Capsazepine

Base Information

• Chemical Name: Capsazepine
• CAS No.: 138977-28-3
• Molecular Formula: C₁₉H₂₁ClN₂O₂S
• Molecular Weight: 376.907
• UNII: LFW48MY844
• DSSTox Substance ID: DTXSID20160852
• Nikkaji Number: J837.194F
• Wikipedia: Capsazepine
• Wikidata: Q5036336
• Pharos Ligand ID: SRZ6FJPSZJHG
• Metabolomics Workbench ID: 65250
• ChEMBL ID: CHEMBL391997
• Mol file: 138977-28-3.mol

Synonyms:capsazepine

Chemical Property of Capsazepine

Chemical Property:

• Appearance/Colour: Light yellow solid
• Vapor Pressure: 4.19E-14mmHg at 25°C
• Melting Point: 155-157 °C
• Refractive Index: 1.671
• Boiling Point: 581.133 °C at 760 mmHg
• PKA: 9.73±0.20(Predicted)
• Flash Point: 305.259 °C
• PSA: 87.82000
• Density: 1.351 g/cm³
• LogP: 3.94540
• Storage Temp.: 2-8°C
• Solubility.: methanol: soluble
• XLogP3: 3.9
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 376.1012268
• Heavy Atom Count: 25
• Complexity: 445

Purity/Quality:

99% ^*data from raw suppliers

Capsazepine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 22-24/25-36-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1CC2=CC(=C(C=C2CN(C1)C(=S)NCCC3=CC=C(C=C3)Cl)O)O
• Description: Transient receptor potential vanilloid type 1 (TRPV1) is a member of the transient receptor potential (TRP) family that is activated or sensitized by a variety of endogenous stimuli as a result of tissue injury and inflammation. TRPV1 is upregulated during inflammation and plays a role in the perception of pain. Capsazepine is a competitive antagonist of transient receptor potential vanilloid type 1 (TRPV1) which blocks the capsaicin-induced uptake of Ca2+ in neonatal rat dorsal root ganglia with an IC50 of 0.42 μM and Chinese hamster ovary cells with an IC50 of 17 nM. It does not block acid- or heat-induced activation of TRPV1 and may block receptors other than TRPV1.
• Uses: Capsazepine has been used as a transient receptor potential vanilloid-1 (TRPV1) antagonist: to study its effect on capsaicin induced extracellular signal-regulated kinase (ERK) phosphorylation to study the role of TRPV1 in central terminals on nociception in ratsfor functional characterization of the TRPV1 in bull spermatozoa A selective vanilloid receptor antagonist (Ki=3.2uM Capsazepine is shown to inhibit the development of mechanical hyperalgesia induced by intraplanar capsaicin injection. Capsazepine is described to block Resiniferatoxin (sc-24015)- and Capsaicin-induced contractions of guinea pig treacheal smooth muscle. Studies investigating the function of the VR1 (TRPV1 receptor) have employed Capsazepine as a tool for perturbing systemic neuronal response to Capsaicin.

Technology Process of Capsazepine

There total 3 articles about Capsazepine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 79.0%

2-(4-chlorophenyl)ethyl isothiocyanate (17608-10-5) + 7,8-dihydroxy-2,3,4,5-tetrahydro-2-benzazepine hydrobromide → capsazepine (138977-28-3)

Guidance literature:

With triethylamine; In tetrahydrofuran; for 18h;

DOI:10.1021/jm00039a006

Reference yield:

7,8-dimethoxy-2,3,4,5-tetrahydro-1H-benzo[c]azepine (95469-38-8) → capsazepine (138977-28-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 58 percent / 48percent aq. HBr / 24 h / Heating

2: 79 percent / Et₃N / tetrahydrofuran / 18 h

With hydrogen bromide; triethylamine; In tetrahydrofuran;

DOI:10.1021/jm00039a006

Reference yield:

7,8-dimethoxy-2,3,4,5-tetrahydro-1H-benzo[c]azepin-1-one (72584-69-1) → capsazepine (138977-28-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 75 percent / B₂H₆ / tetrahydrofuran / 15 h / Heating

2: 58 percent / 48percent aq. HBr / 24 h / Heating

3: 79 percent / Et₃N / tetrahydrofuran / 18 h

With hydrogen bromide; triethylamine; diborane; In tetrahydrofuran;

DOI:10.1021/jm00039a006

upstream raw materials:

2-(4-chlorophenyl)ethyl isothiocyanate

7,8-dimethoxy-2,3,4,5-tetrahydro-1H-benzo[c]azepine

7,8-dimethoxy-2,3,4,5-tetrahydro-1H-benzo[c]azepin-1-one

Refernces

• 1、 Dalence-Guzman, Maria F.,Berglund, Magnus,Skogvall, Staffan,Sterner, Olov. "SAR studies of capsazepinoid bronchodilators. Part 1: The importance of the catechol moiety and aspects of the B-ring structure". . p. 2499 - 2512. Retrieved 2008/09/21.