(1R,2R,3S,5S,8S)-3-(benzoyloxy)-2-(methoxycarbonyl)-8-methyl-8-azabicyclo[3.2.1]octan-8-ium-8-olate

• ChemBase ID: 164938
• Molecular Formular: C17H21NO5
• Molecular Mass: 319.35234
• Monoisotopic Mass: 319.14197278
• SMILES: [C@@H]12CC[C@@H]([N@+]1([O-])C)[C@H]([C@H](C2)OC(=O)c1ccccc1)C(=O)OC
• Canonical SMILES: COC(=O)[C@H]1[C@@H](OC(=O)c2ccccc2)C[C@H]2[N@@+]([C@@H]1CC2)([O-])C
• InChI: InChI=1S/C17H21NO5/c1-18(21)12-8-9-13(18)15(17(20)22-2)14(10-12)23-16(19)11-6-4-3-5-7-11/h3-7,12-15H,8-10H2,1-2H3/t12-,13+,14-,15+,18-/m0/s1
• InChIKey: CQWXYUZZXCRUDE-KCTHJMFYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,2R,3S,5S,8S)-3-(benzoyloxy)-2-(methoxycarbonyl)-8-methyl-8-azabicyclo[3.2.1]octan-8-ium-8-olate
• IUPAC Traditional name: (1R,2R,3S,5S,8S)-3-(benzoyloxy)-2-(methoxycarbonyl)-8-methyl-8-azabicyclo[3.2.1]octan-8-ium-8-olate
• Synonyms: (1R,2R,3S,5S)-3-(Benzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic Acid Methyl Ester 8-Oxide; [1R-(exo,exo)]-3-(Benzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic Acid Methyl Ester 8-Oxide; Cocaine N-Oxide

Database IDs

• CAS Number: 72182-46-8
• PubChem SID: 162259072
• PubChem CID: 71314970

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 1.1577028
• LogD (pH = 7.4): 1.1577325
• Log P: 1.1577328
• Molar Refractivity: 83.2053 cm^3
• Polarizability: 32.342636 Å^3
• Polar Surface Area: 79.48 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - C633510

A thermally labile metabolite of Cocaine (C633500). Controlled Substance.

REFERENCES

• Wang, P. et al.: J. Anal. Toxicol., 23, 62 (1999)
• Huq, F. et al.: J. Pharmacol. Toxicol., 2, 114 (1999)