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

• ChemBase ID: 156498
• Molecular Formular: C16H21NO5
• Molecular Mass: 307.34164
• Monoisotopic Mass: 307.14197278
• SMILES: CN1[C@H]2CC[C@@H]1[C@@H]([C@H](C2)OC(=O)c1ccccc1)C(=O)O.O
• Canonical SMILES: CN1[C@H]2CC[C@@H]1[C@@H]([C@H](C2)OC(=O)c1ccccc1)C(=O)O.O
• InChI: InChI=1S/C16H19NO4.H2O/c1-17-11-7-8-12(17)14(15(18)19)13(9-11)21-16(20)10-5-3-2-4-6-10;/h2-6,11-14H,7-9H2,1H3,(H,18,19);1H2/t11-,12+,13-,14+;/m0./s1
• InChIKey: FFQVHSAKNBCHHT-BHARVXRSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,2R,3S,5S)-3-(benzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acid hydrate
• IUPAC Traditional name: ecgonine benzoate hydrate
• Synonyms: Benzoylecgonine tetrahydrate; 苯甲酰芽子碱 水合物

Database IDs

• CAS Number: 5928-96-1
• EC Number: 208-263-5
• PubChem SID: 24891755; 162250636
• PubChem CID: 71312327

CALCULATED PROPERTIES

• Acid pKa: 3.1464374
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): -0.59588516
• LogD (pH = 7.4): -0.59690845
• Log P: -0.59486806
• Molar Refractivity: 76.3913 cm^3
• Polarizability: 30.082672 Å^3
• Polar Surface Area: 66.84 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• European Hazard Symbols: Toxic (T)
• UN Number: 1544
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3
• Risk Statements: 25
• Safety Statements: 45
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301
• GHS Precautionary statements: P301 + P310
• Personal Protective Equipment: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• RID/ADR: UN 1544 6.1/PG 3
• Drug Control: USDEA Schedule II; Home Office Schedule 2; stupéfiant; kontrollierte Droge in Deutschland; regulated under CDSA - not available from Sigma-Aldrich Canada

Pharmacology Properties

• Gene Information: rat ... Slc6a3(24898)

Product Information

• Grade: drug standard
• Empirical Formula (Hill Notation): C16H19NO4 · 4 H2O

DETAILS

Sigma Aldrich - B4147

Biochem/physiol Actions
Major metabolite of cocaine.