Nicotine
Title: Nicotine
CAS Registry Number: 54-11-5
CAS Name: 3-[(2S)-1-Methyl-2-pyrrolidinyl]pyridine
Additional Names: 1-methyl-2-(3-pyridyl)pyrrolidine; b-pyridyl-a-N-methylpyrrolidine
Trademarks: Habitrol (Novartis); Nicabate (GSK); Nicoderm CQ (GSK); Nicolan (Elan); Nicopatch (Fabre); Nicotinell (Novartis); NiQuitin CQ (GSK); Tabazur (Thžaplix)
Molecular Formula: C10H14N2
Molecular Weight: 162.23
Percent Composition: C 74.04%, H 8.70%, N 17.27%
Literature References: From the dried leaves of Nicotiana tabacum and N. rustica where it occurs to the extent of 2 to 8%, combined with citric and malic acids. Extraction procedure: Gattermann, Wieland, Laboratory Methods of Organic Chemistry (New York, 24th ed., 1937); Schwyzer, Die Fabrikation pharmazeutischer und chemisch-technischer Produkte (Berlin, 1931). Purification: Ratz, Monatsh. Chem. 26, 1241 (1905). Structure and synthesis: Pinner, Ber. 26, 294 (1893); Pictet, Rotschy, Ber. 37, 1225 (1904); Craig, J. Am. Chem. Soc. 55, 2854 (1933); M. Nakane, C. R. Hutchinson, J. Org. Chem. 43, 3922 (1978). Conformation in soln: T. P. Pitner et al., J. Am. Chem. Soc. 100, 246 (1978). HPLC determn in plasma: M. Harlharan et al., Clin. Chem. 34, 724 (1988). Toxicity data: R. B. Barlow, L. J. McLeod, Br. J. Pharmacol. 35, 161 (1969). Review and bibliography: Jackson, Chem. Rev. 29, 123 (1941). Review of pharmacology: R. W. Ryall in Neuropoisons: Their Pathophysiological Actions vol. 2, L. L. Simpson, D. R. Curtis, Eds. (Plenum, New York, 1974) pp 61-97; N. L. Benowitz, Annu. Rev. Med. 37, 21-32 (1986). Clinical trial of long-term efficacy in smoking cessation: T. Blondal et al., Br. Med. J. 318, 285 (1999). Review of clinical experience in Tourette syndrome: A. A. Silver et al., CNS Spectrums 4, 68-76 (1999).
Properties: Colorless to pale yellow, oily liq; very hygroscopic; turns brown on exposure to air or light. Acrid burning taste. Develops odor of pyridine. bp745 247° (partial decompn); bp17 123-125°. Volatile with steam. nD20 1.5282. d420 1.00925. [a]D20 -169.3° (neat); [a]5461 -204.1°. pK1 (15°) 6.16; pK2 10.96. pH of 0.05M soln: 10.2. Forms salts with almost any acid and double salts with many metals and acids. Absorption spectrum: Purvis, J. Chem. Soc. 97, 1035 (1910); Dobbie, Fox, ibid. 103, 1194 (1913). Optical rotatory properties: T. M. Lowry, W. V. Lloyd, J. Chem. Soc. 1929, 1771. Misc with water below 60°; on mixing nicotine with water the volume contracts. Very sol in alc, chloroform, ether, petr ether, kerosene, oils. Distribution of nicotine between water and petroleum oils: Norton, Ind. Eng. Chem., Ind. Ed. 32, 241 (1940). LD50 in mice (mg/kg): 0.3 i.v.; 9.5 i.p.; 230 orally (Barlow, McLeod).
Boiling point: bp745 247° (partial decompn); bp17 123-125°
pKa: pK1 (15°) 6.16; pK2 10.96
Optical Rotation: [a]D20 -169.3° (neat); [a]5461 -204.1°
Index of refraction: nD20 1.5282
Density: d420 1.00925
Toxicity data: LD50 in mice (mg/kg): 0.3 i.v.; 9.5 i.p.; 230 orally (Barlow, McLeod)
 
Derivative Type: Hydrochloride
CAS Registry Number: 21361-93-3
Molecular Formula: C10H14N2.HCl
Molecular Weight: 198.69
Percent Composition: C 60.45%, H 7.61%, N 14.10%, Cl 17.84%
Properties: Deliquesc crystals. [a]D20 +104° (p = 10).
Optical Rotation: [a]D20 +104° (p = 10)
 
Derivative Type: Dihydrochloride
CAS Registry Number: 6019-02-9
Molecular Formula: C10H14N2.2HCl
Molecular Weight: 235.15
Percent Composition: C 51.08%, H 6.86%, N 11.91%, Cl 30.15%
Properties: Deliquesc crystals, very sol in water and alcohol. Nearly insol in ether.
 
Derivative Type: Sulfate
CAS Registry Number: 65-30-5
Additional Names: Nicotine neutral sulfate
Molecular Formula: (C10H14N2)2.H2SO4
Molecular Weight: 422.54
Percent Composition: C 56.85%, H 7.16%, N 13.26%, S 7.59%, O 15.15%
Properties: Six-sided tablets. [a]D20 +88° (p = 70). Sol in water, alcohol.
Optical Rotation: [a]D20 +88° (p = 70)
 
Derivative Type: Bitartrate
CAS Registry Number: 65-31-6
Additional Names: Nicotine tartrate
Molecular Formula: C10H14N2.2C4H6O6
Molecular Weight: 462.41
Percent Composition: C 46.75%, H 5.67%, N 6.06%, O 41.52%
Properties: Dihydrate, crystals. mp 90°. [a]D20 +26° (c = 10). Very sol in water or alcohol.
Melting point: mp 90°
Optical Rotation: [a]D20 +26° (c = 10)
 
Derivative Type: Zinc chloride double salt monohydrate
Molecular Formula: C10H16Cl4N2Zn.H2O
Molecular Weight: 389.48
Percent Composition: C 30.84%, H 4.66%, Cl 36.41%, N 7.19%, Zn 16.79%, O 4.11%
Properties: Also with 4H2O. Very sol in water; sparingly sol in abs alcohol and ether.
 
Derivative Type: Salicylate
CAS Registry Number: 29790-52-1
Trademarks: Eudermol
Molecular Formula: C17H20N2O3
Molecular Weight: 300.35
Percent Composition: C 67.98%, H 6.71%, N 9.33%, O 15.98%
Properties: Six-sided plates, mp 118°. [a]D20 +13° (c = 9). Freely sol in water or alcohol.
Melting point: mp 118°
Optical Rotation: [a]D20 +13° (c = 9)
 
Derivative Type: Polacrilex
CAS Registry Number: 96055-45-7
Trademarks: Nicorette (GSK)
Literature References: Prepn: S. Lichtneckert et al., DE 2136119; eidem, US 3901248 (1972, 1975 both to AB Leo). Review of efficacy in smoking cessation: K. O. Fagerström, Prog. Clin. Biol. Res. 261, 109-128 (1988).
 
CAUTION: Nicotine can be absorbed through the alimentary canal, respiratory tract and intact skin. Potential symptoms of overexposure are nausea, salivation, abdominal pain, vomiting, diarrhea; headache, dizziness, auditory and visual disturbances; confusion, weakness, incoordination; paroxysmal atrial fibrillation; convulsions, dyspnea. Death may result from paralysis of respiratory muscles. See NIOSH Pocket Guide to Chemical Hazards (DHHS/NIOSH 97-140, 1997) p 224; Clinical Toxicology of Commercial Products, R. E. Gosselin et al., Eds. (Williams & Wilkins, Baltimore, 5th ed., 1984) Section III, pp 311-314.
Use: Insecticide; fumigant. In the U.S. a 40% soln of nicotine sulfate, Black Leaf 40, was the commonly used form. As a contact poison it is most effective as soap, i.e., as the laurate, oleate, or naphthenate. As a stomach poison a combination with bentonite has come into use.
Therap-Cat: Treatment of smoking withdrawal syndrome.
Therap-Cat-Vet: Ectoparasiticide. Has been used as an anthelmintic.

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