Benocyclidine

"BTCP" redirects here. For other uses, see BTCP (disambiguation).

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]

Benocyclidine

Clinical data
ATC code	none
Legal status
Legal status	UK: Under Psychoactive Substances Act US: Unscheduled, illegal in Florida and Virginia
Identifiers
IUPAC name 1-[1-(1-Benzothiophen-2-yl)cyclohexyl]piperidine
CAS Number	112726-66-6 N
PubChem CID	123692
ChemSpider	110266 Y
UNII	Q1WR6UP7MW
ChEMBL	ChEMBL279556 Y
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 Y Key:RGSVXQJPSWZXOP-UHFFFAOYSA-N Y
NY (what is this?)  (verify)

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 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 in the United States

Benocyclidine is a Schedule I controlled substance in the state of Florida and Virginia, making it illegal to buy, sell, or possess in these states.^[8][9]

Otherwise, benocyclidine is not scheduled at the federal level in the United States,^[10] but may be considered an analog of PCP, in which case purchase, sale, or possession could be prosecuted under the Federal Analog Act if intended for human consumption.

See also

• Tenocyclidine