529-38-4

Basic information

• Product Name: COCAETHYLENE
• Synonyms: BENZOYLECGONINE ETHYL ESTER;COCAETHYLENE;ECGONINE ETHYL ESTER BENZOATE;(1r-(exo,exo))-te;[1R-(Exo,exo)]-3-(benzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylateacid;3-(benzoyloxy)-8-methyl-8-azabicyclo(3.2.1)octane-2-carboxylicaciethyles;8-Azabicyclo[3.2.1]octane-2-carboxylic acid, 3-(benzoyloxy)-8-methyl-, ethyl ester, [1R-(exo,exo)]-;cocaethyline
• CAS NO: 529-38-4
• Molecular Formula: C₁₈H₂₃NO₄
• Molecular Weight: 317.38
• EINECS: 200-835-2
• Product Categories: Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals
• Mol File: 529-38-4.mol
• Article Data: 3

Chemical Properties

• Melting Point: 1090C
• Boiling Point: 408.8°Cat760mmHg
• Flash Point: 2 °C
• Appearance: /
• Density: 1.2g/cm³
• Vapor Pressure: 6.8E-07mmHg at 25°C
• Refractive Index: 1.562
• Storage Temp.: 2-8°C
• PKA: 9.04±0.60(Predicted)
• CAS DataBase Reference: COCAETHYLENE(CAS DataBase Reference)
• NIST Chemistry Reference: COCAETHYLENE(529-38-4)
• EPA Substance Registry System: COCAETHYLENE(529-38-4)

Safety Data

• Hazard Codes: T,Xn,F
• Statements: 25-36-20/21/22-11
• Safety Statements: 45-36/37-16-26
• RIDADR: UN 2811 6.1/PG 3
• WGK Germany: 3
• RTECS: CL5602980
• Hazardous Substances Data: 529-38-4(Hazardous Substances Data)

Usage

Chemical Properties

COCAETHYLENE is Crystalline Solid

Uses

Different sources of media describe the Uses of 529-38-4 differently. You can refer to the following data:
1. Homolog of Cocaine. Anesthetic (local). High-affinity ligand for dopamine transporter; a metabolite of Cocaine when alcohol is concommitently abused. Controlled substance
2. Homolog of Cocaine (C633500). Anesthetic (local). High-affinity ligand for dopamine transporter; a metabolite of Cocaine when alcohol is concommitently abused. Controlled substance.

InChI:InChI=1/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

Synthetic route

ethyl iodide (75-03-6) + benzylecgonine (519-09-5) → cocaethylene (529-38-4)

Conditions	Yield
With N,N,N,N,-tetramethylethylenediamine In dichloromethane for 72h; Ambient temperature;	72%
With ethanol at 100℃; im Rohr;

ethanol (64-17-5) + benzylecgonine (519-09-5) → cocaethylene (529-38-4)

Conditions	Yield
Stage #1: benzylecgonine With oxalyl dichloride at 20℃; for 0.333333h; Stage #2: ethanol at 20℃; for 12h;	60%
With hydrogenchloride
With hydrogenchloride at 0℃; for 48h;

ethanol (64-17-5) + hydrochloride of l-ecgonine → cocaethylene (529-38-4)

Conditions	Yield
With hydrogenchloride Erhitzen des Reaktionsprodukts mit Benzoylchlorid;
With hydrogenchloride Erhitzen des Reaktionsprodukts mit Benzoylchlorid;

Upstream product

• 64-17-5 ethanol 
• 519-09-5 benzylecgonine 
• 75-03-6 ethyl iodide 
• 98-88-4 benzoyl chloride 

Relevant articles and documents

Convenient synthesis of benzoylecgonine ethyl ester, a homolog of cocaine

Benzoylecgonine reacted with tetramethylethyhlenediamine to form a lipophilic ion pair, which was alkylated in the absence of water. The ethyl ester was readily recrystallized for pharmacological studies.

2β-Substituted Analogues of Cocaine. Synthesis and Inhibition of Binding to the Cocaine Receptor

The potencies of a series of 2β-substituted cocaine analogues to displace -3β-(p-fluorophenyl)tropane-2β-carboxylic acid methyl ester binding in rat striatal membranes demonstrate the requirement for a 2β-substituent with two hydrogen-bond acceptors.The insensitivity of the ester moiety to steric and electronic factors suggests its modification to provide site-specific irreversible ligands.