Tenocyclidine

Tenocyclidine (TCP) is a dissociative anesthetic with psychostimulant effects. It was discovered by a team at Parke-Davis in the late 1950s.[1] 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.

Tenocyclidine
Clinical data
ATC code
  • none
Legal status
Legal status
  • AU: S9 (Prohibited substance)
  • CA: Schedule III
  • DE: Anlage I (Authorized scientific use only)
  • UK: Class A
  • US: Schedule I
  • UN: Psychotropic Schedule I
Identifiers
IUPAC name
  • 1-(1-(2-Thienyl)cyclohexyl)piperidine
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC15H23NS
Molar mass249.42 g·mol−1
3D model (JSmol)
SMILES
  • C1(C2(CCCCC2)N3CCCCC3)=CC=CS1
InChI
  • InChI=1S/C15H23NS/c1-3-9-15(10-4-1,14-8-7-13-17-14)16-11-5-2-6-12-16/h7-8,13H,1-6,9-12H2 Y
  • Key:JUZZEWSCNBCFRL-UHFFFAOYSA-N Y
 NY (what is this?)  (verify)

TCP acts primarily as an NMDA receptor antagonist which blocks the activity of the NMDA receptor, however its increased psychostimulant 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.

See also

References
  1. U.S. Patent 2,921,076 Heterocyclic compounds and methods for producing the same
  2. Stirling JM, Cross AJ, Green AR (January 1989). "The binding of [3H]thienyl cyclohexylpiperidine ([3H]TCP) to the NMDA-phencyclidine receptor complex". Neuropharmacology. 28 (1): 1–7. doi:10.1016/0028-3908(89)90059-2. PMID 2538766. S2CID 35120805.
  3. Javitt DC, Jotkowitz A, Sircar R, Zukin SR (July 1987). "Non-competitive regulation of phencyclidine/sigma-receptors by the N-methyl-D-aspartate receptor antagonist D-(-)-2-amino-5-phosphonovaleric acid". Neuroscience Letters. 78 (2): 193–8. doi:10.1016/0304-3940(87)90632-x. PMID 2888059. S2CID 20766750.


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