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

• ChemBase ID: 126657
• Molecular Formular: C18H23NO4
• Molecular Mass: 317.37952
• Monoisotopic Mass: 317.16270822
• SMILES: O=C(O[C@H]1C[C@H]2N(C)[C@@H]([C@@H]1C(=O)OCC)CC2)c1ccccc1
• Canonical SMILES: CCOC(=O)[C@@H]1[C@H](C[C@H]2N([C@@H]1CC2)C)OC(=O)c1ccccc1
• InChI: InChI=1S/C18H23NO4/c1-3-22-18(21)16-14-10-9-13(19(14)2)11-15(16)23-17(20)12-7-5-4-6-8-12/h4-8,13-16H,3,9-11H2,1-2H3/t13-,14+,15-,16+/m0/s1
• InChIKey: NMPOSNRHZIWLLL-XUWVNRHRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ethyl (1R,2R,3S,5S)-3-(benzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate
• IUPAC Traditional name: cocaethylene
• Synonyms: benzoylecgonine ethyl ester; ethylbenzoylecgonine,; Cocaethylene; Cocaethylene; (1R,2R,3S,5S)-3-(Benzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic Acid Ethyl Ester; Ecgonine Ethyl Ester Benzoate (Ester); Ethyl Benzoylecgonine; Ethylcocaine; Homocaine; Homococaine; 乙基苯酰芽子碱; 可卡乙碱

Database IDs

• CAS Number: 529-38-4
• MDL Number: MFCD00083171
• PubChem SID: 24892289; 162220987
• PubChem CID: 644006; 65034
• CHEMBL: 608806
• Chemspider ID: 559082
• Wikipedia Title: Cocaethylene

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): -0.43166134
• LogD (pH = 7.4): 1.2525958
• Log P: 2.638916
• Molar Refractivity: 85.909 cm^3
• Polarizability: 34.00524 Å^3
• Polar Surface Area: 55.84 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Alcohol; Ether
• Apperance: Crystalline Solid
• Melting Point: 1090C

Safety Information

• RTECS: CL5602980
• European Hazard Symbols: Toxic (T)
• UN Number: 2811
• 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 2811 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

• Admin Routes: Produced from ingestion of cocaine and ethanol
• Dependency Liability: Moderate to High
• Legal Status: CD (UK); Not scheduled specifically, could be prosecuted as an analogue of a scheduled substance.
• Pregnancy Category: C
• Gene Information: mouse ... Slc6a2(20538)rat ... Slc6a3(24898), Slc6a4(25553)

DETAILS

Sigma Aldrich - C0932

Biochem/physiol Actions
多巴胺转运蛋白的高亲和性配体；伴随滥用酒精时可卡因的代谢物

Toronto Research Chemicals - C633400

Homolog of Cocaine (C633500). Anesthetic (local). High-affinity ligand for dopamine transporter; a metabolite of Cocaine when alcohol is concommitently abused. Controlled substance.

REFERENCES

• ElSohly, M., et al.: J. Anal. Toxicol., 15, 46 (1991)
• Hearn, W.L., et al.: J. Neurochem., 56, 698 (1991)
• Shimomura, E., et al.: Clin. Chem., 47, 1040 (1991)
• Wu, A.H.B., et al.: J. Anal. Toxicol., 16, 132 (1991)