N-[2-(4-chlorophenyl)ethyl]-7,8-dihydroxy-2,3,4,5-tetrahydro-1H-2-benzazepine-2-carbothioamide

• ChemBase ID: 105329
• Molecular Formular: C19H21ClN2O2S
• Molecular Mass: 376.90024
• Monoisotopic Mass: 376.1012266
• SMILES: Oc1cc2c(CN(CCC2)C(=S)NCCc2ccc(Cl)cc2)cc1O
• Canonical SMILES: Clc1ccc(cc1)CCNC(=S)N1CCCc2c(C1)cc(O)c(c2)O
• 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

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[2-(4-chlorophenyl)ethyl]-7,8-dihydroxy-2,3,4,5-tetrahydro-1H-2-benzazepine-2-carbothioamide
• IUPAC Traditional name: capsazepine
• Synonyms: N-[2-(4-Chlorophenyl)ethyl]-1,3,4,5-tetrahydro-7,8-dihydroxy-2H-2-benzazepine-2-carbothioamide; CAPSAZEPINE; Capsazepine

Database IDs

• CAS Number: 138977-28-3
• MDL Number: MFCD00153778
• PubChem SID: 24277967; 162092357
• PubChem CID: 2733484
• CHEMBL: 391997
• Chemspider ID: 2015280
• Unique Ingredient Identifier: LFW48MY844
• Wikipedia Title: Capsazepine

CALCULATED PROPERTIES

• Acid pKa: 9.200993
• H Acceptors: 2
• H Donor: 3
• LogD (pH = 5.5): 4.4159565
• LogD (pH = 7.4): 4.409274
• Log P: 4.4160423
• Molar Refractivity: 106.481 cm^3
• Polarizability: 40.8555 Å^3
• Polar Surface Area: 55.73 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Ethyl Acetate; methanol: soluble
• Apperance: Light Yellow Solid; off-white solid
• Melting Point: 155-157°C

Safety Information

• Storage Condition: 2-8°C, Desiccate
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Pharmacology Properties

• Gene Information: human ... TRPV1(7442), TRPV4(59341)rat ... Trpv1(83810)

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C19H21ClN2O2S

DETAILS

MP Biomedicals - 02159796

A competitive antagonist for capsaicin and resiniferatoxin.

Sigma Aldrich - C191

Biochem/physiol Actions
Capsazepine is a specific vanilloid receptor antagonist; synthetic analog of capsaicin.

Toronto Research Chemicals - C175710

A selective vanilloid receptor antagonist (Ki=3.2uM)

REFERENCES

• Dickenson and Dray: Br. J. Pharmacol., 104, 1045 (1991)
• Kwak, et al.: Neuroscience, 86, 619 (1991)
• Szallasi and Blumberg: Pharmacol. Rev., 51, 159 (999)