Compound: NONIVAMIDE
SMILES: O=C(NCc1cc(OC)c(O)cc1)CCCCCCCC
InChIKey: RGOVYLWUIBMPGK-UHFFFAOYSA-N
Synonyms: NONIVAMIDE, 2444-46-4, N-Vanillylnonanamide, Pseudocapsaicin, Pelargonic acid vanillylamide, N-Vanillylnonamide, N-Vanillylpelargonamide, N-(4-Hydroxy-3-methoxybenzyl)nonanamide, Nonanoic acid vanillylamide, Vanillyl pelargonic amide, N-Nonanoyl vanillylamide, Vanillyl-N-nonylamide, Nonylic acid vanillylamide, Pelargonyl vanillylamide, Hydroxymethoxybenzyl pelargonamide, Nonanamide, N-[(4-hydroxy-3-methoxyphenyl)methyl]-, N-[(4-hydroxy-3-methoxyphenyl)methyl]nonanamide, Nonivamida, Nonanoyl vanillylamide, FEMA No. 2787, Nonivamidum, Hansaplast, vanillylnonanamide, Nonanoyl 4-hydroxy-3-methoxybenzylamide, PAVA, DTXSID1034769, Nonylic acid vanillyamide, AH-23491X, NSC-172795, N-((4-Hydroxy-3-methoxyphenyl)methyl)nonanamide, S846B891OR, Nonanamide, N-((4-hydroxy-3-methoxyphenyl)methyl)-, DTXCID9014769, CHEBI:46936, vanillylnonamide, PGA vanillylamide, RefChem:44168, 219-484-1, Vanillyl n-nonoylamide, Nonanamide, N-vanillyl-, Nonivamide [INN], desmethyldihydrocapsaicin, N-Vanillylnonanoamide, Capsaicin (Synthetic), NSC 172795, Capsaicin synthetic, N-((Hydroxy-3-methoxyphenyl)methyl)4-nonanamide, N-vanillyl nonanamide, CHEMBL75124, Nonivamide (INN), NCGC00016089-05, Vanillyl n-Nonylamide, Nonylvanylamide, Nonivamidum [INN-Latin], Nonivamida [INN-Spanish], CAS-2444-46-4, 8-Nordihydrocapsaicin, N-vanillyl-nonanamide, Nonanoylvanillyl Amide, N-((4-Hydroxy-3-methoxyphenyl)methyl)-Nonanamide, N-[(4-Hydroxy-3-methoxyphenyl)methyl]-Nonanamide, EINECS 219-484-1, BRN 2144300, UNII-S846B891OR, Nonivamide CRS, N-Nonylvanylamide, Nonivamide; Pseudocapsaicin; PAVA; Pelargonic acid vallinylamide; Vanillyl N-nonylamide, PAVA spray, Hansaplast (TN), Nonylic vanillamide, Synthetic capsaicin, Nonoyl vanillylamide, MFCD00017286, PSVA, Nonivamide (Standard), Spectrum_000311, Pelargonoyl vanillylamide, SpecPlus_000799, N-Pelargonylvanillylamide, Spectrum2_001091, Spectrum4_000916, Spectrum5_001853, Lopac-V-9130, N-Vanillylnonanamide, 8CI, NONIVAMIDE [MART.], NONIVAMIDE [WHO-DD], Lopac0_001218, SCHEMBL81939, KBioGR_001412, KBioSS_000791, MLS002153373, DivK1c_006895, SPECTRUM2300192, SPBio_001162, N-Pelargonic Acid Vanillylamide, orb1308990, orb3139934, SCHEMBL29425552, FEMA 2787, KBio1_001839, KBio2_000791, KBio2_003359, KBio2_005927, HH 50, HMS2234E23, HMS3374K02, HMS3885C14, HMS5082L05, Pharmakon1600-01506172, ALBB-025790, MSK10400, Tox21_110302, Tox21_301218, BDBM50044767, CCG-39764, EBC-03864, HY-17568R, NSC172795, NSC760391, s3935, SBB072688, AKOS001719931, N-Vanillylnonanamide, >=97%, powder, Tox21_110302_1, AC-4807, DB11324, FC71174, NSC-760391, N-Vanillylnonanamide, analytical standard, NCGC00016089-01, NCGC00016089-02, NCGC00016089-03, NCGC00016089-04, NCGC00016089-06, NCGC00094463-01, NCGC00094463-02, NCGC00094463-03, NCGC00094463-04, NCGC00255553-01, AS-13519, HY-17568, SMR001230764, N-(4-Hydroxy-3-methoxybenzyl)nonanamide #, EU-0101218, M0900, Nonanamide, N-(4-hydroxy-3-methoxybenzyl)-, NS00002166, ST45028933, 4-Hydroxy-3-methoxy-N-(1-oxononyl)-Benzamide, D08282, V 9130, V-3000, AB00053157_06, EN300-1692889, NONIVAMIDE (CONSTITUENT OF CAPSICUM) [DSC], Q420228, SR-01000076196, SR-01000076196-1, BRD-K05907307-001-07-1, N-[(4-Hydroxy-3-methoxyphenyl)methyl]nonanamide, 9CI, Z373586944, N-NONANOYL-4-HYDROXY-3-METHOXYBENZYL-AMIDE [FHFI], Nonivamide, European Pharmacopoeia (EP) Reference Standard, N-Vanillylnonanamide; N-(4-Hydroxy-3-methoxybenzyl)nonanamide, Capsaicin synth.; N-Vanillylpelargonamide; Nonylvanylamide; Pelargonic acid vanillylamide
Theoretical properties:
molecular_formula: C17H27NO3
molecular_weight: 293.4 g/mol
exact_mass: 293.19909372 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 2
hydrogen_bond_acceptor_count: 3
rotatable_bond_count: 10
heavy_atom_count: 21
topological_polar_surface_area: 58.6 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
solubility: Soluble in water (slightly)
Descriptions:
{"pubchem": "Nonivamide is a capsaicinoid that is the carboxamide resulting from the formal condensation of the amino group of 4-hydroxy-3-methoxybenzylamine with the carboxy group of nonanoic acid. It is the active ingredient in many pepper sprays. It has a role as a lachrymator. It is a member of phenols and a capsaicinoid.", "chebi": "A capsaicinoid that is the carboxamide resulting from the formal condensation of the amino group of 4-hydroxy-3-methoxybenzylamine with the carboxy group of nonanoic acid. It is the active ingredient in many pepper sprays.", "chembl": "NONIVAMIDE is a small molecule listed in the ChEMBL database and has reached clinical trial phase 3.0.", "wikipedia": "Nonivamide, also called pelargonic acid vanillylamide or PAVA, is an organic compound and a capsaicinoid. It is an amide of pelargonic acid (n-nonanoic acid) and vanillyl amine.  It is present in chili peppers, but is commonly manufactured synthetically. It is more heat-stable than capsaicin. \nNonivamide is used as a food additive to add pungency to seasonings, flavorings, and spice blends. It is also used in the confectionery industry to create a hot sensation, and in the pharmaceutical industry in some formulations as a cheaper alternative to capsaicin. \nLike capsaicin, it can deter mammals (but not birds or insects) from consuming plants or seeds (e.g. squirrels and bird feeder seeds). This is consistent with nonivamide's role as a TRPV1 ion channel agonist. Mammalian TRPV1 is activated by heat and capsaicin, but the avian form is insensitive to capsaicin.  \nNonivamide is used (under the name PAVA) as the payload in \"less-lethal munitions\" such as the FN Herstal's FN 303 projectiles or as the active ingredient in most pepper sprays, which may be used as a chemical weapon. As a chemical irritant, pepper sprays have been used both as a riot control munition and also a weapon to disperse peaceful demonstrators; they have also been used in other contexts, such as military or police training exercises. While irritants commonly cause only \"transient lacrimation, blepharospasm, superficial pain, and disorientation,\" their use and misuse also presents serious risks of more severe injury and disability."}