ACETYLCHOLINE BROMIDE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C7H16NO2.Br
Molecular Weight	226.111
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[Br-].CC(=O)OCC[N+](C)(C)C

InChI

InChIKey=ZEHGKSPCAMLJDC-UHFFFAOYSA-M

InChI=1S/C7H16NO2.BrH/c1-7(9)10-6-5-8(2,3)4;/h5-6H2,1-4H3;1H/q+1;/p-1

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/books/NBK11143/ | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4027320/ | https://www.ncbi.nlm.nih.gov/pubmed/23040810 | http://www.bausch.com/Portals/77/-/m/BL/United%20States/Files/Package%20Inserts/Pharma/miochol-e-acetylcholine-chloride-intraocular-solution.pdf

Acetylcholine is the neurotransmitter at neuromuscular junctions, at synapses in the ganglia of the visceral motor system, and at a variety of sites within the central nervous system. Whereas a great deal is known about the function of cholinergic transmission at the neuromuscular junction and at ganglionic synapses, the actions of acetylcholine in the central nervous system are not as well understood. Cholinergic system is an important system and a branch of the autonomic nervous system which plays an important role in memory, digestion, control of heart beat, blood pressure, movement and many other functions. Acetylcholine in the brain alters neuronal excitability, influences synaptic transmission, induces synaptic plasticity, and coordinates firing of groups of neurons. Miochol®-E (acetylcholine chloride intraocular solution) is used to obtain miosis of the iris in seconds after delivery of the lens in cataract surgery, in penetrating keratoplasty, iridectomy and other anterior segment surgery where rapid miosis may be required.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Acetylcholinesterase 207 Target ID: CHEMBL220 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28503857	Substrate 661
Muscarinic acetylcholine receptor 160 Target ID: CHEMBL2094109 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4027320/	Agonist 2678
Muscle-type nicotinic acetylcholine receptor 65 Target ID: CHEMBL2362997 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4027320/	Agonist 2678
Neuronal acetylcholine receptors; alpha-3/beta-4, alpha-5, beta-2 4 Target ID: CHEMBL2221346 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4027320/	Agonist 2678

Conditions

Condition	Modality	Targets	Highest Phase	Product
Mydriasis 6 Sources: http://www.bausch.com/Portals/77/-/m/BL/United%20States/Files/Package%20Inserts/Pharma/miochol-e-acetylcholine-chloride-intraocular-solution.pdf	Preventing		Approved 8429	MIOCHOL-E Approved Use To obtain miosis of the iris in seconds after delivery of the lens in cataract surgery, in penetrating keratoplasty, iridectomy and other anterior segment surgery where rapid miosis may be required Launch Date 1993

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
OCTN2 66	ACHE 10 OCTN1 47

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
OCTN2 71	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/11160873/ Page: 6.0	yes

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
ACHE 10	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/020213s010lbl.pdf#page=1 Page: 1.0	major
OCTN1 47	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/22206629/ Page: 1.0	yes

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:15355	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:15355
ZINC	ZINC000003079336	http://zinc15.docking.org/substances/ZINC000003079336
eMolecules	1985299	https://www.emolecules.com/cgi-bin/more?vid=1985299

PubMed

Title	Date	PubMed
Gain of function mutation of the alpha7 nicotinic receptor: distinct pharmacology of the human alpha7V274T variant.	1999 Feb 5	10082212
Diesel exhaust particulate induces airway hyperresponsiveness in a murine model: essential role of GM-CSF.	1999 Nov	10550748
Nitric oxide-compromised hypertension: facts and enigmas.	2000	10805402
Kir3.1/3.2 encodes an I(KACh)-like current in gastrointestinal myocytes.	2000 Feb	10666054
Allosteric interactions of staurosporine and other indolocarbazoles with N-[methyl-(3)H]scopolamine and acetylcholine at muscarinic receptor subtypes: identification of a second allosteric site.	2000 Jul	10860942
Gene transfer of endothelial nitric oxide synthase improves relaxation of carotid arteries from diabetic rabbits.	2000 Mar 7	10704171
Interleukin 10 aggravates experimental autoimmune myasthenia gravis through inducing Th2 and B cell responses to AChR.	2001 Feb 1	11137572
Three-dimensional structure of a complex of galanthamine (Nivalin) with acetylcholinesterase from Torpedo californica: implications for the design of new anti-Alzheimer drugs.	2001 Feb 1	11119642
Inhibition of a Gi-activated potassium channel (GIRK1/4) by the Gq-coupled m1 muscarinic acetylcholine receptor.	2001 Feb 23	11060307
Kinetic evidence for different mechanisms of interaction of black mamba toxins MT alpha and MT beta with muscarinic receptors.	2001 Feb-Mar	10978757
Association study of a nicotinic receptor variant with schizophrenic disorders.	2001 Jan	11150893
Platelet-derived growth factor is involved in the augmentation of airway responsiveness through remodeling of airways in diesel exhaust particulate-treated mice.	2001 Jan	11150003
An altered peptide ligand inhibits the activities of matrix metalloproteinase-9 and phospholipase C, and inhibits T cell interactions with VCAM-1 induced in vivo by a myasthenogenic T cell epitope.	2001 Jan	11149906
Nicotinic agonists stimulate acetylcholine release from mouse interpeduncular nucleus: a function mediated by a different nAChR than dopamine release from striatum.	2001 Jan	11145999
Impaired renal vascular endothelial function in vitro in experimental hypercholesterolemia.	2001 Jan	11137100
Anti-oxidative properties of fluvastatin, an HMG-CoA reductase inhibitor, contribute to prevention of atherosclerosis in cholesterol-fed rabbits.	2001 Jan	11137086
Exercise and the endothelium.	2001 Jan	11136508
Ischemic preconditioning with opening of mitochondrial adenosine triphosphate-sensitive potassium channels or Na/H exchange inhibition: which is the best protective strategy for heart transplants?	2001 Jan	11135172
Specification of neurotransmitter receptor identity in developing retina: the chick ATH5 promoter integrates the positive and negative effects of several bHLH proteins.	2001 Jan	11124117
Environmental familiarization in rats: differential effects of acute and chronic nicotine.	2001 Jan	11124047
Influence of gender and sex hormones on nicotine acute pharmacological effects in mice.	2001 Jan	11123373
Adrenal tyrosine hydroxylase activity and gene expression are increased by intraventricular administration of nicotine.	2001 Jan	11123357
Electrical activation of endothelium evokes vasodilation and hyperpolarization along hamster feed arteries.	2001 Jan	11123230
Increased inactivation of nitric oxide is involved in coronary endothelial dysfunction in heart failure.	2001 Jan	11123219
Capillary recruitment is impaired in essential hypertension and relates to insulin's metabolic and vascular actions.	2001 Jan	11121808
Endothelin receptor blockade improves endothelial function in human internal mammary arteries.	2001 Jan	11121806
Hyperhomocysteinaemia in young adults is not associated with impaired endothelial function.	2001 Jan	11115420
The mechanism of resveratrol-induced vasorelaxation differs in the mesenteric resistance arteries of lean and obese rats.	2001 Jan	11115418
Cholinergic activity of aged rhesus monkeys revealed by positron emission tomography.	2001 Jan	11071714
Decreased choline acetyltransferase immunoreactivity in discrete striatal subregions following chronic haloperidol in rats.	2001 Jan	11071709
Bi-directional activation between human airway smooth muscle cells and T lymphocytes: role in induction of altered airway responsiveness.	2001 Jan 1	11123305
Role of calcium-sensitive K(+) channels and nitric oxide in in vivo coronary vasodilation from enhanced perfusion pulsatility.	2001 Jan 2	11136696
Contributions of Torpedo nicotinic acetylcholine receptor gamma Trp-55 and delta Trp-57 to agonist and competitive antagonist function.	2001 Jan 26	11056174
Aversive hypothalamic stimulation releases acetylcholine in the nucleus accumbens, and stimulation-escape decreases it.	2001 Jan 5	11146052
Combined pre- and postsynaptic action of IgG antibodies in Miller Fisher syndrome.	2001 Jan 9	11148238
Responder characteristics to a single oral dose of cholinesterase inhibitor: a double-blind placebo-controlled study with tacrine in Alzheimer patients.	2001 Jan-Feb	11125238
Gyroxin fails to modify in vitro release of labelled dopamine and acetylcholine from rat and mouse striatal tissue.	2001 Jun	11137545
Location of the polyamine binding site in the vestibule of the nicotinic acetylcholine receptor ion channel.	2001 Mar 2	11104766
Constitutive signaling by Kaposi's sarcoma-associated herpesvirus G-protein-coupled receptor desensitizes calcium mobilization by other receptors.	2001 Mar 9	11116138
Role of rapsyn tetratricopeptide repeat and coiled-coil domains in self-association and nicotinic acetylcholine receptor clustering.	2001 Mar 9	11087759
Evidence for a direct action of Tityus serrulatus scorpion venom on the cardiac muscle.	2001 May	11072050

Patents

Sample Use Guides

In Vivo Use Guide

Miochol®-E (acetylcholine chloride intraocular solution) is instilled into the anterior chamber before or after securing one or more sutures. Instillation should be gentle and parallel to the iris face and tangential to pupil border. If there are no mechanical hindrances, the pupil starts to constrict in seconds and the peripheral iris is drawn away from the angle of the anterior chamber. Any anatomical hindrance to miosis must be released to permit the desired effect of the drug. In most cases, 0.5 to 2 mL produces satisfactory miosis. Note that the syringe filter supplied with Miochol-E has a priming volume of 0.6 mL (approximately). In cataract surgery, use Miochol-E only after delivery of the lens. Aqueous solutions of acetylcholine chloride are unstable. Prepare solution immediately before use. Do not use solution which is not clear and colorless. Discard any solution that has not been used.

Route of Administration: Other

In Vitro Use Guide

Keratocytes were treated with various concentrations of acetylcholine (0.01-1 uM) for 24 h. Acetylcholine enhances keratocyte proliferation through activation of muscarinic acetylcholine receptors.

Name

Type

Language

ACETYLCHOLINE BROMIDE

Systematic Name

English

2-(ACETYLOXY)-N,N,N-TRIMETHYLETHANAMINIUM BROMIDE (1:1)

Systematic Name

English

ACETYLCHOLINE BROMIDE [MI]

Common Name

English

NSC-4678

Code

English

Code System Code Type Description

CAS

66-23-9