gamma-Butyrolactone

gamma-Butyrolactone[1][2]

Names
Preferred IUPAC name
Oxolan-2-one
Other names
Dihydrofuran-2(3H)-one
GBL
Butyrolactone
1,4-Lactone
4-Butyrolactone
4-Hydroxybutyric acid lactone
gamma-Hydroxybutyric acid lactone
Identifiers
CAS Number 96-48-0 (http://www.commonchemistry.org/ChemicalDetail.aspx?ref=96-48-0)

3D model Interactive image (https://chemapps.stolaf.edu/jmol/jmol.php?

(JSmol) model=O%3DC1OCCC1)
ChEBI CHEBI:42639 (https://www.ebi.ac.uk/chebi/searchId.do?chebiId=42639)
ChEMBL ChEMBL95681
(https://www.ebi.ac.uk/chembldb/index.php/compound/inspect/ChEMBL95681)

ChemSpider 7029 (http://www.chemspider.com/Chemical-Structure.7029.html)

DrugBank DB04699 (https://www.drugbank.ca/drugs/DB04699)
ECHA 100.002.282 (https://echa.europa.eu/substance-
InfoCard information/-/substanceinfo/100.002.282)
IUPHAR/BPS 5462 (http://www.guidetopharmacology.org/GRAC/LigandDisplayForward?
tab=summary&ligandId=5462)
KEGG C01770 (http://www.kegg.jp/entry/C01770)
PubChem 7302 (https://pubchem.ncbi.nlm.nih.gov/compound/7302)
CID
RTECS LU3500000
number
UNII OL659KIY4X (https://fdasis.nlm.nih.gov/srs/srsdirect.jsp?regno=OL659KIY4X)

InChI
SMILES
Properties
Chemical C4H6O2
formula
Molar mass 86.09 g·mol−1
Appearance Colorless liquid
Density 1.1286 g/mL (15 °C), 1.1296 g/mL (20 °C)
Melting point −43.53 °C (−46.35 °F; 229.62 K)
Boiling point 204 °C (399 °F; 477 K)
Solubility in Miscible
water
Solubility soluble in CCl4, methanol, ethanol, acetone, benzene, ethyl ether
log P -0.76[3]
Acidity (pKa) 4.5
Refractive 1.435, 1.4341 (20 °C)
index (nD)
Viscosity 1.7 cp (25 °C)
Hazards
Main hazards Harmful
GHS hazard H318, H302, H336
statements
GHS P264, P270, P280, P301+312, P305+351+338, P403+233, P501
precautionary
statements
Flash point 98 °C (208 °F; 371 K) (closed cup)
Lethal dose or concentration (LD, LC):
LD50 17.2 mL/kg (orally, rat)
(median
dose)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C
[77 °F], 100 kPa).
verify (what is ?)
Infobox references
γ-Butyrolactone (GBL) is a hygroscopic colorless, water-miscible liquid with a weak characteristic odor. It is
the simplest 4-carbon lactone. It is mainly used as an intermediate in the production of other chemicals, e.g.
methyl-2-pyrrolidone.[4] GBL In humans it acts as a prodrug for γ-hydroxybutyric acid (GHB), and it is used as
a recreational intoxicant with effects similar to barbiturates.

Contents
Occurrence
Preparation
Reactions
Polymerization
Uses
Pharmacology
Pharmacokinetics
Nutritional supplement
Recreational drug
Dangers
Addictiveness and dependence
Dose
Legal status
See also
References
External links

Occurrence
GBL has been found in extracts from samples of unadulterated wines.[5][6] 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. GBL can be found in cheese flavourings but typically results in a content of 0.0002% GBL in
the final foodstuff.[7]

Preparation
GBL is produced industrially by dehydrogenation of 1,4-butanediol.[4] This route proceeds via dehydration of
GHB.
In the laboratory, it may also be obtained via the oxidation of tetrahydrofuran (THF), for example with
aqueous sodium bromate.[8] An alternative route proceeds from GABA using the sandmeyer reaction.[9]

Reactions
As a lactone, GBL is hydrolyzed under basic conditions, for example in a sodium hydroxide solution into
sodium gamma-hydroxybutyrate, the sodium salt of gamma-hydroxybutyric acid. In acidic water, a mixture of
the lactone and acid forms coexist in an equilibrium. These compounds then may go on to form the polymer
poly(4-hydroxybutyrate). When treated with a non-nucleophilic base, such as lithium diisopropylamide, GBL
undergoes deprotonation alpha to the carbonyl. The related compound caprolactone can be used to make a
polyester in this manner.

Polymerization
The ring-opening polymerization of butyrolactone gives polybutyrolactone. The resulting reverts to the
monomer by thermal cracking.[10][11] It is claimed that poly(GBL) is competitive with commercial biomaterial
poly(4-hydroxybutyrate), or P4HB. It is further claimed that poly(GBL) is cheaper to make than P4HB,
although both are bio-derived.[10][12]

Uses
Butyrolactone is principally a precursor to other chemicals. Reaction with methylamine gives NMP. Ammonia
gives pyrrolidone. It is also used as a solvent in lotions and some polymers.[4]

Butyrolactone, with its wide liquid range, chemical stability and

high dielectric constant, is used in some batteries but primarily is
found in electrolytic capacitors as the organic solvent. In this
capacity, it is frequently mixed with a small ratio of ethylene
glycol, "9:1" being common, to vary internal resistivity.[13]
2-Methyl-4-chlorophenoxybutyric acid
is an herbicide produced from
butyrolactone.
Pharmacology
GBL is not active in its own right; its mechanism of action stems
from its identity as a prodrug of GHB.

The hypnotic effect of GHB is enhanced by combination with alcohol. This combination
(https://en.wikipedia.org/wiki/Gamma-Hydroxybutyric_acid#Combination_with_alcohol) is particularly
toxic (https://en.wikipedia.org/wiki/Gamma-Hydroxybutyric_acid#Overdose), typically leading to
nausea/vomiting and respiratory depression. 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.[14]

Pharmacokinetics
GBL is rapidly converted into GHB by paraoxonase (lactonase) enzymes, found in the blood.[15][16] Animals
which lack these enzymes exhibit no effect from GBL.[15] GBL is more lipophilic (fat soluble) than GHB, and so
is absorbed faster and has higher bioavailability. Because of these pharmacokinetic differences, GBL tends to
be more potent and faster-acting than GHB, but has a shorter 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.[17]

The levels of lactonase enzyme can vary between individuals, meaning that first-time users can show
unpredictable results, even from small doses. In many this manifests as slow onset of effects, followed by
headaches, semi-consciousness which is distinct from GBL sleep in normal users. If the user decides to try
again at a later date, they appear to be able to enjoy the effects normally.

Metabolic pathway of 1,4-butanediol, GBL and GHB.

Nutritional supplement
Due to its property of being a prodrug of GHB which increases sleep related growth hormone (GH) secretion,
[18]
GBL was sold as a nutritional supplement after the scheduling of GHB, under the names Revivarant and
Renewtrient[19] in the U.S. at least until the end of 1999.

Recreational drug
GBL is a prodrug of GHB and its recreational use comes entirely as a result of this.[20] To bypass GHB
restriction laws, home synthesis kits were introduced to transform GBL and/or 1,4-B into GHB.
GBL overdose can cause irrational behaviour,
severe sickness, coma and death.[21] GBL has
a distinctive taste and odour, described as
being comparable to stale water, synthetic
melon aroma or burnt plastic. This differs
significantly from GHB, which is described as
having a decidedly "salty" taste.[22]

Due to the fact that is easily found in

components used in everyday products and
their low value, "a dose costs about seven Jugs of seized GBL.
cents", according to Patrick Nisse, a hospital
doctor, GBL has become quite popular
among young people in nightclubs around France.
[23][24]

Dangers
If taken undiluted by mouth, GBL can cause
esophageal and gastro-intestinal irritation. It is
possible for oral ingestion of GBL to cause nausea and
other similar problems, possibly more so than with
GHB.

GHB has biphasic effects, a euphoric effect at low

doses (the reason for the term liquid ecstasy), and a
sedative effect[25] at higher doses. As a result of this
sedation it can cause unconsciousness.[26] When
combined with alcohol the increased sedation and
risk of vomiting results in a high risk of fatality. Many
harm reduction organisations suggest never mixing
the two drugs as a result.[27][28]

FDA warning against products containing GHB

There have been news reports of several deaths
and its prodrugs, such as GBL.
associated with GBL, usually in combination with
alcohol or other depressants.[29]

Addictiveness and dependence

Frequent use of GHB/GBL, even when taken long-term and in moderate doses, does not appear to cause
significant physical dependency in the majority of its users. In many people, quitting or temporarily abstaining
from use of the drugs is achieved with minimal or no difficulty. However, when consumed in excessive
amounts with a high frequency of dosing, physical and psychological dependence can develop.[30] Management
of GBL dependence involves considering the person's age, comorbidity and the pharmacological pathways of
GBL.[31]

GHB/GBL users can adopt a '24/7' dosing regime.[32] This is where the user has become tolerant to the effects
of the drug, increasing the dosage and frequency of dosage simply to avoid withdrawal symptoms.

For those users who do report withdrawal symptoms upon quitting the use of GHB/GBL, symptoms seem to
depend on the dosage and the length of time the drug was used. Light to moderate users often experience
insomnia and sleep-related problems, whereas heavy, prolonged use can cause severe withdrawal symptoms
similar to Benzodiazepine withdrawal syndrome (BWS).

Dose
A milliliter of pure GBL metabolizes to the equivalent 1.65g of NaGHB, the common form, so doses are
measured in the single milliliter range, either taken all at once or sipped over the course of a night.

Legal status
Australia: GBL is not classified as a drug but as a health-endangering substance. Although legislation to enter
into force on 1 April 2011 will make it possible to handle narcotics for industrial purposes will enable GBL and
1,4-Butanediol to be classified as controlled substances.[33]

Canada: GBL is a Controlled Substance under Schedule VI of the "Controlled Drugs and Substances Act" in
Canada. Schedule VI of the "Controlled Drugs and Substances Act" requires vendors to collect information
regarding purchases of GBL. The Act also prohibits the import and export of GBL into or out of Canada
classifying it as either an indictable offense punishable with up to 10 years in prison or an offense punishable
on summary conviction liable to imprisonment for up to eighteen months.[34] It is not illegal for an individual
to possess GBL in Canada.

Germany: GBL is not listed in the narcotics law, but its distribution is controlled. Possession is not illegal, but
may be punished according to the Medicines Act, when intended to be sold for human consumption or
synthesis of GHB. In recent years, an increase of GBL consumption has been observed due to the prohibition
of GHB.

Hong Kong SAR: GBL is a dangerous drug controlled under Schedule 1 of the Dangerous Drugs Ordinance,
Cap.134 (with exemption clause at Paragraph 16D). Any person who is found to have in his possession of it not
in accordance with this Ordinance can be liable, on conviction upon indictment, a fine of HK$1,000,000 and
to imprisonment for 7 years.

Israel: GBL was classified as a proscribed substance from 2007.[35]

The Netherlands: GBL has been placed on list 1 of the Opiumwet. Therefore, export and import, possession,
manufacturing, sale and transport are forbidden. However, use of drugs forbidden by the Opiumwet is not
considered illegal, but mainly treated as a public health concern.[36]
Poland: GBL is classified as a drug. A license is mandatory for the manufacture, processing, reworking,
importing, distribution of GBL.[37]

Russia: GBL has been classified as a psychotropic substance since 22 February 2012. Its trafficking is limited,
and non-licensed selling, buying or any other use is punishable by imprisonment up to 20 years.

Sweden: GBL is not classified as a drug but as a health-endangering substance. Although recently passed
legislation to enter into force on 1 April 2011 will make it possible to handle narcotics for industrial purposes
will enable GBL and 1,4-Butanediol to be classified as controlled substances.[38]

United Kingdom: Because of their legitimate uses, regulation 4B of the 2001 regulations makes it lawful to
import, export, produce, supply, offer to supply or possess GBL and 1,4-BD. Except where a person does so
knowing or believing that they will be used for the purpose of human ingestion.[7][39]

United States: GBL is regulated as a List I controlled chemical. As a GHB analog, it is also treated as a
controlled substance under Schedule I of the Controlled Substances Act if intended for human consumption.[40]

See also
◾ 1,4-Butanediol
◾ Succinic anhydride

References
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10. Micu, Alexandru (December 12, 2015). "New, fully recyclable and biodegradable plastic could change the
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11. Hong, Miao; Chen, Eugene Y.-X. (2015). "Completely recyclable biopolymers with linear and cyclic
topologies via ring-opening polymerization of γ-butyrolactone". Nature Chemistry. 8 (1): 42–49.
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16. Teiber, J. F.; Draganov, D. I.; Du, B. N. L. (2003). "Lactonase and lactonizing activities of human serum
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(http://www.who.int/medicines/areas/quality_safety/5.4GBLpre-review.pdf) (PDF). 4 Jun 2012.
18. Van Cauter, E.; Plat, L.; Scharf, M. B.; Leproult, R.; Cespedes, S.; l'Hermite-Balériaux, M.; Copinschi, G.
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(https://www.erowid.org/chemicals/ghb/gbl_info2.shtml). Erowid. 1998-11-21. Retrieved 2013-10-10.
20. Meyer, Jerrold; Linda F. Quenzer (2005). Psychopharmacology: Drugs, the Brain and Behavior. Sinauer.
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therapeutic potential of gamma-hydroxybutyric acid". Alcohol. 20 (3): 263–269. doi:10.1016/S0741-8329
(99)00090-7 (https://doi.org/10.1016%2FS0741-8329%2899%2900090-7). PMID 10869868
(https://www.ncbi.nlm.nih.gov/pubmed/10869868).
23. " 'There could be 100 comas in the year': Paris police chief reacts to rise of GBL, GHB overdoses in clubs"
(https://www.residentadvisor.net/news.aspx?id=41494). Resident Advisor. Retrieved 2018-04-19.
24. "Drogue : « L'interdiction de vente au public du GBL n'a rien changé à la consommation »"
(http://www.lemonde.fr/sante/article/2018/04/17/l-interdiction-de-vente-au-public-du-gbl-n-a-rien-change-a-
la-consommation_5286434_1651302.html). Le Monde.fr (in French). Retrieved 2018-04-19.
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hydroxybutyrate (GHB) in rats alone and in combination with other drugs: assessment using biotelemetry".
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(https://www.ncbi.nlm.nih.gov/pubmed/19446408).
26. Edwards, Richard (23 July 2009). "Coroner's 'Russian roulette' warning over GBL party drug"
(https://www.telegraph.co.uk/news/uknews/5895143/Coroners-Russian-roulette-warning-over-GBL-party-
drug.html). The Telegraph. The Telegraph. Retrieved May 1, 2012.
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28. "GHB and GBL" (http://www.gmfa.org.uk/ghb-and-gbl). GMFA. Retrieved 18 August 2014.
29. Casciani, Dominic (23 December 2009). "GBL drug death identified by UK doctors"
(http://news.bbc.co.uk/1/hi/uk/8428802.stm). BBC News. Retrieved May 1, 2012.
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(http://www.psychoactive.org.uk/GHB/addiction.htm) Archived
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40. Information Bulletin: GHB Analogs; GBL, BD, GHV, and GVL
(http://www.justice.gov/archive/ndic/pubs1/1621/index.htm)

External links
◾ Erowid on GBL (http://www.erowid.org/chemicals/ghb/gbl_info1.shtml)
◾ "The paint stripper drug that kills" (http://news.bbc.co.uk/2/hi/uk_news/magazine/4261788.stm). BBC
News. October 7, 2005.
◾ "All About GHB," (http://www.nida.nih.gov/whatsnew/meetings/GHB/default.html) a NIDA Neuroscience
Consortium and OSPC "Cutting Edge" colloquium (27 June 2000 at the Doubletree hotel, Rockville, MD)

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