(2H3)methyl (1R,2R,3S,5S)-3-(benzoyloxy)-8-azabicyclo[3.2.1]octane-2-carboxylate hydrochloride

• ChemBase ID: 175591
• Molecular Formular: C16H20ClNO4
• Molecular Mass: 325.7873
• Monoisotopic Mass: 325.10808581
• SMILES: Cl.[C@@H]12CC[C@@H](N1)[C@H]([C@H](C2)OC(=O)c1ccccc1)C(=O)OC
• Canonical SMILES: COC(=O)[C@@H]1[C@H]2CC[C@H](N2)C[C@@H]1OC(=O)c1ccccc1.Cl
• InChI: InChI=1S/C16H19NO4.ClH/c1-20-16(19)14-12-8-7-11(17-12)9-13(14)21-15(18)10-5-3-2-4-6-10;/h2-6,11-14,17H,7-9H2,1H3;1H/t11-,12+,13-,14+;/m0./s1
• InChIKey: RIPPXFWUYXTRNJ-BHARVXRSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (^2H₃)methyl (1R,2R,3S,5S)-3-(benzoyloxy)-8-azabicyclo[3.2.1]octane-2-carboxylate hydrochloride
• IUPAC Traditional name: (^2H₃)methyl (1R,2R,3S,5S)-3-(benzoyloxy)-8-azabicyclo[3.2.1]octane-2-carboxylate hydrochloride
• Synonyms: 1R,2R,3S,5S)-3-(Benzoyloxy)-8-azabicyclo[3.2.1]octane-2-carboxylic Acid Methyl-d3 Ester Hydrochloride Salt; (-)-Norcocaine-d3 Hydrochloride Salt; N-Demethylcocaine-d3 Hydrochloride Salt; Norcocaine-d3 Hydrochloride

Database IDs

• PubChem SID: 164231501
• PubChem CID: 71751175

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): -1.3176824
• LogD (pH = 7.4): -0.58344674
• Log P: 1.8990601
• Molar Refractivity: 75.8657 cm^3
• Polarizability: 30.330688 Å^3
• Polar Surface Area: 64.63 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: Pale Yellow Foam
• Melting Point: 30-32°C

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - N661502

A minor labelled metabolite of Cocaine. Controlled substance.

REFERENCES

• Jeffcoat, A., et al.: Drug Metab. Dispos., 17, 153 (1989)
• Brzezinski, M., et al.: Biochem. Pharmacol., 48, 1747(1989)
• Cone, E., et al.: Ther. Drug Monit., 20, 556 (1989)
• Jufer, R., et al.: J. Anal. Toxicol., 22, 435 (1989)