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Merck

1091108

USP

Capsaicin

United States Pharmacopeia (USP) 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
UNSPSC Code:
41116107
NACRES:
NA.24
PubChem Substance ID:
329749225
MDL number:
MFCD00017259
Beilstein/REAXYS Number:
2816484

Key Documents

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InChI key

YKPUWZUDDOIDPM-SOFGYWHQSA-N

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+

grade

pharmaceutical primary standard

API family

capsaicin

manufacturer/tradename

USP

mp

62-65 °C (lit.)

application(s)

pharmaceutical (small molecule)

format

neat

storage temp.

2-8°C

Gene Information

human ... TRPV1(7442)

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Analysis Note

These products are for test and assay use only. They are not meant for administration to humans or animals and cannot be used to diagnose, treat, or cure diseases of any kind.  ​

Application

Capsaicin USP reference standard for use in specified quality tests and assays.

Also used to prepare standard solutions for the assay, identification, composition and strength analysis according to the given below monographs of United States Pharmacopeia (USP):
  • Capsaicin
  • Capsicum Oleoresin
  • Capsicum
  • Ginger Tincture

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.
Prototype vanilloid receptor agonist; neurotoxin. Active component of chili peppers.

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.

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

flash_point_f

235.4 °F - closed cup

flash_point_c

113 °C - closed cup

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

1091108-100MG:

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Capsicum Oleoresin
United States Pharmacopeia, 38(4), 730-730 (2019)
Capsaicin
United States Pharmacopeia, 727-727 (2013)
Maija Haanpää et al.
European neurology, 68(5), 264-275 (2012-10-06)
Capsaicin has long been used as a traditional medicine to treat pain and, recently, its mechanism of analgesic action has been discovered. This review article documents the clinical development of capsaicin to demonstrate that pharmacognosy still has a profound influence
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
Astrid J Terkelsen et al.
Anesthesiology, 120(5), 1225-1236 (2014-03-14)
Complex regional pain syndrome is multifactorial. Exaggerated inflammatory responses to limb injury may be involved. The authors hypothesized that capsaicin-induced pain and neurogenic inflammation (skin perfusion and flare area) are increased in patients with complex regional pain syndrome compared with
View All Related Papers

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