Benocyclidine
 | |
| Systematic (IUPAC) name | |
|---|---|
|
1-[1-(1-Benzothiophen-2-yl)cyclohexyl]piperidine | |
| Identifiers | |
| CAS Number |
112726-66-6  |
| ATC code | none |
| PubChem | CID 123692 |
| ChemSpider |
110266  |
| ChEMBL |
CHEMBL279556 |
| Chemical data | |
| Formula | C19H25NS |
| Molar mass | 299.47 g/mol |
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| (what is this?) (verify) | |
Benocyclidine, also known as benzothiophenylcyclohexylpiperidine (BTCP), is a psychoactive recreational drug of the arylcyclohexylamine class which is related to phencyclidine (PCP). It was first described in a patent application naming Marc Caron and colleagues at Duke University in 1997.[1]
It acts as a potent and selective dopamine reuptake inhibitor (DRI) and a psychostimulant.[2][3] Unlike related compounds like phencyclidine and ketamine, benocyclidine is a pure DRI with negligible affinity for the NMDA receptor, and it therefore lacks any anticonvulsant, anesthetic, hallucinogenic, or dissociative effects.[2][3] It has been used to label the dopamine transporter.[4][5]
BCP was also used to try to find a common pharmacophore for DRI type stimulants.[6]
More recently, benocyclidine has been found in several ecstasy tablets, sold as MDMA.[7]
Legal status
United States
Benocyclidine is not scheduled at the federal level in the United States,[8] but may be considered an analog of PCP, in which case purchase, sale, or possession could be prosecuted under the Federal Analog Act.
Florida
"Benocyclidine (BCP) or benzothiophenylcyclohexylpiperidine (BTCP)" is a Schedule I controlled substance in the state of Florida making it illegal to buy, sell, or possess in Florida.[9]
See also
References
- ↑ PCT Patent Application WO199712513 (see also US Patents Nos.5,866,756 and 6,218,595
- 1 2 Vignon J, Pinet V, Cerruti C, Kamenka JM, Chicheportiche R. (1998). "[3H]N-[1-(2-benzo(b)thiophenyl)cyclohexyl]piperidine ([3H]BTCP): a new phencyclidine analog selective for the dopamine uptake complex.". Eur J Pharmacol. 148 (3): 427–436. doi:10.1016/0014-2999(88)90122-7. PMID 3384005.
- 1 2 Chaudieu I, Vignon J, Chicheportiche M, Kamenka JM, Trouiller G, Chicheportiche R. (1989). "Role of the aromatic group in the inhibition of phencyclidine binding and dopamine uptake by PCP analogs.". Pharmacol Biochem Behav. 32 (3): 699–705. doi:10.1016/0091-3057(89)90020-8. PMID 2544905.
- ↑ Filloux F, Hunt MA, Wamsley JK. (1989). "Localization of the dopamine uptake complex using [3H]N-[1-(2-benzo(b)thiophenyl)cyclohexyl]piperidine ([3H]BTCP) in rat brain.". Neurosci Lett. 100 (1–3): 105–110. doi:10.1016/0304-3940(89)90668-X. PMID 2527343.
- ↑ Maurice T, Vignon J, Kamenka JM, Chicheportiche R. (1989). "In vivo labelling of the mouse dopamine uptake complex with the phencyclidine derivative [3H]BTCP". Neurosci Lett. 101 (2): 234–238. doi:10.1016/0304-3940(89)90537-5. PMID 2771169.
- ↑ Froimowitz M, Wu KM, Rodrigo J, George C (2000). "Conformational preferences of the potent dopamine reuptake blocker BTCP and its analogs and their incorporation into a pharmacophore model". J Comput Aided Mol Des 14 (2): 135–46. doi:10.1023/A:1008144707255. PMID 10721502.
- ↑ "EcstasyData Testing Result: Blue Butterfly". Ecstasy and other drug testing. Erowid Center. Retrieved 2 February 2012.
- ↑ 21 CFR — SCHEDULES OF CONTROLLED SUBSTANCES §1308.11 Schedule I.
- ↑ Florida Statutes - Chapter 893 - DRUG ABUSE PREVENTION AND CONTROL
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