Erowid
 
 
Plants - Drugs Mind - Spirit Freedom - Law Arts - Culture Library  
Take a Survey on the use of Breathwork
for Anxiety, Depression, Trauma, or PTSD
Researchers at Johns Hopkins seek responses to an anonymous survey on breathwork. You can participate whether your breathwork experiences helped or not.
(Must be 18+) Take the Survey!
Capsaicin Chemistry
by Erowid



NAME :Capsaicin
CHEMICAL NAME :trans-8-methyl-N-vanillyl-6-nonenamide
ALTERNATE
CHEMICAL NAMES :
(E)-N-[(4-Hydroxy-3-methyoxyphenyl)-methyl]-8-methyl-6-nonenamide;
N-(4-hydroxy-3-methoxybenzyl)-8-methylnontrans-6-enamide;
CHEMICAL FORMULAC18H27NO3
MOLECULAR WEIGHT305.42
MELTING POINT65° C
BOILING POINT210-220° C
From the Merck Index 12th Edition


Capsaicin Molecule


INFORMATION
Compare Capsaicin molecule to another chemical Local File


OFF-SITE LINKS
ScienceLab : Capsaicin Material Safety Data Sheet



MERCK INDEX ENTRY
1811. Capsaicin. (E)-N-[(4-Hydroxy-3-methyoxyphenyl)-methyl]-8-methyl-6-nonenamide; trans-8-methyl-N-vanillyl-6-nonenamide N-(4-hydroxy-3-methoxybenzyl)-8-methylnontrans-6-enamide; Axsain; Mioton; Zostrix. C18H27NO3; mole wt 305.42. C 70.79%, H 8.91%; N 4.59%, O 15.72%. :Pungent principle in fruit of various species of Capsicum, Solanaceae. Isoln from paprika and cayenne: Thresh, Pharm. J. and 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. 43, 597 (1920). Synthesis: Späth, 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. Pharmaoclogy: Molnar et al., Acta Physiol. 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. Letters 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 irritatns: 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, Arzneimittel-Forsch. 15, 718 (1965); Walker, Gavern, Mgf. Chem. Aerosol News 39 (6), 35 (1968); R. M. Virus, G.F. Gebhart, Life Sci. 25, 1273(1979); Y. Monsereenusorn et al., CRC Crit. Rev. Toxicol. 10, 321-339 (1982).

Monoclinic, rectangular plates, scales from petr ether, mp 65°. bp(.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. Use: As a tool in neurobiological research. Therap Cat: Topical Analgesic. Hydrocholoride, C11H15NO2.HCl, crystals from isopopanol/n-hexane, mp 147-148° (Bailey). Crystals from isopropanol/ether, mp 152-153° (Braun). uv max (ethanol): 286 nm (E 2843). LD50 in mice, rats, guinea pigs (mg/gk): 97,49,98 i.p. (Hardman).

Note: This is a controlled substance (hallucinogen) listed in the U.S. Code of Federal Regulations, Title 21 Part 1308.11 (1995).