2-(trimethylazaniumyl)ethyl carbamate

• ChemBase ID: 294
• Molecular Formular: C6H15N2O2+
• Molecular Mass: 147.1955
• Monoisotopic Mass: 147.11335273
• SMILES: O(CC[N+](C)(C)C)C(=O)N
• Canonical SMILES: NC(=O)OCC[N+](C)(C)C
• InChI: InChI=1S/C6H14N2O2/c1-8(2,3)4-5-10-6(7)9/h4-5H2,1-3H3,(H-,7,9)/p+1
• InChIKey: VPJXQGSRWJZDOB-UHFFFAOYSA-O

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(trimethylazaniumyl)ethyl carbamate
• IUPAC Traditional name: carbamyl-choline
• Brand Name: CB; Carbachol USP27; Carbachol chloride; Carbachol hydrochloride; Carbacholin; Carbacholine; Carbacholine chloride; Carbacolina; Carbaminocholine chloride; Carbaminoylcholine chloride; Carbamiotin; Carbamoylcholine chloride; Carbamoylcholine-hydrochloride; Carbamylcholine chloride; Carbastat; Carbastat intraocular; Carbochol; Carbocholin; Carbocholine; Carboptic; Carbyl; Carcholin; Choline carbamate chloride; Choline chloride carbamate; Choline chloride, carbamoyl-; Choline chlorine carbamate; Choline, chloride, carbamate; Coletyl; Doryl; Isopto Carbachol; Jestryl; Karbachol; Karbamoylcholin chlorid; Lentin; Lentine; Miostat; Mistura C; Moryl; P. V. Carbachol; Rilentol; Vasoperif
• Synonyms: Carbachol; Carbamyl-Choline

Database IDs

• CAS Number: 51-83-2
• PubChem SID: 160963757
• PubChem CID: 2551

CALCULATED PROPERTIES

ALOGPS 2.1

• Log P: -2.95
• LOG S: -2.41
• Solubility (Water): 7.06e-01 g/l

JChem

• Log P: -4.5546894
• Molar Refractivity: 50.0222 cm^3
• Polarizability: 15.18228 Å^3
• Polar Surface Area: 52.32 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true
• LogD (pH = 5.5): -4.554689
• LogD (pH = 7.4): -4.5546737
• Acid pKa: 15.226036
• H Acceptors: 1
• H Donor: 1

PROPERTIES

Physical Property

• Solubility: 1 g/ml
• Hydrophobicity(logP): -3.78

DETAILS

DrugBank - DB00411

• Drug Groups: approved
• Description: A slowly hydrolyzed cholinergic agonist that acts at both muscarinic and nicotinic receptors. [PubChem]
• Indication: Primarily used in the treatment of glaucoma, but is also used during ophthalmic surgery.
• Pharmacology: Carbachol is a potent cholinergic (parasympathomimetic) agent which produces constriction of the iris and ciliary body resulting in reduction in intraocular pressure. The exact mechanism by which carbachol lowers intraocular pressure is not precisely known. In the cat and rat, carbachol is well-known for its ability to induce rapid eye movement (REM) sleep when microinjected into the pontine reticular formation. Carbachol elicits this REM sleep-like state via activation of postsynaptic muscarinic cholinergic receptors (mAChRs).
• Toxicity: Oral, mouse: LD₅₀ = 15 mg/kg; Oral, rat: LD₅₀ = 40 mg/kg.
• Affected Organisms: Humans and other mammals
• Absorption: Not well absorbed in the gastro-intestinal tract, and does not cross the blood-brain barrier.
• External Links: Wikipedia; RxList; Drugs.com

DrugBank - DB02487

Drug information: experimental