Benocyclidine
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Benocyclidine
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| Systematic (IUPAC) name | |
| 1-[1-(1-benzothiophen-2-yl)cyclohexyl]piperidine | |
| Clinical data | |
| Pregnancy cat. | ? |
| Legal status | ? |
| Identifiers | |
| CAS number | 112726-66-6  |
| ATC code | None |
| PubChem | CID 123692 |
| ChemSpider | 110266  |
| ChEMBL | CHEMBL279556 |
| Chemical data | |
| Formula | C19H25NS |
| Mol. mass | 299.474 g/mol |
| SMILES | eMolecules & PubChem |
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Benocyclidine (BCP), or benzothiophenylcyclohexylpiperidine (BTCP), is a psychoactive drug and research chemical of the arylcyclohexylamine class. It acts as a potent and selective dopamine reuptake inhibitor (DRI) and a psychostimulant.[1][2] 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.[1][2] It has been used to label the dopamine transporter.[3][4]
BCP was also used to try to find a common pharmacophore for DRI type stimulants.[5]
More recently, benocyclidine has been found in several ecstasy tablets, sold as MDMA. It is often combined with 5-MeO-DiPT, and is said to be extremely dangerous.[6]
See also
References
- ^ a b 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.
- ^ a b 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.
- ^ "Blue Butterfly". Ecstasy and other drug testing. Folley. http://www.ecstasydata.org/view.php?id=2307. Retrieved 2 February 2012.
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