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Chemistry

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Also known as: L-nicotine, 54-11-5, (-)-nicotine, (s)-nicotine, (s)-3-(1-methylpyrrolidin-2-yl)pyridine, Habitrol
Molecular Formula
C10H14N2
Molecular Weight
162.23  g/mol
InChI Key
SNICXCGAKADSCV-JTQLQIEISA-N
FDA UNII
6M3C89ZY6R

Nicotine
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.
Nicotine is a Cholinergic Nicotinic Agonist.
1 2D Structure

Nicotine

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
3-[(2S)-1-methylpyrrolidin-2-yl]pyridine
2.1.2 InChI
InChI=1S/C10H14N2/c1-12-7-3-5-10(12)9-4-2-6-11-8-9/h2,4,6,8,10H,3,5,7H2,1H3/t10-/m0/s1
2.1.3 InChI Key
SNICXCGAKADSCV-JTQLQIEISA-N
2.1.4 Canonical SMILES
CN1CCCC1C2=CN=CC=C2
2.1.5 Isomeric SMILES
CN1CCC[C@H]1C2=CN=CC=C2
2.2 Other Identifiers
2.2.1 UNII
6M3C89ZY6R
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Nicotine Bitartrate

2. Nicotine Tartrate

2.3.2 Depositor-Supplied Synonyms

1. L-nicotine

2. 54-11-5

3. (-)-nicotine

4. (s)-nicotine

5. (s)-3-(1-methylpyrrolidin-2-yl)pyridine

6. Habitrol

7. (s)-(-)-nicotine

8. Nicotrol

9. 3-[(2s)-1-methylpyrrolidin-2-yl]pyridine

10. Nicoderm

11. Nicoderm Cq

12. Fumetobac

13. Prostep

14. Nicotine Polacrilex

15. Flux Maag

16. Ortho N-4 Dust

17. Ortho N-5 Dust

18. Xl All Insecticide

19. Niagara P.a. Dust

20. Nicorette

21. Nicotina

22. Nikotyna

23. Destruxol Orchid Spray

24. 3-(n-methylpyrollidino)pyridine

25. 3-(n-methylpyrrolidino)pyridine

26. L-3-(1-methyl-2-pyrrolidyl)pyridine

27. L(-)-nicotine

28. (-)-3-(1-methyl-2-pyrrolidyl)pyridine

29. Ortho N-4 And N-5 Dusts

30. Nicocide

31. Nicotin

32. Tendust

33. Nico-dust

34. Emo-nik

35. Nico-fume

36. Nicotine Alkaloid

37. Mach-nic

38. Nic-sal

39. Nsc 5065

40. Beta-pyridyl-alpha-n-methylpyrrolidine

41. 3-(2-(n-methylpyrrolidinyl))pyridine

42. Pyridine, 3-(1-methyl-2-pyrrolidinyl)-, (s)-

43. 3-((2s)-1-methylpyrrolidin-2-yl)pyridine

44. 3-(1-methyl-2-pyrollidinyl)pyridine

45. (-)-3-(n-methylpyrrolidino)pyridine

46. S-(-)-nicotine

47. (s)-3-(1-methyl-2-pyrrolidinyl)pyridine

48. 3-(1-methyl-2-pyrrolidinyl)pyridine

49. (s)-3-(n-methylpyrrolidin-2-yl)pyridine

50. 6m3c89zy6r

51. Micotine

52. Chebi:17688

53. Pyridine, 3-((2s)-1-methyl-2-pyrrolidinyl)-

54. Pyridine, 3-[(2s)-1-methyl-2-pyrrolidinyl]-

55. 1-methyl-2-(3-pyridiyl)pyrrolidine

56. Nikotin [german]

57. Nikotyna [polish]

58. Nicotina [italian]

59. Dsstox_cid_930

60. Nicotrol Inhaler

61. Nicotrol Ns

62. Nicotine [for Single Use]

63. Nicotine-l (base)

64. 104062-50-2

65. Destruxol

66. Dsstox_rid_75874

67. Nicotine And Salts

68. Dsstox_gsid_20930

69. Pyrrolidine, 1-methyl-2-(3-pyridal)-

70. (-)-1-methyl-2-(3-pyridyl)pyrrolidine

71. Fumeto Bac

72. Caswell No. 597

73. Pyridine, 3-(tetrahydro-1-methylpyrrol-2-yl)

74. Nicabate

75. Nicotine [bsi:iso]

76. Nicotinum

77. Niquitin

78. Tabazur

79. Exodus

80. Nicotine-d Salicylate

81. Rcra Waste Number P075

82. Cas-54-11-5

83. Dl-tetrahydronicotyrine

84. Ent 3,424

85. Habitrol (tn)

86. Nicotine (usp)

87. Nicotine [iso]

88. Smr000059074

89. Ccris 1637

90. Nicotine (compounds Related To)

91. Hsdb 1107

92. Nicotine [usp:ban]

93. Einecs 200-193-3

94. Methyl-2-pyrrolidinyl)pyridine

95. Mfcd00006369

96. Un1654

97. Rcra Waste No. P075

98. Epa Pesticide Chemical Code 056702

99. Beta-pyridyl-alpha-n-methyl Pyrrolidine

100. Unii-6m3c89zy6r

101. Delta-nicotine

102. Nsc-5065

103. Ai3-03424

104. Nicotine Betadex

105. 1-methyl-2-(3-pyridal)-pyrrolidene

106. Nicotine S(-)

107. A-n-methylpyrrolidine

108. Campbell's Nico-soap

109. 3-n-methylpyrrolidine

110. R)-(+)-nicotine

111. A -n-methylpyrrolidine

112. Chembl3

113. 1uw6

114. Nicotine [hsdb]

115. Alpha-n-methylpyrrolidine

116. Nicotine [mi]

117. Nicotine [un1654]

118. Nicotine [vandf]

119. Nicotinum [hpus]

120. (s)-(-)--nicotine

121. Nicotine [mart.]

122. Bmse000105

123. Nicotine [who-dd]

124. (2s) 3-(1-methyl-pyrrolidin-2-yl)-pyridine

125. Ec 200-193-3

126. Nicotine Polacrilex [usan]

127. S-()-nicotine-pyridine-d4

128. Schembl20192

129. Mls001055457

130. Mls001335905

131. Bidd:gt0599

132. Nicotine [orange Book]

133. Gtpl2585

134. Nicotine [ep Monograph]

135. Dtxsid1020930

136. Nicotine [usp Monograph]

137. Bdbm82070

138. Hms2230h17

139. Hms3259e16

140. Nicotine [un1654] [poison]

141. Zinc391812

142. Hy-b0638

143. Nicotine 10 Microg/ml In Methanol

144. Nicotine Component Of Commit

145. Tox21_201814

146. Tox21_300174

147. Nicotine 100 Microg/ml In Methanol

148. Pdsp1_000113

149. Pdsp1_000465

150. Pdsp2_000463

151. Pdsp2_000555

152. 1-methyl-2-(3-pyridal)-pyrrolidine

153. Akos016843798

154. Nicotine 1000 Microg/ml In Methanol

155. Nicotine Component Of Nicorette

156. 3-(1-methyl-2-pyrrolidinyl)-pyridine

157. Ccg-204892

158. Cs-3999

159. Db00184

160. Nc00577

161. Sb12751

162. Sdccgmls-0066911.p001

163. Sdccgsbi-0050785.p004

164. Ncgc00090693-01

165. Ncgc00090693-02

166. Ncgc00090693-03

167. Ncgc00090693-04

168. Ncgc00090693-05

169. Ncgc00090693-06

170. Ncgc00090693-07

171. Ncgc00090693-08

172. Ncgc00090693-09

173. Ncgc00254095-01

174. Ncgc00259363-01

175. Pyrrolidine, 1-methyl-2-(3-pyridyl)-

176. (-)-nicotine, >=99% (gc), Liquid

177. Sbi-0050785.p003

178. Cas_29790-52-1

179. N0079

180. C00745

181. D03365

182. P10017

183. (-)-.beta.-pyridyl-.alpha.-n-methylpyrrolidine

184. Ab00694322_12

185. (-)-nicotine, Pestanal(r), Analytical Standard

186. 006n369

187. .beta.-pyridyl-.alpha.-n-methyl Pyrrolidine

188. 3-((2s)-1-methyl-2-pyrrolidinyl)pyridine

189. 3-[(1r)-1beta-methylpyrrolidine-2alpha-yl]pyridine

190. J-500021

191. Sr-05000001762-5

192. Brd-k05395900-322-02-1

193. Brd-k05395900-322-04-7

194. Pyridine, 3-(tetrahydro-1-methylpyrrol-2-yl), (s)-

195. Q28086552

196. Z1954805269

197. 434f7990-3240-4a43-acec-e6cc1e495fa0

198. (-)-nicotine Solution, 1.0 Mg/ml, Analytical Standard, For Drug Analysis

199. (s)-(-)-nicotine; 3-[(2s)-1-methyl-2-pyrrolidinyl] Pyridine

200. (-)-nicotine Solution, 100 Mug/ml In Acetonitrile, Pestanal(r), Analytical Standard

201. S(-)-nicotine Solution, 1.0 Mg/ml In Methanol, Ampule Of 1 Ml, Certified Reference Material

2.4 Create Date
2004-09-16
3 Chemical and Physical Properties
Molecular Weight 162.23 g/mol
Molecular Formula C10H14N2
XLogP31.2
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count2
Rotatable Bond Count1
Exact Mass162.115698455 g/mol
Monoisotopic Mass162.115698455 g/mol
Topological Polar Surface Area16.1 Ų
Heavy Atom Count12
Formal Charge0
Complexity147
Isotope Atom Count0
Defined Atom Stereocenter Count1
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Information
1 of 10  
Drug NameHabitrol
PubMed HealthNicotine
Drug ClassesCholinergic, Smoking Cessation Agent
Active IngredientNicotine
Dosage FormFilm, extended release
RouteTransdermal
Strength7mg/24hr; 21mg/24hr; 14mg/24hr
Market StatusOver the Counter
CompanyNovartis

2 of 10  
Drug NameNicoderm cq
PubMed HealthNicotine (Transdermal route)
Drug ClassesCholinergic, Smoking Cessation Agent
Active IngredientNicotine
Dosage FormFilm, extended release
RouteTransdermal
Strength7mg/24hr; 21mg/24hr; 14mg/24hr
Market StatusOver the Counter
CompanySanofi Aventis Us

3 of 10  
Drug NameNicotine
PubMed HealthNicotine
Drug ClassesCholinergic, Smoking Cessation Agent
Drug LabelNICOTROL Inhaler (nicotine inhalation system) consists of a mouthpiece and a plastic cartridge delivering 4 mg of nicotine from a porous plug containing 10 mg nicotine. The cartridge is inserted into the mouthpiece prior to use. Nicotine is a terti...
Active IngredientNicotine
Dosage FormFilm, extended release
RouteTransdermal
Strength7mg/24hr; 21mg/24hr; 14mg/24hr
Market StatusOver the Counter
CompanyAveva

4 of 10  
Drug NameNicotine polacrilex
PubMed HealthNicotine (Into the nose)
Drug ClassesSmoking Cessation Agent
Active IngredientNicotine polacrilex
Dosage FormTroche/lozenge; Gum, chewing
RouteBuccal; Oral
Strengtheq 4mg base; eq 2mg base
Market StatusOver the Counter
CompanyPerrigo R And D; Watson Labs; Ivax Sub Teva Pharms; Perrigo

5 of 10  
Drug NameNicotrol
Drug LabelNICOTROL Inhaler (nicotine inhalation system) consists of a mouthpiece and a plastic cartridge delivering 4 mg of nicotine from a porous plug containing 10 mg nicotine. The cartridge is inserted into the mouthpiece prior to use. Nicotine is a terti...
Active IngredientNicotine
Dosage FormSpray, metered; Inhalant
RouteOral; Nasal
Strength0.5mg/spray; 4mg/cartridge
Market StatusPrescription
CompanyPharmacia And Upjohn; Pfizer

6 of 10  
Drug NameHabitrol
PubMed HealthNicotine
Drug ClassesCholinergic, Smoking Cessation Agent
Active IngredientNicotine
Dosage FormFilm, extended release
RouteTransdermal
Strength7mg/24hr; 21mg/24hr; 14mg/24hr
Market StatusOver the Counter
CompanyNovartis

7 of 10  
Drug NameNicoderm cq
PubMed HealthNicotine (Transdermal route)
Drug ClassesCholinergic, Smoking Cessation Agent
Active IngredientNicotine
Dosage FormFilm, extended release
RouteTransdermal
Strength7mg/24hr; 21mg/24hr; 14mg/24hr
Market StatusOver the Counter
CompanySanofi Aventis Us

8 of 10  
Drug NameNicotine
PubMed HealthNicotine
Drug ClassesCholinergic, Smoking Cessation Agent
Drug LabelNICOTROL Inhaler (nicotine inhalation system) consists of a mouthpiece and a plastic cartridge delivering 4 mg of nicotine from a porous plug containing 10 mg nicotine. The cartridge is inserted into the mouthpiece prior to use. Nicotine is a terti...
Active IngredientNicotine
Dosage FormFilm, extended release
RouteTransdermal
Strength7mg/24hr; 21mg/24hr; 14mg/24hr
Market StatusOver the Counter
CompanyAveva

9 of 10  
Drug NameNicotine polacrilex
PubMed HealthNicotine (Into the nose)
Drug ClassesSmoking Cessation Agent
Active IngredientNicotine polacrilex
Dosage FormTroche/lozenge; Gum, chewing
RouteBuccal; Oral
Strengtheq 4mg base; eq 2mg base
Market StatusOver the Counter
CompanyPerrigo R And D; Watson Labs; Ivax Sub Teva Pharms; Perrigo

10 of 10  
Drug NameNicotrol
Drug LabelNICOTROL Inhaler (nicotine inhalation system) consists of a mouthpiece and a plastic cartridge delivering 4 mg of nicotine from a porous plug containing 10 mg nicotine. The cartridge is inserted into the mouthpiece prior to use. Nicotine is a terti...
Active IngredientNicotine
Dosage FormSpray, metered; Inhalant
RouteOral; Nasal
Strength0.5mg/spray; 4mg/cartridge
Market StatusPrescription
CompanyPharmacia And Upjohn; Pfizer

4.2 Therapeutic Uses

Ganglionic Stimulants; Nicotinic Agonists

National Library of Medicine's Medical Subject Headings online file (MeSH, 1999)


/Nicotine/ is indicated as an aid to smoking cessation for the relief of nicotine withdrawal symptoms. /Nicotine/ therapy should be used as a part of a comprehensive behavioral smoking cessation program. /Included in US product label/[US Natl Inst Health; DailyMed. Current Medication Information for Nicotrol

Nicotine] (August 2007). Available from, as of February 9, 2009: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=5011


In 2 children, use of nicotine polacrilex gum and haloperidol improved symptoms (eg, tics) of tourette's syndrome. /Not included in US product label/

Novak, K.M. (ed.). Drug Facts and Comparisons 59th Edition 2005. Wolters Kluwer Health. St. Louis, Missouri 2005., p. 1344


/EXPL THER/ Pyoderma gangrenosum is potentially a devastating and destructive disorder. There is no uniformly effective or specific therapy for pyoderma gangrenosum. Previous reports of nicotine therapy for pyoderma gangrenosum have suggested it to be efficacious. Unfortunately, previous reports were restricted by the use of commercially available preparations of nicotine, either as a gum or patch formulation. /The authors/ used topical nicotine 0.5% w/w cetamacrogol formula A cream that enables direct application onto the lesion, as well as dose and concentration variation. Two patients with pyoderma gangrenosum treated with topical nicotine 0.5% w/w cetamacrogol formula A cream are described here, both of whom had dramatic clinical resolution of their pyoderma gangrenosum.

PMID:15204166 Patel GK et al; J Dermatolog Treat 15 (2): 122-5 (2004)


For more Therapeutic Uses (Complete) data for NICOTINE (8 total), please visit the HSDB record page.


4.3 Drug Warning

Drugs of Abuse: Contraindicated during Breast-Feeding: Nicotine (smo