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

• ChemBase ID: 130684
• Molecular Formular: C17H21NO5
• Molecular Mass: 319.35234
• Monoisotopic Mass: 319.14197278
• SMILES: CN1[C@H]2CC[C@@H]1[C@H]([C@H](C2)OC(=O)c1cccc(c1)O)C(=O)OC
• Canonical SMILES: COC(=O)[C@H]1[C@H](C[C@H]2N([C@@H]1CC2)C)OC(=O)c1cccc(c1)O
• InChI: InChI=1S/C17H21NO5/c1-18-11-6-7-13(18)15(17(21)22-2)14(9-11)23-16(20)10-4-3-5-12(19)8-10/h3-5,8,11,13-15,19H,6-7,9H2,1-2H3/t11-,13+,14-,15+/m0/s1
• InChIKey: IQXBUEUAOWARGT-PMOUVXMZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (1R,2R,3S,5S)-3-(3-hydroxybenzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate
• IUPAC Traditional name: methyl (1R,2R,3S,5S)-3-(3-hydroxybenzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate
• Synonyms: m-Hydroxycocaine; 间羟基可卡因

Database IDs

• CAS Number: 71387-58-1
• MDL Number: MFCD00274049
• PubChem SID: 162224962
• PubChem CID: 11823332

CALCULATED PROPERTIES

• Acid pKa: 9.320758
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): -1.1265631
• LogD (pH = 7.4): 0.5308791
• Log P: 1.5220572
• Molar Refractivity: 83.1413 cm^3
• Polarizability: 32.79855 Å^3
• Polar Surface Area: 76.07 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• European Hazard Symbols: Harmful (Xn)
• UN Number: 1544
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 2
• Risk Statements: 20/21/22-43
• Safety Statements: 22-26-36/37/39
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H312-H317-H332
• GHS Precautionary statements: P280
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• RID/ADR: UN 1544 6.1/PG 2
• Drug Control: USDEA Schedule II; Home Office Schedule 2; stupéfiant; kontrollierte Droge in Deutschland; regulated under CDSA - not available from Sigma-Aldrich Canada
• Storage Temperature: -20°C