Gamma-hydroxybutyrate

γ-Hydroxybutyric acid
Clinical data


Pregnancy category	B
Routes of administration	Usually by mouth; intravenous
ATC code	N01AX11 (WHO) N07XX04 (WHO)
Legal status
Legal status	AU: S8 (Controlled) CA: Schedule I DE: Anlage III (Prescription only) NZ: Class B UK: Class C US: Schedule I and Schedule III
Pharmacokinetic data
Bioavailability	25% (oral)
Metabolism	95%, mainly liver, also in blood and tissues
Onset of action	Within 5–15 min
Biological half-life	30–60 minutes
Excretion	5%, kidney
Identifiers
IUPAC name 4-Hydroxybutanoic acid
Synonyms	γ-Hydroxybutyric acid γ-Hydroxybutyrate GHB
CAS Number	591-81-1^Y
PubChem (CID)	3037032
IUPHAR/BPS	4711
DrugBank	DB01440^Y
ChemSpider	9984^Y
UNII	30IW36W5B2^Y
KEGG	C00989^Y
ChEBI	CHEBI:30830^Y
ChEMBL	CHEMBL1342^Y
Chemical and physical data
Formula	C₄H₈O₃
Molar mass	104.10 g/mol (GHB) 126.09 g/mol (sodium salt) 142.19 g/mol (potassium salt)
3D model (Jmol)	Interactive image
SMILES O=C(O)CCCO
InChI InChI=1S/C4H8O3/c5-3-1-2-4(6)7/h5H,1-3H2,(H,6,7)^Y Key:SJZRECIVHVDYJC-UHFFFAOYSA-N^Y

γ-Hydroxybutyric acid (GHB), also known as 4-hydroxybutanoic acid, is a naturally occurring neurotransmitter and a psychoactive drug. It is a precursor to GABA, glutamate, and glycine in certain brain areas, and it acts on the GHB receptor and it is a weak agonist at the GABA_B receptor.

GHB has been used in a medical setting as a general anesthetic and as a treatment for cataplexy, narcolepsy and alcoholism. It is also used illegally as an intoxicant, to try to increase athletic performance, and as a date rape drug. It is commonly used in the form of a salt, such as sodium γ-hydroxybutyrate (Na.GHB, sodium oxybate, or Xyrem) or potassium γ-hydroxybutyrate (K.GHB, potassium oxybate).

GHB is also produced as a result of fermentation, and is found in small quantities in some beers and wines, beef and small citrus fruits.

Succinic semialdehyde dehydrogenase deficiency is a disease that causes GHB to accumulate in the blood.

The only common medical use for GHB today are in the treatment of narcolepsy and more rarely alcoholism. It is sometimes used off-label for the treatment of fibromyalgia.

GHB is the active ingredient in the prescription medication sodium oxybate (Xyrem). Sodium oxybate is approved by the U.S. Food and Drug Administration (FDA) for the treatment of cataplexy associated with narcolepsy and excessive daytime sleepiness (EDS) associated with narcolepsy.

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Wikipedia