Chemistry:Tenocyclidine

Short description: Chemical compound

Tenocyclidine

Clinical data
ATC code	none
Legal status
Legal status	AU: S9 (Prohibited substance) BR: F2 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	21500-98-1 N
PubChem CID	62751
DrugBank	DB01520 Y
ChemSpider	56495 Y
UNII	8BQ45Q6VCL
KEGG	D12702 Y
ChEMBL	ChEMBL279676 Y
Chemical and physical data
Formula	C15H23NS
Molar mass	249.42 g·mol−1
3D model (JSmol)	Interactive image
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)

Tenocyclidine (TCP) is a dissociative anesthetic with psychostimulant effects. It was discovered by a team at Parke-Davis in the late 1950s. 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, but less affinity for the sigma receptors. 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 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

• Arylcyclohexylamine
• Benocyclidine (BTCP)