Cocaethylene questions and general metabolic questions

[cdin]

ok, ill keep this short and sweet. The other day i was contemplating the synthesis of cocaethylene by the liver. Is this the ONLY set of drugs to interact and create a new active compound? I've taken many combinations and been struck by the thought "this is certainly like a different substance" like, i dunno, morphethyline or coketamine or candy flips -basically, is there any evidence that combinatory use (of things outside of the classic cocaine and booze combo) creates other novel compounds ?

 

[Reverend Random]

I've been told this process does indeed take part in the liver, but I am gladly corrected if I'm wrong.

Also, since we're talking cocaethylene anyway, is there any sound scientific evidence on whether it's really harmful as people usually claim it is?

 

[sekio]

generally only esters are subject to this kind of transformation... cocaine and mph are the 2 big ones.

the presence of fatty acid ethyl esters is used as a biomarker for ethanol intox

 

[bloodshed344]

generally only esters are subject to this kind of transformation... cocaine and mph are the 2 big ones.

the presence of fatty acid ethyl esters is used as a biomarker for ethanol intox

Well, what about 2C-D?

 

[sekio]

what about it? it's not an ester.

 

[bloodshed344]

what about it? it's not an ester.

Sorry I'm really new to this stuff. So does it have to be connected to the amine to be an ester? I figured using the logic that was presented 2C-D may turn into 2C-E in the presence of ethanol just like MPH to EPH. Would you mind explaining why this doesn't happen and what means it is an ester or not?

 

[sekio]

Read a 1st year organic chem text for more info.

esters are condensation products between carboxylic acids and alcohols, wherein water is lost, and you form a R-CO-OR' type moiety. In the liver, there are enzymes that will break apart these bonds by adding water across them, or "transesterify" the esters by switching the alcohol out for another one. this is what happens in the case of e.g. cocaine to cocaethylene, or methylphenidate to ethylphenidate.

pethidine

methylphenidate

cocaine

note the ester linkage present in all of these, which 2c- compounds don't have.

2c-d


for more info
http://www.chemguide.co.uk/organicprops/esters/background.html

Would you mind explaining why this doesn't happen

ethanol isn't a good reagent for forming carbon-carbon bonds.

 

[bloodshed344]

Thank you, I had no idea that's what it referred to. Simple things like that are the reason my chemistry knowledge is still so limited. I have learned it all through BL talk and studying structure pictures and doing some reading... mostly on the more Structure-Activity related subjects instead of essentials.