Tenocyclidine

{{Short description|Chemical compound}} {{Drugbox | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 470601998 | IUPAC_name = 1-(1-(2-Thienyl)cyclohexyl)piperidine | image = Tenocyclidine.svg | image_class = skin-invert-image | width = 125px

| tradename = | legal_AU = S9 | legal_BR = F2 | legal_BR_comment = <ref>{{Cite web |author=Anvisa |author-link=Brazilian Health Regulatory Agency |date=2023-07-24 |title=RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial |trans-title=Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control|url=https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-804-de-24-de-julho-de-2023-498447451 |url-status=live |archive-url=https://web.archive.org/web/20230827163149/https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-804-de-24-de-julho-de-2023-498447451 |archive-date=2023-08-27 |access-date=2023-08-27 |publisher=Diário Oficial da União |language=pt-BR |publication-date=2023-07-25}}</ref> | legal_CA = Schedule III | legal_UK = Class A | legal_US = Schedule I | legal_DE = Anlage I | legal_UN = P I | routes_of_administration =

| metabolism = | elimination_half-life = | excretion =

| CAS_number_Ref = {{cascite|changed|??}} | CAS_number = 21500-98-1 | ATC_prefix = none | PubChem = 62751 | DrugBank_Ref = {{drugbankcite|correct|drugbank}} | DrugBank = DB01520 | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 56495 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = 8BQ45Q6VCL | ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL = 279676 | KEGG_Ref = {{keggcite|correct|kegg}} | KEGG = D12702

| C=15 | H=23 | N=1 | S=1 | smiles = C1(C2(CCCCC2)N3CCCCC3)=CC=CS1 | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 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 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = JUZZEWSCNBCFRL-UHFFFAOYSA-N }}

'''Tenocyclidine''' ('''TCP''') is a dissociative anesthetic with psychostimulant effects. It was discovered by a team at Parke-Davis in the late 1950s.<ref>{{US patent|2921076}} Heterocyclic compounds and methods for producing the same</ref> 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,<ref name="pmid2538766">{{cite journal | vauthors = Stirling JM, Cross AJ, Green AR | title = The binding of [3H]thienyl cyclohexylpiperidine ([3H]TCP) to the NMDA-phencyclidine receptor complex | journal = Neuropharmacology | volume = 28 | issue = 1 | pages = 1–7 | date = January 1989 | pmid = 2538766 | doi = 10.1016/0028-3908(89)90059-2 | s2cid = 35120805 }}</ref> but less affinity for the sigma receptors.<ref name="pmid2888059">{{cite journal | vauthors = Javitt DC, Jotkowitz A, Sircar R, Zukin SR | title = Non-competitive regulation of phencyclidine/sigma-receptors by the N-methyl-D-aspartate receptor antagonist D-(-)-2-amino-5-phosphonovaleric acid | journal = Neuroscience Letters | volume = 78 | issue = 2 | pages = 193–8 | date = July 1987 | pmid = 2888059 | doi = 10.1016/0304-3940(87)90632-x | s2cid = 20766750 }}</ref> Because of its high affinity for the PCP site of the NMDA receptor complex, the <sup>3</sup>H 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.{{cn|date=February 2022}}

==See also== * Arylcyclohexylamine * Benocyclidine (BTCP)

==References== {{Reflist}}

{{General anesthetics}} {{Dissociatives}} {{Navboxes | title = Pharmacodynamics | titlestyle = background:#ccccff | list1 = {{Ionotropic glutamate receptor modulators}} {{Monoamine reuptake inhibitors}} {{Sigma receptor modulators}} }}

Category:Anesthetics Category:Arylcyclohexylamines Category:Dissociative drugs Category:1-Piperidinyl compounds Category:Thiophenes Category:Designer drugs Category:Dopamine reuptake inhibitors Category:NMDA receptor antagonists Category:Sigma agonists Category:Drugs developed by Parke-Davis