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C191

Capsazepine

Name: Capsazepine
Brand: SIGMA

≥98% (HPLC), solid, TRPV1 antagonist

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):

C₁₉H₂₁ClN₂O₂S

CAS Number:

138977-28-3

Molecular Weight:

376.90

UNSPSC Code:

12352200

PubChem Substance ID:

24277967

NACRES:

NA.77

MDL number:

MFCD00153778

Assay:

≥98% (HPLC)

Form:

solid

Quality level:

100

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Properties

Product Name

Capsazepine, ≥98% (HPLC), solid

Quality Level

100

assay

≥98% (HPLC)

form

solid

color

off-white

solubility

DMSO: >10 mg/mL, clear

storage temp.

2-8°C

SMILES string

Oc1cc2CCCN(Cc2cc1O)C(=S)NCCc3ccc(Cl)cc3

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)

InChI key

DRCMAZOSEIMCHM-UHFFFAOYSA-N

Gene Information

human ... TRPV1(7442), TRPV4(59341)
rat ... Trpv1(83810)

Description

Application

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

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).

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Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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TrpV1 receptor activation rescues neuronal function and network gamma oscillations from Aβ-induced impairment in mouse hippocampus in vitro.

Hugo Balleza-Tapia et al.

eLife, 7 (2018-11-13)

Amyloid-β peptide (Aβ) forms plaques in Alzheimer's disease (AD) and is responsible for early cognitive deficits in AD patients. Advancing cognitive decline is accompanied by progressive impairment of cognition-relevant EEG patterns such as gamma oscillations. The endocannabinoid anandamide, a TrpV1-receptor

Single and combined effects of plant-derived and synthetic cannabinoids on cognition and cannabinoid-associated withdrawal signs in mice.

Alyssa M Myers et al.

British journal of pharmacology, 176(10), 1552-1567 (2018-01-18)

It has been suggested that the non-euphorogenic phytocannabinoid cannabidiol (CBD) can ameliorate adverse effects of Δ9 -tetrahydrocannabinol (THC). We determined whether CBD ameliorates cognitive deficits and withdrawal signs induced by cannabinoid CB1 /CB2 receptor agonists or produces these pharmacological effects

Ablation and regeneration of peripheral and central TRPV1 expressing nerve terminals and the consequence of nociception

Yu SQ and Premkumar LS

Open Medicine : A Peer-Reviewed, Independent, Open-Access Journal, 8(1) (2015)

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Global Trade Item Number

SKU	GTIN
C191-25MG	04061833468883
C191-5MG	04061835370177