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Proserine

Proserine structure

CAS No:
51-60-5
Formula:
C12H19N2O2.CH3O4S
Chemical Name:
Proserine
Synonyms:
Benzenaminium,3-[[(dimethylamino)carbonyl]oxy]-N,N,N-trimethyl-,methyl sulfate (1:1);Ammonium,(m-hydroxyphenyl)trimethyl-,methyl sulfate,dimethylcarbamate;Benzenaminium,3-[[(dimethylamino)carbonyl]oxy]-N,N,N-trimethyl-,methyl sulfate;3-(Dimethylcarbamoxy)phenyl trimethylammonium methyl sulfate;Hodostin;(m-Hydroxyphenyl)trimethylammonium methyl sulfate dimethylcarbamate;(3-Hydroxyphenyl)trimethylammonium methyl sulfate dimethylcarbamic ester;Kirkstigmine methyl sulfate;Leostigmine methyl sulfate;Neoeserine methyl sulfate;Neostigmeth;Neostigmine methosulfate;Neostigmine methyl sulfate;Normastigmin;Philostigmin methyl sulfate;Polstigmine;Proserine methyl sulfate;Stigmanol methyl sulfate;Stigmosan methyl sulfate;Vagostigmine methyl sulfate;Neostigmine mono(methyl sulfate);Prostigmine methyl sulfate;(3-Dimethylcarbamoyloxyphenyl)trimethylammonium methyl sulfate;Eustigmin methyl sulfate;Prostigmin methyl sulfate;Synstigmine;Syntostigmin;Syntostigmin (injection);Vagostigmin;Proserine;GD 65;Stiglyn;Intrastigmina;Metastigmin;NSC 93753;3-[(Dimethylcarbamoyl)oxy]-N,N,N-trimethylanilinium methyl sulfate;Bloxiverz;59954-03-9
Categories:
Organic Chemistry > Amides

Description

Neostigmine methyl sulfate is a reversible inhibitor of acetylcholinesterase, can not cross the blood-brain barrier.

Neostigmine methyl sulfate is an arylammonium sulfate salt. It has a role as an EC 3.1.1.8 (cholinesterase) inhibitor.|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.

Proserine Basic Attributes

Molecular Weight：

334.39

Exact Mass：

334.119843

EC Number：

200-109-5

UNII：

98IMH7M386

NSC Number：

93753

DSSTox ID：

DTXSID40199003

HScode：

2924299090

Characteristics

PSA：

104

XLogP3：

2.11750

Appearance：

white powder

Melting Point：

142-145 °C

Boiling Point：

457ºC

Water Solubility：

H2O: 1g/10mL

Storage Conditions：

−20°C

Toxicity：

Subcutaneous-rat LD50: 0.334 mg/kg; oral-mouse LD50: 7.5 mg/kg

Flammability characteristics：

Combustible, decomposes toxic nitrogen oxides, sulfur oxides gas when burning

Safety Information

Packing level：

Ⅱ

Hazard category：

6.1(a)

Transport codes：

UN 2811 6.1/PG 2

wgk germany：

hazard class code：

28-36/37/38-42/43-26/27/28

safety instructions：

36-45-36/37/39-28A

RTECS Number：

CY1225000

Marks：

T+

Storage features：

Treasury is low temperature, ventilated, dry; stored separately from food raw materials

Stability/Shelf Life：

Stable at normal temperatures and pressures.

Precautionary statement(s)：

Missing Phrase - N15.00950417-P261-P284-P304 + P340-P305 + P351 + P338-P342 + P311

Hazard Statements：

H300-H315-H319-H334-H335

GHS Classification：

|Danger|H300 (43.3%): Fatal if swallowed [Danger Acute toxicity, oral]|P260, P261, P262, P264, P270, P271, P280, P284, P285, P301+P310, P302+P350, P302+P352, P304+P340, P304+P341, P305+P351+P338, P310, P312, P320, P321, P322, P330, P332+P313, P337+P313, P342+P311, P361, P362, P363, P403+P233, P405, and P501|Aggregated GHS information provided by 97 companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Toxicity

Toxicity class：

most toxic

Drug Information

MeSH：

Drugs that inhibit cholinesterases. The neurotransmitter ACETYLCHOLINE is rapidly hydrolyzed, and thereby inactivated, by cholinesterases. When cholinesterases are inhibited, the action of endogenously released acetylcholine at cholinergic synapses is potentiated. Cholinesterase inhibitors are widely used clinically for their potentiation of cholinergic inputs to the gastrointestinal tract and urinary bladder, the eye, and skeletal muscles; they are also used for their effects on the heart and the central nervous system. (See all compounds classified as Cholinesterase Inhibitors.)|Drugs that mimic the effects of parasympathetic nervous system activity. Included here are drugs that directly stimulate muscarinic receptors and drugs that potentiate cholinergic activity, usually by slowing the breakdown of acetylcholine (CHOLINESTERASE INHIBITORS). Drugs that stimulate both sympathetic and parasympathetic postganglionic neurons (GANGLIONIC STIMULANTS) are not included here. (See all compounds classified as Parasympathomimetics.)

MeSH Entry Terms：

Bromide, Neostigmine

Proserine Use and Manufacturing

Methods of Manufacturing

Preparation of neostigmine methylsulphate (General procedure)A 250 ml four neck round bottom flask was charged with 3-dimethylaminophenyl dimethylcarbamate obtained in the example 1, and acetone. Dimethyl sulphate (1.66 eq) was added drop wise to the flask at room temperature. The reaction mixture was stirred overnight, cooled to 5°C to 10°C for 2 hours, filtered and the filtrate was washed with isopropanol. The residue was dried under vacuum at room temperature to get crude neostigmine methylsulphate, which was purified by recrystallisation from isopropanol.Yield - 85percentNature - pale yellow oilHPLC Purity - 99.21percentA clean and dry 1000 ml 4 neck round bottom flask was charged with 3- aminophenyl dimethyl carbamate (50 gm), Calcium carbonate (50 gm) and acetone (300 ml). The reaction mixture was stirred for 5 min. Dimehtyl sulphate (128.3 gm) was added to the reaction mixture and stirred at 25

Uses

Cholinergic; miotic; antidote (curare)

Use Classification：

Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients|Animal Drugs -> FDA Approved Animal Drug Products (Green Book) -> Active Ingredients

Computed Properties

Molecular Weight:334.39
Hydrogen Bond Acceptor Count:6
Rotatable Bond Count:3
Exact Mass:334.11985760
Monoisotopic Mass:334.11985760
Topological Polar Surface Area:104
Heavy Atom Count:22
Complexity:337
Covalently-Bonded Unit Count:2
Compound Is Canonicalized:Yes

Drug Function and Efficacy

It can fully mimetic cholinergic effects by inhibiting the activity of cholinesterase, and can also directly stimulate nicotinic receptors (N2 receptors) on the motor end plates of skeletal muscles. It can promote gastric contraction and increase gastric acid secretion in gastrointestinal smooth muscles, and promote peristalsis of the small and large intestines, especially the colon, thereby preventing intestinal relaxation and promoting the downward movement of intestinal contents. It has a strong excitatory effect on skeletal muscles, but a weak effect on the central nervous system.

This ingredient has been used in drugs with the following functions (note: it does not mean that the ingredient itself has the following health functions)

Related Drugs

Neostigmine Methylsulfate Injection
Ingredients	The main ingredient of this product is neostigmine methylsulfate. Its chemical name is N,N,N-trimethyl-3-[(dimethylamino)formyloxy]anilinium methylsulfate. Molecular formula: C13H22N2O6S Molecular weight: 334.39
Indication	1. This product should not be used in combination with depolarizing muscle relaxants. 2. Certain drugs that can interfere with muscle transmission, such as quinidine, can weaken the effect of this product and should not be used together.
Specifications	1ml:0.5mg
Manufacturer	Zhejiang Xianju Pharmaceutical Co., Ltd.

Compound Naphthoxin Eye Drops
Ingredients	Naphazoline hydrochloride, neostigmine methyl sulfate.
Indication	If you are using other medicines, please consult your physician or pharmacist before using this product.
Specifications	10ml contains naphazoline hydrochloride 0.2mg, vitamin B122mg, vitamin B610mg, neostigmine methylsulfate 0.2mg, chlorpheniramine maleate 1mg, dipotassium glycyrrhizinate 10mg and taurine 10mg
Manufacturer	Shandong Bausch & Lomb Freda Pharmaceutical Co., Ltd.

Compound Aspartame Eye Drops
Ingredients	This product is a compound preparation, each 10 ml contains 78 mg of aspartic acid, 5 mg of vitamin B6, 10 mg of dipotassium glycyrrhizinate, 0.3 mg of naphazoline hydrochloride, 0.5 mg of neostigmine methylsulfate, and 1 mg of chlorpheniramine maleate. Excipients are: panthenol, menthol, benzalkonium chloride, and Tween-80.
Indication	Drug interactions may occur if used with other drugs. Please consult your doctor or pharmacist for details.
Specifications	15ml
Manufacturer	Mentholatum (CHINA) Pharmaceuticals Limited

See More Related Drugs

Registered Holders

ENALTEC LABS PRIVATE LTD

United States
Active
INDOCO REMEDIES LTD

United States
Active
MSN LABORATORIES PRIVATE LTD

United States
Active

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