Pyrolytic fate of piperidinocyclohexanecarbonitrile, a contaminant of phencyclidine, during smoking.
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, [3H]piperidino-[14C]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, H2SO4, or NaOH. Approximately 75% of the 3H was collected in these traps, and 46, 11, and 5% of the 14C was found in the glass wool, H2SO4, 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.
Lue
L P
LP
Department of Pharmacology and Toxicology, Medical College of Virginia, Virginia Commonwealth University, Richmond 23298-0001.
Scimeca
J A
JA
Thomas
B F
BF
Martin
B R
BR
D004340:Drug Contamination; D008401:Gas Chromatography-Mass Spectrometry; D006358:Hot Temperature; D010622:Phencyclidine / Q000031:analogs & derivatives* / Q000032:analysis*; D010623:Phencyclidine Abuse; D012906:Smoke / Q000032:analysis*
D012906:Smoke; C011993:1-piperidinocyclohexanecarbonitrile; D010622:Phencyclidine