Benocyclidine

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Benocyclidine
BTCP structure.png
Systematic (IUPAC) name
1-[1-(1-benzothiophen-2-yl)cyclohexyl]piperidine
Clinical data
Legal status
?
Identifiers
CAS number 112726-66-6 N
ATC code None
PubChem CID 123692
ChemSpider 110266 YesY
ChEMBL CHEMBL279556 YesY
Chemical data
Formula C19H25NS 
Mol. mass 299.47 g/mol
 N (what is this?)  (verify)

Benocyclidine (BTPC), or benzothiophenylcyclohexylpiperidine (BTCP), is a psychoactive recreational drug of the arylcyclohexylamine class. 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 also 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]

Ahmadi TCP and BTCP analogues (2014)[edit]

Ahmadi, Abbas (2014). "Synthesis and Pain Perception of New Analogues of Phencyclidine in NMRI Male Mice". Mini-Reviews in Medicinal Chemistry 14 (1): 64–71. doi:10.2174/1389557513666131119203551.  edit

Ahmadi TCP and BTCP analogues (2014): IV,V,VI,VII.
  1. 2,2,6,6-Tetramethylpiperidine (TMP), or 4-hydroxy-TMP is condensed with cyclohexanone.
  2. enamine-imine tautomerism (c.f. keto-enol tautomerization).
  3. React with organometallic heteroaromatic compounds.

Legal status[edit]

United States[edit]

Benocyclidine is not scheduled at the federal level in the United States and is therefore legal to buy, posses, and sell.[8]

Florida[edit]

"Benocyclidine (BCP) or benzothiophenylcyclohexylpiperidine (BTCP)" is a Schedule I controlled substance in the state of Florida making it illegal to buy, sell, or possess in Florida.[9]

See also[edit]

References[edit]

  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. 
  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. 
  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. 
  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. doi:10.1023/A:1008144707255. PMID 10721502. 
  7. ^ "EcstasyData Testing Result: Blue Butterfly". Ecstasy and other drug testing. Erowid Center. Retrieved 2 February 2012. 
  8. ^ 21 CFR — SCHEDULES OF CONTROLLED SUBSTANCES §1308.11 Schedule I.
  9. ^ Florida Statutes - Chapter 893 - DRUG ABUSE PREVENTION AND CONTROL