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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 (smoking): Shock, vomiting, diarrhea, rapid heart rate, restlessness; decreased milk production. (The Committee on Drugs strongly believes that nursing mothers should not ingest any compounds listed /drugs of abuse/ ... Not only are they hazardous to the nursing infant, but they are also detrimental to the physical and mental health of the mother ... No drug of abuse should be ingested by nursing mothers even though adverse reports are not in the literature.) /from Table 2/

Report of the American Academy of Pediatrics Committee on Drugs in Pediatrics 93 (1): 138 (1994)


Adverse local effects of nicotine polacrilex gum are related principally to the mechanical effects of gum chewing and include traumatic injury to the oral mucosa and/or teeth; irritation and/or tingling of the tongue, mouth, and throat; ulceration of the oral mucosa, including traumatic and aphthous ulcers; esophagitis; jaw-muscle ache; eructation (belching) resulting from unintentional swallowing of air during chewing; gum sticking to teeth; and unpleasant taste. A pruritic, maculopapular rash occurred periorally in at least one patient receiving nicotine polacrilex therapy. Some oral mucosal changes such as stomatitis, glossitis, gingivitis, pharyngitis, aphthous ulcers, and alterations in taste perception can occur during smoking cessation efforts with or without nicotine polacrilex therapy.

American Society of Health System Pharmacists; AHFS Drug Information 2009. Bethesda, MD. (2009)


Unlike the adverse effect profile observed with buccal nicotine polacrilex gum where adverse local effects are most common, local effects occur less commonly than systemic effects with buccal lozenges of the drug. Adverse local effects reported with nicotine polacrilex lozenges in a placebo-controlled study were limited to sore throat, which occurred in 3.6% of patients receiving the drug.

American Society of Health System Pharmacists; AHFS Drug Information 2009. Bethesda, MD. (2009)


Transient and localized pruritus, burning, or erythema on at least one occasion occurred in 35-54% of patients receiving transdermal nicotine therapy in controlled clinical trials. Pruritus or burning generally occurred just after application of a transdermal system and lasted no longer than 30 minutes. Local erythema, which generally resolved without treatment within 24 hours, was observed at least once following removal of a transdermal system in 7-25% of patients in clinical studies. Some degree of edema at the site of application was observed in 3-8% of patients using transdermal systems of nicotine.

American Society of Health System Pharmacists; AHFS Drug Information 2009. Bethesda, MD. (2009)


For more Drug Warnings (Complete) data for NICOTINE (32 total), please visit the HSDB record page.


4.4 Minimum/Potential Fatal Human Dose

The fatal adult dose is 60 mg.

Zenz, C., O.B. Dickerson, E.P. Horvath. Occupational Medicine. 3rd ed. St. Louis, MO., 1994, p. 641


4.5 Drug Indication

For the relief of nicotine withdrawal symptoms and as an aid to smoking cessation.


FDA Label


5 Pharmacology and Biochemistry
5.1 Pharmacology

Nicotine, the primary alkaloid in tobacco products binds stereo-selectively to nicotinic-cholinergic receptors on autonomic ganglia, the adrenal medulla, neuromuscular junctions and in the brain. Nicotine exerts two effects, a stimulant effect exerted at the locus ceruleus and a reward effect in the limbic system. Itranvenous administration of nicotine causes release of acetylcholine, norepinephrine, dopamine, serotonine, vasopressin, beta-endorphin and ACTH. Nicotine is a highly addictive substance. Nicotine also induces peripheral vasoconstriction, tachycardia and elevated blood pressure. Nicotine inhalers and patches are used to treat smoking withdrawl syndrome. Nicotine is classified as a stimulant of autonomic ganglia.


5.2 MeSH Pharmacological Classification

Ganglionic Stimulants

Agents that mimic neural transmission by stimulation of the nicotinic receptors on postganglionic autonomic neurons. Drugs that indirectly augment ganglionic transmission by increasing the release or slowing the breakdown of acetylcholine or by non-nicotinic effects on postganglionic neurons are not included here nor are the nonspecific cholinergic agonists. (See all compounds classified as Ganglionic Stimulants.)


Nicotinic Agonists

Drugs that bind to and activate nicotinic cholinergic receptors (RECEPTORS, NICOTINIC). Nicotinic agonists act at postganglionic nicotinic receptors, at neuroeffector junctions in the peripheral nervous system, and at nicotinic receptors in the central nervous system. Agents that function as neuromuscular depolarizing blocking agents are included here because they activate nicotinic receptors, although they are used clinically to block nicotinic transmission. (See all compounds classified as Nicotinic Agonists.)


Smoking Cessation Agents

Substances that facilitate the cessation of tobacco smoking. (See all compounds classified as Smoking Cessation Agents.)


5.3 FDA Pharmacological Classification
5.3.1 Active Moiety
NICOTINE
5.3.2 FDA UNII
6M3C89ZY6R
5.3.3 Pharmacological Classes
Nicotine [CS]; Cholinergic Nicotinic Agonist [EPC]
5.4 ATC Code

N07BA01

S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355


N - Nervous system

N07 - Other nervous system drugs

N07B - Drugs used in addictive disorders

N07BA - Drugs used in nicotine dependence

N07BA01 - Nicotine


5.5 Absorption, Distribution and Excretion

Absorption

Absorption of nicotine through the buccal mucosa is relatively slow and the high and rapid rise followed by the decline in nicotine arterial plasma concentrations seen with cigarette smoking are not achieved with the inhaler. About 10% of absorbed nicotine is excreted unchanged in urine.


Route of Elimination

About 10% of the nicotine absorbed is excreted unchanged in the urine.


Volume of Distribution

2 to 3 L/kg


Clearance

1.2 L/min [healthy adult smoker]


Nicotine is readily absorbed from respiratory tract, buccal mucous membranes, and skin. ... Both nicotine and its metabolites are rapidly eliminated by the kidneys. The rate of urinary excretion of nicotine is dependent upon pH of urine; excretion diminishes when urine is alkaline. Nicotine is also excreted in milk of lactating women who smoke. Milk of heavy smokers may contain 0.5 mg/L. ...Apparently the gastric absorption of nicotine from tobacco taken by mouth is delayed because of slowed gastric emptying, so that vomiting may remove much of the tobacco remaining in GI tract.

Hardman, J.G., L.E. Limbird, P.B. Molinoff, R.W. Ruddon, A.G. Goodman (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 9th ed. New York, NY: McGraw-Hill, 1996., p. 192


Although nicotine is absorbed rapidly over large section of GI tract, absorption of n-oxide is limited to area relatively high in intestine. n-Oxide is reduced to nicotine in gut and nicotine produced is absorbed low enough in GI tract to avoid first pass phenomenon.

The Chemical Society. Foreign Compound Metabolism in Mammals Volume 3. London: The Chemical Society, 1975., p. 156


Free alkaloid is absorbed rapidly through skin and gastrointestinal and respiratory tracts, but absorption of its acid salts is less complete.

Clayton, G.D., F.E. Clayton (eds.) Patty's Industrial Hygiene and Toxicology. Volumes 2A, 2B, 2C, 2D, 2E, 2F: Toxicology. 4th ed. New York, NY: John Wiley & Sons Inc., 1993-1994., p. 3378


The pharmacokinetics of various commercially available dosage forms of nicotine and nicotine polacrilex differ principally in the rate, site, and extent of absorption of the drug, with absorption being most rapid with intranasal administration of the spray (peak concentrations achieved within 4-15 minutes), followed by chewing the gum (peaks within 25-30 minutes) or oral inhalation (peaks within 15-30 minutes), and then being substantially slower with the transdermal systems (peaks within 2-10 hours). Plasma nicotine concentrations fluctuate least with the transdermal systems and are least like those produced by cigarette smoking, whereas those produced by intranasal administration mimic those of cigarette smoking most closely, although the role of their rise is still somewhat slower and peaks achieved generally are lower than with cigarettes.

American Society of Health System Pharmacists; AHFS Drug Information 2009. Bethesda, MD. (2009)


For more Absorption, Distribution and Excretion (Complete) data for NICOTINE (16 total), please visit the HSDB record page.


5.6 Metabolism/Metabolites

Primarily hepatic, cotinine is the primary metabolite.


Metabolism of nicotine is qualitatively similar following buccal absorption from nicotine polacrilex gum or nicotine oral inhalation and from oral inhalation of cigarette smoke, and reportedly following application of nicotine transdermal systems. Although the exact metabolic fate of nicotine is not clearly established, the drug is metabolized extensively to more than 20 metabolites, but principally in the liver via oxidation of the alpha-carbon and N-oxidation of the pyrrolidine ring to cotinine and nicotine-1'-N-oxide, respectively. These metabolites are not pharmacologically active in humans at blood concentrations attained during cigarette smoking; however, cotinine has been reported to be pharmacologically active in animals, but its potency at equivalent molar concentrations is substantially less than that of nicotine. ... Nicotine may also be metabolized to a lesser extent in the kidneys and lungs.

American Society of Health System Pharmacists; AHFS Drug Information 2009. Bethesda, MD. (2009)


Nicotine-1'-N-oxide is reduced to nicotine by bacterial flora in the large intestine via an N-oxide reductase system and subsequently undergoes enterohepatic circulation and repeat metabolism in the liver.

American Society of Health System Pharmacists; AHFS Drug Information 2009. Bethesda, MD. (2009)


Toxicologically, it is of interest that /the microsomal flavin-containing monooxygenase/ is responsible for the oxidation of nicotine to nicotine-1'-N-oxide, whereas the oxidation of nicotine to cotinine is catalyzed by two enzymes acting in sequence: P450 and a soluble aldehyde dehydrogenase. Thus, nicotine is metabolized by two different routes, the relative contributions of which may vary with both the extrinsic and intrinsic factors.

Hodgson E, Levi PE; A Textbook of Modern Toxicology 2nd ed p.74 (1997)


In vitro studies with rabbit liver microsomes, /NADPH/, and O2, indicated that metabolism of nicotine proceeded through hydroxylation to 5-(3'-pyridyl)-n-methylpyrrolidine-2-ol; oxidation to cotinine; and deamidation of cotinine to 4-(3'-pyridyl)-4-methylamino-butyric acid. No carbon dioxide was observed.

Menzie, C.M. Metabolism of Pesticides. U.S. Department of the Interior, Bureau of Sport Fisheries and Wildlife, Publication 127. Washington, DC: U.S. Government Printing Office, 1969., p. 258


For more Metabolism/Metabolites (Complete) data for NICOTINE (11 total), please visit the HSDB record page.


Nicotine has known thirdhand smoke metabolites that include 2'-Hydroxynicotine, 3-Pyridilacetic Acid, 3-Vinylpyridine, 4-(3-pyridil)-butanoic Acid, 4-(3-pyridyl)-3-butenoic acid, 4-(Methylamino)-1-(3-pyridyl)-1-butanone, 4-(methylnitrosamino)-4-(3-pyridyl) butanal (NNA), 4-Oxo-4-(3-pyridyl)-N-methylbutanamide, 4-Oxo-4-(3-pyridyl)-butanamide, 4-Oxo-4-(3-pyridyl)-butanoic acid (OPBA), 4-hydroxy-4-(3-pyridyl)-butanoic acid (HPBA), 5'-Hydroxy-beta-Nicotyrine, 5'-Hydroxycotinine, 5-(3-pyridyl)-tetrahydrofuran-2-one, Cotinine, Cotinine Methonium Ion, Cotinine N-glucoronide, Cotinine N-oxide, N'- Hydroxymethyl- norcotinine, Nicotine Isomethonium Ion, Nicotine N'oxide, Nicotine N-glucoronide, Nicotine-delta 1' (5') Iminium Ion, Norcotinine, Nornicotine, Trans-3'-Hydroxycotinine, Trans-3'-Hydroxycotinine O glucoronide, and iso-NNAC.

S81 | THSTPS | Thirdhand Smoke Specific Metabolites | DOI:10.5281/zenodo.5394629


Nicotine has known human metabolites that include (S)-Nicotine iminium ion, 2'-Hydroxynicotine, and Nornicotine.

S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560


5.7 Biological Half-Life

Cotinine has a half life of 15-20 hours, while nicotine has a half life of 1-3 hours


Plasma concentrations of nicotine appear to decline in a biphasic manner. The half-life of nicotine in the initial phase is reportedly about 2-3 minutes and the half-life in the terminal phase reportedly averages about 2 hours (range: 1-4 hours).

American Society of Health System Pharmacists; AHFS Drug Information 2009. Bethesda, MD. (2009)


Following removal of a transdermal system of nicotine, plasma nicotine concentrations decline with an apparent half-life averaging 3-6 hours, which exceeds that of nicotine given iv; the slow decline in plasma nicotine concentrations following removal of a transdermal system appears to result from continued absorption of residual drug in the skin.

American Society of Health System Pharmacists; AHFS Drug Information 2009. Bethesda, MD. (2009)


Cotinine is the major metabolite /of nicotine/ and has a plasma half-life of about 10-40 hours.

American Society of Health System Pharmacists; AHFS Drug Information 2009. Bethesda, MD. (2009)


... Following the administration of 0.1 mg nicotine/kg (labeled in 2-(14)C-pyrrolidone) to rats ... radioactivity due to nicotine and cotinine was detected in substantial amounts in plasma samples. Nicotine disappearance was biexponential, with an elimination half life of 1.0 hour. Cotinine appeared as the major metabolite in plasma and had elimination half life of 5.2 hours.

PMID:3667778 Kyerematen GA et al; J Chromatogr 419: 191-203 (1987)


5.8 Mechanism of Action

Nicotine is a stimulant drug that acts as an agonist at nicotinic acetylcholine receptors. These are ionotropic receptors composed up of five homomeric or heteromeric subunits. In the brain, nicotine binds to nicotinic acetylcholine receptors on dopaminergic neurons in the cortico-limbic pathways. This causes the channel to open and allow conductance of multiple cations including sodium, calcium, and potassium. This leads to depolarization, which activates voltage-gated calcium channels and allows more calcium to enter the axon terminal. Calcium stimulates vesicle trafficking towards the plasma membrane and the release of dopamine into the synapse. Dopamine binding to its receptors is responsible the euphoric and addictive properties of nicotine. Nicotine also binds to nicotinic acetylcholine receptors on the chromaffin cells in the adrenal medulla. Binding opens the ion channel allowing influx of sodium, causing depolarization of the cell, which activates voltage-gated calcium channels. Calcium triggers the release of epinephrine from intracellular vesicles into the bloodstream, which causes vasoconstriction, increased blood pressure, increased heart rate, and increased blood sugar.


Nicotine is a ganglionic (nicotinic) cholinergic-receptor agonist. The pharmacologic actions of nicotine are complex and include a variety of effects mediated by stereospecific binding to receptors in autonomic ganglia, the adrenal medulla, the neuromuscular junction, and the brain.

American Society of Health System Pharmacists; AHFS Drug Information 2009. Bethesda, MD. (2009)


The principal pharmacologic effect of small doses of nicotine is initial, transient stimulation of autonomic ganglia; large doses or prolonged neuronal receptor exposure to nicotine results in subsequent persistent depression of receptor activity. Although nicotine has similar dose-related effects at the myoneural (neuromuscular) junction, rapidly developing skeletal muscle paralysis obscures the stimulant phase. The muscle-relaxant properties of nicotine may be mediated through stimulation of Renshaw cells and pulmonary afferent nerves, which results in inhibition of skeletal muscle motor activity; such relaxant effects may contribute to the behavior-reinforcing effects of the drug. Small doses of nicotine directly stimulate sympathetic ganglia and facilitate neurotransmission; however, large doses produce initial ganglionic stimulation, which is quickly followed by inhibition of neurotransmission.

American Society of Health System Pharmacists; AHFS Drug Information 2009. Bethesda, MD. (2009)


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04-Jan-2022
30-May-2025
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DRUG PRODUCT COMPOSITIONS

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DOSAGE - GUM, CHEWING;BUCCAL - EQ 2MG BASE

USFDA APPLICATION NUMBER - 18612

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DOSAGE - GUM, CHEWING;BUCCAL - EQ 4MG BASE

USFDA APPLICATION NUMBER - 20066

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DOSAGE - FILM, EXTENDED RELEASE;TRANSDERMAL -...DOSAGE - FILM, EXTENDED RELEASE;TRANSDERMAL - 14MG/24HR

USFDA APPLICATION NUMBER - 20076

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DOSAGE - FILM, EXTENDED RELEASE;TRANSDERMAL -...DOSAGE - FILM, EXTENDED RELEASE;TRANSDERMAL - 21MG/24HR

USFDA APPLICATION NUMBER - 20076

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DOSAGE - FILM, EXTENDED RELEASE;TRANSDERMAL -...DOSAGE - FILM, EXTENDED RELEASE;TRANSDERMAL - 7MG/24HR

USFDA APPLICATION NUMBER - 20076

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DOSAGE - INHALANT;ORAL - 4MG/CARTRIDGE

USFDA APPLICATION NUMBER - 20714

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DOSAGE - TROCHE/LOZENGE;ORAL - EQ 2MG BASE

USFDA APPLICATION NUMBER - 21330

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DOSAGE - TROCHE/LOZENGE;ORAL - EQ 4MG BASE

USFDA APPLICATION NUMBER - 21330

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ABOUT THIS PAGE

Looking for 54-11-5 / Nicotine API manufacturers, exporters & distributors?

Nicotine manufacturers, exporters & distributors 1

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PharmaCompass offers a list of Nicotine API manufacturers, exporters & distributors, which can be sorted by GMP, USDMF, JDMF, KDMF, CEP (COS), WC, Price,and more, enabling you to easily find the right Nicotine manufacturer or Nicotine supplier for your needs.

Send us enquiries for free, and we will assist you in establishing a direct connection with your preferred Nicotine manufacturer or Nicotine supplier.

PharmaCompass also assists you with knowing the Nicotine API Price utilized in the formulation of products. Nicotine API Price is not always fixed or binding as the Nicotine Price is obtained through a variety of data sources. The Nicotine Price can also vary due to multiple factors, including market conditions, regulatory modifications, or negotiated pricing deals.

API | Excipient name

Nicotine

Synonyms

L-nicotine, 54-11-5, (-)-nicotine, (s)-nicotine, (s)-3-(1-methylpyrrolidin-2-yl)pyridine, Habitrol

Cas Number

54-11-5

Unique Ingredient Identifier (UNII)

6M3C89ZY6R

About 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 Manufacturers

A Nicotine manufacturer is defined as any person or entity involved in the manufacture, preparation, processing, compounding or propagation of Nicotine, including repackagers and relabelers. The FDA regulates Nicotine manufacturers to ensure that their products comply with relevant laws and regulations and are safe and effective to use. Nicotine API Manufacturers are required to adhere to Good Manufacturing Practices (GMP) to ensure that their products are consistently manufactured to meet established quality criteria.

click here to find a list of Nicotine manufacturers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PhamaCompass.

Nicotine Suppliers

A Nicotine supplier is an individual or a company that provides Nicotine active pharmaceutical ingredient (API) or Nicotine finished formulations upon request. The Nicotine suppliers may include Nicotine API manufacturers, exporters, distributors and traders.

click here to find a list of Nicotine suppliers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PharmaCompass.

Nicotine USDMF

A Nicotine DMF (Drug Master File) is a document detailing the whole manufacturing process of Nicotine active pharmaceutical ingredient (API) in detail. Different forms of Nicotine DMFs exist exist since differing nations have different regulations, such as Nicotine USDMF, ASMF (EDMF), JDMF, CDMF, etc.

A Nicotine DMF submitted to regulatory agencies in the US is known as a USDMF. Nicotine USDMF includes data on Nicotine's chemical properties, information on the facilities and procedures used, and details about packaging and storage. The Nicotine USDMF is kept confidential to protect the manufacturer’s intellectual property.

click here to find a list of Nicotine suppliers with USDMF on PharmaCompass.

Nicotine JDMF

The Pharmaceuticals and Medical Devices Agency (PMDA) established the Japan Drug Master File (JDMF), also known as the Master File (MF), to permit Japanese and foreign manufacturers of drug substances, intermediates, excipients, raw materials, and packaging materials (‘Products’) to voluntarily register confidential information about the production and management of their products in Japan.

The Nicotine Drug Master File in Japan (Nicotine JDMF) empowers Nicotine API manufacturers to present comprehensive information (e.g., production methods, data, etc.) to the review authority, i.e., PMDA (Pharmaceuticals & Medical Devices Agency).

PMDA reviews the Nicotine JDMF during the approval evaluation for pharmaceutical products. At the time of Nicotine JDMF registration, PMDA checks if the format is accurate, if the necessary items have been included (application), and if data has been attached.

click here to find a list of Nicotine suppliers with JDMF on PharmaCompass.

Nicotine CEP

A Nicotine CEP of the European Pharmacopoeia monograph is often referred to as a Nicotine Certificate of Suitability (COS). The purpose of a Nicotine CEP is to show that the European Pharmacopoeia monograph adequately controls the purity of Nicotine EP produced by a given manufacturer. Suppliers of raw materials can prove the suitability of Nicotine to their clients by showing that a Nicotine CEP has been issued for it. The manufacturer submits a Nicotine CEP (COS) as part of the market authorization procedure, and it takes on the role of a Nicotine CEP holder for the record. Additionally, the data presented in the Nicotine CEP (COS) is managed confidentially and offers a centralized system acknowledged by numerous nations, exactly like the Nicotine DMF.

A Nicotine CEP (COS) is recognised by all 36 nations that make up the European Pharmacopoeia Convention. Nicotine CEPs may be accepted in nations that are not members of the Ph. Eur. at the discretion of the authorities there.

click here to find a list of Nicotine suppliers with CEP (COS) on PharmaCompass.

Nicotine WC

A Nicotine written confirmation (Nicotine WC) is an official document issued by a regulatory agency to a Nicotine manufacturer, verifying that the manufacturing facility of a Nicotine active pharmaceutical ingredient (API) adheres to the Good Manufacturing Practices (GMP) regulations of the importing country. When exporting Nicotine APIs or Nicotine finished pharmaceutical products to another nation, regulatory agencies frequently require a Nicotine WC (written confirmation) as part of the regulatory process.

click here to find a list of Nicotine suppliers with Written Confirmation (WC) on PharmaCompass.

Nicotine NDC

National Drug Code is a comprehensive database maintained by the FDA that contains information on all drugs marketed in the US. This directory includes information about finished drug products, unfinished drug products, and compounded drug products, including those containing Nicotine as an active pharmaceutical ingredient (API).

Finished drug products

The FDA updates the NDC directory daily. The NDC numbers for Nicotine API and other APIs are published in this directory by the FDA.

Unfinished drugs

The NDC unfinished drugs database includes product listing information submitted for all unfinished drugs, such as active pharmaceutical ingredients (APIs), drugs intended for further processing and bulk drug substances for compounding.

Pharmaceutical companies that manufacture Nicotine as an active pharmaceutical ingredient (API) must furnish the FDA with an updated record of all drugs that they produce, prepare, propagate, compound, or process for commercial distribution in the US at their facilities.

Compounded drug products

The NDC directory also contains data on finished compounded human drug products that contain Nicotine and are produced by outsourcing facilities. While these outsourcing facilities are not mandated to assign a Nicotine NDC to their finished compounded human drug products, they may choose to do so.

click here to find a list of Nicotine suppliers with NDC on PharmaCompass.

Nicotine GMP

Nicotine Active pharmaceutical ingredient (API) is produced in GMP-certified manufacturing facility.

GMP stands for Good Manufacturing Practices, which is a system used in the pharmaceutical industry to make sure that goods are regularly produced and monitored in accordance with quality standards. The FDA’s current Good Manufacturing Practices requirements are referred to as cGMP or current GMP which indicates that the company follows the most recent GMP specifications. The World Health Organization (WHO) has its own set of GMP guidelines, called the WHO GMP. Different countries can also set their own guidelines for GMP like China (Chinese GMP) or the EU (EU GMP).

PharmaCompass offers a list of Nicotine GMP manufacturers, exporters & distributors, which can be sorted by USDMF, JDMF, KDMF, CEP (COS), WC, API price, and more, enabling you to easily find the right Nicotine GMP manufacturer or Nicotine GMP API supplier for your needs.

Nicotine CoA

A Nicotine CoA (Certificate of Analysis) is a formal document that attests to Nicotine's compliance with Nicotine specifications and serves as a tool for batch-level quality control.

Nicotine CoA mostly includes findings from lab analyses of a specific batch. For each Nicotine CoA document that a company creates, the USFDA specifies specific requirements, such as supplier information, material identification, transportation data, evidence of conformity and signature data.

Nicotine may be tested according to a variety of international standards, such as European Pharmacopoeia (Nicotine EP), Nicotine JP (Japanese Pharmacopeia) and the US Pharmacopoeia (Nicotine USP).

Inform the supplier about your product requirements, specifying if you need a product with particular monograph like EP (Ph. Eur.), USP, JP, BP, or any other quality. In addition, clarify whether you need hydrochloride (HCl), anhydricum, base, micronisatum or a specific level of purity. To find reputable suppliers, utilize the filters and select those certified by GMP, FDA, or any other certification as per your requirement.
For your convenience, we have listed synonyms and CAS numbers to help you find the best supplier. The use of synonyms and CAS numbers can be helpful in identifying potential suppliers, but it is crucial to note that they might not always indicate the exact same product. It is important to confirm the product details with the supplier before making a purchase to ensure that it meets your requirements.
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