Neostigmine
Title: Neostigmine
CAS Registry Number: 59-99-4
CAS Name: 3-[[(Dimethylamino)carbonyl]oxy]-N,N,N-trimethylbenzenaminium
Additional Names: (3-dimethylcarbamoxyphenyl) trimethylammonium; synstigmin; proserine
Molecular Formula: [C12H19N2O2]+
Literature References: Synthesis: Aeschlimann, US 1905990 (1933 to Hoffmann-La Roche); Yanagisawa, JP 51 3071 (1951), C.A. 47, 4908g (1953). Pharmacology and pharmacokinetics: T. N. Calvey et al., Br. J. Clin. Pharmacol. 7, 149 (1979). Synergism of neostigmine toxicity by lithium: W. M. Davis, N. S. Hatoum, Toxicology 17, 1 (1980). Toxicity: L. O. Randall, G. Lehmann, J. Pharmacol. Exp. Ther. 99, 16 (1950). Comprehensive description: A. A. Al-Badr, M. Tariq, Anal. Profiles Drug Subs. 16, 403-444 (1987). Clinical evaluation in treatment of acute colonic pseudo-obstruction: R. J. Ponec et al., N. Engl. J. Med. 341, 137 (1999).
 
Derivative Type: Bromide
CAS Registry Number: 114-80-7
Trademarks: Juvastigmin (tabl.) (Dolder); Neoesserin (Ankerpharm); Neostigmin (tabl.) (Ferrosan); Normastigmin (tabl.) (Sigmapharm); Prostigmin (Roche)
Molecular Formula: C12H19BrN2O2
Molecular Weight: 303.20
Percent Composition: C 47.54%, H 6.32%, Br 26.35%, N 9.24%, O 10.55%
Properties: Crystals from alcohol + ether, dec ~167°. One gram dissolves in ~1 ml water. Sol in alc.
 
Derivative Type: Methyl sulfate
CAS Registry Number: 51-60-5
Trademarks: Intrastigmina (Lusofarmaco); Juvastigmin (amp.) (Dolder); Metastigmin (Star); Neostigmin (inj.) (Ferrosan); Normastigmin (amp.) (Sigmapharm); Prostigmin (amp.) (Roche); Stiglyn (Mallinckrodt Vet.)
Molecular Formula: C13H22N2O6S
Molecular Weight: 334.39
Percent Composition: C 46.69%, H 6.63%, N 8.38%, O 28.71%, S 9.59%
Properties: Crystals from alc, mp 142-145°. One gram dissolves in ~10 ml water, less sol in alcohol. LD50 in mice (mg/kg): 0.16 i.v.; 0.42 s.c.; 7.5 orally, (Randall, Lehmann).
Melting point: mp 142-145°
Toxicity data: LD50 in mice (mg/kg): 0.16 i.v.; 0.42 s.c.; 7.5 orally, (Randall, Lehmann)
 
Therap-Cat: Cholinergic; miotic; antidote (curare).
Therap-Cat-Vet: Cholinergic; antidote (curare).
Keywords: Antidote (Curare); Cholinergic; Miotic.

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