Pyrolytic fate of piperidinocyclohexanecarbonitrile, a contaminant of phencyclidine, during smoking

Journal Article · Tue Mar 01 04:00:00 EST 1988 · J. Anal. Toxicol.; (United States)

DOI:https://doi.org/10.1093/jat/12.2.57· OSTI ID:6855840

Lue, L P; Scimeca, J A; Thomas, B F; Martin, B R

The pyrolysis products of 1-(1-piperidino)cyclo-hexanecarbonitrile (PCC), the major contaminant of illicit phencyclidine (PCP), have not been previously reported. In order to quantify PCC in mainstream smoke as well as to identify the pyrolysis products, (/sup 3/H)piperidino-(/sup 14/C)cyano-PCC was synthesized. Marijuana placebo cigarettes were impregnated with this double-labeled PCC and burned with an apparatus that simulated smoking. The mainstream smoke was passed through a series of traps containing glass wool, H/sub 2/SO/sub 4/, or NaOH. Approximately 75% of the /sup 3/H was collected in these traps, and 46, 11, and 5% of the /sup 14/C was found in the glass wool, H/sub 2/SO/sub 4/, and NaOH traps, respectively. Contents of the traps were analyzed by GC/MS. The glass wool trap contained 1-(1-piperidino)-1-cyclo-hexene, PCC, piperidine, and N-acetylpiperidine, and cyanide ion was detected in all three traps. Approximately 47% of the PCC was found intact in mainstream smoke. Approximately 58% was cleaved to form cyanide and 1-(1-piperidino)-1-cyclohexene. The latter was further broken down to cyclohexanone (which represented 21% of the starting material), piperidine (29%), and N-acetylpiperidine (7%), and about 2% remained intact.

• Research Organization: Virginia Commonwealth Univ., Richmond (USA)
• OSTI ID: 6855840
• Journal Information: J. Anal. Toxicol.; (United States), Journal Name: J. Anal. Toxicol.; (United States) Vol. 12:2; ISSN JATOD
• Country of Publication: United States
• Language: English

Related Subjects

550201 -- Biochemistry-- Tracer Techniques
560300* -- Chemicals Metabolism & Toxicology
59 BASIC BIOLOGICAL SCIENCES
63 RADIATION, THERMAL, AND OTHER ENVIRON. POLLUTANT EFFECTS ON LIVING ORGS. AND BIOL. MAT.
AEROSOLS
AMINES
AZINES
CARBON 14 COMPOUNDS
CHEMICAL REACTIONS
CHROMATOGRAPHY
COLLOIDS
CONTAMINATION
CYANIDES
DECOMPOSITION
DISPERSIONS
ENERGY
GAS CHROMATOGRAPHY
HEAT
HETEROCYCLIC COMPOUNDS
ISOTOPE APPLICATIONS
LABELLED COMPOUNDS
MASS SPECTROSCOPY
NITRILES
ORGANIC COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
PIPERIDINES
PYRIDINES
PYROLYSIS
RESIDUES
SEPARATION PROCESSES
SMOKES
SOLS
SPECTROSCOPY
THERMOCHEMICAL PROCESSES
TRACER TECHNIQUES
TRITIUM COMPOUNDS