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In vitro metabolism of 1-phenyl-1-cyclohexene, a pyrolysis product of phencyclidine.

The in vitro metabolism of 1-3H-phenyl-1-cyclohexene (3H-PC) was studied in a crude microsomal preparation from mouse livers. The major routes of metabolism were allylic hydroxylation, oxidation of the allylic alcohol, and epoxidation-hydrolysis. The following metabolites were identified by comparison with reference compounds: 1-phenyl-1-cyclohexen-3-ol (major metabolite), 1-phenyl-1-cyclohexen-3-one (PC-3-one) (major), 1-phenyl-1-cyclohexen-6-ol (minor), 1-phenyl-1-cyclohexen-6-one (minor), and 1-phenylcyclohexane-1,2-diol (PC-1,2-diol) (minor). An additional metabolite, present in abundant quantities, was formed as a result of both allylic hydroxylation and epoxidation-hydrolysis. This triol contained hydroxyl groups at positions 1 and 2 of the cyclohexane ring but the position of the third hydroxyl group could not be established. PC-3-ol and PC-3-one were found to be somewhat more potent than PC in the inverted-screen test, whereas PC-1,2-diol was less effective. However, all three metabolites were considerably less active than PCP in this test.

Animals↗
PubMed1984

Amadori- and N-nitroso-Amadori compounds and their pyrolysis products. Chemical, analytical and biological aspects.

N-(1-Deoxy-D-fructos-1-yl)-L-amino acids (fructose amino acids), Amadori compounds, are formed by reaction of D-glucose and L-amino acids and Amadori rearrangement. They are detected in heat-processed natural products and various foodstuffs and are key products of the Maillard-Browning reaction. N-Nitroso-N-(1-deoxy-D-fructos-1-yl)-L-amino acids (N-NO-fructose amino acids), N-NO-Amadori compounds, are formed in high yields by reacting fructose amino acids with sodium nitrite in acidic aqueous solution. They constitute a new class of non-volatile, bis-beta-oxidized nitrosamine derivatives with unknown biological (mutagenic and/or carcinogenic) activity. N-NO-Fructose amino acids may be formed in nitrite-containing Maillard systems (e.g., cured-meat products, tobacco) or in the human stomach after ingestion of food containing fructose amino acids and nitrite in food or saliva. Thirteen fructose amino acids and 13 N-NO-fructose amino acids (-gly, -ala, -val, -leu, -ileu, -ser, -thr, -met, -asp, -pheala, -tyr, -his, -trp) were prepared and investigated by high-resolution 1H-nuclear magnetic resonance (NMR) and 13C-NMR spectroscopy. The percentage amounts of the sugar ring forms (beta-pyranose, beta-furanose, alpha-furanose and alpha-pyranose) of these compounds in D2O mutarotation equilibrium were determined by 13C-NMR spectroscopy, together with the amounts (%) of E/Z isomers in the case of N-NO-compounds. The nitrosation products of D-fru-L-tyr, D-fru-L-his and D-fru-L-trp were isolated and identified by spectroscopic methods (NMR, infra-red). The N-NO-fructose amino acids can be separated by reversed-phase, ion-pairing, high-performance liquid chromatography. In some case the E/Z isomers are separated.

Amino Acids↗