methane sulfuric acid (1R,3R,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl 3-hydroxy-2-phenylpropanoate

• ChemBase ID: 160892
• Molecular Formular: C18H29NO7S
• Molecular Mass: 403.49036
• Monoisotopic Mass: 403.16647327
• SMILES: C.[C@@H]12CC[C@@H](N1C)C[C@@H](C2)OC(=O)C(CO)c1ccccc1.S(=O)(=O)(O)O
• Canonical SMILES: OS(=O)(=O)O.OCC(c1ccccc1)C(=O)O[C@@H]1C[C@@H]2CC[C@H](C1)N2C.C
• InChI: InChI=1S/C17H23NO3.CH4.H2O4S/c1-18-13-7-8-14(18)10-15(9-13)21-17(20)16(11-19)12-5-3-2-4-6-12;;1-5(2,3)4/h2-6,13-16,19H,7-11H2,1H3;1H4;(H2,1,2,3,4)/t13-,14+,15+,16?
• InChIKey: CEFHIXLHXSXTSB-ODJCEOKHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methane sulfuric acid (1R,3R,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl 3-hydroxy-2-phenylpropanoate
• IUPAC Traditional name: l-atropine; methane; sulfuric acid
• Synonyms: α-(Hydroxymethyl)benzeneacetic Acid (3-endo)-8-Methyl-8-azabicyclo[3.2.1]oct-3-yl Ester Sulfate Hydrate; Atropine Sulfate Hydrate; Atropisol; Atropt; Atropine Sulfate Monohydrate

Database IDs

• CAS Number: 5908-99-6
• PubChem SID: 162255027
• PubChem CID: 71313529

CALCULATED PROPERTIES

• Acid pKa: 15.1457405
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): -1.7801015
• LogD (pH = 7.4): -0.40574417
• Log P: 1.571241
• Molar Refractivity: 80.8164 cm^3
• Polarizability: 32.034832 Å^3
• Polar Surface Area: 49.77 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Water
• Apperance: White Solid
• Melting Point: 190-194°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - A794625

Mydriatic; antispasmodic; used in preanesthetic medication.

REFERENCES

• Brown, R.V., et al.: Br. J. Pharmacol., 15, 170 (1960)
• Shutt, L.E., et al.: Anaesthesia, 34, 476 (1960)
• Hinderling, P.H., et al.: J. Pharm. Sci., 74, 703 (1960)