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Substance Name: Neostigmine [BAN]
RN: 59-99-4
UNII: 3982TWQ96G
InChIKey: ALWKGYPQUAPLQC-UHFFFAOYSA-N

Note

  • A cholinesterase inhibitor used in the treatment of myasthenia gravis and to reverse the effects of muscle relaxants such as gallamine and tubocurarine. Neostigmine, unlike PHYSOSTIGMINE, does not cross the blood-brain barrier.

Molecular Formula

  • C12-H19-N2-O2

Molecular Weight

  • 223.2941
 

Classification Codes

  • Autonomic Agents
  • Cholinergic Agents
  • Cholinesterase Inhibitors
  • Enzyme Inhibitors
  • Neurotransmitter Agents
  • Parasympathomimetics
  • Peripheral Nervous System Agents

Names and Synonyms

Name of Substance

  • Neostigmine
  • Neostigmine [BAN]

MeSH Heading

  • Neostigmine

Synonyms

  • (m-Hydroxyphenyl)trimethylammonium dimethylcarbamate (ester)
  • 3-Trimethylammoniumphenyl N,N-dimethylcarbamate
  • Ammonium, (m-hydroxyphenyl)trimethyl-, dimethylcarbamate (ester)
  • Benzenaminium, 3-(((dimethylamino)carbonyl)oxy)-N,N,N-trimethyl-
  • BRN 3615946
  • CCRIS 3079
  • Eustigmin
  • Eustigmine
  • HSDB 3921
  • Intrastigmina
  • Juvastigmin
  • m-Trimethylammoniumphenyldimethylcarbamate
  • Neostigmin
  • Neostigmine
  • Neostigminum
  • Prostigmin
  • Prostigmine
  • UNII-3982TWQ96G
  • Vagostigmine

Systematic Names

  • Ammonium, (m-hydroxyphenyl)trimethyl-, dimethylcarbamate (ester)
  • Benzenaminium, 3-(((dimethylamino)carbonyl)oxy)-N,N,N-trimethyl-
  • Benzenaminium, 3-(((dimethylamino)carbonyl)oxy)-N,N,N-trimethyl- (9CI)
  • Neostigmine

Registry Numbers

CAS Registry Number

  • 59-99-4

FDA UNII

  • 3982TWQ96G

Related Registry Numbers

  • 114-80-7 (bromide)
  • 51-60-5 (methyl sulfate)

System Generated Number

  • 0000059994

Structure Descriptors

InChI

1S/C12H19N2O2/c1-13(2)12(15)16-11-8-6-7-10(9-11)14(3,4)5/h6-9H,1-5H3/q+1

InChIKey

ALWKGYPQUAPLQC-UHFFFAOYSA-N

Smiles

c1(cc(ccc1)[N+](C)(C)C)OC(N(C)C)=O

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LDLo subcutaneous 769ug/kg (0.769mg/kg) GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS

BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)

GASTROINTESTINAL: ULCERATION OR BLEEDING FROM LARGE INTESTINE
Federation Proceedings, Federation of American Societies for Experimental Biology. Vol. 5, Pg. 184, 1946.
mouse LD50 intraperitoneal 380ug/kg (0.38mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 192, Pg. 88, 1971.
mouse LD50 intravenous 160ug/kg (0.16mg/kg)   International Journal of Neuropharmacology. Vol. 8, Pg. 131, 1969.
mouse LD50 oral 12340ug/kg (12.34mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 117, Pg. 75, 1956.
mouse LD50 subcutaneous 280ug/kg (0.28mg/kg) BEHAVIORAL: TREMOR

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: CYANOSIS
Journal of Pharmacy and Pharmacology. Vol. 34, Pg. 603, 1982.
rabbit LD50 intramuscular 340ug/kg (0.34mg/kg)   Drug and Chemical Toxicology. Vol. 3, Pg. 319, 1980.
rabbit LD50 intravenous 250ug/kg (0.25mg/kg)   "Structure et Activite Pharmacodyanmique des Medicaments du Systeme Nerveux Vegetatif," Bovet, D., and F. Bovet-Nitti, New York, S. Karger, 1948Vol. -, Pg. 452, 1948.
rabbit LD50 subcutaneous 500ug/kg (0.5mg/kg)   "Structure et Activite Pharmacodyanmique des Medicaments du Systeme Nerveux Vegetatif," Bovet, D., and F. Bovet-Nitti, New York, S. Karger, 1948Vol. -, Pg. 452, 1948.
rat LD50 intravenous 225ug/kg (0.225mg/kg) LUNGS, THORAX, OR RESPIRATION: STRUCTURAL OR FUNCTIONAL CHANGE IN TRACHEA OR BRONCHI

SENSE ORGANS AND SPECIAL SENSES: CHROMODACYRORREA: EYE

PERIPHERAL NERVE AND SENSATION: FLACCID PARALYSIS WITHOUT ANESTHESIA (USUALLY NEUROMUSCULAR BLOCKAGE)
Archives Internationales de Pharmacodynamie et de Therapie. Vol. 101, Pg. 205, 1955.

Physical Properties

Physical Property Value Units Temp (deg C) Source
log P (octanol-water) -0.130 (none)   EST
Atmospheric OH Rate Constant 8.96E-12 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.