ethyl (1R,2R,3S,5S)-3-hydroxy-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate

• ChemBase ID: 167944
• Molecular Formular: C11H19NO3
• Molecular Mass: 213.27346
• Monoisotopic Mass: 213.13649347
• SMILES: [C@@H]12CC[C@@H](N1C)[C@H]([C@H](C2)O)C(=O)OCC
• Canonical SMILES: CCOC(=O)[C@H]1[C@@H](O)C[C@H]2N([C@@H]1CC2)C
• InChI: InChI=1S/C11H19NO3/c1-3-15-11(14)10-8-5-4-7(12(8)2)6-9(10)13/h7-10,13H,3-6H2,1-2H3/t7-,8+,9-,10+/m0/s1
• InChIKey: ABDMBNAKYBUEEX-QCLAVDOMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ethyl (1R,2R,3S,5S)-3-hydroxy-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate
• IUPAC Traditional name: ethyl (1R,2R,3S,5S)-3-hydroxy-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate
• Synonyms: (1R,2R,3S,5S)-3-Hydroxy-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic Acid Ethyl Ester; [1R-(exo,exo)]-3-Hydroxy-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic Acid Ethyl Ester; Ethyl Ecgonine; Ecgonine Ethyl Ester

Database IDs

• CAS Number: 70939-97-8
• PubChem SID: 162262077
• PubChem CID: 18656861

CALCULATED PROPERTIES

• Acid pKa: 14.595394
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): -3.0110512
• LogD (pH = 7.4): -1.3790829
• Log P: 0.14361611
• Molar Refractivity: 56.087 cm^3
• Polarizability: 22.4664 Å^3
• Polar Surface Area: 49.77 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - E325570

A metabolite of Cocaine (C633500).Controlled substance.

REFERENCES

• Wolff, K., et al.: Addiction, 94, 1279 (1999)
• Schaffer, M., et al.: J. Anal. Toxicol., 29, 319 (1999)
• Cognard, E., et al.: J. Pharm. Biomed. Anal., 41, 925 (1999)