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Hepatic Transesterifcation with other alcohols?

Jamshyd

Jamshyd

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So we all know the Ethylphenidate and Cocaethylene stories.

Suppose one consumes another alcohol while taking these substances, such as n-Propanol or 2m2b. Would we get the corresponding analogues from the stimulants, or is this phenomenon unique only to Ethanol?
 
I was just wondering this as well, I doubt there is any data documenting the effect as consumption of other simple alcohols is comparatively rare. Also even if it were possible would the product of such a transesterfication even be active? Here is the hypothetical metabolic byproduct of combined methylphenidate and 2-methyl-2-butanol:
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t-Pentylphenidate?
 
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I think the biggest barrier to that is that other alcohols are much more toxic than ethanol, and in order for the transesterification to occur, the relevant alcohol has to reach a notable serum concentration.

The way I understood it was that the esterase isn't a transesterification catalyst, it's an ester hydrolysis catalyst, but since esterification is an equilibrium reaction, the high concentration of ethanol in the blood (much higher than can be achieved safely with other alcohols) causes the equilibrium to shift the "wrong" way in favor of cocaethylene/ethylphenidate/etc. 2-methyl-2-butanol wouldn't cause this effect because it's consumed in much smaller amounts. Propanol is far too toxic to attempt this with, thanks to propanoic acid acting as a wrench in the mechanism of the citric acid cycle.

EDIT: Yeah, butanol -will- dissolve in blood. Bah.
 
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^ Yes, I raised a brow when I read this information. atara, do you have any sources for these claims?

Everything I heard about n-Propanol makes it seem even less toxic than Ethanol.

Also bumping thread in hopes of getting more responses :).
 
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