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-]
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
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
|
Solvent |
mg/mL |
mM |
| Solubility |
| DMSO |
5.0 |
27.37 |
| Water |
36.0 |
197.10 |
| Ethanol |
12.0 |
65.70 |
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.
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.
| 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 |
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.
1: Fornai M, Pellegrini C, Antonioli L, Segnani C, Ippolito C, Barocelli E,
Ballabeni V, Vegezzi G, Al Harraq Z, Blandini F, Levandis G, Cerri S, Blandizzi
C, Bernardini N, Colucci R. Enteric dysfunctions in experimental Parkinson's
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.
