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| Names | |
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| Preferred IUPAC name N-[2-(4-Chlorophenyl)ethyl]-7,8-dihydroxy-1,3,4,5-tetrahydro-2H-2-benzazepine-2-carbothioamide | |
Other names
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| Identifiers | |
3D model (JSmol) | |
| ChEMBL | |
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| UNII | |
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| Properties | |
| C19H21ClN2O2S | |
| Molar mass | 376.9 g/mol |
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |
Capsazepine is a syntheticantagonist ofcapsaicin.[1] It is used as a biochemical tool in the study ofTRPVion channels.
Capsazepine blocks the painful sensation of heat caused by capsaicin (the active ingredient ofchilli pepper) which activates theTRPV1 ion channel. Capsazepine is therefore considered to be a TRPV1antagonist. The TRPV1 channel functions as a pain and temperature sensor inmammalians. Capsazepine blocks the activation of TRPV1 channels by other chemicals, but not by other painful stimuli such as heat. Depending on the pharmacological assay, theIC50 is in thenanomolar to lowmicromolar range. In addition to its effects on TRPV1 channels, it was also shown to activate the noxious chemical sensorTRPA1 channel,[2] inhibit the cold activatedTRPM8 channel,[3]voltage-activated calcium channels[4] andnicotinic acetylcholine receptors.[5] It mainly serves as a tool to study the TRPV1 ion channel.[6]
Capsazepine was discovered by a research group working forNovartis.[1] Its synthesis and chemical properties were published in 1994. It was found by modification of the chemical backbone of capsaicin.[7]
By incorporation of anazobenzene unit, aphotoswitchable version of capsazepine (AC4) was developed in 2013 that allows for optical control ofTRPV1 channels with light.[8][9]
