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Y0000671

Capsaicin

European Pharmacopoeia (EP) Reference Standard

Synonym(s):

8-Methyl-N-vanillyl-trans-6-nonenamide

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About This Item

Linear Formula:
(CH3)2CHCH=CH(CH2)4CONHCH2C6H3-4-(OH)-3-(OCH3)
CAS Number:
404-86-4
Molecular Weight:
305.41
Beilstein/REAXYS Number:
2816484
EC Number:
206-969-8
MDL number:
MFCD00017259
UNSPSC Code:
41116107
PubChem Substance ID:
329831085
NACRES:
NA.24

grade

pharmaceutical primary standard

agency

EP Reference Standard

API family

capsaicin

manufacturer/tradename

EDQM

mp

62-65 °C (lit.)

application(s)

pharmaceutical (small molecule)

format

neat

storage temp.

2-8°C

SMILES string

COc1cc(CNC(=O)CCCC\C=C\C(C)C)ccc1O

InChI

1S/C18H27NO3/c1-14(2)8-6-4-5-7-9-18(21)19-13-15-10-11-16(20)17(12-15)22-3/h6,8,10-12,14,20H,4-5,7,9,13H2,1-3H3,(H,19,21)/b8-6+

InChI key

YKPUWZUDDOIDPM-SOFGYWHQSA-N

Gene Information

human ... TRPV1(7442)

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General description

This product is provided as delivered and specified by the issuing Pharmacopoeia. All information provided in support of this product, including SDS and any product information leaflets have been developed and issued under the Authority of the Issuing Pharmacopoeia. For further information and support please go to the website of the issuing Pharmacopoeia.

Application

Capsaicin EP Reference standard, intended for use in laboratory tests only as specifically prescribed in the European Pharmacopoeia.

Biochem/physiol Actions

Prototype vanilloid receptor agonist. Neurotoxin; activates sensory neurons that give rise to unmyelinated C-fibers, many of which contain substance P. Topical application desensitizes the sensory nerve endings giving a paradoxical antinociceptive effect; systemic administration can be neurotoxic to capsaicin-sensitive cells, especially in newborn animals. Active component of chili peppers.

Packaging

The product is delivered as supplied by the issuing Pharmacopoeia. For the current unit quantity, please visit the EDQM reference substance catalogue.

Other Notes

Sales restrictions may apply.

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Danger

Hazard Classifications

Acute Tox. 2 Oral - Eye Dam. 1 - Resp. Sens. 1 - Skin Irrit. 2 - Skin Sens. 1 - STOT SE 3

target_organs

Respiratory system

Storage Class

6.1A - Combustible, acute toxic Cat. 1 and 2 / very toxic hazardous materials

wgk_germany

WGK 3

flash_point_f

235.4 °F - closed cup

flash_point_c

113 °C - closed cup

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Sigma-Aldrich

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Sigma-Aldrich

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Sigma-Aldrich

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Sigma-Aldrich

D7137

Dihydroxyacetone phosphate dilithium salt

Jennifer Leech et al.
American journal of respiratory and critical care medicine, 188(9), 1069-1075 (2013-10-08)
Antitussive therapies are accompanied by a substantial placebo effect, indicating that inhibitory circuits in the brain have a significant capacity to regulate cough neural processing. However, essentially nothing is known about the identity of these inhibitory circuits or how they
Zohar Bromberg et al.
PloS one, 8(2), e57149-e57149 (2013-03-08)
The heat shock response (HSR) is a highly conserved molecular response to various types of stresses, including heat shock, during which heat-shock proteins (Hsps) are produced to prevent and repair damages in labile proteins and membranes. In cells, protein unfolding
Emma C Y Hilton et al.
The Journal of allergy and clinical immunology, 132(4), 847-855 (2013-06-20)
Inhaled capsaicin elicits cough reproducibly in human subjects and is widely used in the study of cough and antitussive therapies. However, the traditional end points C2 and C5 (the concentrations of capsaicin inducing at least 2 or 5 coughs, respectively)
Helen Sumner et al.
American journal of respiratory and critical care medicine, 187(9), 943-949 (2013-03-09)
Cough is one of the principal symptoms of chronic obstructive pulmonary disease (COPD) but the potential drivers of cough are likely to be multifactorial and poorly understood. To quantify cough frequency in an unselected group of subjects with COPD and
Jessica O'Neill et al.
Pharmacological reviews, 64(4), 939-971 (2012-10-02)
A large number of pharmacological studies have used capsaicin as a tool to activate many physiological systems, with an emphasis on pain research but also including functions such as the cardiovascular system, the respiratory system, and the urinary tract. Understanding
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