NPC personnel in Iran in 2000 and subsequently sent NPC

officials a fax that included a subscription order form and

other ChemPlan materials and which suggested the formation

of a joint venture; (5) attended the same conference in 2001

and sent a letter to NPC with an offer for a ChemPlan

program that would be designed to meet its ends; (6) sent a

64

The District Court concluded Amirnazmi had

“resolved on achieving certain goals for the betterment of

Iran” prior to 2003 and that, although he failed to make

significant headway until well later, “there is no evidence that

[he] ever abandoned or renounced” the plan he had hatched in

the late 1990s. Id. After his encounter with President

Ahmadinejad in 2006, Amirnazmi’s efforts began to bear

fruit. He successfully negotiated another licensing agreement

with NPC in 2008 (after representing that the 1997 agreement

was still valid), and he signed memoranda of understanding

with IBACO and NITD. In the court’s estimation,

Amirnazmi’s efforts to sell ChemPlan to NPC were integral

to his goal of turning Iran into a “chemical powerhouse.”

Thus, it concluded, Amirnazmi’s pre-2003 acts fell squarely

within the scope of his conspiracy to bolster Iran’s chemical

capacities, and evidence of these acts was properly presented

to the jury on the theory that they contributed to a continuing

course of conduct. Id.

Amirnazmi now offers two alternative arguments: (1)

the government failed to prove his pre-2003 conduct was part

of any conspiracy, and (2) even if his early sales to the NPC

were part of a conspiracy to violate IEEPA, that purported

second letter discussing the 2001 conference and urging NPC

to contact him with respect to the proposed joint venture; and

(7) attempted to drum up business in 2002 with his

unsuccessful attempt to have brochures printed in Iran for his

software. Amirnazmi, 648 F. Supp. 2d at 722.

65

conspiracy terminated “well before the subsequent 2008 sale

of ChemPlan.”

The gravamen of Amirnazmi’s contention that his pre-

2003 conduct was not conspiratorial in any way is that the

government failed to demonstrate the existence of an

agreement to violate the statute. See United States v. Gebbie,

294 F.3d 540, 544 (3d Cir. 2002) (listing “an agreement

between two or more persons” as an essential element of a

conspiracy charge under 18 U.S.C. § 371). Amirnazmi claims

the government failed to demonstrate he shared a common

enterprise with NPC “beyond occasionally buying and selling

computer software.” He attempts to divorce his pre-2003 acts

from the overriding contextual narrative and style them as

intermittent transactions between a buyer and a seller working

at arms’ length and without any nefarious joint objective.

However, Amirnazmi declines to confront the evidence that

demonstrates he worked in conjunction with various officials

to provide ChemPlan and BoxScore and had ongoing, regular

contact with assorted NPC agents. The jury may reasonably

infer these business relationships would not have persisted

without at least an understanding in place between the parties

that Amirnazmi would be willing to provide goods and

services in violation of the embargo. See United States v.

McGlory, 968 F.2d 309, 326 (3d Cir. 1992) (concluding that a

reasonable jury could infer from the totality of the evidence

“that the activities of the participants . . . could not have been

carried on except as the result of a preconceived scheme or

common understanding” (internal quotation marks omitted)

(alteration in original)).

66

And Amirnazmi’s alternative contention—that, at best,

the government proved the existence of two separate

conspiracies—is similarly unpersuasive. It miscasts his

unrequited efforts to spark renewed interest in ChemPlan

prior to 2006 as evidence the conspiracy could not have been

“continuing.” This slackening may reveal a disparity in the

vigor with which each side pursued the object of the

conspiracy; NPC seems to have been a somewhat reluctant

collaborator for most of the early part of the past decade.

Nevertheless, the resumption of concerted activity in 2007

came on the heels of Amirnazmi’s continuous efforts to

preserve and strengthen TranTech’s Iranian ties. The

temporary lull in sales does not detract from the District

Court’s conclusion that Amirnazmi’s later actions were part

of the same conspiracy that had begun in the 1990s.

Amirnazmi’s recurrent efforts to strengthen the relationship

were sandwiched between two periods of concerted activity

in which the parties pursued the same unlawful end. The

unaltered nature of the parties’ interests both prior to and after

2003 belies Amirnazmi’s depiction of the facts as evidencing

one conspiracy ceasing and another commencing.

Amirnazmi would have to demonstrate that, even if a

variance led to evidence being admitted that otherwise would

have been barred by the statute of limitations, such evidence

prejudiced a substantial right. As noted, this holds true

whether we conduct a plenary review or review for plain

error. “An error affects substantial rights when it is

prejudicial: It must have affected the outcome of the district

court proceedings.” United States v. Vazquez-Lebron, 582

F.3d 443, 446 (3d Cir. 2009) (internal quotation marks

67

omitted). Here, it appears as though Amirnazmi’s variance

argument is targeted primarily, if not exclusively, at his

conviction for conspiracy in Count One. Because limiting the

jury’s consideration to evidence of Amirnazmi’s post-2006

activities would not have resulted in a different outcome,

Amirnazmi cannot demonstrate his substantial rights were

prejudiced by introduction of this evidence.

Because the District Court neither misinterpreted the

law of conspiracy nor prejudiced a substantial right of

Amirnazmi’s, it did not err in admitting evidence of

Amirnazmi’s pre-2003 conduct.

B.

Lastly, Amirnazmi appeals the District Court’s

decision to allow the government to introduce into evidence

tape recordings and translated transcripts of telephone calls

placed by Amirnazmi to certain family members during his

pretrial imprisonment at the Federal Detention Center

(FDC). 40 Amirnazmi argues the government violated Fed. R.

40

We review a district court’s decision to admit or exclude

evidence, “if premised on a permissible view of the law,” for

an abuse of discretion. United States v. Sokolow, 91 F.3d 396,

402 (3d Cir. 1996). Amirnazmi initially challenged the tape

recordings under the Wiretap Act, 18 U.S.C. § 2510 et seq.

The District Court rejected this argument in its Feb. 6, 2009

Order admitting the tapes, and Amirnazmi declined to renew

this objection in either his Rule 33 motion or in the briefing

materials he has submitted in support of his current appeal.

68

Crim. P. 17(c) by impermissibly using subpoenas as

discovery devices. Rule 17(c), which governs the issuance of

subpoenas duces tecum in federal criminal proceedings, is

“not intended to provide a means of discovery for criminal

cases.” United States v. Nixon, 418 U.S. 683, 698 (1974),

superseded by statute on other grounds as stated in Bourjaily

v. United States, 483 U.S. 171, 177-79 (1987); see also

United States v. Cuthbertson, 630 F.2d 139, 144 (3d Cir.

1980). Rather, the rule was designed “to expedite [a] trial by

providing a time and place before trial for the inspection of

the subpoenaed materials.” Bowman Dairy Co. v. United

States, 341 U.S. 214, 220 (1951). Notably, the Rule 17(c) test

outlined in Nixon pertains to the production of documents in

advance of trial. 418 U.S. at 698-700.

Here, the government served a series of trial subpoenas

on the FDC’s Custodian of Records requiring him to appear

on a specified date and to bring with him copies of

Amirnazmi’s telephonic communications aside from those

shielded by attorney-client privilege. Critically, the dates

returnable of the subpoenas paralleled the then-scheduled trial

dates and noted that the witness was “subject to call.”

Because the subpoenas did not require pre-trial production,

the District Court concluded Nixon was not controlling and

the government had not run afoul of Rule 17(c). Amirnazmi,

however, argues the government implicitly understood that

the FDC would expedite its production of the requested

evidence. That is, based on the alacrity with which the FDC

habitually responds to subpoenas received from the United

States Attorney’s Office, Amirnazmi believes the government

anticipated the FDC turning around the subpoenas in short

69

order and consequently having access to the communications

well in advance of trial. Thus, he argues the protections

embodied in Nixon against the misuse of pre-trial subpoenas

should apply notwithstanding the formal returnable dates on

the subpoenas.

Although the District Court rejected Amirnazmi’s

invitation to adopt a broad reading of Rule 17(c) both at the

suppression hearing and in its denial of his Rule 33 motion,

Amirnazmi again seeks a ruling that Nixon’s gloss on Rule

17(c) applies with equal force to trial subpoenas likely to

yield pre-trial production. Amirnazmi discerns support in

United States v. Noriega, 764 F. Supp. 1480, 1494 (S.D. Fla.

1991), for the broad proposition that trial subpoenas may not

be used to procure advance production of a defendant’s

prison-recorded conversations without first obtaining leave of

court. Significantly, in Noriega, the subpoenas directed the

custodian of records to appear and testify on various dates,

none of which corresponded with scheduled hearings in the

case. Id. at 1482. Because no proceedings were scheduled on

the dates indicated in the subpoenas, the court found it

unmistakable that the subpoenas “constituted a broad

dragnet” designed to “enable the prosecution to examine

these recordings prior to trial in order to obtain additional

discovery against the defendant.” Id. at 1492-93.

Additionally, the court noted that subpoenas are more likely

to be used for impermissible discovery purposes “when

advance production of materials is sought instead of the usual

production at time of trial or other proceeding in which they

are to be used in evidence.” Id. at 1493.

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Here, the government issued subpoenas that complied

with the facial requirements of trial subpoenas. On other

facts, such formalistic compliance may be insufficient to

mask the government’s efforts to make an end run around

Nixon. However, the record before us does not demonstrate

such an impermissible discovery motive. We therefore

conclude that the District Court did not abuse its discretion in

admitting the recordings as evidence. 41

41

Furthermore, Amirnazmi claims the trial was tainted by the

admission of these telephone recordings but does not explain

how the result would have been different were they to have

been excluded. As the District Court astutely noted,

The probative value of these tape recordings

lies in their value as evidence of Defendant’s

state of mind. Yet, the jury was presented with a

plethora of other evidence from which

Defendant’s state of mind could be determined,

including Defendant’s repeated contradictory

statements about his business dealings in Iran,

and the multiple times he was put on notice of

the restrictions on trade with Iran. Therefore,

even assuming the Court erred in admitting

these tape recordings, such error would not have

had a substantial impact on the verdict and

would not warrant a new trial.

648 F. Supp. 2d at 720 n.18.

71

VI.

For the foregoing reasons, we will affirm the jury’s

verdict and the District Court’s imposition of a four-year

prison sentence.

72