ACETYLCHOLINE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C7H16NO2
Molecular Weight	146.2074
Optical Activity	NONE
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	1

SHOW SMILES / InChI

Structure Search

SMILES

CC(=O)OCC[N+](C)(C)C

InChI

InChIKey=OIPILFWXSMYKGL-UHFFFAOYSA-N

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

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
Functional reconstitution and characterization of recombinant human alpha 1-glycine receptors.	2001-06-15	11145968
Gyroxin fails to modify in vitro release of labelled dopamine and acetylcholine from rat and mouse striatal tissue.	2001-06	11137545
Conversion of the ion selectivity of the 5-HT(3a) receptor from cationic to anionic reveals a conserved feature of the ligand-gated ion channel superfamily.	2001-04-06	11139582
Identification of a basolateral sorting signal for the M3 muscarinic acetylcholine receptor in Madin-Darby canine kidney cells.	2001-03-30	11136723
Anti-neuronal nicotinic receptor antibodies in MG patients with thymoma.	2001-02-01	11137585
Lymphotoxin-alpha deficiency completely protects C57BL/6 mice from developing clinical experimental autoimmune myasthenia gravis.	2001-02-01	11137582
Interleukin 10 aggravates experimental autoimmune myasthenia gravis through inducing Th2 and B cell responses to AChR.	2001-02-01	11137572
Nicotine prevents striatal dopamine loss produced by 6-hydroxydopamine lesion in the substantia nigra.	2001-01-12	11150495
Post-ictal analgesia: involvement of opioid, serotoninergic and cholinergic mechanisms.	2001-01-12	11150491
Changes in sensitivity of cholinoceptors and adrenoceptors during transhemispheric cortical reorganisation in rat SmI.	2001-01-12	11150484
Combined pre- and postsynaptic action of IgG antibodies in Miller Fisher syndrome.	2001-01-09	11148238
Site of resting state inhibition of the nicotinic acetylcholine receptor by a hydrophobic inhibitor.	2001-01-09	11141083
Antagonist of nicotinic acetylcholine receptors (nAChR) enhances formalin-induced nociception in rats: tonic role of nAChRs in the control of pain following injury.	2001-01-05	11146056
Aversive hypothalamic stimulation releases acetylcholine in the nucleus accumbens, and stimulation-escape decreases it.	2001-01-05	11146052
exo-2-(Pyridazin-4-yl)-7-azabicyclo[2.2.1]heptanes: syntheses and nicotinic acetylcholine receptor agonist activity of potent pyridazine analogues of (+/-)-epibatidine.	2001-01-04	11141087
Exercise training in coronary artery disease and coronary vasomotion.	2001-01-02	11136704
Role of calcium-sensitive K(+) channels and nitric oxide in in vivo coronary vasodilation from enhanced perfusion pulsatility.	2001-01-02	11136696
beta-Amyloid(1-42) peptide directly modulates nicotinic receptors in the rat hippocampal slice.	2001-01-01	11150356
A noninvasive measurement of reactive hyperemia that can be used to assess resistance artery endothelial function in humans.	2001-01-01	11137850
Bi-directional activation between human airway smooth muscle cells and T lymphocytes: role in induction of altered airway responsiveness.	2001-01-01	11123305
Allergen-specific Th1 cells counteract efferent Th2 cell-dependent bronchial hyperresponsiveness and eosinophilic inflammation partly via IFN-gamma.	2001-01-01	11123294
Projections and pathways of VIP- and nNOS-containing airway neurons in ferret trachea.	2001-01	11152648
Arterial remodeling in chronic sinoaortic-denervated rats.	2001-01	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.	2001-01	11152369
Rapid eye movement sleep deprivation induces an increase in acetylcholinesterase activity in discrete rat brain regions.	2001-01	11151034
Coronary endothelial dysfunction after ischemia and reperfusion: a new therapeutic target?	2001-01	11151023
Dynamic restoration of dystrophin to dystrophin-deficient myotubes.	2001-01	11150969
Effect of dietary vitamin E supplementation on vascular reactivity of thoracic aorta in streptozotocin-diabetic rats.	2001-01	11150923
Association study of a nicotinic receptor variant with schizophrenic disorders.	2001-01	11150893
Platelet-derived growth factor is involved in the augmentation of airway responsiveness through remodeling of airways in diesel exhaust particulate-treated mice.	2001-01	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.	2001-01	11149906
Obesity and body fat distribution induce endothelial dysfunction by oxidative stress: protective effect of vitamin C.	2001-01	11147782
Nicotinic agonists stimulate acetylcholine release from mouse interpeduncular nucleus: a function mediated by a different nAChR than dopamine release from striatum.	2001-01	11145999
Mechanical efficiency of isolated in situ perfused hearts of the eel Anguilla australis.	2001-01	11137449
Impaired renal vascular endothelial function in vitro in experimental hypercholesterolemia.	2001-01	11137100
Anti-oxidative properties of fluvastatin, an HMG-CoA reductase inhibitor, contribute to prevention of atherosclerosis in cholesterol-fed rabbits.	2001-01	11137086
Exercise and the endothelium.	2001-01	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?	2001-01	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.	2001-01	11135005
Extracellular cyclic ADP-ribose potentiates ACh-induced contraction in bovine tracheal smooth muscle.	2001-01	11133499
Specification of neurotransmitter receptor identity in developing retina: the chick ATH5 promoter integrates the positive and negative effects of several bHLH proteins.	2001-01	11124117
Environmental familiarization in rats: differential effects of acute and chronic nicotine.	2001-01	11124047
Influence of gender and sex hormones on nicotine acute pharmacological effects in mice.	2001-01	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.	2001-01	11123358
Adrenal tyrosine hydroxylase activity and gene expression are increased by intraventricular administration of nicotine.	2001-01	11123357
Myocardial stunning in exercise-induced ischemia in dogs: lack of late preconditioning.	2001-01	11123245
Glutathione attenuates coronary constriction to acetylcholine in patients with coronary spastic angina.	2001-01	11123241
Vagosympathetic interactions in ischemia-induced myocardial norepinephrine and acetylcholine release.	2001-01	11123236
Electrical activation of endothelium evokes vasodilation and hyperpolarization along hamster feed arteries.	2001-01	11123230
Responder characteristics to a single oral dose of cholinesterase inhibitor: a double-blind placebo-controlled study with tacrine in Alzheimer patients.	2000-12-23	11125238

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 `Mon Mar 31 18:04:25 GMT 2025` Edited by `admin` on `Mon Mar 31 18:04:25 GMT 2025`
Record UNII	N9YNS0M02X
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ACETYLCHOLINE CATION

Preferred Name

English

ACETYLCHOLINE

Systematic Name

English

Acetylcholine [WHO-DD]

Common Name

English

CHOLINE ACETATE (ESTER)

Common Name

English

ACETYLCHOLINE [VANDF]

Common Name

English

ACETYLCHOLINE [USP IMPURITY]

Common Name

English

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

Systematic Name

English

Classification Tree Code System Code

LOINC

1707-9