Quantification of Phencyclidine in Mainstream Smoke and Identification of Phenylcyclohex-1-ene as Pyrolysis Product

Abstract

Parsley cigarettes containing [3H]phencyclidine were machine smoked, and the mainstream smoke was trapped in glass wool filters. Radioactivity was extracted from these filters with chloroform. The average recoveries of radioactivity were 76, 85, 70, and 69% for cigarettes containing 3, 10, 30, and 50 mg of [3H]phencyclidine hydrochloride, respectively. TLC and GLC-mass spectrometry were employed to identify and quantify compounds in the filter extracts. Approximately one-half of the recovered radioactivity represented a pyrolysis product, phenylcyclohex-1-ene. Formation of this product involved loss of piperidine from phencyclidine. Piperidine, which was not radiolabeled, also may appear in smoke intact. The remainder of the radiolabeled material represented unchanged phencyclidine. Therefore, the percentage of [3H]phencyclidine delivered was ∼40% of the amount smoked. This result was independent of puff frequency and quantity of phencyclidine hydrochloride smoked over the range tested. The [3H] phencyclidine delivery was compared to the quantities of [3H]-±9-tetrahydrocannabinol and [3H]nicotine delivered in mainstream smoke. The recovery of unchanged [3H]-±9-tetrahydrocannabinol from placebo marijuana cigarettes injected with a solution containing 3 mg of ±9-tetrahydrocannabinol was 60%. Tobacco cigarettes injected with [3H]nicotine yielded 70% unchanged nicotine in mainstream smoke.