Carbachol
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    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 317367

CAS#: 51-83-2

Description: Carbachol is a cholinomimetic drug that binds and activates the acetylcholine receptor. Thus it is classified as a cholinergic agonist. It is primarily used for various ophthalmic purposes, such as for treating glaucoma, or for use during ophthalmic surgery. It is generally administered as an ophthalmic solution (i.e. eyedrops).


Chemical Structure

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Carbachol
CAS# 51-83-2

Theoretical Analysis

MedKoo Cat#: 317367
Name: Carbachol
CAS#: 51-83-2
Chemical Formula: C6H15ClN2O2
Exact Mass: 182.08
Molecular Weight: 182.650
Elemental Analysis: C, 39.46; H, 8.28; Cl, 19.41; N, 15.34; O, 17.52

Price and Availability

Size Price Availability Quantity
1g USD 450 2 Weeks
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Synonym: Carbastat, Carboptic, Isopto Carbachol, Miostat, Carbamylcholine

IUPAC/Chemical Name: 2-carbamoyloxyethyl(trimethyl)azanium;chloride

InChi Key: AIXAANGOTKPUOY-UHFFFAOYSA-N

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

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

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Product Data:
Safety Data Sheet (SDS):
Biological target: Carbamoylcholine chloride (Carbachol, Carbamylcholine chloride, Carbastat, Miostat) is a cholinergic agonist that mimics the effect of acetylcholine on both the muscarinic and nicotinic receptors.
In vitro activity: Serosal application of carbachol to T84 cell monolayers mounted in an Ussing chamber caused an immediate increase in short circuit current (Isc) that peaked within 5 min and declined rapidly thereafter, although a small increase in Isc persisted for approximately 30 min. The increase in Isc was detectable with 1 microM carbachol; half-maximal with 10 microM carbachol; and maximal with 100 microM carbachol. Unidirectional Na+ and Cl- flux measurements indicated that the increase in Isc was due to net Cl- secretion. Carbachol did not alter cellular cAMP, but caused a transient increase in free cytosolic Ca2+ ([Ca2+]i) from 117 +/- 7 nM to 160 +/- 15 nM. The carbachol-induced increase in Isc was potentiated by either prostaglandin E1 (PGE1) or vasoactive intestinal polypeptide (VIP), agents that act by increasing cAMP. Measurements of cAMP and [Ca2+]i indicated that the potentiated response was not due to changes in these second messengers. Studies of the effects of these agents on ion transport pathways indicated that carbachol, PGE1, or VIP each increased basolateral K+ efflux by activating two different K+ transport pathways on the basolateral membrane. The pathway activated by carbachol was not sensitive to barium, while that activated by PGE1 or VIP was; furthermore, their action on K+ efflux are additive. Our study indicates that carbachol causes Cl- secretion, and that this action may result from its ability to increase [Ca2+]i and basolateral K+ efflux. Carbachol's effect on Cl- secretion is greatly augmented in the presence of VIP or PGE1, which open a cAMP-sensitive Cl- channel on the apical membrane, accounting for a potentiated response. Reference: J Clin Invest. 1986 Feb;77(2):348-54. https://www.ncbi.nlm.nih.gov/pmc/articles/pmid/3003156/
In vivo activity: Cholinergic regulation of sleep and wakefulness was studied in freely moving rats locally infused with various doses of carbachol into the pontine reticular formation. Induction of REM sleep occurred when carbachol was infused specifically into the posterior oral pontine reticular nucleus (PnO). This effect was observed with 1-10 ng of carbachol, and lasted for at least 6 h. It was antagonized by atropine (100-200 ng) infused into the same site 15 min before carbachol (10 ng), indicating that REM sleep induction resulted from the stimulation of pontine muscarinic receptors. High doses of carbachol (500 ng) did not affect REM sleep but enhanced wakefulness. Cholinergic mechanisms within the PnO may play a critical role in the regulation of REM sleep in the rat. Reference: Neuroreport. 1995 Feb 15;6(3):532-6. https://journals.lww.com/neuroreport/Abstract/1995/02000/Induction_of_rapid_eye_movement_sleep_by_carbachol.31.aspx

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 5.0 27.37
Water 36.0 197.10
Ethanol 12.0 65.70

Preparing Stock Solutions

The following data is based on the product molecular weight 182.65 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
In vitro protocol: 1. Dharmsathaphorn K, Pandol SJ. Mechanism of chloride secretion induced by carbachol in a colonic epithelial cell line. J Clin Invest. 1986 Feb;77(2):348-54. doi: 10.1172/JCI112311. PMID: 3003156; PMCID: PMC423353. 2. Keely SJ, Uribe JM, Barrett KE. Carbachol stimulates transactivation of epidermal growth factor receptor and mitogen-activated protein kinase in T84 cells. Implications for carbachol-stimulated chloride secretion. J Biol Chem. 1998 Oct 16;273(42):27111-7. doi: 10.1074/jbc.273.42.27111. PMID: 9765228.
In vivo protocol: 1. Bourgin P, Escourrou P, Gaultier C, Adrien J. Induction of rapid eye movement sleep by carbachol infusion into the pontine reticular formation in the rat. Neuroreport. 1995 Feb 15;6(3):532-6. doi: 10.1097/00001756-199502000-00031. PMID: 7766858. 2. Nishikawa N, Chakrabarty B, Kitney D, Jabr R, Kanai A, Fry C. Stretch- and carbachol-induced ATP release from bladder wall preparations of young and aged mice. Neurourol Urodyn. 2020 Aug;39(6):1644-1652. doi: 10.1002/nau.24426. Epub 2020 Jun 12. PMID: 32531080; PMCID: PMC7641975.

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1: Fornai M, Pellegrini C, Antonioli L, Segnani C, Ippolito C, Barocelli E,
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disease: alterations of excitatory cholinergic neurotransmission regulating
colonic motility in rats. J Pharmacol Exp Ther. 2015 Nov 18. pii:
jpet.115.228510. [Epub ahead of print] PubMed PMID: 26582732.

2: Sakai H, Sato K, Yuki K, Chiba Y, Narita M. Denatonium and
6-n-propyl-2-thiouracil, agonists of bitter taste receptor, inhibit contraction
of various types of smooth muscles in the rat and mouse. Biol Pharm Bull. 2015
Nov 14. [Epub ahead of print] PubMed PMID: 26567724.