Capsazepine

Capsazepine

Names
Preferred IUPAC name N-[2-(4-Chlorophenyl)ethyl]-7,8-dihydroxy-1,3,4,5-tetrahydro-2H-2-benzazepine-2-carbothioamide
Other names N-(4-Chlorophenethyl)-7,8-dihydroxy-1,3,4,5-tetrahydro-2H-benzo[c]azepine-2-carbothioamide N-(4-Chlorophenethyl)-7,8-dihydroxy-4,5-dihydro-1H-benzo[c]azepine-2(3H)-carbothioamide
Identifiers
CAS Number	138977-28-3 Y
3D model ( JSmol )	Interactive image
ChEMBL	ChEMBL391997 Y
ChemSpider	2015280 Y
IUPHAR/BPS	2461
PubChem CID	2733484
UNII	LFW48MY844 Y
CompTox Dashboard (EPA)	DTXSID20160852
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) Y Key: DRCMAZOSEIMCHM-UHFFFAOYSA-N Y InChI=1/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) Key: DRCMAZOSEIMCHM-UHFFFAOYAH
SMILES Clc1ccc(cc1)CCNC(=S)N3Cc2c(cc(O)c(O)c2)CCC3
Properties
Chemical formula	C19H21ClN2O2S
Molar mass	376.9 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Y verify (what is YN ?) Infobox references

Capsazepine is a synthetic antagonist of capsaicin.^[1] It is used as a biochemical tool in the study of TRPV ion channels.

Pharmacology

Capsazepine blocks the painful sensation of heat caused by capsaicin (the active ingredient of

Capsazepine was discovered by a research group working for Novartis.^[1] Its synthesis and chemical properties were published in 1994. It was found by modification of the chemical backbone of capsaicin.^[7]

Use in biotechnology

By incorporation of an azobenzene unit, a photoswitchable version of capsazepine (AC4) was developed in 2013 that allows for optical control of TRPV1 channels with light.^[8][9]

See also

• Discovery and development of TRPV1 antagonists
• Menthol
• Herkinorin
• JWH-133

References