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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
- All
- Classifications
- Links to Resources
- Names & Synonyms
- Registry Numbers
- Structure Descriptors
- Toxicity
- Physical Properties
Classification Codes
- Autonomic Agents
- Cholinergic Agents
- Cholinesterase Inhibitors
- Enzyme Inhibitors
- Neurotransmitter Agents
- Parasympathomimetics
- Peripheral Nervous System Agents
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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-
- 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+1InChIKey
ALWKGYPQUAPLQC-UHFFFAOYSA-NSmiles
CN(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.