molecular formula C12H19N2O2+ B1678181 Neostigmine CAS No. 59-99-4

Neostigmine

Cat. No.: B1678181
CAS No.: 59-99-4
M. Wt: 223.29 g/mol
InChI Key: ALWKGYPQUAPLQC-UHFFFAOYSA-N
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Preparation Methods

Synthetic Routes and Reaction Conditions: Neostigmine can be synthesized through a multi-step process involving the reaction of dimethylcarbamoyl chloride with 3-dimethylaminophenol in the presence of a base such as sodium hydroxide. The reaction proceeds through the formation of an intermediate, which is then methylated to produce this compound .

Industrial Production Methods: In industrial settings, this compound is often produced as its methylsulfate salt. The process involves the reaction of this compound base with methylsulfuric acid, followed by crystallization and purification steps to obtain the final product .

Chemical Reactions Analysis

Types of Reactions: Neostigmine undergoes various chemical reactions, including hydrolysis, oxidation, and substitution. The hydrolysis of this compound results in the formation of 3-dimethylaminophenol and dimethylcarbamic acid .

Common Reagents and Conditions:

Major Products: The major products formed from these reactions include 3-dimethylaminophenol and dimethylcarbamic acid .

Scientific Research Applications

Neostigmine has a wide range of applications in scientific research:

Properties

IUPAC Name

[3-(dimethylcarbamoyloxy)phenyl]-trimethylazanium
Source PubChem
URL https://pubchem.ncbi.nlm.nih.gov
Description Data deposited in or computed by PubChem

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
Source PubChem
URL https://pubchem.ncbi.nlm.nih.gov
Description Data deposited in or computed by PubChem

InChI Key

ALWKGYPQUAPLQC-UHFFFAOYSA-N
Source PubChem
URL https://pubchem.ncbi.nlm.nih.gov
Description Data deposited in or computed by PubChem

Canonical SMILES

CN(C)C(=O)OC1=CC=CC(=C1)[N+](C)(C)C
Source PubChem
URL https://pubchem.ncbi.nlm.nih.gov
Description Data deposited in or computed by PubChem

Molecular Formula

C12H19N2O2+
Source PubChem
URL https://pubchem.ncbi.nlm.nih.gov
Description Data deposited in or computed by PubChem

Related CAS

114-80-7 (bromide), 51-60-5 (methyl sulfate)
Record name Neostigmine [BAN]
Source ChemIDplus
URL https://pubchem.ncbi.nlm.nih.gov/substance/?source=chemidplus&sourceid=0000059994
Description ChemIDplus is a free, web search system that provides access to the structure and nomenclature authority files used for the identification of chemical substances cited in National Library of Medicine (NLM) databases, including the TOXNET system.

DSSTOX Substance ID

DTXSID1023360
Record name Neostigmine
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Description DSSTox provides a high quality public chemistry resource for supporting improved predictive toxicology.

Molecular Weight

223.29 g/mol
Source PubChem
URL https://pubchem.ncbi.nlm.nih.gov
Description Data deposited in or computed by PubChem

Physical Description

Solid
Record name Neostigmine
Source Human Metabolome Database (HMDB)
URL http://www.hmdb.ca/metabolites/HMDB0015472
Description The Human Metabolome Database (HMDB) is a freely available electronic database containing detailed information about small molecule metabolites found in the human body.
Explanation HMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications.

Solubility

6.77e-02 g/L
Record name Neostigmine
Source Human Metabolome Database (HMDB)
URL http://www.hmdb.ca/metabolites/HMDB0015472
Description The Human Metabolome Database (HMDB) is a freely available electronic database containing detailed information about small molecule metabolites found in the human body.
Explanation HMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications.

Mechanism of Action

Neostigmine is a parasympathomimetic, specifically, a reversible cholinesterase inhibitor. The drug inhibits acetylcholinesterase which is responsible for the degredation of acetylcholine. So, with acetylcholinesterase inhibited, more acetylcholine is present By interfering with the breakdown of acetylcholine, neostigmine indirectly stimulates both nicotinic and muscarinic receptors which are involved in muscle contraction.. It does not cross the blood-brain barrier., ...PHARMACOLOGICAL EFFECTS OF ANTICHOLINESTERASE AGENTS ARE DUE PRIMARILY TO PREVENTION OF HYDROLYSIS OF ACH /ACETYLCHOLINE/ BY ACHE /ACETYLCHOLINESTERASE/ AT SITES OF CHOLINERGIC TRANSMISSION. TRANSMITTER THUS ACCUMULATES, AND THE ACTION OF ACH /ACETYLCHOLINESTERASE/ THAT IS LIBERATED BY CHOLINERGIC IMPULSES OR THAT LEAKS FROM THE NERVE ENDING IS ENHANCED., Neostigmine increased both miniature end-plate potential and end-plate potential amplitudes but did not affect quantal content in isolated frog sciatic nerve-Sartorius muscle prepn. This suggests that cholinesterase inhibition was the only effect., Long term (24-96 hr) treatment of a mouse-derived myogenic cell line (G8) with neostigmine markedly reduced binding of alpha-bungarotoxin (alpha-BuTx) to these cells. Protein synthesis in these cultures was markedly reduced and cell morphology degenerated. Myotubes maintained slightly hyperpolarized resting membrane potentials, and were able to respond to iontophoretic acetylcholine (Ach) application with overshooting action potentials. Degenerative changes at the neuromuscular junction associated with chronic neostigmine treatment in vivo are probably due to a direct action of the anticholinesterase on the muscle, rather than to altered intracleft ACh levels or to presynaptic effects of the anticholinesterase., The intraluminal probe mounted with 2 electrode-strain gauge pairs, 4 cm apart, was used to study the effect of a neutral interview, a stressful interview, a meal (478.7 cal) and neostigmine (0.5 mg, im) on the contractile electrical complex, continuous electrical response activity and their associated contractions in 17 normal subjects. Neostigmine resulted in an incr in contractile electric complex & continuous electric response activity indexes 5-10 and 25-30 min after the injection, respectively. Both the meal and neostigmine incr the percentage of propagated contractile electric complexes during all of the recording periods.
Record name Neostigmine
Source DrugBank
URL https://www.drugbank.ca/drugs/DB01400
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Record name NEOSTIGMINE
Source Hazardous Substances Data Bank (HSDB)
URL https://pubchem.ncbi.nlm.nih.gov/source/hsdb/3921
Description The Hazardous Substances Data Bank (HSDB) is a toxicology database that focuses on the toxicology of potentially hazardous chemicals. It provides information on human exposure, industrial hygiene, emergency handling procedures, environmental fate, regulatory requirements, nanomaterials, and related areas. The information in HSDB has been assessed by a Scientific Review Panel.

CAS No.

59-99-4
Record name Neostigmine
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URL https://commonchemistry.cas.org/detail?cas_rn=59-99-4
Description CAS Common Chemistry is an open community resource for accessing chemical information. Nearly 500,000 chemical substances from CAS REGISTRY cover areas of community interest, including common and frequently regulated chemicals, and those relevant to high school and undergraduate chemistry classes. This chemical information, curated by our expert scientists, is provided in alignment with our mission as a division of the American Chemical Society.
Explanation The data from CAS Common Chemistry is provided under a CC-BY-NC 4.0 license, unless otherwise stated.
Record name Neostigmine [BAN]
Source ChemIDplus
URL https://pubchem.ncbi.nlm.nih.gov/substance/?source=chemidplus&sourceid=0000059994
Description ChemIDplus is a free, web search system that provides access to the structure and nomenclature authority files used for the identification of chemical substances cited in National Library of Medicine (NLM) databases, including the TOXNET system.
Record name Neostigmine
Source DrugBank
URL https://www.drugbank.ca/drugs/DB01400
Description The DrugBank database is a unique bioinformatics and cheminformatics resource that combines detailed drug (i.e. chemical, pharmacological and pharmaceutical) data with comprehensive drug target (i.e. sequence, structure, and pathway) information.
Explanation Creative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode)
Record name Neostigmine
Source EPA DSSTox
URL https://comptox.epa.gov/dashboard/DTXSID1023360
Description DSSTox provides a high quality public chemistry resource for supporting improved predictive toxicology.
Record name NEOSTIGMINE
Source FDA Global Substance Registration System (GSRS)
URL https://gsrs.ncats.nih.gov/ginas/app/beta/substances/3982TWQ96G
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Record name NEOSTIGMINE
Source Hazardous Substances Data Bank (HSDB)
URL https://pubchem.ncbi.nlm.nih.gov/source/hsdb/3921
Description The Hazardous Substances Data Bank (HSDB) is a toxicology database that focuses on the toxicology of potentially hazardous chemicals. It provides information on human exposure, industrial hygiene, emergency handling procedures, environmental fate, regulatory requirements, nanomaterials, and related areas. The information in HSDB has been assessed by a Scientific Review Panel.
Record name Neostigmine
Source Human Metabolome Database (HMDB)
URL http://www.hmdb.ca/metabolites/HMDB0015472
Description The Human Metabolome Database (HMDB) is a freely available electronic database containing detailed information about small molecule metabolites found in the human body.
Explanation HMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications.

Retrosynthesis Analysis

AI-Powered Synthesis Planning: Our tool employs the Template_relevance Pistachio, Template_relevance Bkms_metabolic, Template_relevance Pistachio_ringbreaker, Template_relevance Reaxys, Template_relevance Reaxys_biocatalysis model, leveraging a vast database of chemical reactions to predict feasible synthetic routes.

One-Step Synthesis Focus: Specifically designed for one-step synthesis, it provides concise and direct routes for your target compounds, streamlining the synthesis process.

Accurate Predictions: Utilizing the extensive PISTACHIO, BKMS_METABOLIC, PISTACHIO_RINGBREAKER, REAXYS, REAXYS_BIOCATALYSIS database, our tool offers high-accuracy predictions, reflecting the latest in chemical research and data.

Strategy Settings

Precursor scoring Relevance Heuristic
Min. plausibility 0.01
Model Template_relevance
Template Set Pistachio/Bkms_metabolic/Pistachio_ringbreaker/Reaxys/Reaxys_biocatalysis
Top-N result to add to graph 6

Feasible Synthetic Routes

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