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Details

Stereochemistry ACHIRAL
Molecular Formula C15H23NS
Molecular Weight 249.415
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TENOCYCLIDINE

SMILES

C1CCN(CC1)C2(CCCCC2)C3=CC=CS3

InChI

InChIKey=JUZZEWSCNBCFRL-UHFFFAOYSA-N
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

HIDE SMILES / InChI
Tenocyclidine (TCP) is a dissociative anesthetic drug with psychostimulant and hallucinogenic effects. This drug shows a broad spectrum of pharmacological activity including antidotal effect in organophosphorus compounds poisoning, radioprotective and anticancer effects. It was studied that the antidotal potency could protect acetylcholinesterase (AChE) in the case of organophosphate poisoning. However, the controversial role of TCP in brain protection should be studied further. Tenocyclidine has a high affinity for the N-methyl-D-aspartate (NMDA) receptors. This property allows using of TCP binding (association rate) as a marker of channel opening and thereby permitting measurement of NMDA receptor activation and ligand binding under identical conditions.

Approval Year

PubMed

PubMed

TitleDatePubMed
Anticonvulsant efficacy of N-methyl-D-aspartate antagonists against convulsions induced by cocaine.
1999 May
Beneficial effects of TCP on soman intoxication in guinea pigs: seizures, brain damage and learning behaviour.
2001 Dec
Effects of thienylphencyclidine (TCP) on seizure activity and brain damage produced by soman in guinea-pigs: ECoG correlates of neurotoxicity.
2001 Feb
Decreased density of [3H]TCP binding following antipsychotic drug withdrawal in rats.
2002 Apr 19
Amphetamine inhibits the N-methyl-D-aspartate receptor-mediated responses by directly interacting with the receptor/channel complex.
2002 Mar
Re-evaluation of phencyclidine low-affinity or "non-NMDA" binding sites.
2002 May 1
Molecular mechanisms of inhibition of nicotinic acetylcholine receptors by tricyclic antidepressants.
2003 Dec
Characterization of the non-competitive antagonist binding site of the NMDA receptor in dark Agouti rats.
2004 Aug 6
[An expert study of acute poisoning by phencyclidine derivatives].
2004 May-Jun
In vitro biological efficiency of tenocyclidine-TCP and its adamantane derivative TAMORF.
2006 Dec
Molecular mechanisms and binding site location for the noncompetitive antagonist crystal violet on nicotinic acetylcholine receptors.
2006 Feb 21
The role of antagonism of NMDA receptor-mediated neurotransmission and inhibition of the dopamine reuptake in the neuroendocrine effects of phencyclidine.
2006 Mar 20
Structure-activity relationships of pentacycloundecylamines at the N-methyl-d-aspartate receptor.
2007 Feb 1
Influences of different developmental periods of taurine supplements on synaptic plasticity in hippocampal CA1 area of rats following prenatal and perinatal lead exposure.
2007 May 19
Molecular properties of local anesthetics as predictors of affinity for nicotinic acetylcholine receptors.
2007 Oct
Tenocyclidine treatment in soman-poisoned rats--intriguing results on genotoxicity versus protection.
2008
Engineering and characterization of a mouse/human chimeric anti-phencyclidine monoclonal antibody.
2008 Jan
High specific activity tritiation of TCP and BTCP.
2009 Jun
Inhibition of the histone demethylase LSD1 blocks alpha-herpesvirus lytic replication and reactivation from latency.
2009 Nov
1,2-ethane bis-1-amino-4-benzamidine is active against several brain insult and seizure challenges through anti-NMDA mechanisms targeting the 3H-TCP binding site and antioxidant action.
2010 Jul
Qualitative GC-MS assessment of TCP and TAMORF elimination in rats.
2010 Mar
Name Type Language
TENOCYCLIDINE
HSDB   INN  
INN  
Official Name English
tenocyclidine [INN]
Common Name English
PIPERIDINE, 1-(1-(2-THIENYL)CYCLOHEXYL)-
Systematic Name English
N-(1-(2-THIENYL)CYCLOHEXYL)PIPERIDINE
Systematic Name English
GK-0
Common Name English
THIOPHENE ANALOG OF PHENCYCLIDINE
Common Name English
TCP
Common Name English
TENOCYCLIDINE [HSDB]
Common Name English
THIENYLPHENCYCLIDINE
Common Name English
THIENYLCYCLIDINE
Common Name English
1-(1-(2-THIENYL)CYCLOHEXYL)PIPERIDINE
Systematic Name English
2-THIENYL ANALOG OF PHENCYCLIDINE
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C47796
Created by admin on Fri Dec 15 15:38:22 UTC 2023 , Edited by admin on Fri Dec 15 15:38:22 UTC 2023
DEA NO. 7470
Created by admin on Fri Dec 15 15:38:22 UTC 2023 , Edited by admin on Fri Dec 15 15:38:22 UTC 2023
Code System Code Type Description
SMS_ID
100000082930
Created by admin on Fri Dec 15 15:38:22 UTC 2023 , Edited by admin on Fri Dec 15 15:38:22 UTC 2023
PRIMARY
EPA CompTox
DTXSID3046168
Created by admin on Fri Dec 15 15:38:22 UTC 2023 , Edited by admin on Fri Dec 15 15:38:22 UTC 2023
PRIMARY
INN
4898
Created by admin on Fri Dec 15 15:38:22 UTC 2023 , Edited by admin on Fri Dec 15 15:38:22 UTC 2023
PRIMARY
CHEBI
64610
Created by admin on Fri Dec 15 15:38:22 UTC 2023 , Edited by admin on Fri Dec 15 15:38:22 UTC 2023
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MESH
C012058
Created by admin on Fri Dec 15 15:38:22 UTC 2023 , Edited by admin on Fri Dec 15 15:38:22 UTC 2023
PRIMARY
EVMPD
SUB10896MIG
Created by admin on Fri Dec 15 15:38:22 UTC 2023 , Edited by admin on Fri Dec 15 15:38:22 UTC 2023
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PUBCHEM
62751
Created by admin on Fri Dec 15 15:38:22 UTC 2023 , Edited by admin on Fri Dec 15 15:38:22 UTC 2023
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DRUG BANK
DB01520
Created by admin on Fri Dec 15 15:38:22 UTC 2023 , Edited by admin on Fri Dec 15 15:38:22 UTC 2023
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NCI_THESAURUS
C96892
Created by admin on Fri Dec 15 15:38:22 UTC 2023 , Edited by admin on Fri Dec 15 15:38:22 UTC 2023
PRIMARY
ChEMBL
CHEMBL279676
Created by admin on Fri Dec 15 15:38:22 UTC 2023 , Edited by admin on Fri Dec 15 15:38:22 UTC 2023
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WIKIPEDIA
TENOCYCLIDINE
Created by admin on Fri Dec 15 15:38:22 UTC 2023 , Edited by admin on Fri Dec 15 15:38:22 UTC 2023
PRIMARY
HSDB
7637
Created by admin on Fri Dec 15 15:38:22 UTC 2023 , Edited by admin on Fri Dec 15 15:38:22 UTC 2023
PRIMARY
FDA UNII
8BQ45Q6VCL
Created by admin on Fri Dec 15 15:38:22 UTC 2023 , Edited by admin on Fri Dec 15 15:38:22 UTC 2023
PRIMARY
CAS
21500-98-1
Created by admin on Fri Dec 15 15:38:22 UTC 2023 , Edited by admin on Fri Dec 15 15:38:22 UTC 2023
PRIMARY