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Cocaethylene is a drug formed in the liver when cocaine and alcohol are consumed together. Besides its stimulating and euphoric effects, it is much more toxic than cocaine itself and poses high risk of heart attacks. Agression is a common effect of cocaethylene. With repeated use, cocaethylene builds up in the liver over time causing long term health risks.


[top]Introduction to Cocaethylene

[top]Using Cocaethylene

[top]Ways of administration

[top]Effects of Cocaethylene

Time course of drug effect was reported to last longer and be more enjoyable in test subjects administered both cocaine and alcohol rather than cocaine alone. Cocaethylene causes a more significant rise in heart rate and blood pressure than cocaine, and is therefore considered to be more cardiotoxic because cardiotoxicity is associated with all routes of administration of cocaine.[1]

Studies have also shown that Cocaethylene is only produced within the liver when alcohol is consumed 'before' administration of cocaine.[3]

[top]Combinations with Cocaethylene

[top]Different Uses for Cocaethylene

[top]Pharmacology of Cocaethylene

About 1/6th of the cocaine administered undergoes transesterification and is changed into cocaethylene in the body when taken with alcohol.[2] As much as 24% when cocaine is taken by intravenous route of administration.
[4] When alcohol is present, less cocaine is metabolized into benzoylecgonine and excreted, prolonging the effects of cocaine. [2]

[top]Chemistry of Cocaethylene

Systematic (IUPAC) name:ethyl (2R,3S)-3-benzoyloxy-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate
Synonyms:(1R,2R,3S,5S)-3-(benzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acid ethyl ester, ecgonine ethyl ester benzoate (ester), O-benzoyl-l-ecgonine ethyl ester, ethylbenzoylecgonine, Homocaine
Molecular Formula:C18H23NO4
Molar mass:317.39 g/mol
CAS Registry Number:529-38-4
Melting Point:109C
Boiling Point:no data
Flash Point:no data
Solubility:Solubel in alcohol, ether; almost insoluble in water
Additionnal data:none
Notes:aspect : prisms; crystallized from alcohol

[top]The dangers of Cocaethylene

Concurrent use of cocaine and alcohol has been associated with greater risk of sudden death than after cocaine alone. [5] Cocaethylene is more cardiotoxic than cocaine itself, causing more stress on the cardiovascular system.

[top]Producing Cocaethylene

[top]Forms of Cocaethylene

[top]Legal status of Cocaethylene

There is currently no legal status of Cocaethylene due to the chemical being produced 'in vivo', (produced within a living organism). However, one 'could' be prosecuted due to Cocaethylene being an analogue of a scheduled substance, ie. cocaine. Although more likely to be prosecuted for testing positive for cocaine itself.

[top]History of Cocaethylene

Cocaine was first added to an alcoholic beverage in 1863 [3]by a man called Angelo Mariani.

Angelo Mariani patented a wine called 'Vin Tonique Mariani la Coca de Perou' whilst he was working as a Pharmacist making 'wine tonics' which were given out as medication in order to treat depression, especially within the rich and famous. The success of Mariani's 'Vin Mariani' led to his tonic being sold all over France, with offices also in London and New York.[6]

At the time nobody, not even Angelo Mariani, knew what exactly was making 'Vin Mariani' such a resounding success.

Over a century later, two groups of researchers, one from Barcelona and one from Miami, found out exactly what it was. They discovered, in 1990, that when alcohol was mixed with cocaine the liver actually produced a third compound called Cocaethylene.[1]

They discovered that: "When cocaine is consumed in the absence of alcohol, it is broken down into two principle metabolites: one called benzoylecgonine and one called ecgonine methyl ester. In humans, at least, neither of the two had any stimulant or psychological effects, but cocaethylene does, nearly as much stimulation as cocaine. When the two are consumed together cocaine's stimulating effects are enhanced and prolonged. Vin Mariani's drinkers were, in effect, getting more cocaine than either Mariani or his competitors thought they were providing."[6]

This discovery also explained why only small amounts of Vin Mariani, or any other coca wine, seemed to have such a great effect on its consumers. At the time this seemed unusual in comparison to the amount of coca leaves that were being infused into the wines.

Since this discovery in 1990, there have been several studies on cocaethylene and its effects on the human body. (See above 'Effects of Cocaethylene)

Most of the research undertaken has had some alarming results - cocaethylene, although making its consumer highly euphoric and much more stimulated, was much more deadly and toxic than cocaine use alone.

Today, in light of all the research into exactly how toxic cocaethylene can be, health organisations have started leaflet and poster campaigns, plastering posters all over youth club walls and doctors waiting rooms warning today's generation of these extreme health risks.
Unfortunately due to the social nature of cocaine use, very few heed these warnings and many still consume alcohol along with using cocaine.

[top]More Cocaethylene Sections

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  1. ^ a b Cregler, L. L., & Mark, H. (1986). Medical complications of cocaine abuse. New England Journal of Medicine, 315, 1438 1443.
  2. ^ a b c The pharmacology of cocaethylene in humans following cocaine and ethanol administration
  3. ^ a b Cocaethylene: a unique cocaine metabolite displays high affinity for the dopamine transporter.
  4. ^ Cocaethylene Formation Following Ethanol and Cocaine Administration by Different Routes
  5. ^ Andrews, P., 1997. Cocaethylene toxicity. J. Addict. Dis. 16, 7584.
  6. ^ a b A Brief History of Cocaine, Second Edition By Steven B. Karch, MD, FFFLM, Page 32.

[1]Merck Index, fifteenth edition (2013)

Attached Images
File Type: png cocaethylene.png (17.6 KB, 951 views)
Contributors: John_bob, source, Alfa, NeuroChi
Created by NeuroChi, 02-08-2011 at 04:43
Last edited by John_bob, 08-05-2014 at 13:16
Last comment by source on 01-03-2013 at 04:38
2 Comments, 74,913 Views

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