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Gamma Hydroxybutyric Acid

Catalog No. DB01440 Name DrugBank
CAS Number 591-81-1 Website http://www.ualberta.ca/
M. F. C4H8O3 Telephone (780) 492-3111
M. W. 104.10452 Fax (780) 492-1071
Purity Email david.wishart@ualberta.ca
Storage Chembase ID: 1247

SYNONYMS

IUPAC name
4-hydroxybutanoic acid
IUPAC Traditional name
gamma-hydroxybutyric acid
Brand Name
Xyrem
Synonyms
4-hydroxybutanoic acid
Juice
4-hydroxybutanoate
Sodium oxybate
gamma-Hydroxybutyric acid
GHB
4-Hydroxybutyric acid
4-Hydroxy-butanoic acid
Liquid Ecstasy

DATABASE IDS

PubChem SID 46507548
PubChem CID 3037032
CAS Number 591-81-1

PROPERTIES

DETAILS

Description (English)
Item Information
Drug Groups illicit; approved
Description Gamma Hydroxybutyric Acid, commonly abbreviated GHB, is a therapeutic drug which is illegal in multiple countries. It is currently regulated in the US and sold by Jazz Pharmaceuticals under the name Xyrem. However, it is important to note that GHB is a designated Orphan drug (in 1985). Today Xyrem is a Schedule III drug;
however GHB remains a Schedule I drug and the illicit use of Xyrem falls under penalties of Schedule I. GHB is a naturally occurring substance found in the central nervous system, wine, beef, small citrus fruits and almost all other living creatures in small amounts. It is used illegally under the street names Juice, Liquid Ecstasy or simply G, either as an intoxicant, or as a date rape drug. Xyrem is a central nervous system depressant that reduces excessive daytime sleepiness and cataplexy in patients with narcolepsy.
Indication Used as a general anesthetic, to treat conditions such as insomnia, clinical depression, narcolepsy, and alcoholism, and to improve athletic performance.
Pharmacology GHB has at least two distinct binding sites in the central nervous system. GHB is an agonist at the newly-characterized GHB receptor, which is excitatory, and it is a weak agonist at the GABAB receptor, which is inhibitory. GHB is a naturally-occurring substance that acts in a similar fashion to some neurotransmitters in the mammalian brain. GHB is probably synthesized from GABA in GABAergic neurons, and released when the neurons fire.
Toxicity At higher doses, GHB may induce nausea, dizziness, drowsiness, agitation, visual disturbances, depressed breathing, amnesia, unconsciousness, and death.
Affected Organisms
Humans and other mammals
Half Life 30 to 60 minutes
Elimination Animal studies indicate that metabolism is the major elimination pathway for sodium oxybate, producing carbon dioxide and water via the tricarboxylic acid (Krebs) cycle and secondarily by beta-oxidation. Succinic acid enters the Krebs cycle where it is metabolized to carbon dioxide and water. Fecal and renal excretion is negligible.
5% renal elimination.
Distribution * 190 to 384 mL/kg
Clearance * apparent oral cl=9.1 mL/min/kg [healthy adults receiving a single oral dose of 25 mg/kg]
* 4.5 mL/min/kg [cirrhotic patients without ascites receiving a single oral dose of 25 mg/kg]
* 4.1 mL/min/kg [cirrhotic patients with ascites receiving a single oral dose of 25 mg/kg]
External Links
Wikipedia

REFERENCES