1-(trimethylazaniumyl)propan-2-yl carbamate chloride

• ChemBase ID: 73030
• Molecular Formular: C7H17ClN2O2
• Molecular Mass: 196.67508
• Monoisotopic Mass: 196.09785547
• SMILES: [N+](CC(OC(=O)N)C)(C)(C)C.[Cl-]
• Canonical SMILES: CC(C[N+](C)(C)C)OC(=O)N.[Cl-]
• InChI: InChI=1S/C7H16N2O2.ClH/c1-6(11-7(8)10)5-9(2,3)4;/h6H,5H2,1-4H3,(H-,8,10);1H
• InChIKey: XXRMYXBSBOVVBH-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-(trimethylazaniumyl)propan-2-yl carbamate chloride
• IUPAC Traditional name: carbamyl-β-methylcholine chloride; bethanechol chloride
• Synonyms: n/a; Bethanechol chloride; 2-[(Aminocarbonyl)oxy]-N,N,N-trimethyl-1-propanaminium Chloride; (2-Hydroxypropyl)trimethylammonium Chloride Carbamate; Besacholine; Carbamylmethylcholine Chloride; Mechotane; Mechothane; Mecothane; Mictone; Myocholine; Myotonachol; Myotonine Chloride; NSC 30783; Bethanechol; [1-(trimethylaminiumyl)propan-2-yl] carbamate chloride; Carbamyl-β-methylcholine chloride; Bethanechol chloride; Carbamyl-β-methylcholine chloride

Database IDs

• CAS Number: 590-63-6
• EC Number: 209-686-8
• MDL Number: MFCD00055224
• PubChem SID: 24277823; 162037950
• PubChem CID: 11548

CALCULATED PROPERTIES

• 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

PROPERTIES

Physical Property

• Solubility: ethanol: soluble80 mg/mL (stable for several days at 4°C.); H2O: soluble1.7 g/mL (stable for several days at 4°C.); Methanol
• Apperance: white crystalline; White Solid
• Melting Point: 187-190°C; 209 - 211°C; 218°C(decomposes)
• Hydrophobicity(logP): -4.01

Safety Information

• Storage Condition: -20°C; 2-8°C, Desiccate; Refrigerator, Under Inert Atmosphere
• RTECS: BR5425000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22; R:22
• Safety Statements: 36; S:36/37/39
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥99% (TLC); 95%
• Salt Data: chloride

DETAILS

MP Biomedicals - 02190160

Cholinergic receptor agonist

Selleck Chemicals - S2455

Research Area: Neurological Disease
Biological Activity:
Bethanechol chloride is a selective muscarinic receptor agonist without any effect on nicotinic receptors. It is a parasympathomimetic choline ester. It is not hydrolyzed by cholinesterase and will therefore have a long duration of action. It does not involve the action of the muscarinic M3 receptor subtype in-vitro. [1]

Sigma Aldrich - C5259

Caution
Hygroscopic.
Substrates
Muscarinic acetylcholine receptor agonist that is not a substrate for acetylcholinesterase.

Toronto Research Chemicals - B328900

A selective muscarinic receptor stimulant, used to treat cerebral palsy.

REFERENCES

• http://en.wikipedia.org/wiki/Bethanechol
• Buehler, M., et al.: Res. Vet. Sci., 84, 444 (2008)
• Fliri, A., et al.: J. Med. Chem., 52, 8038 (2008)
• Gohil, V., et al.: Nat. Biotechnol., 28, 249 (2008)