1,4-Butanediol

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1,4-Butanediol
1,4-butanediol.png
200px
IUPAC name 1,4-Butanediol
Identifiers
CAS number 110-63-4
SMILES OCCCCO
Properties
Molecular formula C4H10O2
Molar mass 90.12 g/mol
Density 1.010 g/cm³
Melting point

20 °C

Boiling point

230 °C

Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)

Infobox disclaimer and references

1,4-Butanediol is an alcohol derivative of the alkane butane, carrying two hydroxyl groups. It is a colorless viscous liquid.

Synthesis

Its industrial synthesis starts with acetylene, which is reacted with two molecules of formaldehyde to form 1,4-butynediol, also known as but-2-yne-1,4-diol, a process known as the Reppe synthesis. This product is subsequently hydrogenated to give 1,4-butanediol.

It is also manufactured on an industrial scale by the vapour phase hydrogenation of maleate esters.

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 a soluble ruthenium catalyst, the diol loses H2 and forms 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][7] Abuse has also resulted in addiction and death.[8][9][10]

Pharmacokinetics

1,4-Butandiol 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.[11][12] Because these enzymes are also responsible for metabolizing alcohol there is a strong chance of a dangerous drug interaction.[12][13] 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-butandiol 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.[12]

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.[13]

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 and even where it has not yet been scheduled. Scheduling of 1,4-butanediol on a federal level is highly unlikely considering its common industrial use and many industrial applications.[citation needed]

References

  1. "Ethers, by Lawrence Karas and W. J. Piel". Kirk‑Othmer Encyclopedia of Chemical Technology. (2004). John Wiley & Sons, Inc. Retrieved on 2007-09-05. 
  2. J. Zhao, J. F. Hartwig "Acceptorless, Neat, Ruthenium-Catalyzed Dehydrogenative Cyclization of Diols to Lactones" Organometallics 2005, volume 24, 2441-2446.
  3. Satta R, Dimitrijevic N, Manev H. Drosophila metabolize 1,4-butanediol into gamma-hydroxybutyric acid in vivo. Eur J Pharmacol. 2003 Jul 25;473(2-3):149-52. PMID 12892832
  4. [1]
  5. [2]
  6. [3]
  7. [4]
  8. Zvosec DL, Smith SW, McCutcheon JR, Spillane J, Hall BJ, Peacock EA. Adverse events, including death, associated with the use of 1,4-butanediol. N Engl J Med. 2001 Jan 11;344(2):87-94. PMID 11150358
  9. [5]
  10. [6]
  11. [7]
  12. 12.0 12.1 12.2 Theodore I Benzer, Scott Cameron, Christopher S Russi (8 Jan 2007). Toxicity, Gamma-Hydroxybutyrate. eMedicine.
  13. 13.0 13.1 Poldrugo, F.; Snead, O.C. 3rd. (1984). "1,4 Butanediol, gamma-hydroxybutyric acid and ethanol: relationships and interactions". Neuropharmacology 59 (23): 109-113. PMID 6717752.
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