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Benocyclidine
Systematic (IUPAC) name
1-[1-(1-benzothiophen-2-yl)cyclohexyl]piperidine
Identifiers
CAS number 112726-66-6
ATC code none
PubChem 123692
Chemical data
Formula C19H25NS 
Mol. mass 299.474 g/mol
SMILES eMolecules & PubChem
Therapeutic considerations
Pregnancy cat.  ?
Legal status

Benocyclidine (BCP), or benzothiophenylcyclohexylpiperidine (BTCP), is a psychoactive drug and research chemical of the arylcyclohexylamine and piperidine chemical classes. It acts a potent and selective dopamine reuptake inhibitor (DRI) and is therefore a stimulant.[1][2] 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.[1][2] It has been used to label the dopamine transporter.[3][4]

BCP was also used to try and find a common pharmacophore for DRI type stimulants.[5]

See also

References

  1. ^ 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. PMID 3384005. 
  2. ^ 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. PMID 2544905. 
  3. ^ 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. PMID 2527343. 
  4. ^ 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. PMID 2771169. 
  5. ^ 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. PMID 10721502. http://www.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pubmed&retmode=ref&cmd=prlinks&id=10721502. 
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