methyl (1R,5S)-8-methyl-8-azabicyclo[3.2.1]oct-2-ene-2-carboxylate

• ChemBase ID: 167940
• Molecular Formular: C10H15NO2
• Molecular Mass: 181.2316
• Monoisotopic Mass: 181.11027873
• SMILES: [C@@H]12CC[C@@H](N1C)C(=CC2)C(=O)OC
• Canonical SMILES: COC(=O)C1=CC[C@H]2N([C@@H]1CC2)C
• InChI: InChI=1S/C10H15NO2/c1-11-7-3-5-8(10(12)13-2)9(11)6-4-7/h5,7,9H,3-4,6H2,1-2H3/t7-,9-/m1/s1
• InChIKey: MPSNEAHFGOEKBI-VXNVDRBHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (1R,5S)-8-methyl-8-azabicyclo[3.2.1]oct-2-ene-2-carboxylate
• IUPAC Traditional name: methylecgonidine
• Synonyms: (1R,5S)-8-Methyl-8-azabicyclo[3.2.1]oct-2-ene-2-carboxylic Acid Methyl Ester; (-)-Anhydroecgonine Methyl Ester; (R)-(-)-Anhydroecgonine Methyl Ester; Anhydroecgonine Methyl Ester; EDME; Methyl Ecgonidine; Ecgonidine Methyl Ester

Database IDs

• CAS Number: 43021-26-7
• PubChem SID: 162262073
• PubChem CID: 119478

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): -1.6385471
• LogD (pH = 7.4): 0.12365511
• Log P: 1.1741343
• Molar Refractivity: 50.7424 cm^3
• Polarizability: 19.742533 Å^3
• Polar Surface Area: 29.54 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: Clear Colorless Oil

Safety Information

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

DETAILS

Toronto Research Chemicals - E325300

A metabolite of Cocaine (COC). It is a pyrolysis product formed when crack cocaine is smoked, making this substance a useful biomarker to specifically test for use of crack cocaine, as opposed to powder cocaine which does not form methylecgonidine as a me

REFERENCES

• Casale, J., et al.: J. Pharm. Sci., 83, 1186 (1994)
• Koren, G., et al.: J. Clin. Pharmacol., 32, 671 (1994)
• Mieczkowski, T., et al.: Forensic. Sci. Int., 84, 87 (1994)
• Schaffer, M., et al.: J. Anal. Toxicol., 26, 485 (1994)