{{Short description|Chemical compound}} {{Redirect|BTCP}} {{Drugbox | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 461744968 | IUPAC_name = 1-[1-(1-Benzothiophen-2-yl)cyclohexyl]piperidine | image = Benocyclidine Structure.svg | image_class = skin-invert-image
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'''Benocyclidine''', also known as '''benzo{{wbr}}thiophenyl{{wbr}}cyclo{{wbr}}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.<ref>PCT Patent Application WO199712513 (see also US Patents Nos.5,866,756 and 6,218,595</ref>
It acts as a potent and selective dopamine reuptake inhibitor (DRI) and a psychostimulant.<ref name="pmid3384005">{{cite journal |vauthors=Vignon J, Pinet V, Cerruti C, Kamenka JM, Chicheportiche R | title = [3H]N-[1-(2-benzo(b)thiophenyl)cyclohexyl]piperidine ([3H]BTCP): a new phencyclidine analog selective for the dopamine uptake complex. | journal = Eur J Pharmacol | volume = 148 | issue = 3 | pages = 427–436 | year = 1998 | pmid = 3384005 | doi = 10.1016/0014-2999(88)90122-7 }}</ref><ref name="pmid2544905">{{cite journal |vauthors=Chaudieu I, Vignon J, Chicheportiche M, Kamenka JM, Trouiller G, Chicheportiche R | title = Role of the aromatic group in the inhibition of phencyclidine binding and dopamine uptake by PCP analogs. | journal = Pharmacol Biochem Behav | volume = 32 | issue = 3 | pages = 699–705 | year = 1989 | pmid = 2544905 | doi = 10.1016/0091-3057(89)90020-8 | s2cid = 7672918 }}</ref> 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.<ref name="pmid3384005"/><ref name="pmid2544905"/> It has been used to label the dopamine transporter.<ref name="pmid2527343">{{cite journal |vauthors=Filloux F, Hunt MA, Wamsley JK | title = Localization of the dopamine uptake complex using [3H]N-[1-(2-benzo(b)thiophenyl)cyclohexyl]piperidine ([3H]BTCP) in rat brain. | journal = Neurosci. Lett. | volume = 100 | issue = 1–3 | pages = 105–110 | year = 1989 | pmid = 2527343 | doi = 10.1016/0304-3940(89)90668-X | s2cid = 9985692 }}</ref><ref name="pmid2771169">{{cite journal |vauthors=Maurice T, Vignon J, Kamenka JM, Chicheportiche R | title = In vivo labelling of the mouse dopamine uptake complex with the phencyclidine derivative [3H]BTCP | journal = Neurosci. Lett. | volume = 101 | issue = 2 | pages = 234–238 | year = 1989 | pmid = 2771169 | doi = 10.1016/0304-3940(89)90537-5 | s2cid = 24176107 }}</ref> BCP was used to try to find a common pharmacophore for DRI type stimulants.<ref name="pmid10721502">{{cite journal|vauthors=Froimowitz M, Wu KM, Rodrigo J, George C | title=Conformational preferences of the potent dopamine reuptake blocker BTCP and its analogs and their incorporation into a pharmacophore model | journal=J Comput Aided Mol Des | year= 2000 | volume= 14 | issue= 2 | pages= 135–46 | pmid=10721502| doi=10.1023/A:1008144707255 | bibcode=2000JCAMD..14..135F | s2cid=6754086 }}</ref>
More recently, benocyclidine has been found in several ecstasy tablets, sold as MDMA.<ref name="Ecstasy Data">{{cite web|title=EcstasyData Testing Result: Blue Butterfly|url=http://www.ecstasydata.org/view.php?id=2307|work=Ecstasy and other drug testing|publisher=Erowid Center|access-date=2 February 2012}}</ref>
==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.<ref>{{cite web |title=§ 54.1-3446. Schedule I. |url=https://law.lis.virginia.gov/vacode/title54.1/chapter34/section54.1-3446/ |website=Virginia Law |access-date=14 September 2023}}</ref><ref>{{cite web |url=http://leg.state.fl.us/statutes/index.cfm?App_mode=Display_Statute&URL=0800-0899/0893/0893.html |title=Florida Statutes - Chapter 893 - DRUG ABUSE PREVENTION AND CONTROL}}</ref>
Otherwise, benocyclidine is not scheduled at the federal level in the United States,<ref>{{cite web |url=http://www.deadiversion.usdoj.gov/21cfr/cfr/1308/1308_11.htm |title=21 CFR — SCHEDULES OF CONTROLLED SUBSTANCES §1308.11 Schedule I |access-date=2014-12-17 |archive-date=2009-08-27 |archive-url=https://web.archive.org/web/20090827043725/http://www.deadiversion.usdoj.gov/21cfr/cfr/1308/1308_11.htm |url-status=dead }}</ref> 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
==References== {{Reflist}}
{{Stimulants}} {{Monoamine reuptake inhibitors}} Category:Arylcyclohexylamines Category:Stimulants Category:1-Piperidinyl compounds Category:Benzothiophenes Category:Dopamine reuptake inhibitors