1-(trimethylazaniumyl)propan-2-yl carbamate

• ChemBase ID: 892
• Molecular Formular: C7H17N2O2+
• Molecular Mass: 161.22208
• Monoisotopic Mass: 161.12900279
• SMILES: O(C(C[N+](C)(C)C)C)C(=O)N
• Canonical SMILES: CC(C[N+](C)(C)C)OC(=O)N
• InChI: InChI=1S/C7H16N2O2/c1-6(11-7(8)10)5-9(2,3)4/h6H,5H2,1-4H3,(H-,8,10)/p+1
• InChIKey: NZUPCNDJBJXXRF-UHFFFAOYSA-O

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-(trimethylazaniumyl)propan-2-yl carbamate
• IUPAC Traditional name: carbamyl-β-methylcholine; bethanechol
• Brand Name: Duvoid; Mechotane; Mechothane; Mecothane; Mictone; Mictrol; Myocholine; Myotonachol; Myotonine Chloride; Urabeth; Urecholine; Urecholine Chloride; Uro-Carb
• Synonyms: Amidopropyldimethylbetaine; Beta-Methyl Carbachol Chloride; Besacholine; Bethaine Choline Chloride; Bethanechol Chloride; BTC; Carbamylmethylcholine Chloride; Bethanechol; 2-[(aminocarbonyl)oxy]- ''N'',''N'',''N''-trimethyl- 1-propanaminium

Database IDs

• CAS Number: 674-38-4
• PubChem SID: 160964355; 46507707
• PubChem CID: 2370
• CHEBI ID: 3084
• ATC CODE: N07AB02
• CHEMBL: 1482
• Chemspider ID: 2280
• DrugBank ID: DB01019
• IUPHAR ligand ID: 297
• KEGG ID: C06850
• Unique Ingredient Identifier: 004F72P8F4
• Wikipedia Title: Bethanechol
• Medline Plus: a682849

CALCULATED PROPERTIES

JChem

• Acid pKa: 15.340623
• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): -4.138114
• LogD (pH = 7.4): -4.1381025
• Log P: -4.1381145
• Molar Refractivity: 54.441 cm^3
• Polarizability: 17.012852 Å^3
• Polar Surface Area: 52.32 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -2.79
• LOG S: -2.8
• Solubility (Water): 3.11e-01 g/l

PROPERTIES

Physical Property

• Solubility: 10 mg/mL (chloride salt)

Pharmacology Properties

• Admin Routes: Oral, subcutaneous
• Pregnancy Category: C (US)

DETAILS

DrugBank - DB01019

• Drug Groups: approved
• Description: Bethanechol is a synthetic ester structurally and pharmacologically related to acetylcholine. A slowly hydrolyzed muscarinic agonist with no nicotinic effects, bethanechol is generally used to increase smooth muscle tone, as in the GI tract following abdominal surgery or in urinary retention in the absence of obstruction. It may cause hypotension, cardiac rate changes, and bronchial spasms. [PubChem]
• Indication: For the treatment of acute postoperative and postpartum nonobstructive (functional) urinary retention and for neurogenic atony of the urinary bladder with retention.
• Pharmacology: Bethanechol is a parasympathomimetic (cholinergic) used for the treatment of acute postoperative and postpartum nonobstructive (functional) urinary retention and for neurogenic atony of the urinary bladder with retention. Bethanechol, a cholinergic agent, is a synthetic ester which is structurally and pharmacologically related to acetylcholine. It increases the tone of the detrusor urinae muscle, usually producing a contraction sufficiently strong to initiate micturition and empty the bladder. It stimulates gastric motility, increases gastric tone, and often restores impaired rhythmic peristalsis. Bethanechol chloride is not destroyed by cholinesterase and its effects are more prolonged than those of acetytcholine.
• Affected Organisms: Humans and other mammals
• External Links: Wikipedia; RxList; Drugs.com