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| CAS No.: | 59-99-4 |
|---|---|
| Name: | Neostigmine |
| Molecular Structure: | |
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| Formula: | C12H19N2O2 |
| Molecular Weight: | 223.295 |
| Synonyms: | Prostigmin;Eustigmin;[3-(dimethylcarbamoyloxy)phenyl]-trimethylazanium;Neostigmine;Juvastigmin;Eustigmine;Prostigmine;Neostigminum;Vagostigmine;Intrastigmina;Syntostigmine; |
| Density: | 1.0718 (rough estimate) |
| Boiling Point: | 364.59°C (rough estimate) |
| Safety: | A deadly poison by ingestion, subcutaneous, intramuscular, intravenous, and intraperitoneal routes. When heated to decomposition it emits toxic fumes of NOx and NH3. See also CARBAMATES. |
| PSA: | 29.54000 |
| LogP: | 1.94370 |
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Chemistry
Chemistry informtion about Neostigmine (CAS NO.59-99-4) is:
IUPAC Name: [3-(Dimethylcarbamoyloxy)Phenyl]-Trimethylazanium
Synonyms: 3-[[(Dimethylamino)Carbonyl]Oxy]-N,N,N-Trimethylbenzenaminium ; Eustigmin ; Eustigmine ; Vagostigmine
MF: C12H19N2O2+
MW: 223.291460 g/mol
Following is the molecular structure of Neostigmine (CAS NO.59-99-4) is:
History
Neostigmine was first synthesized by Aeschlimann and Reinert in 1931.It is made by first reacting 3-dimethylaminophenol with N-dimethylcarbamoyl chloride, which forms a dimethylcarbamate. Next, that product is alkylated using dimethylsulfate, which forms neostigmine.
Uses
Neostigmine (CAS NO.59-99-4) is used to improve muscle tone in people with myasthenia gravis and routinely, in anesthesia at the end of an operation, to reverse the effects of non-depolarizing muscle relaxants such as rocuronium and vecuronium. It can also be used for urinary retention resulting from general anaesthesia and to treat curariform drug toxicity. Another indication for use is the Ogilvie syndrome which is a pseudoobstruction of the colon in critically ill patients. Historically, it has been used as a test for early pregnancy. In a non-pregnant female whose menstrual period is delayed, administration of neostigmine can provoke menstrual bleeding. Modern tests which rely on detecting hCG in urine have rendered this application obsolete.Though one of only two treatments available for myasthenia gravis this drug is no longer available to anyone using the Medicare Part D program.
Toxicity Data With Reference
| Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
|---|---|---|---|---|---|
| dog | LDLo | subcutaneous | 769ug/kg (0.769mg/kg) | behavioral: muscle contraction or spasticity) gastrointestinal: changes in structure or function of salivary glands 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) | 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. |
Safety Profile
A deadly poison by ingestion, subcutaneous, intramuscular, intravenous, and intraperitoneal routes. When heated to decomposition it emits toxic fumes of NOx and NH3. See also CARBAMATES.
Specification
Neostigmine is a parasympathomimetic, specifically, a reversible cholinesterase inhibitor.It is available under several trade names such as Prostigmin and Vagostigmin. By interfering with the breakdown of acetylcholine, it indirectly stimulates both nicotinic and muscarinic receptors. Unlike physostigmine, Neostigmine has a quarternary nitrogen; hence, it is more polar and does not enter the CNS. its effect on skeletal muscle is greater than that of physostigmine, and it can stimulate contractility before it paralyzes. Neostigmine has short duration of action, usually thirty minutes to two hours. Neostigmine binds to the anionic site of cholinesterase. The drug blocks the active site of acetylcholinesterase so the enzyme can no longer break down the acetylcholine molecules before they reach the postsynaptic membrane receptors. This allows for the threshold to be reached so a new impulse can be triggered in the next neuron. In myasthenia gravis there are too few acetylcholine receptors so with the acetylcholinesterase blocked, acetylcholine can bind to the few receptors and trigger a muscular contraction. It can induce generic occular side effects including: headache, brow pain, blurred vision, phacodinesis,pericorneal injection, congestive iritis, various allergic reactions, and rarely, retinal detachment and it will cause slowing of the heart rate (bradycardia), for this reason it is usually given along with a parasympatholytic drug such as atropine or glycopyrrolate.Gastrointestial symptoms occur earliest after ingestion and include anorexia, nausea and vomiting, abdominal cramps and diarrhea.