U.S. v. Brown

• Decision Date: 08 July 2005
• Docket Number: No. 03-15459.,No. 03-15413.,03-15413.,03-15459.
• Citation: 415 F.3d 1257
• Parties: UNITED STATES of America, Plaintiff-Appellee, v. Ronald Keith BROWN, Defendant-Appellant. United States of America, Plaintiff-Appellee, v. Kevin Layne Brown, Defendant-Appellant.
• Court: U.S. Court of Appeals — Eleventh Circuit

415 F.3d 1257

UNITED STATES of America, Plaintiff-Appellee, v. Ronald Keith BROWN, Defendant-Appellant.

United States of America, Plaintiff-Appellee, v. Kevin Layne Brown, Defendant-Appellant.

No. 03-15413.

No. 03-15459.

United States Court of Appeals, Eleventh Circuit.

July 8, 2005.

COPYRIGHT MATERIAL OMITTED

Carlos Alfredo Williams (Court-Appointed), Christopher Knight, Fed. Def. Org., Mobile, AL, for Ronald Brown.

David Andrew Sigler, Donna Barrow Dobbins, Mobile, AL, for U.S.

Gordon G. Armstrong, III (Court-Appointed), Gordon G. Armstrong, III, P.C., Mobile, AL, for Kevin Brown.

Appeals from the United States District Court for the Southern District of Alabama.

Before ANDERSON, CARNES and RONEY, Circuit Judges.

CARNES, Circuit Judge:

Two brothers, Ronald and Kevin Brown, were convicted of conspiracy to distribute 1,4-butanediol, an alleged controlled substance analogue, in violation of 21 U.S.C. § 846. Whether the chemical structure of that substance is "substantially similar" to the chemical structure of the schedule I controlled substance gamma hydroxybutyric acid (GHB), such that it is a "controlled substance analogue" as defined by 21 U.S.C. § 802(32)(A), was the key question at trial and it is the key question in this appeal.

The Browns have brought us a number of contentions arising from the dispute over whether 1,4-butanediol is substantially similar to GHB. Some of them involve Daubert v. Merrell Dow Pharmaceuticals, Inc., 509 U.S. 579, 113 S.Ct. 2786, 125 L.Ed.2d 469 (1993), and question the district court's rulings on the admission of expert testimony. The others involve whether the evidence was sufficient to convict the Browns and whether the analogue theory embodied in 21 U.S.C. §§ 802(32)(A) and 813 is unconstitutional.

I.

A.

Ronald and Kevin Brown owned and operated two Internet websites that advertised and sold products for human consumption containing varying amounts of 1,4-butanediol, an industrial solvent that in recent years has been found to be a depressant and can be used as a "date rape" drug. Over a two-year period, FBI agents used an undercover e-mail account to purchase from the Browns approximately 23.5 gallons of products containing 1,4-butanediol. Then, in conjunction with a nationwide operation coordinated by the Department of Justice, law enforcement officers executed search warrants for the Browns' residences and another house where the drugs were thought to be kept. They found 200 gallons of 1,4-butanediol, some pure and some diluted, as well as handwritten notes and recipes for preparing 1,4-butanediol products.

An indictment was returned charging the Browns with one count of conspiracy to distribute and possess with intent to distribute 1,4-butanediol, and with eight counts of distribution and possession with intent to distribute 1,4-butanediol, in violation of 21 U.S.C. §§ 841(a)(1), 813, and 846.

The parties entered into a joint bench trial agreement under which the government dropped the eight possession counts against the Browns. In place of the indictment, the government filed a superseding information charging the Browns with conspiracy to distribute and possess with intent to distribute 1,4-butanediol. The government also sought criminal forfeiture of the Browns' property. The Browns agreed to stipulate to all the facts except the central one of whether the chemical structure of 1,4-butanediol is "substantially similar" to the chemical structure of GHB so as to bring the chemical compound within the definition of "controlled substance analogue" under 21 U.S.C. § 802(32)(A). That one factual issue was left for trial.

In a subsequent joint amendment to the agreement, the Browns waived their right to appeal any resulting conviction and sentence, except as to certain specified issues. The relevant excepted issues for present purposes are whether 1,4-butanediol is substantially similar to GHB as defined by § 802(32)(A)(i), and those additional issues arising from "any rulings by the district court addressing that issue."

B.

The government's position throughout this prosecution has been that, pursuant to 21 U.S.C. § 802(32)(A), 1,4-butanediol is a "controlled substance analogue" of GHB, which Congress added to the statutory list of schedule I controlled substances in 2000. See Hillory J. Farias and Samantha Reid Date-Rape Drug Prohibition Act of 2000, Pub. L. No. 106-172, § 3(a), 114 Stat. 7. Under the Controlled Substance Analogue Enforcement Act of 1986 ("the Analogue Act"), 21 U.S.C. §§ 802 and 813, some chemical compounds that are not themselves listed as schedule I controlled substances are termed "controlled substance analogue[s]" and treated as though they were schedule I substances. Id. § 813 ("A controlled substance analogue shall, to the extent intended for human consumption, be treated, for the purposes of any Federal law as a controlled substance in schedule I."). The Analogue Act 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 stimulant, depressant, or hallucinogenic 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 stimulant, depressant, or hallucinogenic effect on the central nervous system of a controlled substance in schedule I or II.

Id. § 802(32)(A).

We have never decided whether § 802(32)(A) should be read disjunctively or conjunctively. The district court concluded that most courts "have read the statute in the conjunctive which requires the government to prove clause (i) and either clause (ii) or (iii)." United States v. Brown, 279 F.Supp.2d 1238, 1240 (S.D.Ala. 2003) (citation omitted); accord United States v. Turcotte, 405 F.3d 515, 522-23 (7th Cir.2005). Because both parties accept the district court's conjunctive reading of the statute, we will assume for purposes of this appeal that it is the correct one.

The Browns have conceded all along that 1,4-butanediol has the same effect on a person's central nervous system as GHB and thereby meets clause (ii) of § 802(32)(A). In fact, they stipulated in the district court that when ingested 1,4-butanediol is actually transformed into GHB by two naturally occurring enzymes. That leaves only the question of whether 1,4-butanediol meets clause (i). The government says it does; the Browns say it does not.

C.

During the three-day bench trial the government put on two witnesses and the defense put on one. All three of the witnesses testified on the § 802(32)(A)(i) issue: whether the chemical structure of 1,4-butanediol is "substantially similar" to that of GHB.

The government called Dr. James DeFrancesco, a forensic drug chemist with the Drug Enforcement Agency. DeFrancesco holds a Ph.D. in physical-organic chemistry and has conducted several studies of 1,4-butanediol and GHB. The government also called Dr. Richard Irwin, a biochemist with the National Institute of Environmental Health Sciences, a branch of the National Institutes of Health. Irwin holds a Ph.D. in biochemistry and is the author of a peer-reviewed paper on 1,4-butanediol. Those two witnesses were qualified as experts in chemistry without objection from the defense.

DeFrancesco explained that the similarities and differences in the chemical structures of 1,4-butanediol and GHB could be determined by visually comparing two-dimensional representations of the atomic structures of the two chemicals. Based on that visual comparison, both DeFrancesco and Irwin concluded that 1,4-butanediol and GHB are substantially similar because they differ only in the "functional groups" found on the right side of the molecules.

DeFrancesco and Irwin explained that both 1,4-butanediol and GHB are composed of carbon, oxygen, and hydrogen atoms, and each one has an alcohol functional group on its left end. The molecules differ, however, on the right side because a 1,4-butanediol molecule has a second alcohol functional group, making it a dialcohol, while a GHB molecule has a carboxylicacid functional group. Despite those different functional groups, DeFrancesco and Irwin were of the opinion that the chemical structures of the two substances are substantially similar and that 1,4-butanediol is, therefore, a chemical analogue of GHB.

DeFrancesco and Irwin also explained how 1,4-butanediol is converted into GHB in the human body by two naturally occurring enzymes. Irwin testified that this metabolic conversion is a crucial fact in comparing the two substances. He also told the court that the effect of GHB on the body is to depress the central nervous system, while 1,4-butanediol itself has no effect on the central nervous system. Once ingested, however, 1,4-butanediol is rapidly converted to GHB. In fact, GHB can be detected in the bloodstream within two minutes after 1,4-butanediol is ingested. A person can slow down, but cannot prevent, the internal conversion of 1,4-butanediol to GHB. Because 1,4-butanediol is converted into GHB soon after ingestion, consuming it has the same effect on the body as consuming GHB. Indeed, the reason people take (or administer to others) 1,4-butanediol is that it is converted into, and produces the same depressant effects as, GHB.

Irwin acknowledged that the fact one compound metabolizes into another is not enough by itself to establish substantial similarity between their chemical structures. Nonetheless, he testified that the metabolic conversion of 1,4-butanediol into GHB is important when considering the degree of similarity between them. That is because...