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
Spasmolytic constituents of Cedrus deodara (Roxb.) Loud: pharmacological evaluation of himachalol.	1975 Feb	47907
Evidence that a nigral gabaergic--cholinergic balance controls posture.	1979 Jan 1	569589
Neuropharmacology of the parasitic trematode, Schistosoma mansoni.	1983 Jan	6130710
Drug-induced modulation of locomotor hyperactivity induced by picrotoxin in nucleus accumbens.	1984 Oct	6504948
Neuropeptide Y and calcitonin gene-related peptide: effects on glucagon and insulin secretion in the mouse.	1987	3329090
Spinal cholinergic neurons and the expression of morphine withdrawal symptoms in the rat.	1987 Mar	3559705
Novel 'soft' anticholinergic agents.	1988 Feb	3255315
Anatomical analysis of frontal cortex sites at which carbachol induces motor seizures in the rat.	1988 May	3174734
Plasma catecholamines and alpha 1-adrenoceptor function in hemodialysis-associated hypotension.	1990	1966119
Dopaminergic drugs influence the intensity of catalepsy induced by microinjections of carbachol into the reticular formation.	1990 Nov 13	1980731
Studies on the development of tolerance and potential spinal neurotoxicity after chronic intrathecal carbachol-antinociception in the rat.	1991 Feb	2024563
Positive and negative feedback regulation of choline acetyltransferase mRNA levels in Drosophila: a study using temperature-sensitive mutants and embryo cell cultures.	1992 Apr	1317495
Vagus nerve modulates secretin binding sites in the rat forestomach.	1999 Apr	10198350
Myoclonic and tonic seizures elicited by microinjection of cholinergic drugs into the inferior colliculus.	1999 Sep-Oct	10667095
Carbachol blocks beta-amyloid fragment 31-35-induced apoptosis in cultured cortical neurons.	2000 Apr	10758335
Low-affinity M(2) receptor binding state mediates mouse atrial bradycardia: comparative effects of carbamylcholine and the M(1) receptor agonists sabcomeline and xanomeline.	2001 Mar	11181912
The role of endogenous human Trp4 in regulating carbachol-induced calcium oscillations in HEK-293 cells.	2002 Apr 19	11830588
Design, pharmacokinetic, and pharmacodynamic evaluation of soft anticholinergics based on tropyl alpha-phenylcyclopentylacetate.	2002 Feb	11878186
Impaired parasympathetic heart rate control in mice with a reduction of functional G protein betagamma-subunits.	2002 Feb	11788391
Pharmacological characterization of recombinant bovine alpha3beta4 neuronal nicotinic receptors stably expressed in HEK 293 cells.	2003 Jun 12	12770692
Design, pharmacokinetic, and pharmacodynamic evaluation of a new class of soft anticholinergics.	2003 Oct	14620526
Crucial role of histamine for regulation of gastric acid secretion ascertained by histidine decarboxylase-knockout mice.	2003 Oct	12893847
Cyclic AMP/protein kinase a signal attenuates Ca(2+)-induced fibroblast growth factor-1 synthesis in rat cortical neurons.	2004 Aug 15	15264218
Post-seizures amygdaloallocortical microvascular lesion leading to atrophy and memory impairment.	2005 Aug	16023590
Pharmacokinetic and pharmacodynamic evaluations of the zwitterionic metabolite of a new series of N-substituted soft anticholinergics.	2005 Dec	16170596
[Effects of carbachol on apoptosis of peripheral white blood cells and expression of cytokines in rats suffering from gut ischemia/reperfusion injury].	2005 Feb	15698499
Neuronal nitric oxide synthase activity in rat urinary bladder detrusor: participation in M3 and M4 muscarinic receptor function.	2005 Jul	15955028
Effects of ML-7 and Y-27632 on carbachol- and endothelin-1-induced contraction of bovine trabecular meshwork.	2005 Jun	15939040
Actin and non-muscle myosin II facilitate apical exocytosis of tear proteins in rabbit lacrimal acinar epithelial cells.	2005 Oct 15	16219687
Case report: acute unintentional carbachol intoxication.	2006	16740173
Muscarinic acetylcholine receptors mediate oligodendrocyte progenitor survival through Src-like tyrosine kinases and PI3K/Akt pathways.	2006 Apr	16439036
Novelty exploration elicits a reversal of acute stress-induced modulation of hippocampal synaptic plasticity in the rat.	2006 Dec 1	17008368
Muscarinic cholinoceptor activation modulates DNA synthesis and CD40 expression in fibroblast cells.	2006 Jul	16879495
Myosin light chain kinase-independent inhibition by ML-9 of murine TRPC6 channels expressed in HEK293 cells.	2007 Sep	17603544
Structural and functional effects of developmental exposure to ethanol on the zebrafish heart.	2010 Jun	20374213
The validation of an in vitro colonic motility assay as a biomarker for gastrointestinal adverse drug reactions.	2010 Jun 15	20350559
TRPC5 channel sensitivities to antioxidants and hydroxylated stilbenes.	2011 Feb 18	21127073

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

Download

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