BTCP - a compound with cocaine-like properties

[pHarmacist]

1-[1-(2-Benzothiopheneyl)cyclohexyl]piperidine Hydrochloride (BTCP) Yields Two Active Primary Metabolites in Vitro: Synthesis, Identification from Rat Liver Microsome Extracts, and Affinity for the Neuronal Dopamine Transporter
Deleuze-Masquefa, C.; Michaud, M.; Vignon, J.; Kamenka, J.-M.;
J. Med. Chem.; (Article); 1997; 40(25); 4019-4025.

Abstract: 1-[1-(2-Benzo(b)thiopheneyl)cyclohexyl]piperidine hydrochloride (BTCP, 1) and cocaine bind to the neuronal dopamine transporter to inhibit dopamine (DA) reuptake. However, on chronic administration, cocaine produces sensitization, but 1 produces tolerance. Because metabolites of 1 might be responsible for some of its pharmacological properties, we have identified the primary metabolites of 1 produced by rat liver microsomes and determined their affinities for the DA transporter. Five monohydroxylated derivatives (3, 5, 9, 10, 14) and two degradation compounds (15, 16) were identified as metabolites through comparison with synthetic standards in HPLC and GC systems. Standards were obtained utilizing synthetic schemes previously used for the synthesis of phencyclidine metabolites. In vitro, two compounds (3, 5) showed a high affinity for the DA transporter. These active metabolites might be important in the pharmacology of 1.
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http://pharmacist8.tripod.com/BTCP.pdf

[pHarmacist]

Synthesis and biological evaluation of 1-[1-(2-benzo(b)thienyl)cyclohexyl]piperidine homologs at dopamine-uptake and phencyclidine-, and .sigma.-binding sites
Xiao Shu He, Lionel P. Raymon, Mariena V. Mattson, Mohyee E. Eldefrawi, Brian R. de Costa;
J. Med. Chem.; 1993; 36(9); 1188-1193.
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Full-Text:

http://pharmacist8.tripod.com/BTCP-2.pdf