(1R,2R,3S,5S)-3-hydroxy-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acid hydrochloride

• ChemBase ID: 153400
• Molecular Formular: C9H16ClNO3
• Molecular Mass: 221.68124
• Monoisotopic Mass: 221.08187106
• SMILES: CN1[C@H]2CC[C@@H]1[C@@H]([C@H](C2)O)C(=O)O.Cl
• Canonical SMILES: O[C@H]1C[C@@H]2CC[C@H]([C@@H]1C(=O)O)N2C.Cl
• InChI: InChI=1S/C9H15NO3.ClH/c1-10-5-2-3-6(10)8(9(12)13)7(11)4-5;/h5-8,11H,2-4H2,1H3,(H,12,13);1H/t5-,6+,7-,8+;/m0./s1
• InChIKey: HVWQTEPEBQYIFB-PXXJPSRFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,2R,3S,5S)-3-hydroxy-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acid hydrochloride
• IUPAC Traditional name: ecgonine hydrochloride
• Synonyms: (1R,2R,3S,5S)-3-Hydroxy-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic Acid Hydrochloride; 3β-Hydroxy-1αH,5αH-tropane-2β-carboxylic Acid Hydrochloride; L-Ecgonine Hydrochloride; (-)-Ecgonine Hydrochloride; Ecgonine hydrochloride; 芽子碱 盐酸盐

Database IDs

• CAS Number: 5796-31-6
• MDL Number: MFCD00069267
• PubChem SID: 162247539
• PubChem CID: 45157630

CALCULATED PROPERTIES

• Acid pKa: 3.4801822
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -3.0927565
• LogD (pH = 7.4): -3.0912147
• Log P: -3.0901585
• Molar Refractivity: 46.5693 cm^3
• Polarizability: 18.560587 Å^3
• Polar Surface Area: 60.77 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Water
• Apperance: White Solid

Safety Information

• RTECS: YM2785000
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Drug Control: USDEA Schedule II; Home Office Schedule 2; stupéfiant; kontrollierte Droge in Deutschland; regulated under CDSA - not available from Sigma-Aldrich Canada

Product Information

• Empirical Formula (Hill Notation): C9H15NO3 · HCl

DETAILS

Sigma Aldrich - E5137

Biochem/physiol Actions
Minor metabolite of cocaine

Toronto Research Chemicals - E325550

A tropane alkaloid which is both a metabolite and a precursor to Cocaine.

REFERENCES

• Bois, F., et al.: Bioorg. Med. Chem. Lett., 14, 2117 (2004)
• Yoder, K., et al.: Nuc. Med. Biol., 36, 11 (2004)