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DIALOG(R)File 304:The Merck Index Online(SM)/1996S1
(c) 1996,1996 Merck & Co. Inc. All rts. reserv.
06434
Monograph Name: Nicotine
CAS REGISTRY NUMBER: 54-11-5
MOLECULAR FORMULA: C10H14N2 MOLECULAR WEIGHT: 162.23
MOLECULAR COMPOSITION: C 74.03%, H 8.70%, N 17.27%
C.A. CHEMICAL NAME(s): (S)-3-(1-Methyl-2-pyrrolidinyl)pyridine
SYNONYMS:
1-methyl-2-(3-pyridyl)pyrrolidine; .beta. -pyridyl-.alpha.-N-methylpyrrol
idine
BRAND NAME (and COMPANY):
Habitrol (Ciba-Geigy); Nicabate (Marion Merrell Dow); Nicoderm (Alza;
Marion Merrell Dow); Nicolan (Elan); Nicopatch (Fabre); Nicotell TTS
(Ciba-Geigy); Nicotinell (Geigy); Tabazur (Theraplix)
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. Commercial
nicotine is entirely a byproduct of the tobacco industry. 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 through the
zinc chloride double salt: Ratz, Monatsh. 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). Recent synthesis: 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, Brit. 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, Ann. Rev. Med. 37, 21-32 (1986).
PHYSICAL DATA:
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 degrees (partial decompn); bp17 123-125 degrees. Volatile with
steam. nD20 1.5282. d420 1.0097. (.alpha.)D20 -169 degrees. pK1 (15
degrees ) 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). Misc with water below 60 degrees ; 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).
PHYSICAL DATA:
BOILING POINT: (745) 247 degrees (partial decompn); (17) 123-125 degrees
OPTICAL ROTATION: (.alpha. D): -169 degrees
REFRACTIVE INDEX: n(20/D) 1.5282
DENSITY: (20/4) 1.0097
LD50: LD50 in mice (mg/kg): 0.3 i.v.; 9.5 i.p.; 230 orally (Barlow,
McLeod)
DERIVATIVE INFORMATION:
SUBSTANCE: Nicotine Hydrochloride
DERIVATIVE CAS RN: 21361-93-3
DERIVATIVE MOL. FORMULA: C10H14N2.HCl
DERIVATIVE PHYSICAL DATA: deliquesc crystals. (.alpha.)D20 +104 degrees
(p = 10).
OPTICAL ROTATION: (.alpha. D): +104 degrees (p = 10)
SUBSTANCE: Nicotine Dihydrochloride
DERIVATIVE CAS RN: 6019-02-9
DERIVATIVE MOL. FORMULA: C10H14N2.2HCl
DERIVATIVE PHYSICAL DATA: deliquesc crystals, very sol in water and
alcohol. Nearly insol in ether.
SUBSTANCE: Nicotine Sulfate
DERIVATIVE CAS RN: 65-30-5
DERIVATIVE MOL. FORMULA: (C10H14N2)2.H2SO4
DERIVATIVE SYNONYMS: nicotine neutral sulfate
DERIVATIVE PHYSICAL DATA: six-sided tablets. (.alpha.)D20 +88 degrees (p
= 70). Sol in water, alcohol.
OPTICAL ROTATION: (.alpha. D): +88 degrees (p = 70)
SUBSTANCE: Nicotine Bitartrate
DERIVATIVE CAS RN: 65-31-6
DERIVATIVE MOL. FORMULA: C10H14N2.2C4H6O6
DERIVATIVE SYNONYMS: nicotine tartrate
DERIVATIVE PHYSICAL DATA: dihydrate, crystals. mp 90 degrees.
(.alpha.)D20 +26 degrees (c = 10). Very sol in water or alcohol.
MELTING POINT: 90 degrees
OPTICAL ROTATION: (.alpha. D): +26 degrees (c = 10)
SUBSTANCE: Nicotine Zinc chloride double salt monohydrate
DERIVATIVE MOL. FORMULA: C10H16Cl4N2Zn.H2O
DERIVATIVE PHYSICAL DATA: also with 4H2O. Very sol in water; sparingly
sol in abs alcohol and ether.
SUBSTANCE: Nicotine Salicylate
DERIVATIVE CAS RN: 29790-52-1
DERIVATIVE MOL. FORMULA: C17H20N2O3
DERIVATIVE BRAND NAME (COMPANY): Eudermol
DERIVATIVE PHYSICAL DATA: Six-sided plates, mp 118 degrees. (.alpha.)D20
+13 degrees (c = 9). Freely sol in water or alcohol.
MELTING POINT: 118 degrees
OPTICAL ROTATION: (.alpha. D): +13 degrees (c = 9)
SUBSTANCE: Nicotine Polacrilex
DERIVATIVE CAS RN: 96055-45-7
DERIVATIVE BRAND NAME (COMPANY): Nicorette (Lundbeck; Merrell Dow)
NOTES:
Caution: Nicotine can be absorbed from the alimentary canal, the
respiratory tract and intact skin. Percutaneous absorption of the free
alkaloid is much more rapid than the acid salts. Local effects due to
overexposure are burning sensation in mouth and throat, salivation,
nausea, abdominal pain, vomiting and ......... GI reactions are less
severe but do occur after cutaneous and respiratory exposure. The major
systemic effects are a transient stimulation and subsequent depression or
paralysis of the CNS. Symptoms include agitation, headache, sweating,
dizziness, auditory and visual disturbances, confusion, weakness and
incoordination. At first respirations are deep and rapid, the blood
pressure is high and the pulse is slow. CNS excitation may be evidenced by
tremors or clonic-tonic convulsions. As depression develops, the pupils
dilate, the blood pressure falls, and the pulse becomes rapid and
irregular. Faintness, prostration, cyanosis and dyspnea progress to
collapse. Death from paralysis of respiratory muscles usually follows
shortly after collapse. See: 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.
THERAPEUTIC CATEGORY: Treatment of smoking withdrawal syndrome.
THERAPEUTIC CATEGORY VET: Ectoparasiticide. Has been used as an
anthelmintic.
REFERENCE KEYS PRESENT: Conformation; Extraction; HPLC; Pharmacology;
Purification; Review; Structure; Synthesis; Toxicity
DATA KEYS PRESENT: Caution; Molecular weight; Uses; Therap. Cat.; Therap.
Cat. Vet.; Density; Boiling point; Refractive index; Optical rotation;
Lethal dose
DATA KEYS PRESENT IN DERIVATIVE: Melting point; Optical rotation
?t
Nicotine is Very sol in alcohol, chloroform, ether, petr ether,
kerosene, oils.
DIALOG(R)File 304:The Merck Index Online(SM)/1996S1
(c) 1996,1996 Merck & Co. Inc. All rts. reserv.
06434
Monograph Name: Nicotine
CAS REGISTRY NUMBER: 54-11-5
MOLECULAR FORMULA: C10H14N2 MOLECULAR WEIGHT: 162.23
MOLECULAR COMPOSITION: C 74.03%, H 8.70%, N 17.27%
C.A. CHEMICAL NAME(s): (S)-3-(1-Methyl-2-pyrrolidinyl)pyridine
SYNONYMS:
1-methyl-2-(3-pyridyl)pyrrolidine; .beta. -pyridyl-.alpha.-N-methylpyrrol
idine
BRAND NAME (and COMPANY):
Habitrol (Ciba-Geigy); Nicabate (Marion Merrell Dow); Nicoderm (Alza;
Marion Merrell Dow); Nicolan (Elan); Nicopatch (Fabre); Nicotell TTS
(Ciba-Geigy); Nicotinell (Geigy); Tabazur (Theraplix)
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. Commercial
nicotine is entirely a byproduct of the tobacco industry. 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 through the
zinc chloride double salt: Ratz, Monatsh. 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). Recent synthesis: 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, Brit. 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, Ann. Rev. Med. 37, 21-32 (1986).
PHYSICAL DATA:
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 degrees (partial decompn); bp17 123-125 degrees. Volatile with
steam. nD20 1.5282. d420 1.0097. (.alpha.)D20 -169 degrees. pK1 (15
degrees ) 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). Misc with water below 60 degrees ; 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).
PHYSICAL DATA:
BOILING POINT: (745) 247 degrees (partial decompn); (17) 123-125 degrees
OPTICAL ROTATION: (.alpha. D): -169 degrees
REFRACTIVE INDEX: n(20/D) 1.5282
DENSITY: (20/4) 1.0097
LD50: LD50 in mice (mg/kg): 0.3 i.v.; 9.5 i.p.; 230 orally (Barlow,
McLeod)
DERIVATIVE INFORMATION:
SUBSTANCE: Nicotine Hydrochloride
DERIVATIVE CAS RN: 21361-93-3
DERIVATIVE MOL. FORMULA: C10H14N2.HCl
DERIVATIVE PHYSICAL DATA: deliquesc crystals. (.alpha.)D20 +104 degrees
(p = 10).
OPTICAL ROTATION: (.alpha. D): +104 degrees (p = 10)
SUBSTANCE: Nicotine Dihydrochloride
DERIVATIVE CAS RN: 6019-02-9
DERIVATIVE MOL. FORMULA: C10H14N2.2HCl
DERIVATIVE PHYSICAL DATA: deliquesc crystals, very sol in water and
alcohol. Nearly insol in ether.
SUBSTANCE: Nicotine Sulfate
DERIVATIVE CAS RN: 65-30-5
DERIVATIVE MOL. FORMULA: (C10H14N2)2.H2SO4
DERIVATIVE SYNONYMS: nicotine neutral sulfate
DERIVATIVE PHYSICAL DATA: six-sided tablets. (.alpha.)D20 +88 degrees (p
= 70). Sol in water, alcohol.
OPTICAL ROTATION: (.alpha. D): +88 degrees (p = 70)
SUBSTANCE: Nicotine Bitartrate
DERIVATIVE CAS RN: 65-31-6
DERIVATIVE MOL. FORMULA: C10H14N2.2C4H6O6
DERIVATIVE SYNONYMS: nicotine tartrate
DERIVATIVE PHYSICAL DATA: dihydrate, crystals. mp 90 degrees.
(.alpha.)D20 +26 degrees (c = 10). Very sol in water or alcohol.
MELTING POINT: 90 degrees
OPTICAL ROTATION: (.alpha. D): +26 degrees (c = 10)
SUBSTANCE: Nicotine Zinc chloride double salt monohydrate
DERIVATIVE MOL. FORMULA: C10H16Cl4N2Zn.H2O
DERIVATIVE PHYSICAL DATA: also with 4H2O. Very sol in water; sparingly
sol in abs alcohol and ether.
SUBSTANCE: Nicotine Salicylate
DERIVATIVE CAS RN: 29790-52-1
DERIVATIVE MOL. FORMULA: C17H20N2O3
DERIVATIVE BRAND NAME (COMPANY): Eudermol
DERIVATIVE PHYSICAL DATA: Six-sided plates, mp 118 degrees. (.alpha.)D20
+13 degrees (c = 9). Freely sol in water or alcohol.
MELTING POINT: 118 degrees
OPTICAL ROTATION: (.alpha. D): +13 degrees (c = 9)
SUBSTANCE: Nicotine Polacrilex
DERIVATIVE CAS RN: 96055-45-7
DERIVATIVE BRAND NAME (COMPANY): Nicorette (Lundbeck; Merrell Dow)
NOTES:
Caution: Nicotine can be absorbed from the alimentary canal, the
respiratory tract and intact skin. Percutaneous absorption of the free
alkaloid is much more rapid than the acid salts. Local effects due to
overexposure are burning sensation in mouth and throat, salivation,
nausea, abdominal pain, vomiting and ......... GI reactions are less
severe but do occur after cutaneous and respiratory exposure. The major
systemic effects are a transient stimulation and subsequent depression or
paralysis of the CNS. Symptoms include agitation, headache, sweating,
dizziness, auditory and visual disturbances, confusion, weakness and
incoordination. At first respirations are deep and rapid, the blood
pressure is high and the pulse is slow. CNS excitation may be evidenced by
tremors or clonic-tonic convulsions. As depression develops, the pupils
dilate, the blood pressure falls, and the pulse becomes rapid and
irregular. Faintness, prostration, cyanosis and dyspnea progress to
collapse. Death from paralysis of respiratory muscles usually follows
shortly after collapse. See: 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.
THERAPEUTIC CATEGORY: Treatment of smoking withdrawal syndrome.
THERAPEUTIC CATEGORY VET: Ectoparasiticide. Has been used as an
anthelmintic.
REFERENCE KEYS PRESENT: Conformation; Extraction; HPLC; Pharmacology;
Purification; Review; Structure; Synthesis; Toxicity
DATA KEYS PRESENT: Caution; Molecular weight; Uses; Therap. Cat.; Therap.
Cat. Vet.; Density; Boiling point; Refractive index; Optical rotation;
Lethal dose
DATA KEYS PRESENT IN DERIVATIVE: Melting point; Optical rotation
?t
Nicotine is Very sol in alcohol, chloroform, ether, petr ether,
kerosene, oils.
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