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

• ChemBase ID: 1304
• Molecular Formular: C16H19NO4
• Molecular Mass: 289.32636
• Monoisotopic Mass: 289.13140809
• SMILES: O([C@@H]1[C@@H]([C@@H]2N([C@@H](CC2)C1)C)C(=O)O)C(=O)c1ccccc1
• 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-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acid
• IUPAC Traditional name: ecgonine benzoate; benzoylecgonine
• Synonyms: (1R,2R,3S,5S)-3-(Benzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic Acid; Benzoyl Ecgonine; Benzoylecgonine solution; BCG; BEG; Benzoylecgonine hydrate; Benzoylecgonine solution; Benzoylecogonine; Ecgonine benzoate; O-benzoyl-(-)-ecgonine; O-benzoylecgonine; (-)-benzoylecgonine; Benzoylecgonine; 苯甲酰芽子碱 溶液

Database IDs

• CAS Number: 519-09-5
• MDL Number: MFCD00070263
• PubChem SID: 46508112; 160964764; 24892104
• PubChem CID: 448223
• CHEBI ID: 41001
• Chemspider ID: 395095
• DrugBank ID: DB01515
• KEGG ID: C10847
• Unique Ingredient Identifier: 5353I8I6YS
• Wikipedia Title: Benzoylecgonine

CALCULATED PROPERTIES

JChem

• 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

ALOGPS 2.1

• Log P: 1.71
• LOG S: -1.88
• Solubility (Water): 3.82e+00 g/l

PROPERTIES

Physical Property

• Solubility: Chloroform; Ethanol; Methanol
• Apperance: White Solid
• Melting Point: 1950C (dec)
• Flash Point: 11 °C; 51.8 °F

Safety Information

• Storage Condition: Controlled Substance, -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
• GHS Pictograms: GHS02; GHS06; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H225-H301-H311-H331-H370
• GHS Precautionary statements: P210-P260-P280-P301 + P310-P311
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US)
• RID/ADR: UN 1230 3/PG 2
• Drug Control: Home Office Schedule 2; stupéfiant; kontrollierte Droge in Deutschland
• Storage Temperature: 2-8°C

Pharmacology Properties

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

Product Information

• Concentration: 1.0 mg/mL±5% in methanol
• Grade: analytical standard, for drug analysis

DETAILS

DrugBank - DB01515

• Drug Groups: illicit; experimental
• Description: Benzoylecgonine is the major metabolite of cocaine. It is formed by hydrolysis of cocaine in the liver, catalysed by carboxylesterases. It is excreted in the urine of cocaine users after processing in the liver. [Wikipedia]
• Affected Organisms: Humans and other mammals
• External Links: Wikipedia

Toronto Research Chemicals - B208125

A 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)