Carbinol and Carbamate

[Synaps3]

Does a carbamate drug always have the same effect as its carbinol derivative? Does the dose vary? Are carbamates always powders and carbinols liquids?

Anyway, I thought this was interesting because I can really cheaply get the carbinol version of meprobamate (Soma) like 10x cheaper from a chemical site. Would it still work or work too effectively because it doesn't have to get metabolized first?

 

[Hammilton]

Do you have the structure?

Most carbinols aren't liquids. Indole-3-carbinol comes to mind immediately.

Pretty sure you need the carbamate moiety for activity.

Well, cleaving the carbamate to make it a diol might make for an okay depressant. That'd be a heptane-diol which may be too large, it's hard to say. I'm not familiar with carbamate synthesis, if you could just form the carbamate from that alcohol or not. If you wanted to make nitrate esters it'd be easy. It'd probably even make a decent explosive, I'd guess it'd be less sensitive than EGDN but it might still be a secondary.

I've always considered carisoprodol and meprobamate to be ring-opened analogues of barbiturates. They may bind completely differently, I don't know, but that's just how I've looked at them.

 

[Synaps3]

Maybe I am using the wrong term. When I say carbinol, I mean alcohol.

2-methyl-2-propylpropan-1,3-diol CAS 78-26-2
The second molecule here is the alcohol and the third is the carbamate (meprobamate):

It works with the drug ethinamate because 1-ethynylcyclohexanol is active:
So I'm assuming it works with all carbamates.

 

[Hammilton]

I would not make that assumption. With ethinamate you're working with a simpler cyclic molecule and a tertiary alcohol. With carisoprodol you've got a primary diol

I'm not saying that it isn't active, it'll probably do something to you, it may be more toxic and less potent. or just less potent.

 

[sekio]

The logic seems sound enough, but I'd want to know of some other drugs that are active as a carbamate *and* alcohol. Not sure if "meprobamate alcohol" is active in man. Ethanol/uretane and the cyclohexane-acetylene one are definitely active though.

 

[ralf2]

I found some information on this subject in the book Psychotropic agents. It seems that the alcohols related to carbamates in the case of meprobamate will indeed have some activity but will be very short acting.

You can have a preview of the chapter "Chemistry of anxiolytics" here: http://link.springer.com/book/10.1007/978-3-642-67767-0/page/1 it has some short information on this matter. I wish I had the full book though.