CHEBI:70773 - capsazepine

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ChEBI Name capsazepine
ChEBI ID CHEBI:70773
Definition A benzazepine that is 2,3,4,5-tetrahydro-1H-2-benzazepine which is substituted by hydroxy groups at positions 7 and 8 and on the nitrogen atom by a 2-(p-chlorophenyl)ethylaminothiocarbonyl group. A synthetic analogue of capsaicin, it was the first reported capsaicin receptor antagonist.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C19H21ClN2O2S
Net Charge 0
Average Mass 376.90000
Monoisotopic Mass 376.10123
InChI InChI=1S/C19H21ClN2O2S/c20-16-5-3-13(4-6-16)7-8-21-19(25)22-9-1-2-14-10-17(23)18(24)11-15(14)12-22/h3-6,10-11,23-24H,1-2,7-9,12H2,(H,21,25)
InChIKey DRCMAZOSEIMCHM-UHFFFAOYSA-N
SMILES Oc1cc2CCCN(Cc2cc1O)C(=S)NCCc1ccc(Cl)cc1
Roles Classification
Biological Role(s): capsaicin receptor antagonist
Any substance which blocks the painful sensation of heat caused by capsaicin acting on the TRPV1 ion channel.
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ChEBI Ontology
Outgoing capsazepine (CHEBI:70773) has role capsaicin receptor antagonist (CHEBI:70774)
capsazepine (CHEBI:70773) is a benzazepine (CHEBI:35676)
capsazepine (CHEBI:70773) is a catechols (CHEBI:33566)
capsazepine (CHEBI:70773) is a monochlorobenzenes (CHEBI:83403)
capsazepine (CHEBI:70773) is a thioureas (CHEBI:51276)
IUPAC Name
N-[2-(4-chlorophenyl)ethyl]-7,8-dihydroxy-1,3,4,5-tetrahydro-2H-2-benzazepine-2-carbothioamide
Synonyms Sources
2-[2-(4-chlorophenyl)ethylamino-thiocarbonyl]-7,8-dihydroxy-2,3,4,5-tetrahydro-1H-2-benzazepine ChEBI
capsazepin ChEBI
N-(2-[4-chlorophenyl]ethyl)-1,3,4,5-tetrahydro-7,8-dihydroxy-2H-2-benzazepine-2-carbothioamide ChEBI
N-[2-(4-chlorophenyl)ethyl]-1,3,4,5-tetrahydro-7,8-dihydroxy-2H-2-benzazepine-2-carbothioamide ChEBI
N-[2-(4-chlorophenyl)ethyl]-7,8-dihydroxy-1,3,4,5-tetrahydro-2H-2-benzazepine-2-carbothioamide ChEBI
ST50826300 ChEBI
Manual Xrefs Databases
Capsazepine Wikipedia
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Registry Numbers Types Sources
138977-28-3 CAS Registry Number ChemIDplus
7047754 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
1422598 PubMed citation Europe PMC
14757700 PubMed citation Europe PMC
15032662 PubMed citation Europe PMC
18230728 PubMed citation Europe PMC
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8027976 PubMed citation Europe PMC
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Last Modified
25 February 2016