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Nicotine

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Definition: Nicotine is highly toxic alkaloid. It is the prototypical agonist at nicotinic cholinergic receptors where it dramatically stimulates neurons and ultimately blocks synaptic transmission. Nicotine is also important medically because of its presence in tobacco smoke.  /biosyn permitted if by plant   
Pharmacological Action Ganglionic Stimulants; Nicotinic Agonists 		Other names Tartrate, Nicotine; Bitartrate, Nicotine; Nicotine Tartrate; Nicotine BitartrateDrugs* : NICOTROL; NICOTINE; NICODERM CQ; HABITROL; PROSTEP
 
SubstanceCAS Registry & nameCategoriesSourceDrugs*
fulleronicotine  0   *Fullerenes Nicotine/*analogs & derivatives. Chem Commun (Camb). 2009 Feb 21;(7):758-60
7,8-difluoro-1,2,3,4,5,6- hexahydro-1,5-methano-3-benzazocine  0   Nicotine/*analogs & derivatives Alkaloids. Org Lett 2006 Dec 21;8(26):5947-50
2,4,5,6-tetradeuterocotinine  0   Nicotine/*analogs & derivatives. Clin Pharmacol Ther 2006 Nov;80(5):457-67
3',3'-dideuteronicotine  0   Nicotine/*analogs & derivatives. Clin Pharmacol Ther 2006 Nov;80(5):457-67
4-(dimethylphenylsilyl)nicotine  0   *Silanes Nicotine. Org Lett. 2005 Oct 27;7(22):5059-62
4-hydroxynicotine  0   Nicotine/*analogs & derivatives. Org Lett. 2005 Oct 27;7(22):5059-62
5'-acetoxy-N'-nitrosonornicotine  0   *Nitrosamines Nicotine/*analogs & derivatives. Chem Res Toxicol 2006 Mar;19(3):426-35
N-(n-dec-9-enyl)nicotinium  0   Nicotine/*analogs & derivatives. AAPS J 2005;7(1):E201-17
N-(n-oct-3-enyl)nicotinium  0   Nicotine/*analogs & derivatives. AAPS J 2005;7(1):E201-17
N-n-octylnicotinium  0   Nicotine/*analogs & derivatives. AAPS J 2005;7(1):E201-17
N'-formylnornicotine  0   Nicotine/*analogs & derivatives. Phytochemistry 2005 Oct;66(20):2432-40
6-(2-phenylethyl)nicotine  0   Nicotine/*analogs & derivatives. Bioorg Med Chem Lett 2005 Jul 1;15(13):3237-40
N-methyl-nicotine  0   Nicotine/*analogs & derivatives. Biol Reprod. 2005 Mar;72(3):628-32
6-hydroxynicotine  0   Nicotine/*analogs & derivatives. Nucleic Acids Res 2005;33(12) (dup#1):e107
SIB1663  0   Nicotine/analogs & derivatives. Brain Res 2004 Apr 2;1003(1-2):42-53
6-n-propylnicotine  0   Nicotine/*analogs & derivatives. Bioorg Med Chem Lett 2002 Oct 21;12(20):3005-7
homoazanicotine  0   Nicotine/*analogs & derivatives Ligands. J Med Chem 2002 Oct 10;45(21):4724-31
1-benzyl-4-phenylnicotinamidinium  0   Nicotine/*analogs & derivatives. J Am Chem Soc 2002 Aug 7;124(31):9181-8
5-methoxynicotine  0   Nicotine/*analogs & derivatives. Eur J Pharmacol 2002 Jan 25;435(2-3):171-80
K(s-nic)5(Ga2(N,N'-bis-(2,3-dihydroxybenzoyl)-1,4-phenylenediamine)3)  0   *Organometallic Compounds Nicotine/*analogs & derivatives. Inorg Chem 2001 May 7;40(10):2216-7
N-n-decylnicotinium  0   Nicotine/*analogs & derivatives Receptors, Nicotinic/antagonists & inhibitors. Br J Pharmacol 1999 Nov;128(6):1291-9
5'-hydroxycotinine-N-oxide  0   Cotinine/*analogs & derivatives Nicotine/metabolism. Xenobiotica 1999 Aug;29(8):793-801
5-iodonicotine  0   Nicotine/*analogs & derivatives Iodine Radioisotopes. Biol Pharm Bull 1995 Nov;18(11):1463-6
5-fluoronicotine  35286-36-3   Nicotine/*analogs & derivatives. Neurochem Res 1995 Sep;20(9):1089-94
4'-methylnicotine  74805-00-8   Nicotine/*analogs & derivatives. J Med Chem 1994 Oct 14;37(21):3542-53
5-isothiocyanonicotine  156577-11-6   Nicotine/*analogs & derivatives. Biochem Pharmacol 1994 Jun 1;47(11):1965-7
nicotine N-glucuronide  152306-59-7   *Glucuronates Nicotine/*analogs & derivatives Pyridinium Compounds. J Chromatogr 1993 Nov 17;621(1):49-53
2,3,3a,4,5,9b-hexahydro-1-methyl-1H-pyrrolo(3,2-h)isoquinoline  151330-10-8   *Isoquinolines Nicotine/*analogs & derivatives. J Med Chem 1993 Oct 29;36(22):3381-5
pseudooxynicotine  2055-23-4   *Butanones Nicotine/*analogs & derivatives. Ann N Y Acad Sci 1993 May 28;686:213-28
N-octanoylnornicotine  38854-10-3   Nicotine/*analogs & derivatives Aromatase Inhibitors. Endocr Res 1991;17(3-4):409-19
N'-methylnicotinium  17479-21-9   Nicotine/*analogs & derivatives. Pharmacol Biochem Behav 1991;38(4):843
N'-propylnornicotine  91907-45-8   Nicotine/*analogs & derivatives. J Chromatogr 1990;525(2):349
N-methyl-N'-oxonicotinium  105740-40-7   Nicotine/*analogs & derivatives. Drug Metab Dispos 1986;14(5):574
nicotinium molybdophosphate resin  104062-50-2   *Organometallic Compounds Nicotine/*analogs & derivatives Cation Exchange Resins Molybdenum. Bull Environ Contam Toxicol 1986;36(6):924
N-methylnicotinium  24554-05-0   *Pyridinium Compounds Nicotine/*analogs & derivatives. J Chromatogr 1985;347(3):405
N-methylnornicotinium  97729-48-1   Nicotine/*analogs & derivatives. Drug Metab Dispos 1985;13(3):348
3,4-dihydrometanicotine  3000-74-6   Nicotine/*analogs & derivatives. Klin Wochenschr 1984;62 suppl 2:92
nicotine imine  74710-78-4   Nicotine/*analogs & derivatives. Adv Exp Med Biol 1982;136B:1121
N-4-azido-2-nitrophenylnornicotine  74660-84-7 Pyridine, 3-(1-(4-azido-2-nitrophenyl)-2-pyrrolidinyl)-, (S)  Nicotine/*analogs & derivatives. Ann NY Acad Sci 1980;346:419
nicotine 1-N-oxide  63551-14-4 3-(1-methyl-2-pyrrolidinyl)pyridine, N-oxide  *Cyclic N-Oxides Nicotine/*analogs & derivatives. Appl Environ Microbiol 1979;38(5):836
N-methylnicoton  59551-30-3 2(1H)-Pyridinone, 1-methyl-3-(1-methyl-2-pyrrolidinyl)-, (S)  Nicotine/*analogs & derivatives. Arch Pharm (Weinheim) 309(3):197;1976
metanicotine  538-79-4   Nicotine/*analogs & derivatives. J Pharmacol Exp Ther 196(3):685;1976
N'-carbomethoxynornicotine  56078-08-1 1-Pyrrolidinecarboxylic acid, 2-(3-pyridinyl)-, methyl ester, (S)  Nicotine/*analogs & derivatives. J Nat Can Inst 54(5):1238;1975
nicotine monomethiodide  22083-76-7   Nicotine/*analogs & derivatives. Naunyn Schmiedebergs Arch Pharmacol 22(282):R69;1974
nornicotine  5746-86-1   Nicotine/*analogs & derivatives.
Pharma Action Insecticides 		Environ N-Nitroso Cpds Anal Forum W1 121k No. 14:227;1976; J Org Chem 41(21):3438;1976
cytisine  485-35-8 1,2,3,4,5,6-hexahydro-1,5-methano-8H- pyrido(1,2-a)(1,5)diazocin-8-one  *Alkaloids Azocines Quinolizines Nicotine/antagonists & inhibitors. Acta Polon Pharm 29(5):490;1972; Biokhimiia 43(7):1150;1978
5'-cyanonicotine  42459-12-1 2-Pyrrolidinecarbonitrile, 1-methyl-5-(3-pyridinyl)  Nicotine/*analogs & derivatives. J Biol Chem 248(8):2796;1973

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Sources: NLM Medical Subject Headings, NIH UMLS, Drugs@FDA, FDA AERS original data copyright United States Government. No endorsement implied. Last modified 6/6/2012
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