I was sitting around on the computer, trying to get my internets to work again and after everything was fixed, the first thing I did was hit one of my favorite blogs: post doc ergo propter doc. I dunno who this “post doc” is, but if it’s female, I want to date it. If it’s male, I still may want to date it, but it would have to put this dress on and let me call it Judy. [All this time and I never knew?] PDEPD links to a great site on one of the internets that tells you what kind of drug you are. According to this test, I am like the drug Ecstasy.

Your Personality Is Like Ecstasy

Now… that’s just fuckin’ retarded. I pretty much hate everything. Nay, this test is bogus and I hate it, but it did remind me that drug of the week is today and I said it would be Chloral Hydrate and I would hate myself (even more) if I forgot to do it. So, here it is.

chloralhydratestructure.gifChloral Hydrate is the original ye olde apothecary’s Mickæe Fynn, slipped into many a knight’s ale, whereupon they would awaken with their holey vestibules asunder and in an unusable state as a perverse drunken bachelor dressed as a bar wench made off with his purse and garter. Oh Glory Be!

It has roots dating back to 1832 where the Barron Justus von Liebig discovered it by bubbling chlorine gas through ethanol. Like all good drugs it was shelved, rediscovered in 1869 as a way to induce sleep, and being unabashedly abused by 1880. The drug’s popularity was immense and the utility it provided for evil people would pass on to other nefarious agents like Rohypnol and GHB. This was the big feel-good drug boom of the late 20th 19th and early 20th century. Yes, finally after they were putting patients first they suddenly found that they had answers that mattered and then everywhere you looked yesterday’s promises were the day after that’s miracles. Sadly, new addicts, having fallen victim to the ravages of the multitude of wars, were re-victimized by a drug called Laudanum. Chloral Hydrate was turning out to be quite addictive itself. Their alternatives came from Bayer in the form of the “non-addictive” Heroin. Our soft drinks had cocaine in them; even the cough syrups were being abused (*gasp*) all of it it was, of course, medicinal.

temporance.jpg

Drugs were the new rampage of the early 20th century and to say that the synthetic drug boom started with Chloral Hydrate is a pretty big damn stretch for which I have absolutely no evidence, but that’s not going to stop me because I can’t find anything that contradicts it right now. (Why is aspirin considered the first synthetic drug? Acetylsalicylic acid was invented in1897. Chloral Hydrate was known to induce sleep almost 30 years before and was actually synthesized some 40 years before that) WHAT WE DO KNOW (or I think I know) is that Chloral Hydrate was the 1st in class of being the 1st in class. It was the first and, for a little while, the only drug used to treat crazy people that didn’t involve opium, alcohol or large cranial drills. To this day it is still being used and can be found in the migraine medication Midrin (Amidrine).

Chloral Hydrate is absorbed fully upon consuming and is metabolized to trichloroethanol by an alcohol dehydrogenase and trichloroacteic acid by an aldehyde dehydrogenase using nicotinamide adenine dinucleotide (NAD) as a cofactor. It is assumed that the trichloroethanol is really what gets you grooving. The metabolites are excreted when you tinkle and poo.

Chloral Hydrate Mechanism

The synthesis is described on the internet and will not be described here in fear of replication by retards. Needless to say, the syntheses on the web are horribly dangerous. If you wana do it, be my guest. I’m not your father and I won’t be scraping the residues of your head off my kitchen ceiling when you discover just how bad of an idea it is to boil ethanol and sulfuric acid on a stove top. The mechanisms that I’ve come up with are prolly all wrong, but radical chemistry isn’t my forte. I’m sure someone smarter than me will immediatly post in the comments with something reasonably smart along with the deserved derogatory statement. In the first mechanism the oxidation occurs by abstraction of the hydrogen on the alcohol to form an alkoxy radical which is followed up by the abstraction of another proton to create a tertiary radical which immediately closes to form the aldehyde. Alternately the process could go in reverse and make a tertiary radical and then abstract the hydrogen from the alcohol and collapse to make the aldehyde. Thirdly, we can toss caution to the wind and say that the tertiary radical is formed and exchanged with a chloride and upon abstraction of some other hydrogen, the collapse leads to the enol or the aldehyde. With radicals, it’s always hard to say, but my inclination is to go with 3 relative to 1… only because I don’t know which is more stable, the tertiary radical or the alkoxy radical. 2 sounds too cumbersome and three component reactions are poo-pooed in my book. Ultimately the reaction terminates with trichloroacetaldehyde which is stable after hydrolysis to the diol.

Oh, and it may cause cancer.