Carbachol

Structural formula
General
Non-proprietary name	Carbachol
other names	(2-carbamoyloxyethyl) trimethylammonium chloride; Carbamoylcholine; Carbamylcholine; Choline carbamate; Choline urethane;
Molecular formula	C 6 H 15 ClN 2 O 2
Brief description	yellowish, odorless solid
External identifiers / databases
EC number	200-127-3
ECHA InfoCard	100,000.117
PubChem	5831
DrugBank	DB00411
Wikidata	Q419401
Drug information
ATC code	S01 EB02 , N07 AB01
Drug class	Parasympathomimetics
properties
Molar mass	182.65 g mol −1
Physical state	firmly
Melting point	200 ° C
solubility	easy in water (1000 g l −1 )
safety instructions
	Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances danger
H and P phrases	H: 300
	P: 264-301 + 310
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Carbachol is a drug from the group of parasympathomimetics and a structural analog of the neurotransmitter acetylcholine . Instead of an acetyl group there is a carbamoyl group [ Carba m (o) yl chol in], which gives the drug increased chemical stability (i.e. resistance to hydrolysis). It is therefore only very poorly cleaved by acetylcholinesterase and has a longer half-life than the therapeutically insignificant acetylcholine.

It was first used in 1932 and is chemically an ester of choline with carbamic acid.

Carbachol mimics the activity of the parasympathetic nervous system by binding to the muscarinic receptor (directly effective parasympathomimetic) and is used, for example, in ophthalmology (ophthalmology) as an antiglaucoma agent. It is applied locally in the form of eye drops in order to reduce systemic side effects. Carbachol shows a preference for the therapeutically important muscarinic acetylcholine receptors , whereby the nicotinic subtype is only poorly bound.

Extraction and presentation

Carbachol can be prepared by reacting 2-chloroethyl chloroformate with ammonia and trimethylamine .

Trade names

Monopreparations

Isopto-Carbachol (D), Miostat (CH)

Individual evidence

↑ ^a ^b ^c ^d Entry on carbachol in the GESTIS substance database of the IFA , accessed on February 10, 2017(JavaScript required) .
↑ Carbamoylcholine chloride purum data sheet from Sigma-Aldrich , accessed on October 20, 2016 ( PDF ).

↑ Spektrum.de: Carbachol - Lexicon of Neuroscience - Spectrum of Science , accessed on September 16, 2016.

↑ Entry on Carbachol at Vetpharm, accessed on September 16, 2016.

^ Ruben Vardanyan, Victor Hruby: Synthesis of Essential Drugs . Elsevier, 2006, ISBN 978-0-08-046212-7 , pp. 182 ( limited preview in Google Book search).

[GESTIS-1] Entry on carbachol in the GESTIS substance database of the IFA , accessed on February 10, 2017(JavaScript required) .

[Sigma-2] Carbamoylcholine chloride purum data sheet from Sigma-Aldrich , accessed on October 20, 2016 ( PDF ).

[spektrum.de-3] Spektrum.de: Carbachol - Lexicon of Neuroscience - Spectrum of Science , accessed on September 16, 2016.

[vetpharm-4] Entry on Carbachol at Vetpharm, accessed on September 16, 2016.

[Ruben_Vardanyan,_Victor_Hruby-5] Ruben Vardanyan, Victor Hruby: Synthesis of Essential Drugs . Elsevier, 2006, ISBN 978-0-08-046212-7 , pp. 182 ( limited preview in Google Book search).