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Carbachol

CAS No.
51-83-2
Chemical Name:
Carbachol
Synonyms
Doryl;Moryl;tl457;Carba;Lentin;TL 457;Carbyl;carbach;Jestryl;Lentine
CBNumber:
CB1685095
Molecular Formula:
C6H15N2O2.Cl
Molecular Weight:
182.65
MDL Number:
MFCD00012011
MOL File:
51-83-2.mol
MSDS File:
SDS
Last updated:2024-03-14 15:18:25

Carbachol Properties

Melting point 210 °C (dec.) (lit.)
Density 1.2798 (rough estimate)
refractive index 1.5557 (estimate)
storage temp. Desiccate at RT
solubility H2O: 1 g/mL
form crystalline
pka pKa 4.8 (Uncertain)
color white
Water Solubility 1.0 G/ML
Sensitive Hygroscopic
Merck 14,1779
BRN 3917459
Stability Hygroscopic
CAS DataBase Reference 51-83-2(CAS DataBase Reference)
FDA UNII 8Y164V895Y
NIST Chemistry Reference Carbachol(51-83-2)
ATC code N07AB01,S01EB02
EPA Substance Registry System Carbachol chloride (51-83-2)

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS06
Signal word  Danger
Hazard statements  H300
Precautionary statements  P301+P330+P331+P310
Hazard Codes  T
Risk Statements  25-36/37/38
Safety Statements  45-36/37/39-28A-26
RIDADR  UN 2811 6.1/PG 2
WGK Germany  3
RTECS  GA0875000
TSCA  Yes
HazardClass  6.1
PackingGroup  II
HS Code  29239000
Toxicity LD50 in mice (mg/kg): 15 orally, 0.3 i.v. (Molitor)
NFPA 704
1
4 0

Carbachol price More Price(26)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 212385-M Carbachol - CAS 51-83-2 - Calbiochem An unsubstituted carbamoyl ester that acts as an agonist for nicotinic and muscarinic acetylcholine receptors. 51-83-2 100mg $90.9 2024-03-01 Buy
Sigma-Aldrich 1092009 Carbachol United States Pharmacopeia (USP) Reference Standard 51-83-2 200mg $436 2024-03-01 Buy
TCI Chemical C0596 Carbamylcholine Chloride >99.0%(T) 51-83-2 10g $132 2024-03-01 Buy
TCI Chemical C0596 Carbamylcholine Chloride >99.0%(T) 51-83-2 25g $240 2024-03-01 Buy
Alfa Aesar L06674 Carbachol, 99% 51-83-2 1g $47.9 2024-03-01 Buy
Product number Packaging Price Buy
212385-M 100mg $90.9 Buy
1092009 200mg $436 Buy
C0596 10g $132 Buy
C0596 25g $240 Buy
L06674 1g $47.9 Buy

Carbachol Chemical Properties,Uses,Production

Description

Unlike acetylcholine and methacholine, carbachol contains a carbamino functional group instead of an acetyl group, which is not responsive to hydrolysis by cholinesterase. In vitro studies have shown that the rate of hydrolysis is at least twice as slow as that of acetylcholine.

Chemical Properties

Carbachol chloride is a crystalline odorless powder which, on standing in an open container, develops a faint odor resembling that of an aliphatic amine.

Chemical Properties

white crystalline powder

Originator

Miostat,Alcon,US,1979

Uses

Carbachol is a cholinergic agonist and is used for the treatment of glaucoma. It is also used as ophthalmic solution (eye drops) during ophthalmic surgery.

Uses

cholinergic, miotic

Uses

Carbamylcholine Chloride is a cholinergic receptor agonist. Studies show that Carbamylcholine Chloride is resistant to the action of cholinesterases. Carbamylcholine Chloride also displays antiapoptotic effects in cerebellar granule neurons.

Uses

Carbachol is a powerful cholinic ester that stimulates both muscarinic and nicotinic receptors, as well as exhibits all of the pharmacological properties of acetylcholine while in addition resulting in vasodilation, a decrease in heart rate, an increase in tone and contractability of smooth muscle, stimulation of salivary, ocular, and sweat glands as well as autonomic ganglia and skeletal muscle. For this reason, use of carbachol, like acetylcholine, is limited. The exception is that it is used in ophthalmological practice and postoperational intestines and bladder atony. Upon administration in the eye, the pupil constricts and the intraocular pressure is reduced. It is used for severe chronic glaucoma.

Definition

An acetylcholine counterfit molecule that is not inactivated by acetylcholinesterase and is a slowly hydrolyzed cholinergic agonist that acts at both muscarinic and nicotinic receptors.

Manufacturing Process

About 14 g of choline chloride are stirred with a solution of about 20 g of phosgene in 100 g of chloroform for about two hours at room temperature. The mixture becomes a two-phase liquid mixture. Hydrochloric acid and excess phosgene are removed by distillation in vacuo. Chloroform is added to the syrup, and the mixture is then added to a solution of excess ammonia in chloroform which was cooled with solid carbon dioxide-acetone. The mixture is filtered, and the solid is extracted with hot absolute alcohol. The solid in the alcoholic solution is precipitated with ether, and filtered. It is recrystallized from a methyl alcohol-ether mixture; the carbaminoyl-choline chloride obtained has a melting point of about 208°-210°C.

brand name

Carbastat (Novartis); Miostat (Alcon).

Therapeutic Function

Cholinergic

General Description

Carbachol forms a carbamylester in the active site of AChE, which is hydrolyzedmore slowly than an acetyl ester. This slower hydrolysis ratereduces the amount of free enzyme and prolongs the durationof ACh in the synapse. Carbachol also stimulates theautonomic ganglia and causes contraction of skeletal musclebut differs from a true muscarinic agent in that it does nothave cardiovascular activity despite the fact that it seems toaffect M2 receptors.

General Description

Prismatic crystals or powder. Odorless, but develops a faint odor of aliphatic amine upon standing in an open container. Cholinergic, parasympathomimetic, used chiefly in large animals, especially for colic in the horse.

Air & Water Reactions

Hygroscopic.

Reactivity Profile

Carbachol is a carbamate ester. Carbamates are chemically similar to, but more reactive than amides. Like amides they form polymers such as polyurethane resins. Carbamates are incompatible with strong acids and bases, and especially incompatible with strong reducing agents such as hydrides. Flammable gaseous hydrogen is produced by the combination of active metals or nitrides with carbamates. Strongly oxidizing acids, peroxides, and hydroperoxides are incompatible with carbamates.

Hazard

Deadly poison; may cause lowered blood pressure, venous dilation, nausea or vomiting, sweating and lachrymation; a parasympathetic nerve stimulant.

Health Hazard

Highly toxic by mouth.

Fire Hazard

When heated to decomposition, Carbachol emits very toxic fumes of chloride and nitrogen oxides. The aqueous solution is stable even when heated.

Biological Activity

Cholinergic receptor agonist that is resistant to the action of cholinesterases. Blocks apoptosis in cerebellar granule neurons.

Biochem/physiol Actions

Non-selective cholinergic agonist that is resistant to the action of cholinesterases; inhibits apoptotic death of cultured neurons, and may induce apoptosis in thymocytes.

Clinical Use

Carbachol is a miotic and has been used to reduce the intraoculartension of glaucoma when a response cannot beobtained with pilocarpine or neostigmine. Penetration of thecornea is poor but can be enhanced by the use of a wettingagent in the ophthalmic solution. In addition to its topicaluse for glaucoma, carbachol is used during ocular surgery,when a more prolonged miosis is required than can be obtainedwith ACh chloride.

Synthesis

Carbachol, 2-carbamoyloxy-N,N,N-trimethylethyl ammonium chloride (13.1.7), is made by reacting 2-chloroethanol with phosgene, which forms 2-chloroethyl chloroformate (13.1.5). Upon reaction with ammonia, it turns into the corresponding amide (13.1.6), which is further reacted with an equimolar quantity of trimethylamine, giving carbachol (13.1.7) [9¨C13].

Synthesis_51-83-2

Potential Exposure

Used in veterinary medicine as a cholinergic; parasympathomimetic, used chiefly in large animals, especially for colic in the horse

First aid

If this chemical gets into the eyes, remove anycontact lenses at once and irrigate immediately for at least15 min, occasionally lifting upper and lower lids. Seek medical attention immediately. If this chemical contacts theskin, remove contaminated clothing and wash immediatelywith soap and water. Seek medical attention immediately. Ifthis chemical has been inhaled, remove from exposure,begin rescue breathing (using universal precautions, including resuscitation mask) if breathing has stopped and CPR ifheart action has stopped. Transfer promptly to a medicalfacility. When this chemical has been swallowed, get medical attention. Give large quantities of water and inducevomiting. Do not make an unconscious person vomit.

storage

Desiccate at RT

Shipping

UN3249 Medicine, solid, toxic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials. UN2811 Toxic solids, organic, n.o.s., Hazard Class: 6.1; Labels: 6.1- Poisonous materials, Technical Name Required.

Incompatibilities

Carbachol chloride is a carbamate ester. Esters are generally incompatible with nitrates. Moisture may cause hydrolysis or other forms of decomposition. Carbamates are incompatible with strong acids and bases, and especially incompatible with strong reducing agents such as hydrideds and active metals. Contact with active metals or nitrides form flammable gaseous hydrogen. Incompatible with strongly oxidizing acids, peroxides, and hydroperoxides.

Waste Disposal

It is inappropriate and possibly dangerous to the environment to dispose of expired or waste pharmaceuticals by flushing them down the toilet or discarding them to the trash. Household quantities of expired or waste pharmaceuticals may be mixed with wet cat litter or coffee grounds, double-bagged in plastic, discard in trash. Larger quantities shall carefully take into consideration applicable DEA, EPA, and FDA regulations. If possible return the pharmaceutical to the manufacturer for proper disposal being careful to properly label and securely package the material. Alternatively, the waste pharmaceutical shall be labeled, securely packaged, and transported by a state licensed medical waste contractor to dispose by burial in a licensed hazardous or toxic waste landfill or incinerator.

Carbachol Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from Carbachol manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Carbachol pictures 2023-08-29 Carbachol
51-83-2
US $0.00 / KG 1KG 99% 50000KG/month Hebei Mojin Biotechnology Co., Ltd
Carbachol pictures 2023-03-09 Carbachol
51-83-2
US $20.00 / kg 1kg 99% 5000 Ton Hebei Duling International Trade Co. LTD
Carbachol pictures 2023-01-13 Carbachol
51-83-2
US $0.00 / KG 1KG 98%min 30tons/month WUHAN FORTUNA CHEMICAL CO., LTD
  • Carbachol pictures
  • Carbachol
    51-83-2
  • US $0.00 / KG
  • 99%
  • Hebei Mojin Biotechnology Co., Ltd
  • Carbachol pictures
  • Carbachol
    51-83-2
  • US $20.00 / kg
  • 99%
  • Hebei Duling International Trade Co. LTD
  • Carbachol pictures
  • Carbachol
    51-83-2
  • US $0.00 / KG
  • 98%min
  • WUHAN FORTUNA CHEMICAL CO., LTD
2-(aminocarbonyl)oxy-n,n,n-trimethyl-ethanaminiuchloride 2-[(aminocarbonyl)oxy]-n,n,n-trimethyl-ethanaminiuchloride 2-[(Aminocarbonyl)oxy]-N,N,N-trimethyle-thanaminiumchloride carbach Carbacholin Carbacholine Carbacholine chloride carbacholinechloride carbacholum carbacholumchloratum Carbacolina Carbamic acid, ester with choline chloride Doryl doryl(pharmaceutical) Ethanaminium, 2-[(aminocarbonyl)oxy]-N,N,N-trimethyl-, chloride gamma-Carbamoyl choline chloride gamma-carbamoylcholinechloride Isopto Carbachol Jestryl Karbachol Karbamoylcholin chlorid karbamoylcholinchlorid Lentin Lentine lentine(french) Miostat Mistura C Moryl P. V. Carbachol Rilentol TL 457 tl457 Vasoperif (2-Hydroxyethyl)trimethylammonium chloride carbamate, Carbachol, Carbamylcholine chloride Carbamoylcholine chloride purum, >=99.0% (AT) Carbachol (200 mg) Carba Carbachol (2-Carbamoyloxyethyl)trimethylammonium Chloride Choline Chloride Carbamate Cholin Chloride Carbamylcholine chloride,99% 2-(carbaMoyloxy)-N,N,N-triMethylethanaMiniuM chloride Ethanaminium,2-[(aminocarbonyl)oxy]-N,N,N-trimethyl-, chloride (1:1) CHOLINE CHLORIDE CARBAMATE CHOLINE CHLORIDE CARBAMATER CHOLINCHLORIDE CARBAMATE LABOTEST-BB LT00645774 LABOTEST-BB LT00455354 CARBAMYLCHOLINCHLORIDE CARBAMYLCHOLINE CHLORIDE CARBAMOYLCHOLINE CHLORIDE CARBACHOL CARBACHOL CHLORIDE 2-((aminocarbonyl)oxy)-n,n,n,-trimethyl-ethanaminiuchloride 2-((Aminocarbonyl)oxy)-N,N,N-trimethylethanaminium chloride 2-((aminocarbonyl)oxy)-n,n,n-trimethylethanaminiumchloride 2-((aminocarbonyl)oxy)-n,n,n-trimethylethanaminumchloride carbamicacid,esterwithcholinechloride Carbaminocholine chloride