Transesterification and the formation of methanol.

[Haoma]

This would mean if one were to ingest ethyl alcohol with cocaine or methylphenidate then a by product of this would be methanol. Would this amount of methanol be relevant? I don't think at methylphenidate doses it really would be a worry, but I'm thinking more along the lines of coke binges.

Sorry I tried to link a pic but can't figure it out. What it basically shows is R'OH+R"OCOR=R"OH+R'OCOR.

 

[sekio]

The amount of methanol formed from the degradation of esters like aspartame/methylphenidate is very small.

 

[Haoma]

The wiki says that even 10 mL is enough to cause permanent blindness, I don't know how much methanol would be produced relative to the molecule it is effecting but 10 mL doesn't seem like it would be hard to produce with excessive amounts of alcohol and cocaine intake. Does anyone have any numbers on how much Transesterification happens?

 

[Roger&Me]

A 40mg dose of methylphenidate will produce ~0.007mL of methanol, assuming 100% deesterification.

 

[sekio]

To put that in perspective, 1 kg of apple juice (~1L) contains 200mg (0.15ml) of methanol. Even cocaine can hydrolise to 1/10 its weight in methanol (1g pure cocaine alkaloid + water = 100mg methanol).

Your body has built-in metabolic processes that generate and remove methanol naturally anyway. It's only if you start consuming it in large doses (i.e. 10ml+) that it becomes a problem - from conversion to formic acid / formaldehyde.

Plenty of drugs/flavours/fragrances are methyl esters/amines etc, but due to the fact that a methyl group doesn't really weigh all that much, the total amount of methanol ingested is very low, and can be handled safely.