529-38-4

Usage

Uses

Used in Pharmaceutical Applications:
COCAETHYLENE is used as a local anesthetic for its numbing effects on specific areas of the body. Its high-affinity for the dopamine transporter makes it a subject of interest in the study of addiction and substance abuse, as well as potential applications in the development of new medications for treating such conditions.
Used in Research and Development:
In the field of neuroscience and addiction research, COCAETHYLENE is used as a research compound to better understand the mechanisms of drug addiction, particularly in cases where Cocaine and alcohol are abused simultaneously. This knowledge can contribute to the development of more effective treatments and interventions for substance abuse disorders.
Used in Regulatory and Forensic Analysis:
As a controlled substance, COCAETHYLENE is also used in regulatory and forensic analysis to detect and monitor its presence in cases of drug abuse, trafficking, and other related criminal activities. This helps law enforcement and regulatory agencies to enforce drug control policies and protect public health.
Used in Chemical and Material Science:
COCAETHYLENE, being a crystalline solid, may have potential applications in the field of chemical and material science, where its unique properties can be studied and utilized for the development of new materials or processes. However, further research would be required to explore these possibilities.

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 academic research and scientific papers

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.

Cocaethylene, the in vivo product of cocaine and ethanol, is a narcotic more potent than its precursors

The molecular conformation and supramolecular architecture of cocaethylene [systematic name: ethyl (1R,2R,3S,5S)-3-benzoyloxy-8-methyl-8-azabicyclo- [3.2.1]octane-2-carboxylate], C18H23NO4, have been determined for the first time. Cocaethylene is a narcotic produced in vivo when cocaine and ethanol are administered concomitantly. The intra- and intermolecular features of cocaethylene and its less potent narcotic precursor cocaine are very similar. The only molecular difference is in the conformation of the methyl group of the ethoxycarbonyl group. Similar to cocaine, the carboxylate atoms and the α-C atom are coplanar in cocaethylene, but the methyl C atom of the ethyl group is bent by ca 90° away from this plane in the narcotic reported here. The main supramolecular motif is a one-dimensional chain stabilized by weak C-H.O contacts.

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.