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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

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

CN(C)C(=O)Oc1cccc(c1)[N+](C)(C)C

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LDLo subcutaneous 769ug/kg (0.769mg/kg) GASTROINTESTINAL: ULCERATION OR BLEEDING FROM LARGE INTESTINE

BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)

GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS		 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) LUNGS, THORAX, OR RESPIRATION: CYANOSIS

BEHAVIORAL: TREMOR

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD		 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) PERIPHERAL NERVE AND SENSATION: FLACCID PARALYSIS WITHOUT ANESTHESIA (USUALLY NEUROMUSCULAR BLOCKAGE)

SENSE ORGANS AND SPECIAL SENSES: CHROMODACYRORREA: EYE

LUNGS, THORAX, OR RESPIRATION: STRUCTURAL OR FUNCTIONAL CHANGE IN TRACHEA OR BRONCHI		 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.