Compound Selection

Formula: C18H27NO3

MW: 305.42

CAS: 404-86-4

TNP NUMBER: TNP00277

MDL NUMBER: MFCD00017259

IUPAC: (6E)-N-[(4-hydroxy-3-methoxyphenyl)methyl]-8-methylnon-6-enamide

Smiles: C(NC(CCCC\C=C\C(C)C)=O)c1cc(OC)c(cc1)O

Pungent principle in fruit of various species of Capsicum, Solanaceae

THERAPEUTIC CATEGORY: Topical analgesic

ACCEPTORS: 3

DONORS: 2

ROTATION BONDS: 10

N+O: 4

Chiral Centers: 0

LogP: 4.19

LogS: -4.6

LIPINSKI: 4

Monograph Number: 0001774

Title: Capsaicin

CAS Registry Number: 404-86-4

CAS Name: (6E)-N-[(4-Hydroxy-3-methoxyphenyl)methyl]-8-methyl-6-nonenamide

Additional Names: trans-8-methyl-N-vanillyl-6-nonenamide; N-(4-hydroxy-3-methoxybenzyl)-8-methylnon-trans-6-enamide

Trademarks: Axsain (Bioglan); Mioton (Pharmakhim); Zacin (Bioglan); Zostrix (GenDerm)

Molecular Formula: C18H27NO3

Molecular Weight: 305.41.

Percent Composition: C 70.79%, H 8.91%, N 4.59%, O 15.72%

Literature References: Pungent principle in fruit of various species of Capsicum, Solanaceae. Isoln from paprika and cayenne: Thresh, Pharm. J. Trans. 7, 21 (1876); Micko, Z. Nahr. Genussm. 1, 818 (1898). See Beilstein 13, suppl. I, 322. Early structure study: Nelson, J. Am. Chem. Soc. 42, 597 (1920). Synthesis: Spath, Darling, Ber. 63, 737 (1930); L. Crombie et al., J. Chem. Soc. 1955, 1025; O. P. Vig et al., Indian J. Chem. 17B, 558 (1979). Constitution and biosynthesis: D. J. Bennet, E. W. Kirby, J. Chem. Soc. C 1968, 442. Pharmacology: J. Molnar et al., Acta Physiol. Acad. Sci. Hung. 35, 369 (1969). Capsaicin is a powerful irritant; initial administration causes intense pain. Prolonged treatment causes insensitivity to painful stimuli and induces selective degeneration of certain primary sensory neurons: G. Jancso et al., Nature 270, 741 (1977); R. Gamse, Arch. Pharmacol. 320, 205 (1982); P. Holzer et al., Neurosci. Lett. 31, 253 (1982). Neuronal depletion of substance P, q.v.: T. M. Jessell et al., Brain Res. 152, 183 (1978); T. L. Yaksh et al., Science 206, 481 (1979). Capsaicin pretreatment also induces long-lasting desensitization of airway mucosa to various mechanical and chemical irritants: J. M. Lundberg, A. Saria, Nature 302, 251 (1983). Preliminary clinical evaluation in chronic postherpetic neuralgia: J. E. Bernstein et al., J. Am. Acad. Dermatol. 17, 93 (1987). Reviews: Molnar, Arzneim.-Forsch. 15, 718 (1965); Walker, Gavern, Manuf. Chem. Aerosol News 39 (6), 35 (1968); R. M. Virus, G. F. Gebhart, Life Sci. 25, 1273 (1979); Y. Monsereenusorn et al., Crit. Rev. Toxicol. 10, 321-339 (1982).

Properties: Monoclinic, rectangular plates, scales from petr ether, mp 65. bp0.01 210-220 (air-bath temp). uv max: 227, 281 nm (e 7000, 2500). Burning taste, one part in 100,000 can be detected by tasting. Practically insol in cold water. Freely sol in alc, ether, benzene, chloroform; slightly sol in CS2.

Melting point: mp 65

Boiling point: bp0.01 210-220 (air-bath temp)

Absorption maximum: uv max: 227, 281 nm (e 7000, 2500)

Use: As a tool in neurobiological research.

Therap-Cat: Topical analgesic.

Therap-Cat-Vet: Topical analgesic.

Synonyms: (E)-8-METHYL-NON-6-ENOIC ACID 4-HYDROXY-3-METHOXY-BENZYLAMIDE;(E)-CAPSAICIN;(E)-N-([4-HYDROXY-3-METHOXYPHENYL]METHYL)8-METHYL-6-NONEAMIDE;(E)-N-[(4-HYDROXY-3-METHOXYPHENYL)METHYL]-8-METHYL-6-NONENAMIDE;CAPSAICIN;CAPSAICINE;CAPSAICIN, NATURAL;FEMA 3404

CAS:404-86-4

MF:C18H27NO3

MW:305.41

EINECS:206-969-8

Product Categories:INORGANIC & ORGANIC CHEMICALS;Anilines, Aromatic Amines and Nitro Compounds;Miscellaneous Natural Products;Natural Plant Extract;Intermediates & Fine Chemicals;Pharmaceuticals;Vanilloid/TRPV channel Capsaicin

Chemical Properties: mp 62-65 C(lit.) bp 210-220 C FEMA 3404 Fp 113 C storage temp. 2-8C solubility H2O: insoluble Water Solubility insoluble Merck 1768 Stability:Stable. Incompatible with strong oxidizing agents.

CAS DataBase Reference: 404-86-4(

CAS DataBase Reference: ) EPA Substance Registry System6-Nonenamide, N-[(4-hydroxy-3-methoxyphenyl) methyl]-8-methyl-, (6E)-(404-86-4) T,T+ Risk Statements 25-37/38-41-42/43-36/37/38 Safety Statements 22-26-28-36/39-45-36/37/39 RIDADR UN 2811 6.1/PG 2 WGK Germany 3 RTECS RA8530000 F 10-21 HazardClass 6.1(a) PackingGroup II Hazardous Substances Data404-86-4(Hazardous Substances Data) (E)-N-[(4-Hydroxy-3-methoxyphenyl)methyl]-8-methyl-6-nonenamide Capsaicin

Usage And Synthesis:

Chemical Properties: Off-White Crystalline Solid UsageA representative lot is a 5:1 E:Z mixture. It is used as a tool in neurobiological research. Prototype vanilloid receptor agonist. Topical analgesic. Biological ActivityPrototypic vanilloid receptor agonist (pEC 50 values are 7.97 and 7.10 at rat and human VR1 receptors respectively). Excites a subset of primary afferent sensory neurons, with subsequent antinociceptive and anti-inflammatory effects. Reversibly inhibits aggregation of platelets. Also available as part of the Vanilloid TRPV1 Receptor Tocriset . Capsaicin

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