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

Key Documents

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Product Name

Capsazepine, ≥98% (HPLC), solid

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

assay

≥98% (HPLC)

form

solid

color

off-white

solubility

DMSO: >10 mg/mL, clear

storage temp.

2-8°C

Quality Level

100

Gene Information

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

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Bioactive Small Molecule Inhibitors

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Show Differences

1 of 4

This Item	211280	Z0127	S2694
Sigma-Aldrich C191 Capsazepine	Sigma-Aldrich 211280 Capsazepine	Sigma-Aldrich Z0127 Zatebradine hydrochloride	Sigma-Aldrich S2694 SB-408124
form solid	form solid	form powder	form solid
assay ≥98% (HPLC)	assay ≥97% (HPLC)	assay ≥98% (HPLC)	assay ≥98% (HPLC)
Quality Level 100	Quality Level 100	Quality Level 100	Quality Level 100
storage temp. 2-8°C	storage temp. 10-30°C	storage temp. 2-8°C	storage temp. 2-8°C
solubility DMSO: >10 mg/mL, clear	solubility DMSO: soluble, methanol: soluble	solubility H₂O: >10 mg/mL	solubility DMSO: >10 mg/mL
color off-white	color off-white	color white	color off-white

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[1]
to study the role of TRPV1 in central terminals on nociception in rats[2]
for functional characterization of the TRPV1 in bull spermatozoa[3]

Biochem/physiol Actions

Capsazepine is a synthetic analog of capsaicin and a transient receptor potential vanilloid-1 (TRPV1) antagonist.[1] 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).[4] Capsazepine recovers impaired lung mechanics during endotoxemia and it may be a potential therapeutic target for acute lung injury (ALI).[5]

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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Certificates of Analysis (COA)

Lot/Batch Number

0000388599

0000276793

0000069287

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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)

Capsazepine: a competitive antagonist of the sensory neurone excitant capsaicin.

S Bevan et al.

British journal of pharmacology, 107(2), 544-552 (1992-10-01)

1. Capsazepine is a synthetic analogue of the sensory neurone excitotoxin, capsaicin. The present study shows the capsazepine acts as a competitive antagonist of capsaicin. 2. Capsazepine (10 microM) reversibly reduced or abolished the current response to capsaicin (500 nM)

Synthesis and SAR of novel capsazepine analogs with significant anti-cancer effects in multiple cancer types.

Jorge De La Chapa et al.

Bioorganic & medicinal chemistry, 27(1), 208-215 (2018-12-12)

We previously demonstrated that capsazepine (CPZ), a synthetic transient receptor potential Vanilloid subtype 1 (TRPV1) antagonist, has significant anti-cancer effects in vivo. The purpose of this study was to develop more potent analogs based upon CPZ pharmacophore and structure-activity relationships

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

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

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