1,4-butanediol (Date rape drug or solvent for kids' toys?)

There are a lot of stories bouncing around about a toy in Australia, Bindeez, which are apparently little beads that adhere to one another when you wet them. There are a ton of news sources getting very confused, but Reuters seems to have gotten it: they are contaminated with 1,4-butanediol, which your body metabolizes into GHB (a banned so-called "date rape drug.")

i-5f815971441c0b01d339ad8ad719541d-butanediol.png

Humans evolved in the presence of ethanol - beverage ethanol is recent, evolutionarily speaking, but much of life creates a little bit of ethanol. It'd be much more toxic than it is if we didn't have a set of enzymes to deal with it, oxidizing it to acetic acid (which yields food energy). These enzymes can chew on essentially any alcohol - which can cause problems.

i-7f98d9a9b6283de5dedb80f511884900-ghb-gaba-gbl.gif

The top molecule above is GHB. It mimics the next one down, GABA, which is an endogenous neurotransmitter (it is on this system that Valium works its magic).

Your ethanol-metabolizing enzymes can convert 1,4-butanediol into GHB. This is the "date rape drug" angle that got what's just another (although no less upsetting) contaminated toy story so much press.

Finally, that bottom molecule, GBL, is an industrial solvent and organic intermediate. It, too, will be metabolized into GHB. Following the GHB ban 1,4-butanediol and GBL have been used as substitutes, since at least some becomes GHB in your body. In many areas, this has resulted in what are really solvents to be controlled as though they were drugs. To be fair, they amount to drugs as well - this is why legislating simple small molecules can be so puzzling - they rarely do just one thing.

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Dude, I love your molecules of the day. Reading your column gives me a chemistry tidbit each day that I actually has a real-life application to it. Love it.

The obvious answer is to ban all chemicals, duh!

:)

Arrest, convict, and imprison any child who ingests 1,4-butaendiol for being a recreational pharmaceutical drug synthesis laboratory. If they urinate, EPA and Haz-Mat will fine them to perdition's gate. The solution to societies' ills is enforcement not correction.

There's no way to rule innocent men. The only power any government has is the power to crack down on criminals. Well, when there aren't enough criminals, one makes them. One declares so many things to be a crime that it becomes impossible for men to live without breaking laws. Ayn Rand.

Hello,

I've just finished a section on naming alcohols in my A-Level Chemistry course. We were taught that when naming polyhydric alcohols, you put the parent alkane first, then the position, then the hydroxyl group. If that's right, this would be butane-1,4-diol.

Which is right? butane-1,4-diol or 1,4-butanediol ?

Which is correct: phloroglucinol, cyclohexane-1,3,5-trione, or 1,3,5-trihydroxybenzene? Know formal nomenclature, know colloquial short cuts. Using an acronym of a surname, two adjectives and two nouns as a verb is unconscionably awful! How many samples did you FTNMR today? If we were pendantic like CAS, IUPAC, or Roberts and Caserio we'd be poor communicators on the fly.

I really dig your blog, and you're excellent (and informative) molecule for the day. Would you consider a pronunciation key for those of us who like to sound smart?

Apparently, the manufacturer replaced 1,5-pentanediol with the 1,4-butanediol. oops.

Freddie, both are "acceptable" but there are the IUPAC rules that some of us occasionally follow. Using butane-1,4-diol is more useful when there are other substituents on the molecule. It's less confusing. But, as I tell my students, using something like 1,4-butanediol conveys the same exact structural information. The IUPAC purest may not like it, but it works. The use of common names, however, is a totally different story.

Um... not to go all raver and stuff but it would be nice if a blog that is supposed to be spreading knowledge would refrain from spreading the incorrect meme that GHB and similar drugs have anything to do with date rape.

Can someone tell me how spraying a coating of 1,5-pentanediol can make anything "stick" together. I'm not aware of any chemical reaction between water and 1,5-pentanediol that would result in a "glue".

Is it possible that there's a third component to this coating that's "activated" when sprayed with water? Isocynatates come to mind (think super glue) and I wonder if that's being kept out of the media by ignorance or intention.

Peace...

>JjV<
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By John Vaccaro (not verified) on 22 Nov 2007 #permalink