1,4-Butanediol, also called Butane-1,4-diol (other names include 1,4-B, BD, BDO and 1,4-BD),[5] is a
primary alcohol and an
organic compound with the
formula HOCH2CH2CH2CH2OH. It is a colorless
viscousliquid first synthesized in 1890 via acidic hydrolysis of N,N'-dinitro-1,4-butanediamine by Dutch chemist Pieter Johannes Dekkers, who called it "tetramethylene glycol".[6][7]
World production of butane-1,4-diol was claimed to be about one million metric tons per year and market price is about US$ 2,000 (€1,600) per ton (2005). In 2013, worldwide production was claimed to be billions of pounds (consistent with approximately one million metric tons).[14]
Butane-1,4-diol is also used as a
recreational drug known by some users as "One Comma Four", "Liquid Fantasy", "One Four Bee" or "One Four B-D-O".
Some
federal courts in the USA have stated that 1,4-butanediol exerts effects similar to its metabolite gamma-hydroxybutyrate (GHB), but several other federal courts have ruled that it does not.
Pharmacokinetics
Butane-1,4-diol is rapidly converted into gamma-hydroxybutyric acid 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.[17] While co-administration of
ethanol and GHB already poses serious risks, co-administration of
ethanol with 1,4-butanediol will interact considerably and has many other potential risks. This is because the same enzymes that are responsible for metabolizing alcohol also metabolize 1,4-butanediol so there is a strong chance of a dangerous
drug interaction.[17][18] Emergency room patients who overdose on both
ethanol and 1,4-butanediol often present with symptoms of
alcohol 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.[17]
Pharmacodynamics
Butane-1,4-diol seems to have two types of pharmacological actions. The major psychoactive effects of 1,4-butanediol are because it is metabolized into GHB; however there is a study suggesting that 1,4-butanediol may have potential alcohol-like pharmacological effects on its own.[18] The study arrived at this conclusion based on the finding that butane-1,4-diol coadministered with ethanol led to potentiation of some of the behavioral effects of ethanol. However, potentiation of ethanol's effects may simply be caused by competition for the
alcohol dehydrogenase and
aldehyde dehydrogenase enzymes with co-administered 1,4-butanediol. The shared metabolic rate-limiting steps thus leads to slowed metabolism and clearance for both compounds including ethanol's known toxic metabolite
acetaldehyde.
Another study found no effect following intracerebroventricular injection of butane-1,4-diol in rats.[19] This contradicts the hypothesis of butane-1,4-diol having inherent alcohol-like pharmacological effects.
Like gamma-hydroxybutyric acid, butane-1,4-diol is safe only in small amounts. Adverse effects in higher doses include nausea, vomiting, dizziness, sedation, vertigo, and potentially death if ingested in large amounts. Anxiolytic effects are diminished and side effects increased when used in combination with alcohol.
Legality
While butane-1,4-diol is not currently
scheduled federally in the United States,[20] a number of states have classified 1,4-butanediol as a controlled substance. Individuals have been prosecuted for possession of 1,4-butanediol under the
Federal Analog Act as substantially similar to GHB.[21] A federal case in New York in 2002 ruled that 1,4-butanediol could not be considered an
analog of GHB under federal law,[22] but that decision was later overturned by the Second Circuit.[23] A jury in Federal District Court in Chicago found that 1,4-butanediol was not an analog of GHB under federal law, which was not disputed on the case's appeal to the Seventh Circuit Court of Appeals, however this finding did not affect the outcome of the case.[24] In the
United Kingdom, 1,4-butanediol was scheduled in December 2009 (along with another GHB precursor,
gamma-butyrolactone) as a
Class C controlled substance. In Germany, the drug is not explicitly illegal, but might also be treated as illegal if used as a drug. It is controlled as a Schedule VI
precursor in
Canada.
A toy called "
Bindeez" ("Aqua Dots" in North America) was recalled by the distributor in November 2007 because of the presence of butane-1,4-diol. The toy consists of small beads that stick to each other by sprinkling water. Butane-1,4-diol was detected by
GC-MS.[25] The production plant seems to have intended to cut costs by replacing less toxic
pentane-1,5-diol with butane-1,4-diol. ChemNet China listed the price of butane-1,4-diol 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.[26]
2021 poisoning at Darmstadt Technical University
In August 2021, several people fell severely ill after consuming drinks at building L2.01 at the Lichtwiese Campus of
Darmstadt Technical University, Germany. Seven showed severe symptoms, two were transported to a hospital in
Frankfurt am Main, and a 30-year-old person was, for a time, in a critical state. Butane-1,4-diol had been detected in milk packages, as well as in water filters. At the location, detectives also found
bromophenols and
dicyclohexylamine.[27]
^
abPoldrugo, Flavio; Snead III, O. Carter (1984), "1,4-butanediol, γ-hydroxybutyric acid and ethanol: Relationships and interactions", Neuropharmacology, 23 (1): 109–13,
doi:
10.1016/0028-3908(84)90226-0,
PMID6717752,
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^Carter, LP; Koek, W; France, CP (2006), "Lack of effects of GHB precursors GBL and 1,4-BD following i.c.v. Administration in rats", The European Journal of Neuroscience, 24 (9): 2595–600,
doi:
10.1111/j.1460-9568.2006.05146.x,
PMID17100847,
S2CID24609982
^United States v. Turcotte, 405 F.3d 515 (7th Cir. 2005) "With specific regard to 1,4 Butanediol, the jury has returned a special verdict which states that 1,4-Butanediol is not a Schedule I Narcotic Drug Controlled Substance analogue, because 1,4-Butanediol's chemical structure is not significantly similar to the chemical structure of GHB.