propan-2-yl (1R,2R,3S,5S)-3-(benzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate

• ChemBase ID: 160952
• Molecular Formular: C19H25NO4
• Molecular Mass: 331.4061
• Monoisotopic Mass: 331.17835829
• SMILES: [C@@H]12CC[C@@H](N1C)[C@H]([C@H](C2)OC(=O)c1ccccc1)C(=O)OC(C)C
• Canonical SMILES: CC(OC(=O)[C@H]1[C@H](C[C@H]2N([C@@H]1CC2)C)OC(=O)c1ccccc1)C
• InChI: InChI=1S/C19H25NO4/c1-12(2)23-19(22)17-15-10-9-14(20(15)3)11-16(17)24-18(21)13-7-5-4-6-8-13/h4-8,12,14-17H,9-11H2,1-3H3/t14-,15+,16-,17+/m0/s1
• InChIKey: NGJWCZYRIKMKEP-VVLHAWIVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: propan-2-yl (1R,2R,3S,5S)-3-(benzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate
• IUPAC Traditional name: isopropyl (1R,2R,3S,5S)-3-(benzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate
• Synonyms: (1R,2R,3S,5S)-3-(Benzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic Acid 1-Methylethyl Ester; [1R-(exo,exo)]-3-(Benzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic Acid; Benzoyl Ecgonine Isopropyl Ester

Database IDs

• CAS Number: 137819-55-7
• PubChem SID: 162255087
• PubChem CID: 15109306

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 0.027180176
• LogD (pH = 7.4): 1.7312707
• Log P: 3.055491
• Molar Refractivity: 90.3278 cm^3
• Polarizability: 35.843838 Å^3
• Polar Surface Area: 55.84 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - B208130

A 2β-substituted analog of cocaine as potential cocaine antagonist.Controlled substance.

REFERENCES

• Arthur, C., et al.: Anal. Chem., 62, 2145 (1990)
• Lewin, A.H., et al.: J. Med. Chem., 35, 135 (1990)
• Lloyd, J., et al.: J. Forensic Sci., 48, 130 (1990)