Benocyclidine
Clinical data
ATC code
  • none
Legal status
Legal status
Identifiers
  • 1-[1-(1-Benzothiophen-2-yl)cyclohexyl]piperidine
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC19H25NS
Molar mass299.48 g·mol−1
3D model (JSmol)
  • C1(SC(C2(CCCCC2)N3CCCCC3)=C4)=C4C=CC=C1
  • 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 checkY
  • Key:RGSVXQJPSWZXOP-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

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]

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

References

  1. ^ PCT Patent Application WO199712513 (see also US Patents Nos.5,866,756 and 6,218,595
  2. ^ 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.
  3. ^ 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. S2CID 7672918.
  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. S2CID 9985692.
  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. S2CID 24176107.
  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. Bibcode:2000JCAMD..14..135F. doi:10.1023/A:1008144707255. PMID 10721502. S2CID 6754086.
  7. ^ "EcstasyData Testing Result: Blue Butterfly". Ecstasy and other drug testing. Erowid Center. Retrieved 2 February 2012.
  8. ^ "§ 54.1-3446. Schedule I." Virginia Law. Retrieved 14 September 2023.
  9. ^ "Florida Statutes - Chapter 893 - DRUG ABUSE PREVENTION AND CONTROL".
  10. ^ "21 CFR — SCHEDULES OF CONTROLLED SUBSTANCES §1308.11 Schedule I". Archived from the original on 2009-08-27. Retrieved 2014-12-17.
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