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Benocyclidine

From Wikipedia, the free encyclopedia
(Redirected fromBTCP)
Chemical compound
"BTCP" redirects here. For other uses, seeBTCP (disambiguation).
Pharmaceutical compound
Benocyclidine
Clinical data
ATC code
  • none
Legal status
Legal status
Identifiers
  • 1-[1-(1-Benzothiophen-2-yl)cyclohexyl]piperidine
CAS Number
PubChemCID
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 asbenzothiophenylcyclohexylpiperidine (BTCP), is apsychoactiverecreational drug of thearylcyclohexylamine class which is related tophencyclidine (PCP). It was first described in a patent application naming Marc Caron and colleagues at Duke University in 1997.[1]

It acts as apotent andselectivedopamine reuptake inhibitor (DRI) and apsychostimulant.[2][3] Unlike relatedcompounds likephencyclidine andketamine, benocyclidine is a pure DRI with negligibleaffinity for theNMDA receptor, and it therefore lacks anyanticonvulsant,anesthetic,hallucinogenic, ordissociative effects.[2][3] It has been used to label thedopamine transporter.[4][5] BCP was used to try to find a commonpharmacophore for DRI type stimulants.[6]

More recently, benocyclidine has been found in several ecstasy tablets, sold asMDMA.[7]

Legal status in the United States

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Benocyclidine is a Schedule Icontrolled substance in the state ofFlorida andVirginia, making it illegal to buy, sell, or possess in these states.[8][9]

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

See also

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References

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  1. ^PCT Patent Application WO199712513 (see also US Patents Nos.5,866,756 and 6,218,595
  2. ^abVignon 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. ^abChaudieu 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. Retrieved2 February 2012.
  8. ^"§ 54.1-3446. Schedule I."Virginia Law. Retrieved14 September 2023.
  9. ^"Florida Statutes - Chapter 893 - DRUG ABUSE PREVENTION AND CONTROL".
  10. ^"21 CFR — SCHEDULES OF CONTROLLED SUBSTANCES §1308.11 Schedule I". Archived fromthe original on 2009-08-27. Retrieved2014-12-17.
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