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

• ChemBase ID: 164936
• Molecular Formular: C17H21NO4
• Molecular Mass: 303.35294
• Monoisotopic Mass: 303.14705816
• SMILES: [C@@H]12CC[C@@H](N1C)[C@H]([C@H](C2)OC(=O)c1ccccc1)C(=O)OC
• Canonical SMILES: COC(=O)[C@H]1[C@H](C[C@H]2N([C@@H]1CC2)C)OC(=O)c1ccccc1
• InChI: InChI=1S/C17H21NO4/c1-18-12-8-9-13(18)15(17(20)21-2)14(10-12)22-16(19)11-6-4-3-5-7-11/h3-7,12-15H,8-10H2,1-2H3/t12-,13+,14-,15+/m0/s1
• InChIKey: ZPUCINDJVBIVPJ-LJISPDSOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (1R,2R,3S,5S)-3-(benzoyloxy)-8-(^2H₃)methyl-8-azabicyclo[3.2.1]octane-2-carboxylate
• IUPAC Traditional name: methyl (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 Methyl Ester; (-)-Cocaine-d3; Cocaine-d3 Muriate; Ecgonine-d3 Methyl Ester Benzoate; NSC 25263-d3; Cocaine N-Methyl-d3

Database IDs

• CAS Number: 138704-14-0
• PubChem SID: 162259070
• PubChem CID: 10638361

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): -0.8337083
• LogD (pH = 7.4): 0.82485026
• Log P: 2.282108
• Molar Refractivity: 81.1604 cm^3
• Polarizability: 32.167484 Å^3
• Polar Surface Area: 55.84 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform
• Apperance: White to Off-White Solid
• Melting Point: 91-930C

Safety Information

• Storage Condition: Controlled Substance, -20°C Freezer

DETAILS

Toronto Research Chemicals - C633502

Inhibits the dopamine, norepinephrine, and serotonin transporters. Unlike amphetamines, it has no effect on catecholamine release. Controlled substance. Anesthetic (local).

REFERENCES

• Blakely, R.D., et al.: Curr. Opin. Neurobiol., 10, 328 (2000)
• Cowell, R. M., et al.: Eur. J. Pharmacol., 389, 59 (2000)
• Fleckenstein, A.E., Eur. J. Pharmacol., 406, 1 (2000)
• Torres, G.E., et al.: Nat. Rev. Neurosci., 4, 13 (2000)