909 F.3d 372
11th Cir.2018Background
- Jason Phifer was convicted for possession with intent to distribute ethylone, charged as a "positional isomer" of temporarily scheduled Schedule I drug butylone under 21 U.S.C. § 841.
- The DEA's regulations list butylone and its "optical, positional, and geometric isomers" among temporarily scheduled substances; the only regulatory definition of "positional isomer" appears in 21 C.F.R. § 1300.01(b) but includes the clause "As used in § 1308.11(d)..."
- Phifer's defense: the technical (scientific) meaning of "positional isomer"—as explained by his expert using McMurry's Organic Chemistry—requires the same carbon skeleton, which ethylone and butylone do not share (they are skeletal isomers), so ethylone was not criminally covered.
- Government/DEA position: the DEA’s regulatory definition (and contemporaneous DEA materials) treats ethylone as a positional isomer of butylone, so the regulatory definition governs and supports conviction.
- The district court instructed the jury using the DEA definition; Phifer was convicted and appealed. The Eleventh Circuit found the regulatory language ambiguous as to whether § 1300.01(b)’s definition applies to § 1308.11(h) and vacated the conviction.
Issues
| Issue | Plaintiff's Argument (Phifer) | Defendant's Argument (Government/DEA) | Held |
|---|---|---|---|
| Whether the DEA's § 1300.01(b) definition of "positional isomer" applies to temporary listings in § 1308.11(h) | The § 1300.01(b) definition is limited by its phrase "As used in § 1308.11(d)" and thus does not govern § 1308.11(h); the scientific (McMurry) definition should control | The regulatory definition (and DEA materials) is the sole regulatory meaning and applies across part 1308, encompassing § 1308.11(h) | Regulation ambiguous; court cannot conclusively read it on this record |
| Whether courts should defer to the DEA's interpretation (Auer deference) in a criminal case | The rule of lenity and fair-warning concerns bar Auer deference in criminal prosecutions | Auer/Ehlert permit deference to the agency's reasonable interpretation of its ambiguous regulation | Auer deference unavailable in criminal cases here: bound by Diamond Roofing; must resolve ambiguity in defendant's favor if penal |
| How to resolve the technical meaning of "positional isomer" | Court should adopt the scientific definition presented by Phifer's expert (McMurry) or otherwise apply scientific consensus | Court should accept DEA's interpretation and contemporaneous agency materials identifying ethylone as a positional isomer | Remand: district court must hold an evidentiary (Daubert-style) hearing to determine which definitions of "positional isomer" are generally accepted; instruct jury on all such definitions and let jury decide factual application; if any reasonable ambiguity exists, lenity favors acquittal |
| Whether retrial is barred by double jeopardy | Retrial would violate double jeopardy | Retrial allowed because conviction was vacated on appeal for legal error | Retrial permitted; no double jeopardy bar because conviction set aside on appeal for error (Lockhart) |
Key Cases Cited
- Touby v. United States, 500 U.S. 160 (1991) (explains DEA/Attorney General temporary scheduling authority under the CSA)
- Auer v. Robbins, 519 U.S. 452 (1997) (deference to agency interpretation of ambiguous regulation)
- Ehlert v. United States, 402 U.S. 99 (1971) (deferred to agency construction of regulation in criminal context but did not consider rule of lenity)
- Diamond Roofing Co. v. Occupational Safety & Health Review Comm'n, 528 F.2d 645 (5th Cir. 1976) (Auer deference precluded where regulation imposes criminal or civil penalties; fair warning requirement)
- McDermott Int'l, Inc. v. Wilander, 498 U.S. 337 (1991) (when undefined term of art appears in statute, courts presume established technical meaning applies)
- Daubert v. Merrell Dow Pharm., Inc., 509 U.S. 579 (1993) (district court gatekeeping for admissibility and reliability of expert scientific evidence)
- Lockhart v. Nelson, 488 U.S. 33 (1988) (double jeopardy does not bar retrial after conviction is vacated on appeal)
- Bass v. United States, 404 U.S. 336 (1971) (rule of lenity: ambiguous criminal laws must be construed in defendant's favor)