Tenocyclidine

Tenocyclidine
Clinical data
ATC code	none;
Legal status
Legal status	AU: S9 (Prohibited substance); BR: Class F2 (Prohibited psychotropics); 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 ;
PubChem CID	62751;
DrugBank	DB01520 ;
ChemSpider	56495 ;
UNII	8BQ45Q6VCL;
KEGG	D12702 ;
ChEMBL	ChEMBL279676 ;
CompTox Dashboard (EPA)	DTXSID3046168 ;
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 ; Key:JUZZEWSCNBCFRL-UHFFFAOYSA-N ;
	(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.^[2] 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,^[3] but less affinity for the sigma receptors.^[4] 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.

References

^ Anvisa (2023-07-24). "RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-07-25). Archived from the original on 2023-08-27. Retrieved 2023-08-27.
^ U.S. patent 2,921,076 Heterocyclic compounds and methods for producing the same
^ 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.
^ 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.

[1] Anvisa (2023-07-24). "RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-07-25). Archived from the original on 2023-08-27. Retrieved 2023-08-27.

[2] U.S. patent 2,921,076 Heterocyclic compounds and methods for producing the same

[pmid2538766-3] 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.

[pmid2888059-4] 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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See also

References