904 F.3d 947
11th Cir.2018Background
- Jason Alexander Phifer was convicted for possession with intent to distribute ethylone, charged as a "positional isomer" of butylone under the Controlled Substances Act schedules.
- The DEA had temporarily scheduled butylone (and its "positional isomers") in 2014; the DEA's only regulatory definition of "positional isomer" appears in 21 C.F.R. § 1300.01(b), phrased "As used in § 1308.11(d)..." though § 1308.11(h) lists temporary schedules including butylone.
- Phifer's defense: under the common scientific (McMurry) definition, positional isomers require the same carbon skeleton and ethylone is a skeletal isomer, not a positional isomer; thus ethylone was not a controlled substance as charged.
- The district court instructed the jury using the DEA definition and excluded Phifer’s requested McMurry definition; the jury convicted Phifer.
- On appeal the Eleventh Circuit held the regulation ambiguous about whether the § 1300.01(b) definition applies to § 1308.11(h) and rejected Auer deference in criminal cases, requiring the district court to determine scientific definitions at a hearing.
- The court vacated Phifer’s conviction and remanded, directing the district court to hold an evidentiary (Daubert-style) hearing to identify all definitions of "positional isomer" generally accepted in the scientific community and to instruct the jury accordingly; if ethylone fails to qualify under any such accepted definition, verdict must be not guilty under the rule of lenity.
Issues
| Issue | Phifer's Argument | Government's Argument | Held |
|---|---|---|---|
| Whether the DEA regulatory definition in 21 C.F.R. § 1300.01(b) of "positional isomer" governs the term as used in § 1308.11(h) (temporary schedules) | The § 1300.01(b) definition is limited to § 1308.11(d) by its own phrase "As used in § 1308.11(d)" and thus does not govern § 1308.11(h); absent a regulatory definition, the scientific (McMurry) meaning controls | The DEA's lone regulatory definition should apply across Part 1308; agency materials (DEA website) identify ethylone as a positional isomer of butylone, so the conviction stands | The regulation is ambiguous on whether the § 1300.01(b) definition applies to § 1308.11(h); ambiguity cannot be resolved in favor of agency interpretation in a criminal case without more proceedings |
| Whether Auer (Seminole Rock) deference requires accepting the DEA’s interpretation of its ambiguous regulation in a criminal prosecution | Auer deference is inapplicable in criminal cases where ambiguity implicates criminal liability; rule of lenity controls | Government urges deference to the DEA under Auer because the agency consistently identified ethylone as a positional isomer | The court (bound by Fifth Circuit precedent) holds Auer deference does not apply in criminal cases; rule of lenity and fair-warning concerns require courts to resolve ambiguity themselves |
| What process the court must use to determine the operative meaning of the technical term "positional isomer" for criminal application | The scientific definition (McMurry) should be used; at minimum a fair process to determine generally accepted scientific meanings is required | The DEA’s prior website listing and regulatory definition show the agency’s intended meaning; the court could defer or accept stipulated definitions | The district court must hold an evidentiary (Daubert-style) hearing to identify all definitions generally accepted in the scientific community and then instruct the jury on each such definition; jury decides factual application; rule of lenity requires acquittal if the substance fails at least one accepted definition |
| Whether retrial is barred by double jeopardy after vacatur of conviction | Retry would violate double jeopardy | Government says retrial is permitted because conviction was vacated on appeal for trial error | Court holds retrial is permitted; vacatur for error allows retrial absent prosecutorial misconduct |
Key Cases Cited
- Touby v. United States, 500 U.S. 160 (1991) (delegation to DEA and temporary scheduling authority under CSA)
- Auer v. Robbins, 519 U.S. 452 (1997) (deference to agency interpretation of its own ambiguous regulation)
- Ehlert v. United States, 402 U.S. 99 (1971) (applied agency construction of regulation in criminal case)
- Bowles v. Seminole Rock & Sand Co., 325 U.S. 410 (1945) (Seminole Rock deference doctrine)
- Diamond Roofing Co. v. Occupational Safety & Health Review Comm’n, 528 F.2d 645 (5th Cir. 1976) (agency interpretation cannot cure regulatory vagueness where criminal or civil sanctions attach)
- McDermott Int’l, Inc. v. Wilander, 498 U.S. 337 (1991) (use established technical meanings when statutory term is of art)
- Daubert v. Merrell Dow Pharm., Inc., 509 U.S. 579 (1993) (trial court's gatekeeping for expert scientific evidence)
- Kumho Tire Co. v. Carmichael, 526 U.S. 137 (1999) (Daubert gatekeeping applies to all expert testimony)
- Bass v. United States, 404 U.S. 336 (1971) (rule of lenity: ambiguous criminal statutes construed in favor of defendants)
- Lockhart v. Nelson, 488 U.S. 33 (1988) (vacatur on appeal permits retrial)