What led me down this rabbit hole was wondering why street speed is racemic when pharmaceutical dexamphetamine for ADHD is made by triple reduction of l-phenylalanine, which is really similar to how those zany yanks make meth from Sudafed, only with fewer explosions and cut with lactose monohydrate instead of Persil.
And figured the street guys were probably somehow attaching benzene to isopropylamine.
Which would give you racemic amphetamine (janky shit like Adderall. What is it with the US and their “we found this in a crack house but it’ll probably help” approach to ADHD meds) but also MAYBE 2-phenyl 2–aminopropane.
Which is not chiral but also a structural isomer of amphetamine and I have absolutely no idea what it does.
You mentioning the triple reduction here was eye-opening for me: I was today years old (as they say) before I recognized that.
But then again, I went through a lot of time in my previous life as a chemist studiously ignoring most pharmaceutical chemistry as a series of rabbit holes that didn't interest me. I'm getting over that, now, and paying catch-up, but in a much more informal way.
@like jam or bootlaces Obvious when you think about it. Phenylalanine is just phenethylamine with methanoic acid on the alpha carbon.
So a single reduction turns it into an aldehyde
Double into an alcohol
And triple into ... well just methane
At which point it's literally just amphetamine.
And you make dexamphetamine from levophenylalanine because I guess the priority between the amino and carboxylic acid functional groups is the other way round to methyl and amino.
Sarah Brown
in reply to Sarah Brown • •What led me down this rabbit hole was wondering why street speed is racemic when pharmaceutical dexamphetamine for ADHD is made by triple reduction of l-phenylalanine, which is really similar to how those zany yanks make meth from Sudafed, only with fewer explosions and cut with lactose monohydrate instead of Persil.
And figured the street guys were probably somehow attaching benzene to isopropylamine.
Which would give you racemic amphetamine (janky shit like Adderall. What is it with the US and their “we found this in a crack house but it’ll probably help” approach to ADHD meds) but also MAYBE 2-phenyl 2–aminopropane.
Which is not chiral but also a structural isomer of amphetamine and I have absolutely no idea what it does.
like jam or bootlaces
in reply to Sarah Brown • • •You mentioning the triple reduction here was eye-opening for me: I was today years old (as they say) before I recognized that.
But then again, I went through a lot of time in my previous life as a chemist studiously ignoring most pharmaceutical chemistry as a series of rabbit holes that didn't interest me. I'm getting over that, now, and paying catch-up, but in a much more informal way.
Sarah Brown
in reply to like jam or bootlaces • •@like jam or bootlaces Obvious when you think about it. Phenylalanine is just phenethylamine with methanoic acid on the alpha carbon.
So a single reduction turns it into an aldehyde
Double into an alcohol
And triple into ... well just methane
At which point it's literally just amphetamine.
And you make dexamphetamine from levophenylalanine because I guess the priority between the amino and carboxylic acid functional groups is the other way round to methyl and amino.