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Tenocyclidine

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
Tenocyclidine
Clinical data
ATC code
  • none
Legal status
Legal status
Identifiers
  • 1-(1-(2-Thienyl)cyclohexyl)piperidine
CAS Number
PubChemCID
DrugBank
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UNII
KEGG
ChEMBL
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC15H23NS
Molar mass249.42 g·mol−1
3D model (JSmol)
  • C1(C2(CCCCC2)N3CCCCC3)=CC=CS1
  • 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 checkY
  • Key:JUZZEWSCNBCFRL-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Tenocyclidine (TCP) is adissociativeanesthetic withpsychostimulant effects. It was discovered by a team atParke-Davis in the late 1950s.[2] It is similar in effects tophencyclidine (PCP) but is considerably more potent. TCP has slightly different binding properties to PCP, with more affinity for theNMDA receptors,[3] but less affinity for thesigma receptors.[4] Because of its high affinity for the PCP site of the NMDA receptor complex, the3Hradiolabelled form of TCP is widely used in research into NMDA receptors.

TCP acts primarily as anNMDA 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 adopamine reuptake inhibitor (DRI). Due to its similarity in effects to PCP, TCP was placed into theSchedule I list of illegal drugs in the 1970s, although it was only briefly used in the 1970s and 1980s and is now little known.[citation needed]

See also

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References

[edit]
  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. Retrieved2023-08-27.
  2. ^U.S. patent 2,921,076 Heterocyclic compounds and methods for producing the same
  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.
  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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