CARBACHOL

Details

Stereochemistry	ACHIRAL
Molecular Formula	C6H15N2O2.Cl
Molecular Weight	182.649
Optical Activity	NONE
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=AIXAANGOTKPUOY-UHFFFAOYSA-N

InChI=1S/C6H14N2O2.ClH/c1-8(2,3)4-5-10-6(7)9;/h4-5H2,1-3H3,(H-,7,9);1H

HIDE SMILES / InChI

Molecular Formula	C6H15N2O2
Molecular Weight	147.1955
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.accessdata.fda.gov/drugsatfda_docs/label/2016/016968s029lbl.pdf

Carbachol is a potent cholinergic (parasympathomimetic) agent which produces constriction of the iris and ciliary body resulting in reduction in intraocular pressure.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Muscarinic acetylcholine receptor 162 Target ID: CHEMBL2094109 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26535008 \| https://www.ncbi.nlm.nih.gov/pubmed/8401322 \| https://www.ncbi.nlm.nih.gov/pubmed/16879496 \| https://www.ncbi.nlm.nih.gov/pubmed/3689439	Agonist 2752
Acetylcholinesterase 209 Target ID: CHEMBL220 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19006330 \| https://www.ncbi.nlm.nih.gov/pubmed/18602908	Substrate 661		6.0 mM [Kd]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Elevated intraocular pressure 9 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/016968s029lbl.pdf	Preventing		Approved 8583	MIOSTAT Approved Use Intraocular use for obtaining miosis during surgery. In addition, MIOSTAT (carbachol intraocular solution, USP) reduces the intensity of intraocular pressure elevation in the first 24 hours after cataract surgery. Launch Date 1972

Sourcing

Vendor/Aggregator	ID	URL
1PlusChem LLC	1P00DELC
A2B Chem	AG24640
AA Blocks	AA00DE1W
AAA Chemistry	AR-1C8722
ABI Chem	AC1L1DXK
ABI Chem	AC1Q65QH
AbovChem LLC	HY-B1208
Acros Organics	10824
Alfa Chemistry	L06674
Angene	AGN-PC-0JK7E6
ApexBio Technology	B7196
BLD Pharm	BD01104798	http://www.bldpharm.com/products/462-58-8.html
Boerchem	BC224240	http://www.boerchem.com/?product_37788.html
Cayman Chemical	14486
Chemieliva Pharmaceutical Co., Ltd	PBCM1311157
ChemMol	44007155	http://www.chemmol.com/chemmol/44007155.html
ChemMol	49425868	http://www.chemmol.com/chemmol/49425868.html
ChemMol	99086802	http://www.chemmol.com/chemmol/99086802.html
Chemodex	C0306
Chemspace	CSSS00160769827	https://chem-space.com/CSSS00160769827
ChemTik	CTK1D5875
Compound Cloud	2551
Compound Cloud	5831
eMolecules	193736093
eMolecules	260329458
eMolecules	300019310
eMolecules	489054
Enamine	BBV-39898943
Enamine	EN300-122286
Fluorochem	358106
Fluorochem	393337
Hangzhou Yuhao Chemical Technology	HL1007
Lab Network	LN01343758
mcule	MCULE-5642570831	https://mcule.com/MCULE-5642570831/
Molnova	M14811
MolPort	MolPort-003-666-136
MolPort	MolPort-044-724-528
NCI Plated 2007	32865
Norris Pharm	NSZB-A219779
NovoSeek	2551
Princeton BioMolecular Research	OSSL_751146
Ryan Scientific	L-Adrenaline
Sigma Aldrich	1092009\|USP
Sigma Aldrich	C2409
Sigma Aldrich	C4382
Sigma Aldrich	PHR1511\|SIAL
Sigma Aldrich	Y0000113\|SIAL
Smolecule	S570329	https://www.smolecule.com/products/s570329
TargetMol	T0105
Tetrahedron	TS15068
TimTec	SBB057998
TimTec	ST50993883
TimTec	ST51007309
Tocris	2810
Toronto Research Chemicals	C175970
Toronto Research Chemicals	H939590
Vitas-M Laboratory	STL371210
Yuhao Chemical	HL1007	http://www.chemyuhao.com/51-83-2.html
ZINC	ZINC000003079342	http://zinc15.docking.org/substances/ZINC000003079342

PubMed

Title	Date	PubMed
Characterisation of acetylcholinesterase release from neuronal cells.	2013-03-25	23047022
Antispasmodic effects of eugenol on rat airway smooth muscle.	2011-12	21077946
Interaction of bispyridinium compounds with the orthosteric binding site of human α7 and Torpedo californica nicotinic acetylcholine receptors (nAChRs).	2011-09-25	21703337
TRPC5 channel sensitivities to antioxidants and hydroxylated stilbenes.	2011-02-18	21127073
Aggravation of seizure-associated microvascular injuries by ibuprofen may involve multiple pathways.	2010-12	21121909
Zinc oxide nanoparticle disruption of store-operated calcium entry in a muscarinic receptor signaling pathway.	2010-10	20708676
Molecular basis of inhibition of substrate hydrolysis by a ligand bound to the peripheral site of acetylcholinesterase.	2010-09-06	20493829
Prediction of functionally selective allosteric interactions at an M3 muscarinic acetylcholine receptor mutant using Saccharomyces cerevisiae.	2010-08	20466821
The validation of an in vitro colonic motility assay as a biomarker for gastrointestinal adverse drug reactions.	2010-06-15	20350559
Structural and functional effects of developmental exposure to ethanol on the zebrafish heart.	2010-06	20374213
Carbachol induces headache, but not migraine-like attacks, in patients with migraine without aura.	2010-03	19614687
Cholinergic responses of ophthalmic arteries in M3 and M5 muscarinic acetylcholine receptor knockout mice.	2009-10	19407017
Histamine H1 receptor induces cytosolic calcium increase and aquaporin translocation in human salivary gland cells.	2009-08	19443731
Muscarinic receptors prevent oxidative stress-mediated apoptosis induced by domoic acid in mouse cerebellar granule cells.	2009-04	19200344
The cholinomimetic agent carbachol induces headache in healthy subjects.	2009-02	19143771
Enhanced proliferation of SNU-407 human colon cancer cells by muscarinic acetylcholine receptors.	2008-11-30	19017493
Monitoring the reaction of carbachol with acetylcholinesterase by thioflavin T fluorescence and acetylthiocholine hydrolysis.	2008-09-25	18602908
Metabotropic receptor-activated calcium increases and store-operated calcium influx in mouse Müller cells.	2008-07	18316702
A novel assay of Gi/o-linked G protein-coupled receptor coupling to potassium channels provides new insights into the pharmacology of the group III metabotropic glutamate receptors.	2008-04	18171729
Myosin light chain kinase-independent inhibition by ML-9 of murine TRPC6 channels expressed in HEK293 cells.	2007-09	17603544
[Effects of carbachol on apoptosis of intestinal epithelial cells after gut ischemia/reperfusion in rat].	2007-08	17708838
Endogenous RGS proteins modulate SA and AV nodal functions in isolated heart: implications for sick sinus syndrome and AV block.	2007-05	17277016
Theoretical and experimental investigation of calcium-contraction coupling in airway smooth muscle.	2006	17272850
Regeneration of cardiomyocytes from bone marrow: Use of mesenchymal stem cell for cardiovascular tissue engineering.	2003-03	19002953
Studies on the development of tolerance and potential spinal neurotoxicity after chronic intrathecal carbachol-antinociception in the rat.	1991-02	2024563
Dopaminergic drugs influence the intensity of catalepsy induced by microinjections of carbachol into the reticular formation.	1990-11-13	1980731
Catalepsy induced by carbachol microinjected into the pontine reticular formation of rats.	1990-07-31	2234502
Renal function during onset of carbachol-induced hypertension in conscious rats.	1990	2148214
Plasma catecholamines and alpha 1-adrenoceptor function in hemodialysis-associated hypotension.	1990	1966119
Anatomical analysis of frontal cortex sites at which carbachol induces motor seizures in the rat.	1988-05	3174734
The effect of cholinergic stimulation in the nucleus accumbens on locomotor behavior.	1988-02-16	3359231
Novel 'soft' anticholinergic agents.	1988-02	3255315
Cardiovascular effects of cholinergic agents in the ventral-lateral midbrain periaqueductal gray of the rat.	1987-12	3437936
Spinal cholinergic neurons and the expression of morphine withdrawal symptoms in the rat.	1987-03	3559705
Neuropeptide Y and calcitonin gene-related peptide: effects on glucagon and insulin secretion in the mouse.	1987	3329090
Cholinergic induction of seizures in the rat prefrontal cortex.	1986-06-23	3724361
Subclassification of muscarinic receptors in the heart, urinary bladder and sympathetic ganglia in the pithed rat. Selectivity of some classical agonists.	1985-12	4094621
A crucial epileptogenic site in the deep prepiriform cortex.	1985-10-17	4058572
Drug-induced modulation of locomotor hyperactivity induced by picrotoxin in nucleus accumbens.	1984-10	6504948
Cardiovascular characterization of UL-FS 49, 1,3,4,5-tetrahydro-7,8-dimethoxy-3-[3-][2-(3,4-dimethoxyphenyl)ethyl] methylimino]propyl]-2H-3-benzazepin-2-on hydrochloride, a new "specific bradycardic agent".	1984-09-03	6499920
Seizures induced by carbachol, morphine, and leucine-enkephalin: a comparison.	1983-04	6301361
Neuropharmacology of the parasitic trematode, Schistosoma mansoni.	1983-01	6130710
[Effects of atropine and scopolamine on the aggressive behavior and convulsions induced by carbachol and eserine injected into the cerebral ventricles of the cat].	1980	6446956
Evidence that a nigral gabaergic--cholinergic balance controls posture.	1979-01-01	569589
Muscarine- and carbachol-induced aggressions: fear and irritable kinds of aggressions.	1977-12-28	414283
Midbrain interaction with the hypothalamus in expression of aggressive behavior in cats.	1977	563160
Motor disturbances produced by intrastriatal injection of cyclic AMP and cyclic GMP.	1976-11	189712
Spasmolytic constituents of Cedrus deodara (Roxb.) Loud: pharmacological evaluation of himachalol.	1975-02	47907
Sustained atrial fibrillation induced by carbachol, methacholine and bethanechol.	1971-04	4397202
Avoidance learning: long-lasting deficits after temporal lobe seizure.	1969-12-12	5350349

Patents

Sample Use Guides

In Vivo Use Guide

MIOSTAT (CARBACHOL INTRAOCULAR SOLUTION, USP) 0.01% Aseptically remove the sterile vial from the blister package by peeling the backing paper and dropping the vial onto a sterile tray. Withdraw the contents into a dry sterile syringe, and replace the needle with an atraumatic cannula prior to intraocular instillation. No more than one-half milliliter should be gently instilled into the anterior chamber for the production of satisfactory miosis. It may be instilled before or after securing sutures. Miosis is usually maximal within two to five minutes after application.

Route of Administration: Other

In Vitro Use Guide

In the dose-course studies, carbachol showed significant increase in phosphorylation of MYPT1 at Thr696 (p-MYPT1) from concentrations of 15-100 μM based on Western blot results (p < 0.05, ANOVA test). In the time-course studies, treatment of cells with 15 μM of carbachol significantly enhanced the expression of p-MYPT1 from 3 to 15 h (p < 0.05, ANOVA test) and induced the expression of Rho A from 10 to 120 min (p < 0.05, ANOVA test).

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:49:17 GMT 2025` Edited by `admin` on `Mon Mar 31 17:49:17 GMT 2025`
Record UNII	8Y164V895Y
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CARBASTAT

Preferred Name

English

CARBACHOL

Official Name

English

CARBACHOL [USP-RS]

Common Name

English

CARBACHOL [EP MONOGRAPH]

Common Name

English

CARBACHOLINE CHLORIDE

Systematic Name

English

MIOSTAT

Brand Name

English

CARBACHOL [EP IMPURITY]

Common Name

English

CARBACHOL [MART.]

Common Name

English

NSC-32865

Code

English

ETHANAMINIUM, 2-((AMINOCARBONYL)OXY)-N,N,N-TRIMETHYL-, CHLORIDE

Systematic Name

English

CARBACHOL [VANDF]

Common Name

English

CARBACHOL [HSDB]

Common Name

English

Choline chloride, carbamate

Systematic Name

English

CARBACHOL CHLORIDE

Common Name

English

Carbachol [WHO-DD]

Common Name

English

CARBACHOL [JAN]

Common Name

English

carbachol [INN]

Common Name

English

CARBACHOL [MI]

Common Name

English

CARBACHOL [USP MONOGRAPH]

Common Name

English

CARBACHOL [ORANGE BOOK]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C29705