Tenocyclidine

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Tenocyclidine
Tenocyclidine.svg
Systematic (IUPAC) name
1-(1-(2-Thienyl)cyclohexyl)piperidine
Clinical data
Legal status
  • Schedule I / Class A
Identifiers
CAS number 21500-98-1 N
ATC code None
PubChem CID 62751
DrugBank DB01520
ChemSpider 56495 YesY
UNII 8BQ45Q6VCL YesY
ChEMBL CHEMBL279676 YesY
Chemical data
Formula C15H23NS 
Mol. mass 249.416 g/mol
 N (what is this?)  (verify)

Tenocyclidine (TCP) was discovered by a team at Parke Davis in the late 1950s.[1] It is a dissociative anesthetic drug with stimulant and hallucinogenic effects. It is similar in effects to phencyclidine (PCP) but is considerably more potent. TCP has slightly different binding properties to PCP, with more affinity for the NMDA receptors,[2] but less affinity for the sigma receptors.[3] Because of its high affinity for the PCP site of the NMDA receptor complex, the 3H radiolabelled form of TCP is widely used in research into NMDA receptors.

TCP acts primarily as an NMDA receptor antagonist which blocks the activity of the NMDA receptor, however its increased stimulant effects compared to PCP suggests it also has relatively greater activity as a dopamine reuptake inhibitor (DRI). Due to its similarity in effects to PCP, TCP was placed into the Schedule I list of illegal drugs in the 1970s, although it was only briefly used in the 1970s and 1980s and is now little known.

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.

See also[edit]

References[edit]

  1. ^ U.S. Patent 2,921,076 Heterocyclic compounds and methods for producing the same
  2. ^ Stirling JM, Cross AJ, Green AR. The binding of [3H]thienyl cyclohexylpiperidine ([3H]TCP) to the NMDA-phencyclidine receptor complex. Neuropharmacology. 1989 Jan;28(1):1-7.
  3. ^ Javitt DC, Jotkowitz A, Sircar R, Zukin SR. Non-competitive regulation of phencyclidine/sigma-receptors by the N-methyl-D-aspartate receptor antagonist D-(-)-2-amino-5-phosphonovaleric acid. Neuroscience Letters. 1987 Jul 22;78(2):193-8.