| gamma-Butyrolactone | |
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| 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 | [96-48-0] |
| RTECS number | LU3500000 |
| SMILES | O=C1CCCO1 |
| Properties | |
| Molecular formula | C4H6O2 |
| Molar mass | 86. IUPAC Nomenclature is a system of naming Chemical compounds and of describing the science of Chemistry in general CAS registry numbers are unique numerical identifiers for Chemical compounds Polymers biological sequences mixtures and Alloys They are also referred to Registry of Toxic Effects of Chemical Substances ( RTECS) is a Database of Toxicity information compiled from the open scientific literature without reference A chemical formula is a way of expressing information about the Atoms that constitute a particular Chemical compound, and how the relationship between those atoms changes Molar mass, symbol M, is the Mass of one mole of a substance ( Chemical element or Chemical compound) 089 g/mol |
| Appearance | Colorless liquid |
| Density | 1. The density of a material is defined as its Mass per unit Volume: \rho = \frac{m}{V} Different materials usually have different 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 |
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gamma-Butyrolactone (γ-butyrolactone or GBL) is a hygroscopic colorless oily liquid with a weak characteristic odor and is soluble in water. The melting point of a solid is the temperature range at which it changes state from solid to Liquid. The boiling point of a liquid is the temperature at which the Vapor pressure of the liquid equals the environmental pressure surrounding the liquid Solubility is the characteristic Physical property referring to the ability of a given substance the Solute, to dissolve in a Solvent. Water is a common Chemical substance that is essential for the survival of all known forms of Life. A material safety data sheet ( MSDS) is a form containing data regarding the properties of a particular substance Occupational safety and health is a cross-disciplinary area concerned with protecting the Safety, Health and welfare of people engaged in R-phrases (short for Risk Phrases) are defined in Annex III of European Union Directive 67/548/EEC: Nature of special risks attributed to dangerous R-phrases (short for Risk Phrases) are defined in Annex III of European Union Directive 67/548/EEC: Nature of special risks attributed to dangerous R-phrases (short for Risk Phrases) are defined in Annex III of European Union Directive 67/548/EEC: Nature of special risks attributed to dangerous S-phrases are defined in Annex IV of European Union Directive 67/548/EEC: Safety advice concerning dangerous substances and preparations. S-phrases are defined in Annex IV of European Union Directive 67/548/EEC: Safety advice concerning dangerous substances and preparations. S-phrases are defined in Annex IV of European Union Directive 67/548/EEC: Safety advice concerning dangerous substances and preparations. The flash point of a flammable liquid is the lowest Temperature at which it can form an ignitable mixture in air In Chemistry, the standard state of a material is its state at 1 bar (100 Kilopascals exactly Hygroscopy is the ability of a substance to attract Water Molecules from the surrounding environment through either absorption or Adsorption GBL is a common solvent and reagent in chemistry and is used as an aroma compound, as a stain remover, as a superglue remover, as a paint stripper, and as a solvent in some wet aluminium electrolytic capacitors. A solvent is a liquid or gas that dissolves a solid liquid or gaseous Solute, resulting in a Solution. A reagent or reactant is a substance or compound consumed during a Chemical reaction. Chemistry (from Egyptian kēme (chem meaning "earth") is the Science concerned with the composition structure and properties Cyanoacrylate is the generic name for cyanoacrylate based fast-acting Glues such as ethyl-2-cyanoacrylate (commonly sold under trade names like Superglue and Krazy Paint stripper, or paint remover, is the generic name given to Solvent mixtures designed to remove Paint and other finishes and also to clean the underlying A solvent is a liquid or gas that dissolves a solid liquid or gaseous Solute, resulting in a Solution.
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Occurrence
GBL has been 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.
Preparation
GBL can be synthesized from gamma-hydroxybutyric acid (GHB) by removal of water or by distillation from such a mixture. gamma -Hydroxybutyric acid, 4-hydroxybutanoic acid, GHB, or fantasy is a naturally-occurring substance found in the Central nervous It may also be obtained via oxidation of tetrahydrofuran (THF). "THF" redirects here For other uses see THF (disambiguation. One such process, which affords GBL in yields of up to 80%, utilises bromine generated in situ from an aqueous solution of sodium bromate and potassium hydrogen sulfate. In situ (ɪn siːˈtuː is a Latin phrase meaning in the place. Sodium bromate (molecular formula NaBrO3 is a strong Oxidant, mainly used in continuous or batch Dyeing processes involving sulfur or vat dyes and Potassium bisulfate is the Potassium salt of Bisulfate anion with the molecular formula KHSO4 [1]
Chemistry
GBL is a lactone. lactone is a cyclic Ester in Organic chemistry. It is the condensation product of an Alcohol group and a Carboxylic acid It is hydrolyzed under basic conditions, for example in a sodium hydroxide solution into sodium gamma-hydroxybutyrate, the sodium salt of gamma-hydroxybutyric acid. Hydrolysis is a Chemical reaction during which one or more water molecules are split into hydrogen and hydroxide ions which may go on to participate in further reactions In Chemistry, a base is most commonly thought of as an aqueous substance that can accept Protons This refers to the Brønsted-Lowry theory of acids and Sodium hydroxide ( Na[[hydroxide OH]]) also known as Lye, caustic soda and (incorrectly according to IUPAC nomenclature In Chemistry, a solution is a Homogeneous Mixture composed of two or more substances Sodium (ˈsoʊdiəm is an element which has the symbol Na( Latin natrium, from Arabic natrun) atomic number 11 atomic mass 22 A salt, in Chemistry, is defined as the product formed from the neutralisation reaction of Acids and bases. Under acidic conditions it forms an equilibrium mixture of both compounds. In a Chemical process, chemical equilibrium is the state in which the chemical activities or Concentrations of the reactants and products have no net change
Pharmacology
GBL is not active in its own right, its mechanism of action stems from its identity as a prodrug of GHB. gamma -Hydroxybutyric acid, 4-hydroxybutanoic acid, GHB, or fantasy is a naturally-occurring substance found in the Central nervous A prodrug is a pharmacological substance ( drug) that is administered in an inactive (or significantly less active form
The hypnotic effect of GHB is enhanced by combination with alcohol. A 2003 rat study showed that GBL in combination with ethanol showed a potentiated hypnotic effect, as the sleep-timing measure was longer than both of the individual components combined. [2]
Pharmacokinetics
GBL is rapidly converted into GHB by lactamase enzymes found in the blood. Beta-lactamases are Enzymes ( produced by some bacteria and are responsible for their resistance to Beta-lactam antibiotics like Penicillins GBL is more lipophilic (fat soluble) than GHB, and so is absorbed faster and has higher bioavailability; the paradox is that this can mean that GBL has a faster onset of effects than GHB itself, even though it is a prodrug. In Pharmacology, bioavailability is used to describe the fraction of an administered Dose of unchanged drug that reaches the Systemic circulation, one of The levels of lactamase enzyme can vary between individuals, and GBL is not active in its own right, so people who have never tried GBL before may have delayed or fewer effects than expected; however, once someone has taken GBL a few times, the production of lactamase enzymes is increased and he/she will feel the effects like normal.
Because of these pharmacokinetic differences, GBL tends to be more potent and faster-acting than GHB, and has around the same duration; whereas the related compound 1,4-butanediol (1,4-B) tends to be slightly less potent, slower to take effect but longer-acting than GHB.
Recreational use
GBL is a prodrug of GHB. A prodrug is a pharmacological substance ( drug) that is administered in an inactive (or significantly less active form To bypass GHB restriction laws, home synthesis kits were introduced to transform GBL and/or 1,4-B into GHB. GBL can also be used as a recreational drug by itself. [3]
GBL overdose can cause severe sickness, coma and death. In Medicine, a coma (from the Greek koma, meaning deep sleep is a profound state of Unconsciousness. Death is the termination of the biological functions that define living Organisms It refers both to a specific
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.
Dose
A milliliter of pure GBL metabolizes to roughly 1. 6g of GHB, so doses are measured in the single milliliter range, either taken all at once or sipped over the course of a night.
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. At the end of 2006, a campaign began to reduce the number of people using GBL in the area. The effects of this campaign are yet to be seen.
See also
- gamma-Hydroxybutyrate (GHB)
- 1,4-Butanediol (1,4-B)
References
- ^ Metsger, L. gamma -Hydroxybutyric acid, 4-hydroxybutanoic acid, GHB, or fantasy is a naturally-occurring substance found in the Central nervous ; Bittner, S. Autocatalytic Oxidation of Ethers with Sodium Bromate, Tetrahedron 2000, 56, 1905-1910
- ^ Sassenbroek, Van (Jun), “Characterization of the pharmacokinetic and pharmacodynamic interaction between gamma-hydroxybutyrate and ethanol in the rat.”, Toxicological Sciences, PMID 12700396
- ^ Meyer, Jerrold; Linda F. Quenzer (2005). Psychopharmacology: Drugs, the Brain and Behavior. Psychopharmacology (from Greek grc ψῡχή psȳkhē, "breath life soul" grc φάρμακον pharmakon, "drug" and grc -λογία Sinauer, pp. 370. ISBN 0-87893-534-7.
External links
- Erowid on GBL
- Forum on GBL's Legal Status
- BBC News story: The paint stripper drug that kills, October 7, 2005.
- “All About GHB," a NIDA Neuroscience Consortium and OSPC “Cutting Edge” colloquium (27 June 2000 at the Doubletree hotel, Rockville, MD) Organized by Drs. Jerry Frankenheim and Minda Lynch in response to the rapid ascent of GHB and its precursors, GBL and 1,4-butanediol, as public health concerns.
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