CAPSAZEPINE

ChemicalBook > CAS DataBase List > CAPSAZEPINE

Product Name: CAPSAZEPINE
CAS No.: 138977-28-3
Chemical Name: CAPSAZEPINE
Synonyms: Capsazepin;CAPSAZEPINE;capasazepine;Capsazepine,98%;CAPSAZEPINE SYNTHETIC ANALOG OF C;8-dihydroxy-2H-2-benzazepine-2-carbothioamide;7;8-DIHYDROXY-2H-2-BENZAZEPINE-2-CARBOTHIOAMIDE;N-(4-Chlorophenethyl)-7,8-dihydroxy-4,5-dihydro-1H-benzo[c]azepine-2(3H)-carbothioamide;2-[[2-(4-Chlorophenyl)ethylamino]thiocarbonyl]-2,3,4,5-tetrahydro-1H-2-benzazepine-7,8-diol;N-[2-(CHLOROPHENYL)ETHYL]-1,3,4,5-TETRAHYDRO-7,8-DIHYDROXY-2H-2-BENZAZEPINE-2-CARBOTHIOAMIDE
CBNumber: CB0144302
Molecular Formula: C19H21ClN2O2S
Formula Weight: 376.9
MOL File: 138977-28-3.mol

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CAPSAZEPINE Property

Melting point:: 155-157°C
Boiling point:: 581.1±60.0 °C(Predicted)
Density: 1.350±0.06 g/cm3(Predicted)
storage temp.: 2-8°C
solubility: methanol: soluble
pka: 9.73±0.20(Predicted)
form: solid
color: off-white
InChIKey: DRCMAZOSEIMCHM-UHFFFAOYSA-N
CAS DataBase Reference: 138977-28-3(CAS DataBase Reference)

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Safety

Hazard Codes: Xn
Risk Statements: 20/21/22-36/37/38
Safety Statements: 22-24/25-36-26
RIDADR: 2811
WGK Germany: 3
HazardClass: 6.1(a)
PackingGroup: II

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Hazard and Precautionary Statements (GHS)

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: C191
Product name: Capsazepine
Purity: ≥98% (HPLC), solid
Packaging: 5mg
Price: $240
Updated: 2024/03/01

Sigma-Aldrich

Product number: C191
Product name: Capsazepine
Purity: ≥98% (HPLC), solid
Packaging: 25mg
Price: $844
Updated: 2024/03/01

Alfa Aesar

Product number: J63055
Product name: Capsazepine, 99+%
Packaging: 10mg
Price: $321
Updated: 2024/03/01

Alfa Aesar

Product number: J63055
Product name: Capsazepine, 99+%
Packaging: 50mg
Price: $1347.65
Updated: 2024/03/01

Cayman Chemical

Product number: 10007518
Product name: Capsazepine
Purity: ≥98%
Packaging: 1mg
Price: $32
Updated: 2024/03/01

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CAPSAZEPINE Chemical Properties,Usage,Production

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.

Chemical Properties

Light Yellow Solid

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 rats
for functional characterization of the TRPV1 in bull spermatozoa

Uses

A selective vanilloid receptor antagonist (Ki=3.2uM

Uses

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.

Definition

ChEBI: 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 caps icin, it was the first reported capsaicin receptor antagonist.

Hazard

A poison.

Biological Activity

Selective vanilloid receptor antagonist (K i = 3.2 μ M). Inhibits carrageenan inflammation-induced hyperalgesic responses in the rat. Also activates amiloride-sensitive epithelial Na + channel ENaC δ . Also available as part of the Vanilloid TRPV1 Receptor Tocriset™ .

Biochem/physiol Actions

Capsazepine is a synthetic analog of capsaicin and a transient receptor potential vanilloid-1 (TRPV1) antagonist. It exhibits anti-proliferative and anti-cancer effects in various cancer types including oral squamous cell carcinoma, non-small cell lung cancer (NSCLC), breast cancer, and prostate cancer cell lines (HSC-3, H460, MDA-231, and PC-3 respectively). Capsazepine recovers impaired lung mechanics during endotoxemia and it may be a potential therapeutic target for acute lung injury (ALI).

storage

Room temperature

References

1. c. s. walpole, s. bevan, g. bovermann, j. j. boelsterli, r. breckenridge, j. w. davies, g. a. hughes, i. james, l. oberer, j. winter and et al., j med chem 1994, 37, 1942-1954. 2. r. j. docherty, j. c. yeats and a. s. piper, br j pharmacol 1997, 121, 1461-1467. 3. h. j. behrendt, t. germann, c. gillen, h. hatt and r. jostock, br j pharmacol 2004, 141, 737-745. 4. l. liu and s. a. simon, neurosci lett 1997, 228, 29-32. 5. b. sung, s. prasad, j. ravindran, v. r. yadav and b. b. aggarwal, free radic biol med 2012, 53, 1977-1987.

CAPSAZEPINE Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from CAPSAZEPINE manufacturers

Zhuozhou Wenxi import and Export Co., Ltd

Product: CAPSAZEPINE 138977-28-3
Price: US $15.00-10.00/KG
Min. Order: 1KG
Purity: 99%+ HPLC
Supply Ability: Monthly supply of 1 ton
Release date: 2021-08-10

138977-28-3, CAPSAZEPINERelated Search:

1-BENZYL-3-PHENETHYL-2-THIOUREA 2,3,4,5-Tetrahydro-1H-2-benzazepine Hydrochloride 2,3,4,5-TETRAHYDRO-1H-BENZO[C]AZEPIN-8-OL CAPSAZEPINE 1-(3-PHENYLPROPYL)-2-THIOUREA N,N'-DI-N-PROPYLTHIOUREA 2-PHENYLETHYLTHIOUREA

CAPSAZEPINE

N-[2-(CHLOROPHENYL)ETHYL]-1,3,4,5-TETRAHYDRO-7,8-DIHYDROXY-2H-2-BENZAZEPINE-2-CARBOTHIOAMIDE

N-[2-(4-CHLOROPHENYL)ETHYL]-1,3,4,5-TETRAHYDRO-7,8-DIHYDROXY-2H-2-BENZAZEPINE-2-CARBOTHIOAMIDE

CAPSAZEPINE SYNTHETIC ANALOG OF C

2-[[2-(4-Chlorophenyl)ethylamino]thiocarbonyl]-2,3,4,5-tetrahydro-1H-2-benzazepine-7,8-diol

Capsazepine,98%

7;8-DIHYDROXY-2H-2-BENZAZEPINE-2-CARBOTHIOAMIDE

8-dihydroxy-2H-2-benzazepine-2-carbothioamide

capasazepine

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

Capsazepin

N-(4-Chlorophenethyl)-7,8-dihydroxy-4,5-dihydro-1H-benzo[c]azepine-2(3H)-carbothioamide

138977-28-3

38977-28-3

C19H21ClN2O2S

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Vanilloid/TRPV channel

Ion Channels

Amines

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