United States Court of Appeals

FOR THE EIGHTH CIRCUIT

___________

No. 02-1681

___________

United States of America, *

*

Appellee, *

* Appeal from the United States

v. * District Court for the

* District of Minnesota.

Thomas William Washam, *

*

Appellant. *

___________

Submitted: October 10, 2002

Filed: December 11, 2002 

___________

Before LOKEN, BEAM and MELLOY, Circuit Judges.

___________

BEAM, Circuit Judge.

A jury found Thomas William Washam ("Washam") guilty of two counts of

distributing a controlled substance analogue of gamma-hydroxybutyric acid (GHB)

in violation of 21 U.S.C. §§ 841(a)(1), 813 and 802(32). Washam appeals the

judgment and the denial of his motion to dismiss the indictment, claiming a violation

of his Fifth Amendment due process rights. Washam argues that the definition of a

controlled substance analogue in 21 U.S.C. § 802(32) ("Analogue Statute") denies
1

The Honorable Ann D. Montgomery, United States District Judge for the

District of Minnesota.

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him due process because it is unconstitutionally vague as applied to the facts of his

conviction. We disagree and affirm the district court.1

 

I. BACKGROUND

In August of 2000, Washam began working for "Nutri-Tech," a nutrition store

located in College Station, Texas. While at Nutri-Tech, Washam began using and

selling products containing 1,4-Butanediol. Washam researched 1,4-Butanediol in

order to ascertain its legality, and he determined that a similar substance, GHB, was

illegal and that another similar substance, gamma-butyrolactone (GBL), was an illegal

analogue to GHB, but 1,4-Butanediol was not listed as an illegal substance. Through

the owner of Nutri-Tech, Washam began importing 1,4-Butanediol from Mexico for

sale in the United States for human consumption.

With the help of Kyle Anderson, who was being charged with possession of

GBL in an unrelated case, the government set up an undercover purchase of 1,4-

Butanediol from Washam. Washam agreed to sell Anderson 1500 four-ounce bottles

of 1,4-Butanediol for $55,000. Washam shipped 540 bottles to Anderson via FedEx,

which was received on July 13, 2001. A second shipment of bottles from Washam

to Anderson was never located. On July 13, Washam also met Anderson and an

undercover officer, Robert Nance, at a hotel in St. Paul, Minnesota. During this

meeting, Washam delivered 501 bottles to Anderson and indicated that he knew the

substance he was selling was to be used for human consumption, and that it was

illegal as such. Officer Nance gave Washam the cash and then placed him under

arrest.
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At trial, the central issue was whether 1,4-Butanediol is a controlled substance

analogue of GHB, as defined in the Analogue Statute. The government offered the

opinions of two experts. Dr. Richard Irwin, a research scientist with the National

Institutes of Health, testified that the human body converts 1,4-Butanediol into GHB

and that at least two deaths had been attributed to the use of the substance.

Dr. James DeFrancesco, a Drug Enforcement Administration ("DEA") chemist,

also testified for the government. He said that 1,4-Butanediol and GHB are both

linear compounds containing four carbons and that there is only one difference

between the substances on one side of their molecules. He stated that this difference

does not preclude a substantially similar chemical structure and that his opinion, and

the official opinion of the DEA, was that 1,4-Butanediol was an analogue of GHB

under the definition in the Analogue Statute.

Washam also presented two experts. Dr. J. Thomas Ippoliti, a chemistry

professor at the University of St. Thomas, testified that the difference between 1,4-

Butanediol and GHB was in their respective functional groups. Functional groups

allow chemists to differentiate between chemical structures and to determine a

chemical's physical properties and reactivity. This difference in functional groups

means that the two chemicals are not substantially similar in chemical structure. 

Dr. Jordan Holtzman, a physician with a Ph.D. in pharmacology, testified that

1,4-Butanediol metabolizes into GHB through a two-step process in the body. MSG,

a food additive, also metabolizes into GHB in the body. Dr. Holtzman stated that

GHB and 1,4-Butanediol are very different substances outside of the body. GHB

works as a neurotransmitter, while 1,4-Butanediol does not, and GHB is 100 billion

times more acidic than 1,4-Butanediol. Dr. Holtzman testified that 1,4-Butanediol

and GHB are not substantially similar in chemical structure.
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The jury heard all of this expert testimony, was instructed to determine whether

1,4-Butanediol is a controlled substance analogue under the Analogue Statute,

determined that it was a controlled substance analogue, and found Washam guilty of

distributing a controlled substance analogue. Washam appeals this determination,

claiming that the definition of a controlled substance analogue in 21 U.S.C. § 802(32)

is void for vagueness because it fails to provide notice of the conduct proscribed and

because it lends itself to arbitrary enforcement. 

II. DISCUSSION

We review a constitutional challenge to a federal statute de novo. United

States v. Whiting, 165 F.3d 631, 633 (8th Cir. 1999).

The Fifth Amendment guarantees every citizen the right to due process.

Stemming from this guarantee is the concept that vague statutes are void. Connally

v. Gen. Constr. Co., 269 U.S. 385, 391 (1926). "[A] statute which either forbids or

requires the doing of an act in terms so vague that men of common intelligence must

necessarily guess at its meaning and differ as to its application, violates the first

essential of due process of law." Id. "Void for vagueness simply means that criminal

responsibility should not attach where one could not reasonably understand that his

contemplated conduct is proscribed." United States v. Nat'l Dairy Prods. Corp., 372

U.S. 29, 32-33 (1963). "[L]aws [must] give the person of ordinary intelligence a

reasonable opportunity to know what is prohibited, so that he may act accordingly.

Vague laws may trap the innocent by not providing fair warning." Grayned v. City

of Rockford, 408 U.S. 104, 108 (1972). "[V]agueness challenges to statutes which

do not involve First Amendment freedoms must be examined in the light of the facts

of the case at hand." United States v. Mazurie, 419 U.S. 544, 550 (1975).

In determining whether a statute is unconstitutionally vague on the facts at

hand, we apply a two-part test. First, the statute must provide adequate notice of the
2

While there is some debate as to how this provision is to be read, we agree

with the courts who have read the three requirements in the conjunctive. Thus, part

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proscribed conduct. Kolender v. Lawson, 461 U.S. 352, 357 (1983). Second, the

statute must not lend itself to arbitrary enforcement. Id. at 358. Washam argues that

section 802(32) violates both parts of this test because the statute does not provide

adequate notice of proscribed conduct and because it allows for arbitrary

enforcement. 

A.

A penal statute is void if it does not sufficiently define a criminal offense so

that ordinary people can understand what conduct is prohibited. Kolender, 461 U.S.

at 357. This inquiry looks at what a person of "common intelligence" would

"reasonably" understand the statute to proscribe, not what the particular defendant

understood the statute to mean. Nat'l Dairy Prods., 372 U.S. at 32-33; Connally, 269

U.S. at 391. The statute in question in this case defines a controlled substance

analogue as a substance: 

(i) the chemical structure of which is substantially similar to the

chemical structure of a controlled substance in schedule I or II; 

(ii) which has a stimulant, depressant, or hallucinogenic effect on the

central nervous system that is substantially similar to or greater than the

. . . effect on the central nervous system of a controlled substance in

schedule I or II; or 

(iii) with respect to a particular person, which such person represents or

intends to have a stimulant, depressant, or hallucinogenic effect on the

central nervous system that is substantially similar to or greater than the

. . . effect on the central nervous system of a controlled substance in

schedule I or II.

21 U.S.C. § 802(32)(A).2
(i) must be satisfied and either part (ii) or part (iii) must also be satisfied. See United

States v. Forbes, 806 F. Supp. 232, 235-36 (D. Colo. 1992).

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Washam argues that there is no consensus in the scientific community

regarding whether 1,4-Butanediol has a "substantially similar" chemical structure to

GHB under provision (i) of this definition, and thus the definition is

unconstitutionally vague as applied. The government argues that Washam had actual

notice that his conduct was illegal and so he cannot claim that the statute is void for

vagueness as applied to him. Additionally the government argues that a person of

common intelligence has sufficient notice under the statute that 1,4-Butanediol is a

controlled substance analogue. We agree with the government.

We think the government's "actual notice" argument has some appeal and is

supported by United States v. Saffo. 227 F.3d 1260, 1270 (10th Cir. 2000), cert.

denied, 532 U.S. 974 (2001). In Saffo, the defendant challenged a statute as

unconstitutionally vague. The court held that the defendant could not sustain the

challenge because she concealed her activities and lied to DEA agents, which showed

that she had actual knowledge of the illegality of her actions. Id. Thus, the defendant

was not in "a situation where she 'could not reasonably understand that [her]

contemplated conduct [was] proscribed.'" Id. (quoting Parker v. Levy, 417 U.S. 733,

757 (1974)) (first alteration in original). Similarly, the evidence in the present case

shows that Washam knew his conduct was illegal because even though the shipping

label said not to ingest, Washam told the buyers how much to ingest, he charged an

exorbitant mark-up price on the chemical, and he commented about other chemicals

that were legal for human consumption.

Additionally, even if we overlook Washam's actual knowledge that his conduct

was illegal, we still find that the Analogue Statute is not vague as applied to him

because a person of ordinary intelligence would have reasonably known that selling

1,4-Butanediol for human consumption violated the statute. See Grayned, 408 U.S.
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at 108-09. The term "substantially similar," as used in the statute, does not mean

"exactly the same." There obviously will be differences in chemical structures

between an "analogue" chemical and a schedule I or II chemical. If two chemicals'

structures are exactly the same, the chemical in question would no longer be an

"analogue," but instead it would be the same chemical as the listed chemical. Thus,

some level of difference is acceptable between an analogue's chemical structure and

a proscribed chemical's structure. 

We have held that all experts need not agree on whether two drugs' chemical

structures are "substantially similar" in order to affirm a conviction under the

Analogue Statute. United States v. McKinney, 79 F.3d 105, 108 (8th Cir. 1996),

vacated on other grounds, 520 U.S. 1226 (1997); but see Forbes, 806 F. Supp. at 237

(application of Analogue Statute to alphaethyltryptamine void for vagueness because

government's own witnesses differed as to whether the chemical had a substantially

similar structure to a controlled substance). Rather than unanimous expert

ratification, we look to whether the statute gave adequate warning, under a specific

set of facts, that the defendant's behavior was a criminal offense. McKinney, 79 F.3d

at 108.

The difficulty is determining when "some notice" is enough notice. In United

States v. Fisher, the Eleventh Circuit determined that defendants had enough notice

that GBL is a chemical analogue to GHB. 289 F.3d 1329, 1339 (11th Cir. 2002). In

coming to this conclusion, the court found it relevant that GBL was a listed chemical

and that Congress had stated that GBL was a chemical analogue to GHB in its

proposed rules. Id. at 1336. When Congress commented that GBL was a chemical

analogue to GHB, it also mentioned that 1,4-Butanediol was the same sort of

analogue. 

If taken for human consumption, GBL and other chemicals, including

1,4-butanediol, are swiftly converted into GHB by the body. Abuse of
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these and other GHB-like substances is a significant law enforcement

and public health problem. GBL and 1,4-butanediol are structurally and

pharmacologically similar to GHB and are often substituted for GHB.

Under certain circumstances they may satisfy the definition of a

controlled substance analogue. 

Placement of Gamma-Butyrolactone in List I of the Controlled Substances Act (21

U.S.C. § 802(34)), 65 Fed. Reg. 21645 (April 24, 2000) (codified at 21 C.F.R. §

1310). This piece of explicit notice, in addition to the fact that 1,4-Butanediol turns

into GHB in the body and has the same effect as GHB, aids us in concluding that

there is sufficient notice that 1,4-Butanediol is a chemical analogue of GHB. See

Fisher, 289 F.3d at 1336.

B.

The second part of the statutory due process inquiry is whether the statute lends

itself to arbitrary enforcement. Kolender, 461 U.S. at 358. Congress must provide

minimal requirements to guide law enforcement in order to prevent police officers,

prosecutors, and juries from pursuing their "personal predilections." Id. Indeed, the

United States Supreme Court has noted:

It would certainly be dangerous if the legislature could set a net large

enough to catch all possible offenders, and leave it to the courts to step

inside and say who could be rightfully detained, and who should be set

at large. This would, to some extent, substitute the judicial for the

legislative department of the government.

United States v. Reese, 92 U.S. 214, 221 (1875). 

There is some superficial appeal to Washam's comparison between 1,4-

Butanediol and MSG, the common food additive that also becomes GHB in the
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human body. But Washam's conclusion that the Analogue Statute lends itself to

arbitrary enforcement because it allows for a distinction between the two substances

is flawed. The statute does not allow for arbitrary enforcement because the statute

itself requires a two-step inquiry before law enforcement may extend its application

to a new chemical. The first step in the statute is to determine whether a chemical is

substantially similar in chemical structure to a listed chemical. 21 U.S.C. §

802(32)(A)(i). Beyond this inquiry is the requirement that the chemical either has

the same effect as the listed chemical on the human body, or it is intended to have

such an effect. Id. § 802(32)(A)(ii), (iii). Utilizing these two steps, MSG could not

be proscribed by the Analogue Statute. While MSG may be substantially similar in

physical and chemical structure to GHB, just as is 1,4-Butanediol, MSG does not

have similar effects on the human body, nor do food producers intend for MSG to

have the same effect as GHB. Thus, MSG would not satisfy the second prong of the

statute. To the contrary, 1,4-Butanediol is substantially similar in physical and

chemical structure to GHB and it has a similar effect on the human body as GHB.

This violates the statute. Thus, applying the Analogue Statute to 1,4-Butanediol and

not to MSG is not proof of arbitrary enforcement, rather it is proof that the statute is

narrowly drawn to proscribe only those chemicals which are dangerous and intended

to be used in an illegal manner.

In United States v. Roberts, No. 01CR410, 2002 WL 31014834 (S.D.N.Y. Sept.

9, 2002), cited by Washam, the district court held that the Analogue Statute was

unconstitutionally vague as applied to 1,4-Butanediol because it violated both prongs

of the void for vagueness test. This decision is incorrect on both points. The court

in Roberts held that there was insufficient notice because of the lack of consensus

among experts in the field as to whether the two chemicals were substantially similar,

that experts could not agree on which methodology to use to determine substantial

similarity, that 1,4-Butanediol was not designated a List I chemical and that no

warning letters were sent to distributors of 1,4-Butanediol like those sent to

distributors of GBL. Id. at *4-*5. While all of these are factors to be considered,
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they do not mandate, either individually or in the aggregate, a finding that there was

no adequate notice that 1,4-Butanediol was an analogue of GHB. We have already

stated that experts need not agree for there to be a finding that a chemical is an

analogue to GHB. McKinney, 79 F.3d at 108. Further, Congress did not state that

distributors of analogues must be warned prior to enforcement of the statute. Nor did

Congress state or intend that only List I chemicals may be considered analogues. 

Additionally, the court in Roberts held that effects on the human body could

not be considered in determining whether the chemicals were "substantially similar"

under the first part of the statute. Roberts, 2002 WL 31014834 at *5. We disagree.

While the effects on the human body must be similar in order to satisfy the second

part of the statute, this does not prevent consideration of the effects on the human

body when determining whether the chemical satisfies the "substantially similar"

requirement of the first portion of the law. In this regard, we think it is

extraordinarily relevant that 1,4-Butanediol transforms into GHB upon ingestion with

similar physical results.

The court in Roberts also found that the Analogue Statute, as applied to 1,4-

Butanediol, is unconstitutionally vague because it allows for arbitrary enforcement.

Id. In coming to this conclusion, the court rested its decision on the fact that several

other products, such as Gamma Aminobutyric Acid (GABA) and succinic acid were

as similar to GHB as 1,4-Butanediol, differing only in one functional group. Id. The

court, however, failed to recognize that this problem was addressed by the Analogue

Statute because the statute requires a showing of structural similarity and similar

effect on the human body (or intent for there to be such an effect). Obviously,

GABA, succinic acid, and MSG (cited by Washam for the same proposition) do not

have the same dangerous effects on the body that GHB does. Otherwise, the FDA

would not have approved the substances for human consumption. Congress does

address the problem of these other similar substances in its use of the two-part test.

This prevents arbitrary enforcement. 
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One of Congress' purposes for passing the Analogue Statute was to prohibit

innovative drugs that are not yet listed as controlled substances. McKinney, 79 F.3d

at 107. However, Congress did not limit the Analogue Statute's application to newly

designed drugs. The language of the statute shows that Congress intended to

proscribe all drugs that are similar in chemical structure and effect to illegal drugs.

We are confident that Congress intended to prohibit use of dangerous substances such

as 1,4-Butanediol when it passed the Analogue Statute. 

III. CONCLUSION

The Analogue Statute is not void for vagueness as applied to 1,4-Butanediol

because Congress provided adequate notice of the proscribed conduct and prevented

arbitrary enforcement through the terms of the statute. Therefore, we affirm the

district court. 

A true copy.

Attest:

CLERK, U.S. COURT OF APPEALS, EIGHTH CIRCUIT.