(1R,2R,3S,5S)-3-(benzoyloxy)-8-(2H3)methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acid

• ChemBase ID: 132082
• Molecular Formular: C16H19NO4
• Molecular Mass: 289.32636
• Monoisotopic Mass: 289.13140809
• SMILES: CN1[C@H]2CC[C@@H]1[C@H]([C@H](C2)OC(=O)c1ccccc1)C(=O)O
• Canonical SMILES: CN1[C@H]2CC[C@@H]1[C@H]([C@H](C2)OC(=O)c1ccccc1)C(=O)O
• InChI: InChI=1S/C16H19NO4/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)/t11-,12+,13-,14+/m0/s1
• InChIKey: GVGYEFKIHJTNQZ-RFQIPJPRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,2R,3S,5S)-3-(benzoyloxy)-8-(^2H₃)methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acid; (1R,2R,3S,5S)-3-(benzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acid
• IUPAC Traditional name: (1R,2R,3S,5S)-3-(benzoyloxy)-8-(^2H₃)methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acid; ecgonine benzoate
• Synonyms: Benzoylecgonine-N-methyl-d3 solution; (1R,2R,3S,5S)-3-(Benzoyloxy)-8-(methyl-d3)-8-azabicyclo[3.2.1]octane-2-carboxylic Acid; O-Benzoyl-(-)-ecgonine-d3; (-)-Benzoylecgonine-d3; O-Benzoylecgonine-d3; Benzoyl Ecgonine-d3; Benzoylecgonine-d3 solution; 苯甲酰芽子碱-N-甲基-d3 溶液; 苯甲酰芽子碱-d3 溶液

Database IDs

• CAS Number: 115732-68-8
• EC Number: 200-659-6
• MDL Number: MFCD00058542
• PubChem SID: 162226359; 24882026; 24882027; 24891696
• PubChem CID: 71308514

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

Physical Property

• Solubility: Chloroform; Ethanol; Methanol
• Apperance: White Solid
• Melting Point: 158-1600C
• Flash Point: 11 °C; 51.8 °F; 52 °F
• Mass Shift: M+3

Safety Information

• Storage Condition: -20°C Freezer
• European Hazard Symbols: Flammable (F); Toxic (T)
• UN Number: 1230
• German water hazard class: 1
• Hazard Class: 3
• Packing Group: 2
• Risk Statements: 11-23/24/25-39/23/24/25
• Safety Statements: 16-36/37-45; 7-16-36/37-45
• GHS Pictograms: GHS02; GHS06; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H225-H301 + H311 + H331-H370; H225-H301-H311-H331-H370
• GHS Precautionary statements: P210-P260-P280-P301 + P310-P311
• RID/ADR: UN 1230 3/PG 2
• Drug Control: Home Office Schedule 2; stupéfiant; kontrollierte Droge in Deutschlandregulated under CDSA - not available from Sigma-Aldrich Canada; regulated under CDSA - not available from Sigma-Aldrich Canada
• Storage Temperature: -20°C; 2-8°C

Product Information

• Concentration: 0.1 mg/mL in methanol; 1 mg/mL in methanol; 100 μg/mL in methanol
• Grade: analytical standard, for drug analysis; drug standard
• Isotopic Purity: 99 atom % D
• Empirical Formula (Hill Notation): C16D3H16NO4

DETAILS

Toronto Research Chemicals - B208127

A labelled metabolite of Cocaine. Controlled substance.

REFERENCES

• Wolff, K., et al.: Addiction, 94, 1279 (1999)
• Schaffer, M., et al.: J. Anal. Toxicol., 29, 319 (1999)
• Cognard, E., et al.: J. Pharm. Biomed. Anal., 41, 925 (1999)