U.S. v. Roberts

• Decision Date: 01 April 2004
• Docket Number: Docket No. 02-1604.,Docket No. 02-1605.
• Citation: 363 F.3d 118
• Parties: UNITED STATES of America, Appellant, v. Todd Kelly ROBERTS, aka "Dr. Conan", Michael Toback, Defendants-Appellees.
• Court: U.S. Court of Appeals — Second Circuit

363 F.3d 118

UNITED STATES of America, Appellant, v. Todd Kelly ROBERTS, aka "Dr. Conan", Michael Toback, Defendants-Appellees.

Docket No. 02-1604.

Docket No. 02-1605.

United States Court of Appeals, Second Circuit.

Argued: May 27, 2003.

Decided: April 1, 2004.

Laurie A. Korenbaum, Assistant United States Attorney (Christine H. Chung, Assistant U.S. Attorney, on the brief), for James B. Comey, United States District Attorney for the Southern District of New York, for Appellant.

Richard Collins, Collins, McDonald & Gann, P.C., Carle Place, N.Y.; Edward P. Jenks, Mineola, N.Y., for Defendant-Appellee Todd Kelly Roberts.

Kenneth Saltzman, (Andrew A. Rubin, on the brief), Mancuso, Rubin & Fufidio, White Plains, N.Y., for Defendant-Appellee Michael Toback.

Before: WALKER, Chief Judge, CALABRESI, Circuit Judge, and KORMAN, District Judge.^*

CALABRESI, Circuit Judge.

The government appeals from the judgment of the district court (Sweet, J.), dismissing the indictments against the defendants on the ground that the definition of "controlled substance analogue," 21 U.S.C. § 802(32)(A), as applied to 1,4-butanediol, is unconstitutionally vague. We conclude that, because 1,4-butanediol both (a) differs from gamma hydroxybutyric acid ("GHB"), a Schedule I controlled substance, by only two atoms and (b) converts into GHB upon ingestion, it is sufficiently clear that 1,4-butanediol is "substantially similar [in] chemical structure" to GHB, as that term is used in § 802(32)(A)'s definition of "controlled substance analogue," and, hence, that the definition as applied in this case does not violate the Constitution. The defendants do not contest that 1,4-butanediol meets the other statutory criteria for being a controlled substance analogue. We therefore vacate the dismissal of the indictments and remand for further proceedings.

BACKGROUND

On April 26, 2001, a grand jury in the Southern District of New York returned indictments against Todd Kelly Roberts and Michael Toback, charging that Roberts and Toback conspired to distribute and distributed 1,4-butanediol for human consumption, in violation of 21 U.S.C. §§ 802(32)(A), 812, 813, 841(a)(1), 841(b)(1)(C), and 846. The government charges that Toback made retail sales of 1,4-butanediol from a New York City health food store. It also charges that Toback obtained the 1,4-butanediol from the Barin Corporation and that Roberts is the president of that company.

1,4-butanediol has a long history of use as an industrial solvent. In recent years it has been discovered to be a depressant, inducing a deep sleep. According to the government, this property has caused it to be used as a "date rape" drug. Though 1,4-butanediol has not been listed as a controlled substance, see 21 U.S.C. § 812; 21 C.F.R. §§ 1308.11-1308.15, the government contends that it is a "controlled substance analogue" of GHB, which Congress listed as a Schedule I controlled substance in 2000. See Hillory J. Farias and Samantha Reid Date-Rape Drug Prohibition Act of 2000, Pub.L. No. 106-172, § 3(a)(1), 114 Stat. 7 (2000) ("Pub.L. No. 106-172"). Under the Controlled Substance Analogue Enforcement Act of 1986 (the "Act"), 21 U.S.C. §§ 802(32)(A), 813 (2000), some substances that have not been listed as controlled substances, but that are sufficiently similar to a listed substance, are, under certain additional circumstances, treated as Schedule I controlled substances for the purposes of federal drug law.

After their indictment, the defendants submitted Rule 12(b) motions to dismiss. See Fed.R.Crim.P. 12(b). In these, they argued, inter alia, that the Act was so vague (as applied to 1,4-butanediol) that the defendants' prosecution violated the Fifth Amendment's guarantee of due process. On December 14, 2001, the district court (Sweet, J.) granted a hearing on the matter and issued a preliminary ruling on how the Act's definition of "controlled substance analogue" should be interpreted.

The 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.

21 U.S.C. § 802(32)(A). The interpretive question that the district court addressed in its December 14, 2001 order was whether the three subsections of the definition should be read in the disjunctive or in the conjunctive. Under the disjunctive reading, a substance that satisfies one or more of the subsections is a "controlled substance analogue." According to the conjunctive reading, the definition requires two things: first, (i) that the substance be chemically similar and, second, (ii) that it have a similar or greater psychopharmacological effect or (iii) that it be intended to have or be represented as having such an effect. Before the district court, the government argued for the disjunctive reading, the defendants for the conjunctive.

The district court found that the language of the statute did not unambiguously lend itself to either reading, because the "which" in (ii) and (iii) appears at the beginning of those clauses, suggesting that it might refer not to "substance" in the preface of the definition, but instead to "chemical structure" in (i). Having found the provision ambiguous, the district court examined the purpose and legislative history of the Act and concluded that the conjunctive reading was the correct one. Other courts that have considered the question have come to the same conclusion. United States v. Hodge, 321 F.3d 429, 432-39 (3d Cir.2003) (providing an extensive analysis of the plain meaning and legislative history of 21 U.S.C. § 802(32)(A)); United States v. Washam, 312 F.3d 926, 930 n. 2 (8th Cir.2002) (adopting the conjunctive reading); United States v. McKinney, 79 F.3d 105, 107-08 (8th Cir.1996), vacated on other grounds, 520 U.S. 1226, 117 S.Ct. 1816, 137 L.Ed.2d 1025 (1997) (paraphrasing the test in the conjunctive without discussion); United States v. Forbes, 806 F.Supp. 232, 236 (D.Colo.1992) (stating that the conjunctive reading is required to avoid unintended results and is supported by the Act's legislative history). But see United States v. Fisher, 289 F.3d 1329, 1338 (11th Cir.2002) (expressly declining to decide whether the conjunctive or disjunctive reading governs); United States v. Granberry, 916 F.2d 1008, 1010 (5th Cir.1990) (stating the test in the disjunctive without discussion). Because the government has not appealed this holding of the district court, we assume that the conjunctive reading is correct.

On June 17, 2002, the district court held a hearing on the defendants' void-for-vagueness argument. The defendants did not contest that 1,4-butanediol satisfied clause (ii) of the definition of "controlled substance analogue" — which requires a stimulant, depressant, or hallucinogenic effect on the central nervous system that is similar to or greater than that of a controlled substance. At issue was only whether it was sufficiently clear that 1,4-butanediol satisfied clause (i) of that definition — requiring a "chemical structure [that is] substantially similar to the chemical structure of a controlled substance."

Two defense experts, Drs. Haley and Schuster, and one government expert, Dr. DiBerardino, testified at the June 17, 2002 hearing. Haley and Schuster are both professors of chemistry. DiBerardino has a degree in polymer chemistry and is employed by the DEA. The experts agreed on the following facts as to the chemical makeup of 1,4-butanediol and GHB. (1) The molecules of 1,4-butanediol and GHB differ by two atoms: an oxygen atom in GHB is replaced by two hydrogen atoms in 1,4-butanediol. (2) The different atoms are located in a "functional group" of the molecule, which is a section of the molecule that is especially important in determining the substance's properties. In this case, the difference means that 1,4-butanediol is an alcohol while GHB is an acid and that the chemicals have different reactivity, acidity levels, and melting and boiling points. (3) While the difference between 1,4-butanediol and GHB appears minor on a two-dimensional chart, the molecules have different three-dimensional structures. The four-carbon chain in 1,4-butanediol is linear, while in GHB the chain folds over itself. (4) The nuclear magnetic resonance (NMR) spectrograms of 1,4-butanediol and GHB are significantly different. (5) Despite the difference in functional groups, upon ingestion, 1,4-butanediol is metabolized, in two steps, into GHB.

The experts, however, disagreed on whether 1,4-butanediol was "substantially similar [in] chemical structure" to GHB. The defense experts argued that 1,4-butanediol and GHB were not substantially similar in chemical structure for the following reasons: (1) chemists treat alcohols and acids as belonging to fundamentally different categories; (2) 1,4-butanediol is linear, while GHB folds over on itself; and (3) chemists commonly use NMR spectrograms to classify chemicals and the NMR spectrograms of 1,4-butanediol and GHB are significantly different. The prosecution expert, DiBerardino, argued that functional groups concerned a molecule's various properties and reactivity, but not its structure, and emphasized the similarity of the two-dimensional diagrams.

On September 9, 2002, the district court issued an opinion granting the...