ACETYLCHOLINE CHLORIDE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C7H16NO2.Cl
Molecular Weight	181.66
Optical Activity	NONE
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=JUGOREOARAHOCO-UHFFFAOYSA-M

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

HIDE SMILES / InChI

Molecular Formula	C7H16NO2
Molecular Weight	146.2074
Charge	1
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	ClH
Molecular Weight	36.461
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

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 209 Target ID: CHEMBL220 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28503857	Substrate 661
Muscarinic acetylcholine receptor 162 Target ID: CHEMBL2094109 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4027320/	Agonist 2752
Muscle-type nicotinic acetylcholine receptor 65 Target ID: CHEMBL2362997 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4027320/	Agonist 2752
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 2752

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 8583	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 71	ACHE 10 OCTN1 55

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
OCTN2 71	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/11160873/ Page: 6.0	yes

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
ACHE 10	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/020213s010lbl.pdf#page=1 Page: 1.0	major
OCTN1 55	substrate 4014 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
eMolecules	1985299	https://www.emolecules.com/cgi-bin/more?vid=1985299
ZINC	ZINC000003079336	http://zinc15.docking.org/substances/ZINC000003079336

PubMed

Title	Date	PubMed
SCH 23390 affords protection against soman-evoked seizures in the freely moving guinea-pig: a concomitant neurochemical, electrophysiological and behavioural study.	2001	11114407
Influence of nitric oxide donors and of the alpha(2)-agonist UK-14,304 on acetylcholine release in the pig gastric fundus.	2001	11114406
Anti-neuronal nicotinic receptor antibodies in MG patients with thymoma.	2001 Feb 1	11137585
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
Depletion of phosphatidylinositol 4,5-bisphosphate by activation of phospholipase C-coupled receptors causes slow inhibition but not desensitization of G protein-gated inward rectifier K+ current in atrial myocytes.	2001 Feb 23	11104770
Projections and pathways of VIP- and nNOS-containing airway neurons in ferret trachea.	2001 Jan	11152648
Arterial remodeling in chronic sinoaortic-denervated rats.	2001 Jan	11152375
Effects of LY117018 and the estrogen analogue, 17alpha-ethinylestradiol, on vascular reactivity, platelet aggregation, and lipid metabolism in the insulin-resistant JCR:LA-cp male rat: role of nitric oxide.	2001 Jan	11152369
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
Mechanical efficiency of isolated in situ perfused hearts of the eel Anguilla australis.	2001 Jan	11137449
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
Cortical acetylcholine release elicited by stimulation of histamine H1 receptors in the nucleus basalis magnocellularis: a dual-probe microdialysis study in the freely moving rat.	2001 Jan	11135005
Extracellular cyclic ADP-ribose potentiates ACh-induced contraction in bovine tracheal smooth muscle.	2001 Jan	11133499
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
A new hypoglycemic agent, JTT-608, evokes protein kinase A-mediated Ca(2+) signaling in rat islet beta-cells: strict regulation by glucose, link to insulin release, and cooperation with glucagon-like peptide-1(7-36)amide and pituitary adenylate cyclase-activating polypeptide.	2001 Jan	11123358
Adrenal tyrosine hydroxylase activity and gene expression are increased by intraventricular administration of nicotine.	2001 Jan	11123357
Myocardial stunning in exercise-induced ischemia in dogs: lack of late preconditioning.	2001 Jan	11123245
Glutathione attenuates coronary constriction to acetylcholine in patients with coronary spastic angina.	2001 Jan	11123241
Vagosympathetic interactions in ischemia-induced myocardial norepinephrine and acetylcholine release.	2001 Jan	11123236
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
Stress and gastrointestinal tract. II. Stress and intestinal barrier function.	2001 Jan	11123192
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
Vasoactive intestinal peptide: cardiovascular effects.	2001 Jan	11121793
Role of calcium and calmodulin in ciliary stimulation induced by acetylcholine.	2001 Jan	11121381
Effects of nicotine and cotinine on porcine arterial endothelial cell function.	2001 Jan	11120631
Pharmacological agents for the treatment of urinary incontinence due to overactive bladder.	2001 Jan	11116281
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
Contractile properties of the elasmobranch rectal gland.	2001 Jan	11104711
CHRNB2 is the second acetylcholine receptor subunit associated with autosomal dominant nocturnal frontal lobe epilepsy.	2001 Jan	11104662
beta-Amyloid(1-42) peptide directly modulates nicotinic receptors in the rat hippocampal slice.	2001 Jan 1	11150356
Bi-directional activation between human airway smooth muscle cells and T lymphocytes: role in induction of altered airway responsiveness.	2001 Jan 1	11123305
Allergen-specific Th1 cells counteract efferent Th2 cell-dependent bronchial hyperresponsiveness and eosinophilic inflammation partly via IFN-gamma.	2001 Jan 1	11123294
Changes in sensitivity of cholinoceptors and adrenoceptors during transhemispheric cortical reorganisation in rat SmI.	2001 Jan 12	11150484
Impairment of maze learning in rats by restricting environmental space.	2001 Jan 12	11121873
Exercise training in coronary artery disease and coronary vasomotion.	2001 Jan 2	11136704
Role of calcium-sensitive K(+) channels and nitric oxide in in vivo coronary vasodilation from enhanced perfusion pulsatility.	2001 Jan 2	11136696
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
Location of the polyamine binding site in the vestibule of the nicotinic acetylcholine receptor ion channel.	2001 Mar 2	11104766
Identification of a basolateral sorting signal for the M3 muscarinic acetylcholine receptor in Madin-Darby canine kidney cells.	2001 Mar 30	11136723
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

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.

Substance Class	Chemical Created by `admin` on `Wed Apr 02 08:20:07 GMT 2025` Edited by `admin` on `Wed Apr 02 08:20:07 GMT 2025`
Record UNII	AF73293C2R
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ACETYLCHOLINE CHLORIDE

Official Name

English

MIOCHOL

Preferred Name

English

Choline acetate (ester) chloride

Common Name

English

ACETYLCHOLINE CHLORIDE [ORANGE BOOK]

Common Name

English

ACETYLCHOLINE CHLORIDE [EP MONOGRAPH]

Common Name

English

ACETYLCHOLINE CHLORIDE FOR INJECTION [JAN]

Common Name

English

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

Systematic Name

English

acetylcholine chloride [INN]

Common Name

English

ACETYLCHOLINE CHLORIDE [MI]

Common Name

English

ETHANAMINIUM, 2-(ACETYLOXY)-N,N,N-TRIMETHYL-, CHLORIDE

Systematic Name

English

ACETYLCHOLINE CHLORIDE [MART.]

Common Name

English

ACETYLCHOLINE CHLORIDE [USP IMPURITY]

Common Name

English

ACETYLCHOLINE CHLORIDE [USP-RS]

Common Name

English

ACETYLCHOLINE CHLORIDE [VANDF]

Common Name

English

ACETYLCHOLINE CHLORIDE [USP MONOGRAPH]

Common Name

English

Acetylcholine chloride [WHO-DD]

Common Name

English

NSC-755845

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C47796