1.0 2009-07-23 18:26:09 UTC 2026-05-14 18:24:11 UTC T3D3085 Capsaicin SmallMolecule Capsaicin belongs to the methoxyphenols, a subclass of phenols within the organic compounds. This exogenous compound has the formula C18H27NO3 and an average molecular weight of 305.41 g/mol. At room temperature, it exists as a solid. It is classified as a benzenoid and is further identified as an alkaloid (PMC7833388), an agonist (PMC6391190), and a xenobiotic (PMC13418474). Capsaicin is found in 40 recorded sources across various sectors, including healthcare, pharmaceuticals and veterinary products (such as anesthetics, medical devices, and topical products for joint and muscular pain), food, food processing and cookware, building and construction, household cleaning and consumer products, textiles, leather and furnishings, and electrical and electronic equipment. Exposure routes include oral, inhalation, cutaneous, topical, percutaneous, transdermal, and touch. Industrially, it is used as a flavouring and nutrient, a deodorizer, and a softener and conditioner. Biologically, capsaicin acts as a non-narcotic analgesic, an analgesic (PMC7609673), and a voltage-gated sodium channel blocker. Its protein targets include the modulator of Prostaglandin G/H synthase 1 (PTGS1), Cannabinoid receptor 1 (CNR1), Cannabinoid receptor 2 (CNR2), and Prohibitin-2 (PHB2). It also targets Transient receptor potential cation channel subfamily A member 1 (TRPA1) and Transient receptor potential cation channel subfamily V member 1 (TRPV1); the latter interaction with sensory neurons produces burning and painful sensations by binding to the vanilloid receptor 1 (VR1), allowing cations to pass through the cell membrane and depolarize the neuron. While associated with an increase in pain (PMC7833388), it is used as a treatment for pain (PMC11859530) and has therapeutic effects on pain (PMC12684957), hypertension (PMC6175881), glioblastoma (PMC10786984), and prostate cancer (PMC10786984). Household Toxin Plant Toxin Food Toxin Natural Toxin Organic Compound Amine Ether Amide Food Toxin Plant Toxin Metabolite Lachrymator Household Toxin Natural Compound Human Neurotoxin PFAS Phytotoxin (E)-8-Methyl-N-vanillyl-6-nonenamide(8cl) (E)8-methyl-N-vanillyl-6-Nonenamide Axsain E-Capsaicin epsilon-Capsaicin Isodecenoate Isodecenoic acid Isodecenoic acid vanillylamide N-(4-HYDROXY-3-METHOXYBENZYL)-8-METHYL-6-NONENAMIDE N-(4-Hydroxy-3-methoxybenzyl)-8-methylnon-trans-6-enamide Styptysat trans-8-Methyl-N-vanillyl-6-nonenamide Transacin Zostrix C18H27NO3 305.4119 305.199093735 (6E)-N-[(4-hydroxy-3-methoxyphenyl)methyl]-8-methylnon-6-enamide capsaicin 404-86-4 COC1=C(O)C=CC(CNC(=O)CCCC\C=C\C(C)C)=C1 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+ YKPUWZUDDOIDPM-SOFGYWHQSA-N Organic compounds Benzenoids Phenols Methoxyphenols Methoxyphenols 1-hydroxy-2-unsubstituted benzenoids Alkyl aryl ethers Anisoles Carbonyl compounds Hydrocarbon derivatives Methoxybenzenes N-acyl amines Organic oxides Organonitrogen compounds Organopnictogen compounds Phenoxy compounds Secondary carboxylic acid amides 1-hydroxy-2-unsubstituted benzenoid Alkyl aryl ether Anisole Aromatic homomonocyclic compound Carbonyl group Carboxamide group Carboxylic acid derivative Ether Fatty acyl Fatty amide Hydrocarbon derivative Methoxybenzene Methoxyphenol Monocyclic benzene moiety N-acyl-amine Organic nitrogen compound Organic oxide Organic oxygen compound Organonitrogen compound Organooxygen compound Organopnictogen compound Phenol ether Phenoxy compound Secondary carboxylic acid amide Aromatic homomonocyclic compounds Capsaicinoids and derivatives capsaicinoid Detected and Not Quantified Exogenous Extracellular Membrane Capsaicin Drug Metabolism Action Pathway SMP0144114 Solid White powder. melting_point 65°C logp 3.80 ALOGPS logs -4.56 ALOGPS solubility 8.41e-03 g/l ALOGPS logp 3.75 ChemAxon pka_strongest_acidic 9.93 ChemAxon pka_strongest_basic -0.52 ChemAxon iupac (6E)-N-[(4-hydroxy-3-methoxyphenyl)methyl]-8-methylnon-6-enamide ChemAxon average_mass 305.4119 ChemAxon mono_mass 305.199093735 ChemAxon smiles COC1=C(O)C=CC(CNC(=O)CCCC\C=C\C(C)C)=C1 ChemAxon formula C18H27NO3 ChemAxon 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+ ChemAxon inchikey YKPUWZUDDOIDPM-SOFGYWHQSA-N ChemAxon polar_surface_area 58.56 ChemAxon refractivity 90.32 ChemAxon polarizability 36.32 ChemAxon rotatable_bond_count 9 ChemAxon acceptor_count 3 ChemAxon donor_count 2 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Oral (ingestion) (L1817) ; dermal (L1817) The burning and painful sensations associated with capsaicin result from its chemical interaction with sensory neurons. Capsaicin, as a member of the vanilloid family, binds to the vanilloid receptor 1 (VR1). VR1 permits cations to pass through the cell membrane and into the cell when activated. The resulting depolarization of the neuron stimulates it to signal the brain. By binding to the VR1 receptor, the capsaicin molecule produces the same sensation that excessive heat or abrasive damage would cause, explaining why the spiciness of capsaicin is described as a burning sensation. (L1246) LD50: 47200 ug/kg (Oral, Mouse) (T13) LD50: 6500 ug/kg (Intraperitoneal, Mouse) (T13) LD50: 9000 ug/kg (Subcutaneous, Mouse) (T13) LD50: 400 ug/kg (Intravenous, Mouse) (T13) LD50: 7800 ug/kg (Intramuscular, Mouse) (T13) LD50: 1600 ug/kg (Intratracheal, Mouse) (T13) Not listed by IARC. Capsaicin is the active component of chili peppers (genus Capsicum). It is a powerful irritant that is commonly used in food products to give them added spice. Capsaicin is also used in topical ointments to relieve the pain of peripheral neuropathy and can be found in pepper spray. (L1246) #<HealthEffect::ActiveRecord_Associations_CollectionProxy:0x00007f726e49f330> Capsaicin is a powerful irritant and causes burning or stinging pain to the skin. Ingestion of large amounts can cause nausea, vomiting, abdominal pain and burning diarrhea. Eye exposure produces intense tearing, pain, conjunctivitis and blepharospasm. (L1246) Capsaicin should be washed off the skin using soap, shampoo, or other detergents, or rubbed off with oily compounds such as vegetable oil, paraffin oil, petroleum jelly, creams, or polyethylene glycol. Burning and pain symptoms can be effectively relieved by cooling from ice, cold water, cold surfaces, or a flow of air. In severe cases, eye burn might be treated symptomatically with topical ophthalmic anaesthetics, while mucous membrane burn can be treated with lidocaine gel. Capsaicin-induced asthma might be treated with nebulized bronchodilators or oral antihistamines or corticosteroids. (L1246) DB06774 HMDB02227 1548943 CHEMBL294199 1265957 C06866 3374 CAPSAICIN Capsaicin 244 http://en.wikipedia.org/wiki/Capsaicin 8621114 17584831 17959343 Lewis RJ Sr. (ed) (2004). Sax's Dangerous Properties of Industrial Materials. 11th Edition. Hoboken, NJ: Wiley-Interscience, Wiley & Sons, Inc. Wikipedia. Capsaicin. Last Updated 16 July 2009. : http://en.wikipedia.org/wiki/Capsaicin Wikipedia. Phytotoxin. Last Updated 7 August 2009.: http://en.wikipedia.org/wiki/Phytotoxin BE0000095 Inhibitory >10 uM BindingDB 86537 BE0001023 The burning and painful sensations associated with capsaicin result from its chemical interaction with sensory neurons. Capsaicin, as a member of the vanilloid family, binds to the vanilloid receptor 1 (VR1). VR1 permits cations to pass through the cell membrane and into the cell when activated. The resulting depolarization of the neuron stimulates it to signal the brain. By binding to the VR1 receptor, the capsaicin molecule produces the same sensation that excessive heat or abrasive damage would cause, explaining why the spiciness of capsaicin is described as a burning sensation. (L1246) Wikipedia. Capsaicin. Last Updated 16 July 2009. : http://en.wikipedia.org/wiki/Capsaicin BE0000061 Inhibitory >10 uM BindingDB 20461 BE0000017 IC50 3.8 uM BindingDB 20461 BE0001122 Receptor-activated non-selective cation channel involved in detection of pain and possibly also in cold perception and inner ear function. Has a central role in the pain response to endogenous inflammatory mediators and to a diverse array of volatile irritants, such as mustard oil, garlic and acrolein, an irritant from tears gas and vehicule exhaust fumes. Acts also as a ionotropic cannabinoid receptor by being activated by delta(9)-tetrahydrocannabinol (THC), the psychoactive component of marijuana. Not involved in menthol sensation. May be a component for the mechanosensitive transduction channel of hair cells in inner ear, thereby participating in the perception of sounds. Probably operated by a phosphatidylinositol second messenger system (By similarity). Activation of cation channels in the membrane of sensory neurons, the so called TRP receptors (TRP = transient receptor potential) Lachrymation: http://aok.pte.hu/en/download/index/14785 BE0009007