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Author Topic: Few quick chlormethiazole questions  (Read 83 times)

Tsathoggua

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Few quick chlormethiazole questions
« on: May 15, 2010, 09:00:28 PM »
Anybody remember heminevrin (chlormethiazole) as a downer blast from the past?

Synthesis is pretty simple IIRC going from thiamine, my question is, can sulfur monochloride or disulfur dichloride accomplish the chlorination step, substituting thionyl chloride.

And, are other (pseudo)halide substitutions, fluoro, bromo, iodo, cyano, nitro etc active?
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I'm hyperbolic, hypergolic, viral, chiral. So motherfucking twisted my laevo is on the right side.

jon

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Re: Few quick chlormethiazole questions
« Reply #1 on: May 15, 2010, 11:03:17 PM »
buy some it's crap then you wwon't  bothrer with it

Tsathoggua

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Re: Few quick chlormethiazole questions
« Reply #2 on: May 16, 2010, 03:20:53 PM »
I have had it, my doc was once generous enough to script me a fuckoff great bottle of the stuff, gave me a choice between chlordiazepoxide and heminevrin for the purpose intended, knowing the former to be utter shit, I picked the latter, and enjoyed the hell out of it.

Apart from the godsawful stench produced by an ill advised binge on the substance in question knocking out sulfur metabolites enough to stun a small rhino from 50 paces, damn I didn't see that coming, and it ruined a good belt, a fleece and several tops.

As long as one doesn't binge on it though, I enjoyed it quite a lot.
Nomen mihi Legio est, quia multi sumus

I'm hyperbolic, hypergolic, viral, chiral. So motherfucking twisted my laevo is on the right side.

Vesp

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Re: Few quick chlormethiazole questions
« Reply #3 on: May 16, 2010, 06:16:55 PM »
If I remember correctly, which I may not -- didn't some place, such as RS or phrixus-sci have a pretty good discussion on this synthesis? Hopefully it was somewhere else, as both those places are gone, however archives are around so they might be worth checking out. I also remember thinking that the synthesis would not be all that hard to accomplish.
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Sedit

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Re: Few quick chlormethiazole questions
« Reply #4 on: May 16, 2010, 06:38:13 PM »
My first instinct would be to perform an acid hydrolysis of Thiamine followed by clorination of the correct partion. There are many things that could go wrong such as N chlorination or Hydrolysis not producing the correct product but its what first instincts tell me. Its not something I have really looked into much since I have never heard of the substance.

I wounder if the OH on Thiamine was halogenated if it would be an active compound.
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jon

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Re: Few quick chlormethiazole questions
« Reply #5 on: May 16, 2010, 09:03:19 PM »
its cleaved with nahso3 and something preciptates the thiol is phase separated and chlinated socl2 does the job nicely socl2 is found in those new fangled lithium batteries.

Quantum Dude

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Re: Few quick chlormethiazole questions
« Reply #6 on: May 16, 2010, 09:30:05 PM »
Studies of Crystalline Vitamin B1. III. Cleavage of Vitamin with Sulfite
Robert R. Williams, Robert E. Waterman, John C. Keresztesy, and Edwin R. Buchman
J. Am. Chem. Soc., 1935, 57 (3), 536-537

jon

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Re: Few quick chlormethiazole questions
« Reply #7 on: May 17, 2010, 01:48:03 AM »
the reaction can also be done in hydrochloric acid i dunno what that does to the thaizole ring probablbly jack shit because it's aromatic can't get the ref but it's pretty harsh conditions i liked it at fisrt then it was just another librium
as in the ole spirit of patrick henry "give me librium or give me meth!
i think it was done hot under pressure at 130 or so fr sur hours you could crack that nut easy or you could save yourself a lot of hassle and buy some unscheduled benzo for like 5 bucks a gram in china or 15 here phenazepam comes to mind ahh yes i remember well dont drink on that shit!!!

mumbles

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Re: Few quick chlormethiazole questions
« Reply #8 on: May 17, 2010, 10:23:11 AM »
Its simple to make but you will really stink so...
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