1.0 2011-09-21 00:16:47 UTC 2025-11-19 02:42:05 UTC FDB022606 Cotinine N-oxide Cotinine N-oxide is a minor metabolite of nicotine, cotinine formation being the major pathway of nicotine metabolism in smokers. Cotinine N-oxide accounts for less than 5% of the nicotine dose. Cotinine N-oxide can be reduced back to the parent amine in vivo. Nicotine is a naturally occurring alkaloid found in many plants. The principal sources of nicotine exposure are through the use of tobacco, nicotine containing gum and nicotine replacement therapies. Nicotine is an amine composed of pyridine and pyrrolidine rings. It has been shown that nicotine crosses biological membranes and the blood brain barrier easily. The absorbed nicotine is extensively metabolized in the liver to form a wide variety of metabolites including and cotinine N-oxide. Nicotine has been shown to affect a wide variety of biological functions ranging from gene expression, regulation of hormone secretion and enzyme activities. (PMID: 16359169, 15109883) [HMDB] (5S)-1-methyl-5-(1-oxido-3-pyridinyl)-2-pyrrolidinone (S)-1-methyl-5-(1-oxido-3-pyridinyl)-2-Pyrrolidinone (S)-1-methyl-5-(3-pyridinyl)-2-Pyrrolidinone N-oxide cotinine N-oxide Cotinine-N-oxide C10H12N2O2 192.2145 192.089877638 3-[(2S)-1-methyl-5-oxopyrrolidin-2-yl]pyridin-1-ium-1-olate 3-[(2S)-1-methyl-5-oxopyrrolidin-2-yl]pyridin-1-ium-1-olate 36508-80-2 CN1[C@@H](CCC1=O)C1=C[N+]([O-])=CC=C1 InChI=1S/C10H12N2O2/c1-11-9(4-5-10(11)13)8-3-2-6-12(14)7-8/h2-3,6-7,9H,4-5H2,1H3/t9-/m0/s1 CIPULDKLIIVIER-VIFPVBQESA-N belongs to the class of organic compounds known as pyrrolidinylpyridines. Pyrrolidinylpyridines are compounds containing a pyrrolidinylpyridine ring system, which consists of a pyrrolidine ring linked to a pyridine ring. Pyrrolidinylpyridines Organic compounds Organoheterocyclic compounds Pyridines and derivatives Pyrrolidinylpyridines Aromatic heteromonocyclic compounds Alkaloids and derivatives Azacyclic compounds Carbonyl compounds Heteroaromatic compounds Hydrocarbon derivatives Lactams N-alkylpyrrolidines Organic oxides Organonitrogen compounds Organopnictogen compounds Pyridinium derivatives Pyrrolidine-2-ones Tertiary carboxylic acid amides 2-pyrrolidone Alkaloid or derivatives Aromatic heteromonocyclic compound Azacycle Carbonyl group Carboxamide group Carboxylic acid derivative Heteroaromatic compound Hydrocarbon derivative Lactam N-alkylpyrrolidine Organic nitrogen compound Organic oxide Organic oxygen compound Organonitrogen compound Organooxygen compound Organopnictogen compound Pyridinium Pyrrolidine Pyrrolidinylpyridine Pyrrolidone Tertiary carboxylic acid amide Solid logp -0.66 ALOGPS logs -1.24 ALOGPS solubility 1.10e+01 g/l ALOGPS logp -1 ChemAxon pka_strongest_basic 0.8 ChemAxon iupac 3-[(2S)-1-methyl-5-oxopyrrolidin-2-yl]pyridin-1-ium-1-olate ChemAxon average_mass 192.2145 ChemAxon mono_mass 192.089877638 ChemAxon smiles CN1[C@@H](CCC1=O)C1=C[N+]([O-])=CC=C1 ChemAxon formula C10H12N2O2 ChemAxon inchi InChI=1S/C10H12N2O2/c1-11-9(4-5-10(11)13)8-3-2-6-12(14)7-8/h2-3,6-7,9H,4-5H2,1H3/t9-/m0/s1 ChemAxon inchikey CIPULDKLIIVIER-VIFPVBQESA-N ChemAxon polar_surface_area 45.77 ChemAxon refractivity 52.97 ChemAxon polarizability 19.5 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 2 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::NmrOneD 95998 Specdb::NmrOneD 95999 Specdb::NmrOneD 96000 Specdb::NmrOneD 96001 Specdb::NmrOneD 96002 Specdb::NmrOneD 96003 Specdb::NmrOneD 96004 Specdb::NmrOneD 96005 Specdb::NmrOneD 96006 Specdb::NmrOneD 96007 Specdb::NmrOneD 96008 Specdb::NmrOneD 96009 Specdb::NmrOneD 96010 Specdb::NmrOneD 96011 Specdb::NmrOneD 96012 Specdb::NmrOneD 96013 Specdb::NmrOneD 96014 Specdb::NmrOneD 96015 Specdb::NmrOneD 96016 Specdb::NmrOneD 96017 Specdb::CMs 14622 Specdb::CMs 171022 Specdb::MsIr 1254 Specdb::MsIr 1255 Specdb::MsMs 103863 Specdb::MsMs 103864 Specdb::MsMs 103865 Specdb::MsMs 170016 Specdb::MsMs 170017 Specdb::MsMs 170018 Specdb::MsMs 3041128 Specdb::MsMs 3041129 Specdb::MsMs 3041130 Specdb::MsMs 3102371 Specdb::MsMs 3102372 Specdb::MsMs 3102373 HMDB01411 #<Reference:0x000055ce332332d0> #<Reference:0x000055ce33233118> #<Reference:0x000055ce33232f60> #<Reference:0x000055ce33232da8> #<Reference:0x000055ce33232bf0> Anatidae Type 1 specific Anatidae 8830 Beefalo Type 1 specific Bos taurus X Bison bison 297284 Bison Type 1 specific Bison bison 9901 Buffalo Type 1 specific Bubalus bubalis 89462 Cattle (Beef, Veal) Type 1 specific Bos taurus 9913 Chicken Type 1 specific Gallus gallus 9031 Columbidae (Dove, Pigeon) Type 1 specific Columbidae 8930 Deer Type 1 specific Cervidae 9850 Domestic goat Type 1 specific Capra aegagrus hircus 9925 Domestic pig Type 1 specific Sus scrofa domestica 9825 Elk Type 1 specific Cervus canadensis 1574408 Emu Type 1 specific Dromaius novaehollandiae 8790 European rabbit Type 1 specific Oryctolagus 9984 Greylag goose Type 1 specific Anser anser 8843 Guinea hen Type 1 specific Numida meleagris 8996 Horse Type 1 specific Equus caballus 9796 Mallard duck Type 1 specific Anas platyrhynchos 8839 Mountain hare Type 1 specific Lepus timidus 62621 Mule deer Type 1 specific Odocoileus 9871 Ostrich Type 1 specific Struthio camelus 8801 Pheasant Type 1 specific Phasianus colchicus 9054 Quail Type 1 specific Phasianidae 9005 Rabbit Type 1 specific Leporidae 9979 Rock ptarmigan Type 1 specific Lagopus muta 64668 Sheep (Mutton, Lamb) Type 1 specific Ovis aries 9940 Squab Type 1 specific Columba 8931 Turkey Type 1 specific Meleagris gallopavo 9103 Velvet duck Type 1 specific Melanitta fusca 371864 Wild boar Type 1 specific Sus scrofa 9823