benocyclidine

{{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

| tradename =

| licence_EU =

| pregnancy_category =

| legal_UK = PSA

| legal_US = Unscheduled, illegal in Florida and Virginia

| routes_of_administration =

| bioavailability =

| metabolism =

| elimination_half-life =

| excretion =

| CAS_number_Ref = {{cascite|changed|??}}

| CAS_number = 112726-66-6

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = Q1WR6UP7MW

| ATC_prefix = none

| ATC_suffix =

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 279556

| PubChem = 123692

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 110266

| C=19 | H=25 | N=1 | S=1

| smiles = C1(SC(C2(CCCCC2)N3CCCCC3)=C4)=C4C=CC=C1

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 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

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = RGSVXQJPSWZXOP-UHFFFAOYSA-N

}}

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.PCT Patent Application WO199712513 (see also US Patents Nos.5,866,756 and 6,218,595

It acts as a potent and selective dopamine reuptake inhibitor (DRI) and a psychostimulant.{{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 }}{{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 }} 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. It has been used to label the dopamine transporter.{{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 }}{{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 }} BCP was used to try to find a common pharmacophore for DRI type stimulants.{{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 }}

More recently, benocyclidine has been found in several ecstasy tablets, sold as MDMA.{{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}}