Capsaicin (CED0001531)

Record Information
Version1.0
Creation Date2009-07-23 18:26:09 UTC
Update Date2026-05-14 18:24:11 UTC
Accession NumberCHEM002422
Identification
Common NameCapsaicin
ClassSmall Molecule
Description
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).
Contaminant Type
  • Amide
  • Amine
  • Ether
  • Food Toxin
  • Household Toxin
  • Human Neurotoxin
  • Lachrymator
  • Metabolite
  • Natural Compound
  • Organic Compound
  • PFAS
  • Phytotoxin
  • Plant Toxin
Chemical Structure
Synonyms
ValueSource
(e)-8-Methyl-N-vanillyl-6-nonenamideChEBI
Isodecenoic acid vanillylamideChEBI
trans-8-Methyl-N-vanillyl-6-nonenamideChEBI
ZostrixChEBI
Isodecenoate vanillylamideGenerator
(e)-8-Methyl-N-vanillyl-6-nonenamide(8CL)HMDB
(e)8-Methyl-N-vanillyl-6-nonenamideHMDB
AxsainHMDB
e-CapsaicinHMDB
epsilon-CapsaicinHMDB
IsodecenoateHMDB
Isodecenoic acidHMDB
N-(4-Hydroxy-3-methoxybenzyl)-8-methylnon-trans-6-enamideHMDB
StyptysatHMDB
TransacinHMDB
GelcenHMDB
Link brand OF capsaicinHMDB
8 Methyl N vanillyl 6 nonenamideHMDB
Capsicum farmayaHMDB
CapzasinHMDB
Flemming brand OF capsaicinHMDB
8-Methyl-N-vanillyl-6-nonenamideHMDB
CapsinHMDB
KatrumHMDB
Medicis brand OF capsaicinHMDB
Smaller brand OF capsaicinHMDB
Thompson brand OF capsaicinHMDB
Vinas brand OF capsaicinHMDB
Alacan brand OF capsaicinHMDB
Antiphlogistine rub a-535 capsaicinHMDB
CapsaicineHMDB
CapsidolHMDB
Carter horner brand OF capsaicinHMDB
Centrum brand OF capsaicinHMDB
Elan brand OF capsaicinHMDB
ZacinHMDB
Chemical FormulaC18H27NO3
Average Molecular Mass305.412 g/mol
Monoisotopic Mass305.199 g/mol
CAS Registry Number404-86-4
IUPAC Name(6E)-N-[(4-hydroxy-3-methoxyphenyl)methyl]-8-methylnon-6-enamide
Traditional Namecapsaicin
SMILESCOC1=C(O)C=CC(CNC(=O)CCCC\C=C\C(C)C)=C1
InChI IdentifierInChI=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+
InChI KeyYKPUWZUDDOIDPM-SOFGYWHQSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub ClassMethoxyphenols
Direct ParentMethoxyphenols
Alternative Parents
Substituents
  • Methoxyphenol
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Phenol ether
  • Alkyl aryl ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Monocyclic benzene moiety
  • Fatty acyl
  • Fatty amide
  • N-acyl-amine
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Carboxylic acid derivative
  • Ether
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Organopnictogen compound
  • Organic oxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
Applications
Biological Roles
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point65°C
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0084 g/LALOGPS
logP3.8ALOGPS
logP3.75ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)9.93ChemAxon
pKa (Strongest Basic)-0.52ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area58.56 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity90.32 m³·mol⁻¹ChemAxon
Polarizability36.32 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-052o-9860000000-4151cd60d08276e5122aNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-03mi-9576000000-fb9f159d71790f546865Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-0901000000-adba1bb6f254087febe8Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-0900000000-5be0e66854b20d7a5a03Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-0900000000-4337ff26dcbd2a77725eNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-0900000000-c94a246143850aa73e44Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014r-0950000000-3d145ef428e054b3e535Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014r-0950000000-c3ca097a6480ab798ff3Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-000i-0900000000-4e8f98d1f848f30117d7Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-000i-0900000000-58fab2fdd15893ea71e7Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-000i-0900000000-296a0cb1555da4f1ccd7Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03di-0209000000-a91e6403d5a0c0b67c2eNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03di-0209000000-dd0879d3f4f3a8b022c3Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-0149000000-d6a9f6e70ae7cd7aec38Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-0149000000-6fcf63c3bf44a4efc5bdNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-06sl-0075690000-b562b766019cc7cbd98fNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-01x3-0094560000-f354077f4cd51e45b945Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004i-0002900000-ce1ea9819252343543cdNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004i-0002911000-6c37470f794c89a66410Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-000i-0900000000-00619747b8012ce6aa64Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-000i-0900000000-3ca73f5212a7643b45d2Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03dr-0956000000-d0dbf319e1bb02a1aa21Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03dr-0958000000-a53fd50bc48a51d95c1cNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004i-0096000000-265377cd56468981c3a3Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004i-0096000000-da1cc255516c9c58c6f6Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0aou-9400000000-9db1381553cf09ff0defNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4l-9000000000-3221421682adf6813fa4Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-1900000000-ec3f28211e6f4bd5b26aNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-0900000000-fecdda27de4427466449Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-000i-0900000000-4a9136d4275cafa3fc71Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-000i-0900000000-63bd0649b4c9b86f5dd5Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-000i-2900000000-09f8170f413239ce4050Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-000i-0900000000-05d9a31d125479487a6dNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-0912000000-95e090cebb8f95d7fe89Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-0900000000-6fb8b34936b848190c39Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0f79-4900000000-ade1e8ba842adf972c83Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-0419000000-80bfd538da9be3f08fe0Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-0922000000-00b0b7b3e9df2464d425Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-7900000000-8b112ae03b8d84d338f3Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-052r-0914000000-4d92046e13d9a4b8011bNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-052r-2900000000-ec7ee9d2a2bd31098e6cNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-052r-4900000000-2497c77329f4162ef036Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-1900000000-cb56867af6eb20d30a02Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0fr6-7901000000-d4a6ac2cb2a203a0c689Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udl-9826000000-e934aee6c92533ea2ebcNot AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityThe 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. (4)
Carcinogenicity (IARC Classification)Not listed by IARC.
Minimum Risk LevelNot Available
SymptomsCapsaicin 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. (4)
TreatmentCapsaicin 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. (4)
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
47200.0ug/kgNot AvailableMouseLD50OralexperimentalT13
6500.0ug/kgNot AvailableMouseLD50IntraperitonealexperimentalT13
9000.0ug/kgNot AvailableMouseLD50SubcutaneousexperimentalT13
400.0ug/kgNot AvailableMouseLD50IntravenousexperimentalT13
7800.0ug/kgNot AvailableMouseLD50IntramuscularexperimentalT13
1600.0ug/kgNot AvailableMouseLD50IntratrachealexperimentalT13
516.0Log mg/kg[290:920]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
hypertensionhas_therapeutic_effect_onNot AvailablePMC6175881 , PMC6175881 , PMC6175881
painassociated_withincreasePMC7833388
painis_treatment_forNot AvailablePMC11859530
painhas_therapeutic_effect_onNot AvailablePMC12684957
Prostate cancerhas_therapeutic_effect_onNot AvailablePMC10786984
glioblastomahas_therapeutic_effect_onNot AvailablePMC10786984
Exposure Sources
Source IDSourceSectorReference
7PesticidesAgriculture & land managementNot Available
19Indoor airAir, dust & atmospheric transportNot Available
120Wires and cablesElectrical & Electronic EquipmentNot Available
121Printed circuit boardsElectrical & Electronic EquipmentNot Available
125BatteriesElectrical & Electronic EquipmentNot Available
130SemiconductorsElectrical & Electronic EquipmentNot Available
138LubricantsEnergy, oil & gasNot Available
147Food packagingFood, food processing & cookwareNot Available
174LubricantsIndustrial manufacturing & chemical processingNot Available
234Medical devicesHealthcare, pharmaceuticals & veterinary productsNot Available
364Topical products for joint and muscular painHealthcare, pharmaceuticals & veterinary productsNot Available
369AnestheticsHealthcare, pharmaceuticals & veterinary productsNot Available
451Carpets and RugsTextiles, leather & furnishingsNot Available
454Synthetic textilesTextiles, leather & furnishingsNot Available
490Personal care & cosmeticsNot Available
492Cell phonesElectrical & Electronic EquipmentNot Available
493CapacitorsElectrical & Electronic EquipmentNot Available
495CeilingsBuilding & ConstructionNot Available
496FencingBuilding & ConstructionNot Available
497FloorsBuilding & ConstructionNot Available
499RoofsBuilding & ConstructionNot Available
505AmplifiersElectrical & Electronic EquipmentNot Available
506AntennasElectrical & Electronic EquipmentNot Available
510Communication Cables Or ConductorsElectrical & Electronic EquipmentNot Available
516Electric Hearing AidsElectrical & Electronic EquipmentNot Available
527MagnetsElectrical & Electronic EquipmentNot Available
529Power CablesElectrical & Electronic EquipmentNot Available
539Video GamesElectrical & Electronic EquipmentNot Available
546Molasses And Treatment Of MolassesFood, food processing & cookwareNot Available
548Preparation Of VinegarFood, food processing & cookwareNot Available
549Preparation Of Wine Or Sparkling WineFood, food processing & cookwareNot Available
550Preparation Of WortFood, food processing & cookwareNot Available
551Processing FishFood, food processing & cookwareNot Available
552Processing MeatsFood, food processing & cookwareNot Available
553Treatment Of HopsFood, food processing & cookwareNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
560Other Smoking RequisitesHousehold cleaning & consumer productsNot Available
562Pipe AccessoriesHousehold cleaning & consumer productsNot Available
564Soap DispensersHousehold cleaning & consumer productsNot Available
567Tobacco Product CasesHousehold cleaning & consumer productsNot Available
568Tobacco Product Moisture ControlHousehold cleaning & consumer productsNot Available
578Making CigarsIndustrial manufacturing & chemical processingNot Available
583Anchoring EquipmentMarine, shipping & aquacultureNot Available
584BuoysMarine, shipping & aquacultureNot Available
587Gun Or Missile LaunchersMarine, shipping & aquacultureNot Available
593Nautical InstrumentsMarine, shipping & aquacultureNot Available
597ChemosterilantsAgriculture & land managementNot Available
607Rodenticides(1)Agriculture & land managementNot Available
608RodenticidesAgriculture & land managementNot Available
612Body Washing Or Cleaning ImplementsPersonal care & cosmeticsNot Available
616Face Mask CosmeticsPersonal care & cosmeticsNot Available
634BucklesTextiles, leather & furnishingsNot Available
643HeadwearTextiles, leather & furnishingsNot Available
651Purses Money Bags WalletsTextiles, leather & furnishingsNot Available
661UmbrellasTextiles, leather & furnishingsNot Available
Pathways
1 pathway
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Transient receptor potential cation channel subfamily V member 1 structureClick to view 3D structureTransient receptor potential cation channel subfamily V member 1Q8NER1HumansPredicted (SEA)0.934191
Click to view 3D structureTransient receptor potential cation channel subfamily V member 1O35433Rattus norvegicusPredicted (SEA)0.467095
Cannabinoid receptor 1 structureClick to view 3D structureCannabinoid receptor 1P21554HumansPredicted (SEA)5.2159
Cannabinoid receptor 2 structureClick to view 3D structureCannabinoid receptor 2P34972HumansPredicted (SEA)5.60514
Click to view 3D structureTransient receptor potential cation channel subfamily V member 2Q9WUD2Rattus norvegicusPredicted (SEA)2.64687
Cytochrome P450 1A2 structureClick to view 3D structureCytochrome P450 1A2P05177HumansPredicted (SEA)20.3965
Prostaglandin G/H synthase 1 structureClick to view 3D structureProstaglandin G/H synthase 1P23219HumansPredicted (SEA)7.16213
Cytochrome P450 2C9 structureClick to view 3D structureCytochrome P450 2C9P11712HumansPredicted (SEA)100.036
Lysine-specific histone demethylase 1A structureClick to view 3D structureLysine-specific histone demethylase 1AO60341HumansPredicted (SEA)6.30579
Polyunsaturated fatty acid 5-lipoxygenase structureClick to view 3D structurePolyunsaturated fatty acid 5-lipoxygenaseP09917HumansPredicted (SEA)20.8636
Cytochrome P450 2B6 structureClick to view 3D structureCytochrome P450 2B6P20813HumansPredicted (SEA)5.3716
Cytochrome P450 2C8 structureClick to view 3D structureCytochrome P450 2C8P10632HumansPredicted (SEA)27.1694
Bile salt export pump structureClick to view 3D structureBile salt export pumpO95342HumansPredicted (SEA)5.0602
Bifunctional epoxide hydrolase 2 structureClick to view 3D structureBifunctional epoxide hydrolase 2P34913HumansPredicted (SEA)19.7737
Cytochrome P450 3A4 structureClick to view 3D structureCytochrome P450 3A4P08684HumansPredicted (SEA)300.732
Click to view 3D structureBifunctional epoxide hydrolase 2P34914Mus musculusPredicted (SEA)7.70707
Click to view 3D structureCannabinoid receptor 1P20272Rattus norvegicusPredicted (SEA)26.2352
Click to view 3D structureFatty-acid amide hydrolase 1O00519HumansPredicted (SEA)40.8708
Transient receptor potential cation channel subfamily M member 8 structureClick to view 3D structureTransient receptor potential cation channel subfamily M member 8Q7Z2W7HumansPredicted (SEA)6.30579
Cytochrome P450 2C19 structureClick to view 3D structureCytochrome P450 2C19P33261HumansPredicted (SEA)180.065
Click to view 3D structureBifunctional epoxide hydrolase 2P80299Rattus norvegicusPredicted (SEA)7.62922
Click to view 3D structureCarbonic anhydrase 2Q3I4V7Cryptococcus neoformansPredicted (SEA)19.7737
Click to view 3D structureCarbonic anhydraseQ5AJ71Candida albicans (strain SC5314 / ATCC MYA-2876) (Yeast)Predicted (SEA)23.0434
Click to view 3D structurePROBABLE TRANSMEMBRANE CARBONIC ANHYDRASE (CARBONATE DEHYDRATASE) (CARBONIC DEHYDRATASE)P96878Mycobacterium tuberculosisPredicted (SEA)19.9294
Carbonic anhydrase 9 structureClick to view 3D structureCarbonic anhydrase 9Q16790HumansPredicted (SEA)141.763
Cannabinoid receptor 2 structureClick to view 3D structureCannabinoid receptor 2P34972HumansKnownNot Available
Transient receptor potential cation channel subfamily V member 1 structureClick to view 3D structureTransient receptor potential cation channel subfamily V member 1Q8NER1HumansKnownThe 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)
Cannabinoid receptor 1 structureClick to view 3D structureCannabinoid receptor 1P21554HumansKnownNot Available
Prostaglandin G/H synthase 1 structureClick to view 3D structureProstaglandin G/H synthase 1P23219HumansKnownNot Available
Transient receptor potential cation channel subfamily A member 1 structureClick to view 3D structureTransient receptor potential cation channel subfamily A member 1O75762HumansKnownReceptor-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)
Concentrations
Not Available
External Links
DrugBank IDDB06774
HMDB IDHMDB0002227
FooDB IDFDB012411
Phenol Explorer ID712
KNApSAcK IDC00052221
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkCapsaicin
Chemspider ID1265957
ChEBI ID3374
PubChem Compound ID1548943
Kegg Compound IDC06866
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceGannett, Peter M.; Nagel, Donald L.; Reilly, Pam J.; Lawson, Terence; Sharpe, Jody; Toth, Bela. Capsaicinoids: their separation, synthesis, and mutagenicity. Journal of Organic Chemistry (1988), 53(5), 1064-71.
MSDSLink
General References
1. Gannett, Peter M.; Nagel, Donald L.; Reilly, Pam J.; Lawson, Terence; Sharpe, Jody; Toth, Bela. Capsaicinoids: their separation, synthesis, and mutagenicity. Journal of Organic Chemistry (1988), 53(5), 1064-71.
2. Gannett, Peter M.; Nagel, Donald L.; Reilly, Pam J.; Lawson, Terence; Sharpe, Jody; Toth, Bela. Capsaicinoids: their separation, synthesis, and mutagenicity. Journal of Organic Chemistry (1988), 53(5), 1064-71.
3. Surh YJ, Lee SS: Capsaicin in hot chili pepper: carcinogen, co-carcinogen or anticarcinogen? Food Chem Toxicol. 1996 Mar;34(3):313-6.
4. Simpson DM, Estanislao L, Brown SJ, Sampson J: An open-label pilot study of high-concentration capsaicin patch in painful HIV neuropathy. J Pain Symptom Manage. 2008 Mar;35(3):299-306. Epub 2007 Oct 23.