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

• ChemBase ID: 164935
• Molecular Formular: C18H23NO4
• Molecular Mass: 317.37952
• Monoisotopic Mass: 317.16270822
• SMILES: [C@@H]12CC[C@@H](N1C)[C@H]([C@H](C2)OC(=O)c1ccccc1)C(=O)OCC
• Canonical SMILES: CCOC(=O)[C@H]1[C@H](C[C@H]2N([C@@H]1CC2)C)OC(=O)c1ccccc1
• InChI: InChI=1S/C18H23NO4/c1-3-22-18(21)16-14-10-9-13(19(14)2)11-15(16)23-17(20)12-7-5-4-6-8-12/h4-8,13-16H,3,9-11H2,1-2H3/t13-,14+,15-,16+/m0/s1
• InChIKey: NMPOSNRHZIWLLL-XUWVNRHRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ethyl (1R,2R,3S,5S)-3-(benzoyloxy)-8-(^2H₃)methyl-8-azabicyclo[3.2.1]octane-2-carboxylate
• IUPAC Traditional name: ethyl (1R,2R,3S,5S)-3-(benzoyloxy)-8-(^2H₃)methyl-8-azabicyclo[3.2.1]octane-2-carboxylate
• Synonyms: (1R,2R,3S,5S)-3-(Benzoyloxy)-8-(methyl-d3)-8-azabicyclo[3.2.1]octane-2-carboxylic Acid Ethyl Ester; Ecgonine-d3 Ethyl Ester Benzoate (Ester); Ethyl Benzoylecgonine-d3; Ethylcocaine-d3; Homocaine-d3; Homococaine-d3; Cocaethylene-d3

Database IDs

• PubChem SID: 162259069
• PubChem CID: 71314968

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): -0.43166134
• LogD (pH = 7.4): 1.2525958
• Log P: 2.638916
• Molar Refractivity: 85.909 cm^3
• Polarizability: 34.00524 Å^3
• Polar Surface Area: 55.84 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Alcohol; Ether
• Apperance: Crystalline Solid
• Melting Point: 1090C

DETAILS

Toronto Research Chemicals - C633402

Homolog of Cocaine (C633500). Anesthetic (local). High-affinity ligand for dopamine transporter; a metabolite of Cocaine when alcohol is concommitently abused. Controlled substance.

REFERENCES

• ElSohly, M., et al.: J. Anal. Toxicol., 15, 46 (1991)
• Hearn, W.L., et al.: J. Neurochem., 56, 698 (1991)
• Shimomura, E., et al.: Clin. Chem., 47, 1040 (1991)
• Wu, A.H.B., et al.: J. Anal. Toxicol., 16, 132 (1991)