United States v. Phifer, No. 17-10397

CourtUnited States Courts of Appeals. United States Court of Appeals (11th Circuit)
Writing for the CourtROSENBAUM, Circuit Judge
Citation904 F.3d 947
Decision Date21 September 2018
Docket NumberNo. 17-10397
Parties UNITED STATES of America, Plaintiff-Appellee, v. Jason Alexander PHIFER, Defendant- Appellant

904 F.3d 947

UNITED STATES of America, Plaintiff-Appellee,
v.
Jason Alexander PHIFER, Defendant- Appellant,

No. 17-10397

United States Court of Appeals, Eleventh Circuit.

September 21, 2018


ROSENBAUM, Circuit Judge:

There's no easy way around it. We're just going to have to science the heck out

904 F.3d 950

of this case.1 And when we're done with that, we're going to have to law the heck out of it.

Defendant-Appellant Jason Alexander Phifer was convicted of possession with intent to distribute a controlled substance, in violation of 21 U.S.C. § 841(a)(1) and 21 U.S.C. § 841(b)(1)(C). The substance involved was ethylone.

But as it turns out, ethylone constitutes a controlled substance — and Phifer was therefore convicted of an existing crime — only if ethylone is a "positional isomer" of butylone. Phifer says it's not. To support his position, he urges that "positional isomer" means what he characterizes as the scientific term of art. The Drug Enforcement Administration ("DEA") disagrees and contends that its regulatory definition of "positional isomer" governs, and even if it doesn't, ethylone is a positional isomer of butylone under other scientific definitions. If the DEA is right that the regulatory definition necessarily governs, Phifer's conviction stands. But if not, we must set aside Phifer's conviction.

After careful consideration and a crash course in organic chemistry, we conclude that the DEA's regulatory definition of "positional isomer" does not unambiguously apply to the use of that term as it pertains to butylone and ethylone in this case. We therefore vacate Phifer's conviction and remand for further proceedings consistent with this opinion.

I.

The Controlled Substances Act, 21 U.S.C. §§ 801-971 ("CSA" or "Act"), established five schedules of controlled substances, which the CSA regulates or prohibits. Touby v. United States, 500 U.S. 160, 162, 111 S.Ct. 1752, 114 L.Ed.2d 219 (1991); see 21 U.S.C. § 812. The Act assigns to the Attorney General the task of adding substances to the schedules. Touby, 500 U.S. at 162, 111 S.Ct. 1752; 21 U.S.C. § 811(a). But before the Attorney General may do so, he or she must follow certain procedures, including engaging in notice-and-comment rule-making, that typically require six to twelve months to complete. Touby, 500 U.S. at 163, 111 S.Ct. 1752; see 21 U.S.C. §§ 811(a)-(c), 877.

Because of that time lag, by the time a specific chemical formulation of a given drug was scheduled, people were able to design and sell drugs that behaved similarly to that substance but differed slightly in chemical composition, without risk of criminal liability. Touby, 500 U.S. at 163, 111 S.Ct. 1752. To address this problem, Congress amended the CSA to allow the Attorney General to place a substance on a schedule on a temporary basis when the Attorney General deems it "necessary to avoid an imminent hazard to the public safety." Id. (quoting 21 U.S.C. § 811(h)) (quotation marks omitted). Under this process, within thirty days after a new drug is identified, a new drug can be added to a schedule on a temporary basis. Id. at 164, 111 S.Ct. 1752.

The Attorney General delegated to the DEA the power to add drugs to the schedules — including the power to schedule controlled substances on a temporary basis. Id. (citing 28 C.F.R. § 0.100(b) (1990)). Under this authority, in March of 2014, the DEA Administrator issued an order temporarily designating butylone (1-(1,3-benzodioxol-5-yl)-2-(methylamino)butan-1-one) as a Schedule I controlled substance.2 79

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Fed. Reg. 12,938-12,943 (Mar. 7, 2014). Substances qualify for Schedule I if they have a "high potential for abuse," "no currently accepted medical use in treatment in the United States," and no "accepted safety for use of the drug or other substance under medical supervision." 21 U.S.C. § 812(b)(1). Butylone is a synthetic cathinone3 and acts, among other ways, as a hallucinogen. See 79 Fed. Reg. 12,938; Synthetic Cathinones ("Bath Salts"), Nat'l Inst. on Drug Abuse, https://www.drugabuse.gov/publications/drugfacts/synthetic-cathinones-bath-salts (last visited Sept. 20, 2018).

The list of drugs on Schedule I appears at 21 C.F.R. § 1308.11.4 Subsections (b) through (g) of this regulation identify substances placed permanently on Schedule I. See 21 C.F.R. § 1308.11(b)-(g). Among these substances permanently listed, certain hallucinogens are set forth at subsection (d). Meanwhile, substances temporarily listed — which may include all types of drugs, including hallucinogens — are identified at subsection (h). See 21 C.F.R. § 1308.11(h). At the time relevant to Phifer's case, butylone, along with "its optical, positional, and geometric isomers, salts and salts of isomers," appeared at 21 C.F.R. § 1308.11(h).

Section 1300.01(b) of Title 21 of the Code of Federal Regulations defines the term "isomer" and provides the sole regulatory definition for the term "positional isomer," as used in Schedule I. See 21 C.F.R. § 1300.01(b). The DEA added the definition for "positional isomer" to § 1300.01(b) for the first time by final rule that became effective on January 2, 2008. See 72 Fed. Reg. 67,850, 67851-52 (Dec. 3, 2007). Section 1300.01(b) defines "isomer," in relevant part, as "(1) [t]he optical isomer, except as used in § 1308.11(d) ... of this chapter. As used in § 1308.11(d) of this chapter, the term `isomer' means any optical, positional, or geometric isomer." Id. The definition of "isomer" then goes on in subsection (2) to define the term "positional isomer," a definition we will discuss in a moment.

But first, we note the DEA's reasons for adding a definition of only "positional isomer" but not definitions for other types of isomers: "The terms `optical isomer' and `geometric isomer' are specifically defined and well understood scientific terms, and it is easy to determine whether one substance is an optical or geometric isomer of another." 72 Fed. Reg. at 67,850. In contrast, the DEA acknowledged, "[t]he term `positional isomer" ... is not universally

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defined, and, therefore, is subject to scientific interpretation." Id. For this reason, the DEA established its own definition of the term for purposes of the CSA. Id.

To better understand the issue in this case, we must delve into the science behind the DEA's definition. Isomers are "[m]olecules that share the same chemical formula but have their atoms connected differently, or arranged differently in space." Hydrocarbon structures and isomers, Khan Academy, https://www.khanacademy.org/science/biology/properties-of-carbon/hydrocarbon-structures-and-functional-groups/a/hydrocarbon-structures-and-isomers (last visited Sept. 20, 2018). The way that the atoms are arranged or connected determines the type of isomers the molecules form. See id.

Two fundamental types of isomers exist: stereoisomers and constitutional isomers, which are also known as structural isomers. Isomers, Khan Academy, https://www.khanacademy.org/science/biology/properties-of-carbon/hydrocarbon-structures-and-functional-groups/v/isomers (last visited Sept. 20, 2018). Each isomer type, in turn, has sub-types. Optical and geometric isomers, which are mentioned in the DEA's definition of "isomer," are sub-types of stereoisomers. Positional isomers — also noted in the DEA's definition of "isomer" — are a sub-type of constitutional isomers. We concern ourselves here with only positional isomers.5

Unlike in stereoisomers, the atoms in constitutional isomers differ in how they are connected. See Bond-line Structures, Khan Academy, https://www.khanacademy.org/science/organic-chemistry/gen-chem-review/bond-line-structures/v/structural-constitutional-isomers-new, at 2:45-2:59 (last visited Sept. 20, 2018). So although constitutional isomers share the same constituent atoms in the same numbers, those atoms are bonded together in different orders. See Hydrocarbon structures and isomers, Khan Academy, https://www.khanacademy.org/science/biology/properties-of-carbon/hydrocarbon-structures-and-functional-groups/a/hydrocarbon-structures-and-isomers (last visited Sept. 20, 2018). The diagram below shows a basic example of a constitutional isomer:

Tabular or graphical material not displayable at this time.

Hydrocarbon structures and isomers, https://www.khanacademy.org/science/biology/properties-of-carbon/hydrocarbon-structures-and-functional-groups/a/hydrocarbon-structures-and-isomers (last visited Sept. 20, 2018). As this illustration demonstrates, the four carbon atoms in

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butane are connected to each other in a chain (so no carbon atom is bonded to more than two other carbon atoms), whereas one of the four carbon atoms in isobutane has three bonds to other carbon atoms. Similarly, while only two carbon atoms in butane are each bonded to three hydrogen atoms, in isobutane, three carbon atoms are each bonded to three hydrogen atoms, and one carbon atom is bonded to a single hydrogen atom. As a result, although both of these molecules share the same chemical formula (C4H10), they are different substances.

As we have noted, a positional isomer is a type of constitutional isomer. In relevant part, the DEA has defined the term "positional isomer" in ...

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