Capsaicin

Capsaicin
Capsaicin
Heat	Above peak; (pure capsaicin is toxic)
Scoville scale	16,000,000 SHU

Capsaicin
Names
Pronunciation	/kæpˈseɪsɪn/ or /kæpˈseɪəsɪn/
	Preferred IUPAC name (6E)-N-[(4-Hydroxy-3-methoxyphenyl)methyl]-8-methylnon-6-enamide
	Other names (E)-N-(4-Hydroxy-3-methoxybenzyl)-8-methylnon-6-enamide; 8-Methyl-N-vanillyl-trans-6-nonenamide; trans-8-Methyl-N-vanillylnon-6-enamide; (E)-Capsaicin; Capsicine; Capsicin; CPS; Drug
Identifiers
CAS Number	404-86-4 ;
3D model (JSmol)	Interactive image;
Beilstein Reference	2816484
ChEBI	CHEBI:3374 ;
ChEMBL	ChEMBL294199 ;
ChemSpider	1265957 ;
DrugBank	DB06774;
ECHA InfoCard	100.006.337
EC Number	206-969-8;
IUPHAR/BPS	2486;
KEGG	C06866 ;
PubChem CID	1548943;
UNII	S07O44R1ZM ;
CompTox Dashboard (EPA)	DTXSID9020241 ;
	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+ Key: YKPUWZUDDOIDPM-SOFGYWHQSA-N ; InChI=1/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+ Key: YKPUWZUDDOIDPM-SOFGYWHQBQ;
	SMILES O=C(NCc1cc(OC)c(O)cc1)CCCC/C=C/C(C)C;
Properties
Chemical formula	C18H27NO3
Molar mass	305.418 g·mol−1
Appearance	Crystalline white powder
Odor	Highly pungent
Melting point	62 to 65 °C (144 to 149 °F; 335 to 338 K)
Boiling point	210 to 220 °C (410 to 428 °F; 483 to 493 K) 0.01 Torr
Solubility in water	0.0013 g/100 mL
Solubility	Soluble in alcohol, ether, benzene; Slightly soluble in CS2, HCl, petroleum;
Vapor pressure	1.32×10−8 mm Hg at 25 °C
UV-vis (λmax)	280 nm
Structure
Crystal structure	Monoclinic
Pharmacology
ATC code	M02AB01 (WHO) N01BX04 (WHO)
License data	EU EMA: by INN;
Legal status	US: ℞-only;
Hazards
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H301, H302, H315, H318
Precautionary statements	P264, P270, P280, P301+P310, P301+P312, P302+P352, P305+P351+P338, P310, P321, P330, P332+P313, P362, P405, P501
NFPA 704 (fire diamond)	2 1 0
Safety data sheet (SDS)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Capsaicin (8-methyl-N-vanillyl-6-nonenamide) (/kæpˈseɪ.ə.sɪn/, rarely /kæpˈseɪsɪn/)^[6]^[7]^[8] is an active component of chili peppers, which are plants belonging to the genus Capsicum. It is a potent irritant for mammals, including humans, for which it produces a sensation of burning in any tissue with which it comes into contact. Capsaicin and several related amides (capsaicinoids) are produced as secondary metabolites by chili peppers, likely as deterrents against eating by mammals and against the growth of fungi.^[9] Pure capsaicin is a hydrophobic, colorless, highly pungent (i.e., spicy) crystalline solid.^[2]^[10]^[11]

^ "Capsaicin". ChemSpider. Royal Society of Chemistry. 2018. Retrieved 9 June 2018.
^ ^a ^b ^c ^d "Capsaicin". PubChem, US National Library of Medicine. 27 May 2023. Retrieved 1 June 2023.
^ "Qutenza- capsaicin kit". DailyMed. 10 January 2023. Retrieved 22 February 2023.
^ "Drug Approval Package: Qutenza (capsaicin) NDA #022395". U.S. Food and Drug Administration (FDA). 3 October 2013. Retrieved 22 February 2023.
^ Govindarajan VS, Sathyanarayana MN (1991). "Capsicum—production, technology, chemistry, and quality. Part V. Impact on physiology, pharmacology, nutrition, and metabolism; structure, pungency, pain, and desensitization sequences". Critical Reviews in Food Science and Nutrition. 29 (6): 435–474. doi:10.1080/10408399109527536. PMID 2039598.
^ "Capsaicin".
^ "Definition of CAPSAICIN".
^ "The American Heritage Dictionary entry: Capsaicin".
^ "What Made Chili Peppers So Spicy?". Talk of the Nation. 15 August 2008.
^ David WI, Shankland K, Shankland K, Shankland N (1998). "Routine determination of molecular crystal structures from powder diffraction data". Chemical Communications (8): 931–932. doi:10.1039/a800855h.
^ Lozinšek M (1 April 2025). "Single-crystal structure of the spicy capsaicin". Acta Crystallographica Section C Structural Chemistry. 81 (4): 188–192. doi:10.1107/S2053229625001706. ISSN 2053-2296. PMC 11970115. PMID 40052876.

[1] "Capsaicin". ChemSpider. Royal Society of Chemistry. 2018. Retrieved 9 June 2018.

[pubchem-2] "Capsaicin". PubChem, US National Library of Medicine. 27 May 2023. Retrieved 1 June 2023.

[Qutenza_FDA_label-3] "Qutenza- capsaicin kit". DailyMed. 10 January 2023. Retrieved 22 February 2023.

[4] "Drug Approval Package: Qutenza (capsaicin) NDA #022395". U.S. Food and Drug Administration (FDA). 3 October 2013. Retrieved 22 February 2023.

[pmid2039598-5] Govindarajan VS, Sathyanarayana MN (1991). "Capsicum—production, technology, chemistry, and quality. Part V. Impact on physiology, pharmacology, nutrition, and metabolism; structure, pungency, pain, and desensitization sequences". Critical Reviews in Food Science and Nutrition. 29 (6): 435–474. doi:10.1080/10408399109527536. PMID 2039598.

[6] "Capsaicin".

[7] "Definition of CAPSAICIN".

[8] "The American Heritage Dictionary entry: Capsaicin".

[totn-9] "What Made Chili Peppers So Spicy?". Talk of the Nation. 15 August 2008.

[10] David WI, Shankland K, Shankland K, Shankland N (1998). "Routine determination of molecular crystal structures from powder diffraction data". Chemical Communications (8): 931–932. doi:10.1039/a800855h.

[11] Lozinšek M (1 April 2025). "Single-crystal structure of the spicy capsaicin". Acta Crystallographica Section C Structural Chemistry. 81 (4): 188–192. doi:10.1107/S2053229625001706. ISSN 2053-2296. PMC 11970115. PMID 40052876.

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