1,4-Butanediol

1,4-Butanediol is the organic compound with the formula HOCH₂CH₂CH₂CH₂OH. This colorless viscous liquid is derived from butane by placement of alcohol groups at each end of the chain. It is one of four stable isomers of butanediol.

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Synthesis

In its industrial synthesis, acetylene reacts with two equivalents of formaldehyde to form 1,4-butynediol, also known as but-2-yne-1,4-diol. This type of process is illustrative of what is known as Reppe Chemistry. Hydrogenation of 1,4-butynediol gives 1,4-butanediol.

It can also be manufactured on an industrial scale by the vapour phase hydrogenation of the esters and anhydrides of maleic acid and succinic acid.

Uses

1,4-Butanediol is used industrially as a solvent and in the manufacture of some types of plastics and fibers. In organic chemistry, 1,4-butanediol is used for the synthesis of γ-butyrolactone (GBL). In the presence of phosphoric acid and high temperature, it dehydrates to the important solvent tetrahydrofuran.^[1] At about 200 °C in the presence of soluble ruthenium catalysts, the diol undergoes dehydrogenation to form butyrolactone.^[2]

It is also used as a recreational drug known by some users as "One Comma Four", "One Four Bee" or "One Four B-D-O". It exerts effects similar to γ-hydroxybutyrate (GHB), which is a metabolic product of 1,4-butanediol.^[3]

Anecdotal reports indicate that 1,4-butanediol produces a strong toxic feeling not present with GHB when ingested.^[4][5] These reports also indicate that it may cause damage to the liver as well as to other vital organs.^[6][4] Abuse has also resulted in addiction and death.^[7][8][9]

Pharmacokinetics

1,4-Butanediol is converted into GHB by the enzymes alcohol dehydrogenase and aldehyde dehydrogenase and differing levels of these enzymes may account for differences in effects and side effects between users.^[4][10] Because these enzymes are also responsible for metabolizing alcohol there is a strong chance of a dangerous drug interaction.^[10][11] Emergency room patients who overdose on both alcohol and 1,4-butanediol often present with symptoms of ethanol intoxication initially and as the ethanol is metabolized the 1,4-butanediol is then able to better compete for the enzyme and a second period of intoxication ensues as the 1,4-butanediol is converted into GHB.^[10]

2007 contamination of Bindeez toy

See also: Bindeez

A toy called Bindeez (Aqua Dots in North America) was recalled by the distributor in November 2007 because of the presence of 1,4-butanediol. The toy consists of small beads that stick to each other by sprinkling water. 1,4-Butanediol, which is metabolized to gamma-hydroxybutyric acid in vivo, was detected by GC-MS.^[12] The production plant seems to have intended to cut costs by replacing 1,5-pentanediol. ChemNet China lists the price of 1,4 butanediol at between about US$1,350-$2,800 per metric ton, while the price for 1,5-pentanediol is about US$9,700 per metric ton.^[13]

Pharmacodynamics

1,4-Butanediol seems to have two types of pharmacological actions. The major psychoactive effects of 1,4-butanediol are due to the fact that it is metabolized into GHB, however there is some evidence that 1,4-butanediol may have inherent alcohol-like pharmacological effects that are not due to this conversion.^[11]

Legality

While 1,4-butanediol is not currently scheduled federally in the United States, a number of states have classified 1,4-butanediol as a controlled substance. Scheduling of 1,4-butanediol on a federal level is highly unlikely considering its common industrial use and many industrial applications.^{[citation needed]}

See also

• 2,3-Butanediol
• 1,3-Propanediol
• Ethylene glycol

References