Benocyclidine

Benocyclidine, also known as benzo​thiophenyl​cyclo​hexylpiperidine (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]

Benocyclidine

Clinical data
ATC code	none
Legal status
Legal status	UK: Under Psychoactive Substances Act
Identifiers
IUPAC name 1-[1-(1-Benzothiophen-2-yl)cyclohexyl]piperidine
CAS Number	112726-66-6
PubChem CID	123692
ChemSpider	110266
UNII	Q1WR6UP7MW
ChEMBL	ChEMBL279556
CompTox Dashboard (EPA)	DTXSID0042581
Chemical and physical data
Formula	C19H25NS
Molar mass	299.48 g·mol^−1
3D model (JSmol)	Interactive image
SMILES C1(SC(C2(CCCCC2)N3CCCCC3)=C4)=C4C=CC=C1
InChI InChI=1S/C19H25NS/c1-5-11-19(12-6-1,20-13-7-2-8-14-20)18-15-16-9-3-4-10-17(16)21-18/h3-4,9-10,15H,1-2,5-8,11-14H2 Key:RGSVXQJPSWZXOP-UHFFFAOYSA-N
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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

• Tenocyclidine

References

1. PCT Patent Application WO199712513 (see also US Patents Nos.5,866,756 and 6,218,595
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.
3. 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.
4. 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.
5. 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.
6. 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.
7. "EcstasyData Testing Result: Blue Butterfly". Ecstasy and other drug testing. Erowid Center. Retrieved 2 February 2012.
8. 21 CFR — SCHEDULES OF CONTROLLED SUBSTANCES §1308.11 Schedule I.
9. Florida Statutes - Chapter 893 - DRUG ABUSE PREVENTION AND CONTROL