8-methyl-8-azabicyclo[3.2.1]oct-2-ene-2-carboxylic acid

• ChemBase ID: 160662
• Molecular Formular: C9H13NO2
• Molecular Mass: 167.20502
• Monoisotopic Mass: 167.09462866
• SMILES: C12CCC(N1C)C(=CC2)C(=O)O
• Canonical SMILES: CN1C2CCC1C(=CC2)C(=O)O
• InChI: InChI=1S/C9H13NO2/c1-10-6-2-4-7(9(11)12)8(10)5-3-6/h4,6,8H,2-3,5H2,1H3,(H,11,12)
• InChIKey: HZGRVVUQEIBCMS-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 8-methyl-8-azabicyclo[3.2.1]oct-2-ene-2-carboxylic acid
• IUPAC Traditional name: ecgonidine
• Synonyms: (1R,5S)-8-Methyl-8-azabicyclo[3.2.1]oct-2-ene-2-carboxylic Acid; (1R)-8-methyl-8-Azabicyclo[3.2.1]oct-2-ene-2-carboxylic Acid; Anhydroecgonine; Ecgonidine; Anhydro Ecgonine

Database IDs

• CAS Number: 484-93-5
• PubChem SID: 162254797
• PubChem CID: 101709

CALCULATED PROPERTIES

• Acid pKa: 3.71554
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): -1.9388651
• LogD (pH = 7.4): -1.9376084
• Log P: -1.9349588
• Molar Refractivity: 45.9733 cm^3
• Polarizability: 17.655323 Å^3
• Polar Surface Area: 40.54 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - A638800

An alkaloid related to Ecgonine and Cocaine ( (C633500). It is a metabolite of Methylecgonidine (a pylolytic product of cocaine) and is used as a biomarker for crack cocaine use.

REFERENCES

• Fandino, A. et al.: Chem. Res. Toxicol., 15, 1543 (2002)
• Scheidweiler, K.B. et al.: J. Pharmacol. Exp. Therap., 307, 1179 (2002)
• Paul, B. et al.: Biomed. Chrom., 19, 677 (2002)