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Substance Name: Capsaicin [USP:INN]
RN: 404-86-4
UNII: S07O44R1ZM
InChIKey: YKPUWZUDDOIDPM-SOFGYWHQSA-N

Note

  • An alkylamide found in CAPSICUM that acts at TRPV CATION CHANNELS.

Molecular Formula

  • C18-H27-N-O3

Molecular Weight

  • 305.4153
 

Classification Codes

  • Analgesic (Topical)
  • Antineuralgic, Specific Pain Syndromes, Topical
  • Antipruritics
  • Dermatologic Agents
  • Mutation Data
  • Natural Product
  • Peripheral Nervous System Agents
  • Sensory System Agents
  • Tumor Data
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Names and Synonyms

Name of Substance

  • Capsaicin
  • Capsaicin [USP:INN]

MeSH Heading

  • Capsaicin

Synonyms

  • (E)-8-Methyl-N-vanillyl-6-nonenamide
  • (E)-N-((4-Hydroxy-3-methoxyphenyl)-methyl)-8-methyl-6-nonenamide
  • 4-13-00-02588 (Beilstein Handbook Reference)
  • 6-Nonenamide, (E)-N-((4-hydroxy-3-methoxy-phenyl)methyl)-8-methyl
  • 6-Nonenamide, 8-methyl-N-vanillyl-, (E)-
  • 6-Nonenamide, N-((4-hydroxy-3-methoxyphenyl)methyl)-8-methyl-, (E)-
  • 8-Methyl-N-vanillyl-6-nonenamide, (E)-
  • ALGRX 4975
  • Ausanil
  • BRN 2816484
  • Capsaicin
  • Capsaicine
  • Caswell No. 158
  • CCRIS 1588
  • EINECS 206-969-8
  • EPA Pesticide Chemical Code 070701
  • FEMA No. 3404
  • HSDB 954
  • Isodecenoic acid vanillylamide
  • N-((4-Hydroxy-3-methoxyphenyl)methyl)-8-methyl-6-nonenamide, (E)-
  • N-(4-Hydroxy-3-methoxybenzyl)-8-methylnon-trans-6-enamide
  • NCI-C56564
  • NGX 4010
  • NGX-4010
  • NSC 56353
  • Qutenza
  • Styptysat
  • trans-8-Methyl-N-vanillyl-6-nonenamide
  • UNII-S07O44R1ZM
  • Zostrix

Systematic Names

  • 6-Nonenamide, 8-methyl-N-vanillyl-, (E)-
  • 6-Nonenamide, N-((4-hydroxy-3-methoxyphenyl)methyl)-8-methyl-, (6E)-
  • 6-Nonenamide, N-((4-hydroxy-3-methoxyphenyl)methyl)-8-methyl-, (E)-
  • Capsaicin

Superlist Names

  • Capsaicin
  • Capsaicin [in oleoresin of capsicum]

Registry Numbers

CAS Registry Number

  • 404-86-4

FDA UNII

  • S07O44R1ZM

Other Registry Number

  • 912457-62-6

System Generated Number

  • 0000404864

Structure Descriptors

InChI

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+

InChIKey

YKPUWZUDDOIDPM-SOFGYWHQSA-N

Smiles

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

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LDLo intravenous 1600ug/kg (1.6mg/kg)   FAO Nutrition Meetings Report Series. Vol. 48A, Pg. 60, 1970.
guinea pig LD50 intraperitoneal 1100ug/kg (1.1mg/kg) BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)

BEHAVIORAL: EXCITEMENT

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD		 Toxicon. Vol. 18, Pg. 215, 1980.
hamster LD50 intraperitoneal > 120mg/kg (120mg/kg)   Toxicon. Vol. 18, Pg. 215, 1980.
mouse LD50 intramuscular 7800ug/kg (7.8mg/kg) BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)

BEHAVIORAL: EXCITEMENT

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD		 Toxicon. Vol. 18, Pg. 215, 1980.
mouse LD50 intraperitoneal 6500ug/kg (6.5mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)

BEHAVIORAL: EXCITEMENT		 Toxicon. Vol. 18, Pg. 215, 1980.
mouse LD50 intratracheal 1600ug/kg (1.6mg/kg) BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)

BEHAVIORAL: EXCITEMENT

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD		 Toxicon. Vol. 18, Pg. 215, 1980.
mouse LD50 intravenous 400ug/kg (0.4mg/kg)   Yakhak Hoe Chi. Journal of the Pharmaceutical Society. Vol. 25(3), Pg. 101, 1981.
mouse LD50 oral 47200ug/kg (47.2mg/kg)   Yakhak Hoe Chi. Journal of the Pharmaceutical Society. Vol. 25(3), Pg. 101, 1981.
mouse LD50 rectal > 218mg/kg (218mg/kg)   Toxicon. Vol. 18, Pg. 215, 1980.
mouse LD50 skin > 512mg/kg (512mg/kg)   Toxicon. Vol. 18, Pg. 215, 1980.
mouse LD50 subcutaneous 9000ug/kg (9mg/kg) BEHAVIORAL: EXCITEMENT

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)		 Toxicon. Vol. 18, Pg. 215, 1980.
rabbit LD50 intraperitoneal > 50mg/kg (50mg/kg)   Toxicon. Vol. 18, Pg. 215, 1980.
rat LD50 intraperitoneal 9500ug/kg (9.5mg/kg) BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)

BEHAVIORAL: EXCITEMENT

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD		 Toxicon. Vol. 18, Pg. 215, 1980.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 65 deg C   EXP
log P (octanol-water) 4.000 (none)   EST
Atmospheric OH Rate Constant 1.14E-10 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.