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Details

Stereochemistry ACHIRAL
Molecular Formula C6H15N2O2
Molecular Weight 147.1955
Optical Activity NONE
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 1

SHOW SMILES / InChI
Structure of CARBAMOYLCHOLINE

SMILES

C[N+](C)(C)CCOC(N)=O

InChI

InChIKey=VPJXQGSRWJZDOB-UHFFFAOYSA-O
InChI=1S/C6H14N2O2/c1-8(2,3)4-5-10-6(7)9/h4-5H2,1-3H3,(H-,7,9)/p+1

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

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

CNS Activity

Curator's Comment: Carbachol does not pass the blood-brain-barrier (BBB) however it produces cholinergic effects on brain blood vessels from the luminal side, whereas the effects on dural and extracranial vessels are from both the luminal and abluminal side since they are devoid of BBB

Originator

Curator's Comment: reference retrieved from https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1550933/

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
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

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Avoidance learning: long-lasting deficits after temporal lobe seizure.
1969 Dec 12
[Tremor following intracerebral carbachol injection. 1.Carbachol sensitivity of various brain structures].
1975
Spasmolytic constituents of Cedrus deodara (Roxb.) Loud: pharmacological evaluation of himachalol.
1975 Feb
A crucial epileptogenic site in the deep prepiriform cortex.
1985 Oct 17-23
Novel 'soft' anticholinergic agents.
1988 Feb
Chick optic lobe contains a developmentally regulated alpha2alpha5beta2 nicotinic receptor subtype.
2000 Aug
Cardiovascular studies on different classes of soft drugs.
2000 Mar
PLD pathway involved in carbachol-induced Cl- secretion: possible role of TNF-alpha.
2001 Apr
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
Regional differences in functional receptor distribution and calcium mobilization in the intact human lens.
2001 Sep
The role of endogenous human Trp4 in regulating carbachol-induced calcium oscillations in HEK-293 cells.
2002 Apr 19
The relationship between hippocampal acetylcholine release and cholinergic convulsant sensitivity in withdrawal seizure-prone and withdrawal seizure-resistant selected mouse lines.
2002 Aug
Regeneration of cardiomyocytes from bone marrow: Use of mesenchymal stem cell for cardiovascular tissue engineering.
2003 Mar
Post-seizures amygdaloallocortical microvascular lesion leading to atrophy and memory impairment.
2005 Aug
Pharmacokinetic and pharmacodynamic evaluations of the zwitterionic metabolite of a new series of N-substituted soft anticholinergics.
2005 Dec
Theoretical and experimental investigation of calcium-contraction coupling in airway smooth muscle.
2006
Muscarinic cholinoceptor activation modulates DNA synthesis and CD40 expression in fibroblast cells.
2006 Jul
Gene transfer of neuronal nitric oxide synthase into intracardiac Ganglia reverses vagal impairment in hypertensive rats.
2007 Feb
Endogenous RGS proteins modulate SA and AV nodal functions in isolated heart: implications for sick sinus syndrome and AV block.
2007 May
Structural and functional effects of developmental exposure to ethanol on the zebrafish heart.
2010 Jun
Patents

Patents

Sample Use Guides

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 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 17:59:37 GMT 2025
Edited
by admin
on Mon Mar 31 17:59:37 GMT 2025
Record UNII
54Z8M50D6Q
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CARBAMOYLCHOLINE
Systematic Name English
CARBACHOLINE
Preferred Name English
ETHANAMINIUM, 2-((AMINOCARBONYL)OXY)-N,N,N-TRIMETHYL-
Systematic Name English
CARBAMYLCHOLINE
Systematic Name English
CHOLINE CARBAMATE
Systematic Name English
Classification Tree Code System Code
NDF-RT N0000175884
Created by admin on Mon Mar 31 17:59:37 GMT 2025 , Edited by admin on Mon Mar 31 17:59:37 GMT 2025
NDF-RT N0000175369
Created by admin on Mon Mar 31 17:59:37 GMT 2025 , Edited by admin on Mon Mar 31 17:59:37 GMT 2025
Code System Code Type Description
EPA CompTox
DTXSID0048397
Created by admin on Mon Mar 31 17:59:37 GMT 2025 , Edited by admin on Mon Mar 31 17:59:37 GMT 2025
PRIMARY
DRUG BANK
DB00411
Created by admin on Mon Mar 31 17:59:37 GMT 2025 , Edited by admin on Mon Mar 31 17:59:37 GMT 2025
PRIMARY
PUBCHEM
2551
Created by admin on Mon Mar 31 17:59:37 GMT 2025 , Edited by admin on Mon Mar 31 17:59:37 GMT 2025
PRIMARY
DAILYMED
54Z8M50D6Q
Created by admin on Mon Mar 31 17:59:37 GMT 2025 , Edited by admin on Mon Mar 31 17:59:37 GMT 2025
PRIMARY
RXCUI
1546387
Created by admin on Mon Mar 31 17:59:37 GMT 2025 , Edited by admin on Mon Mar 31 17:59:37 GMT 2025
PRIMARY RxNorm
CAS
462-58-8
Created by admin on Mon Mar 31 17:59:37 GMT 2025 , Edited by admin on Mon Mar 31 17:59:37 GMT 2025
PRIMARY
FDA UNII
54Z8M50D6Q
Created by admin on Mon Mar 31 17:59:37 GMT 2025 , Edited by admin on Mon Mar 31 17:59:37 GMT 2025
PRIMARY
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