gamma-Butyrolactone
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| gamma-Butyrolactone | |
|---|---|
| Image:GBL chemical structure.png | |
| IUPAC name | Dihydrofuran-2(3H)-one |
| Other names | GBL, butyrolactone, 1,4-lactone, 4-butyrolactone, 4-hydroxybutyric acid lactone, and gamma-hydroxybutyric acid lactone |
| Identifiers | |
| CAS number | |
| RTECS number | LU3500000 |
| SMILES | O=C1CCCO1 |
| Properties | |
| Molecular formula | C4H6O2 |
| Molar mass | 86.089 g/mol |
| Appearance | Colorless liquid |
| Density | 1.144 g/mL |
| Melting point |
-45 °C |
| Boiling point |
204 - 205 °C |
| Solubility in water | Hygroscopic |
| Hazards | |
| MSDS | External MSDS |
| Main hazards | Harmful |
| R-phrases | R22 R36 |
| S-phrases | S26 S36 |
| Flash point | 98 °C (closed cup) |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references | |
gamma-Butyrolactone, also known as GBL, butyrolactone, 1,4-lactone, 4-butyrolactone, 4-hydroxybutyric acid lactone, and gamma-hydroxybutyric acid lactone, is a hygroscopic colorless oily liquid with a weak characteristic odor and is soluble in water. gamma-Butyrolactone is a common solvent and reagent in chemistry and is used as an aroma compound, as a stain remover, as a paint stripper, as a solvent in some wet aluminum electrolytic capacitors, and as a gamma-hydroxybutyric acid (GHB) precursor and substitute.
Chemistry
gamma-Butyrolactone is a lactone. It is hydrolyzed under basic conditions, for example in a sodium hydroxide solution into sodium gamma-hydroxybutyrate, the sodium salt of gamma-hydroxybutyric acid. Under acidic conditions it forms an equilibrium mixture of both compounds. gamma-Butyrolactone can be synthesized from gamma-hydroxybutyric acid by removal of water or by distillation from such a mixture. It may also be obtained via oxidation of tetrahydrofuran (THF). One such process, which affords GBL in yields of up to 80%, utilises bromine generatedin situ from an aqueous solution of sodium bromate and potassium hydrogen sulfate[1].
A Natural Component In Wine
The compound gamma-butyrolactone (GBL) was found in extracts from samples of unadulterated wines. This finding indicates that GBL is a naturally occurring component in some wines and may be present in similar products. The concentration detected was approximately 5 μg/mL and was easily observed using a simple extraction technique followed by GC/MS analysis. These results illustrate the need to carefully examine an allegedly adulterated sample's matrix before determining a sample was laced with GBL.
Recreational use
GBL is a prodrug of GHB. Metabolism takes place in stomach and blood plasma. GBL is longer acting and has a shorter onset than GHB. Otherwise, effects are similar to GHB, although weight for weight it is significantly more powerful, meaning dosage must be lowered accordingly. If ingested undiluted through the oral route, GBL can irritate innards. It is possible for oral ingestion of GBL to cause nausea and other similar problems, possibly more so than with GHB.
Restricting the use of GBL
Although GBL is an unclassified drug in the United Kingdom, risk to people's lives is being recognised on the London Gay Scene, where use is more prevalent than other parts of the country[citation needed]. At the end of 2006, a campaign began to reduce the number of people using GBL in the area[citation needed]. The effects of this campaign are yet to be seen.
References
See also
- gamma-Hydroxybutyrate (GHB)
External links
- Erowid on GBL
- GHB alternatives
- BBC News story: The paint stripper drug that kills, October 7, 2005.
fr:Gamma-butyrolactonefi:GBL sv:GBL
Acknowledgement and Attribution Regarding Sources of Content
Some of the initial content on this page may be incorporated in part from copyleft sources in the public domain including wikis such as Wikipedia and AskDrWiki. Drug information for patients came from the The National Library of Medicine. Infectious disease information may have come from the Centers for Disease Control (CDC). Differential Diagnoses are drawn from clinicians as well as an amalgamation of 3 sources: 1.The Disease Database; 2. Kahan, Scott, Smith, Ellen G. In A Page: Signs and Symptoms. Malden, Massachusetts: Blackwell Publishing, 2004:3; 3. Sailer, Christian, Wasner, Susanne. Differential Diagnosis Pocket. Hermosa Beach, CA: Borm Bruckmeir Publishing LLC, 2002:7 .
