gamma-Hydroxybutyric acid

γ-hydroxybutyric acid
Clinical data
Other names	γ-hydroxybutyric acid; γ-hydroxybutyrate; GHB; fishies;
Routes of; administration	By mouth, intravenous
Drug class	Depressant, ; Sedative, Psycholeptic, ; Hypnotic, ; GABA analogue
ATC code	N01AX11 (WHO) N07XX04 (WHO);
Legal status
Legal status	AU: S8 (Controlled drug); BR: Class B1 (Psychoactive drugs); CA: Schedule I; DE: Prescription only (Anlage III for higher doses); NZ: Class B; UK: Class B; US: Schedule I / Schedule III (Xywav and Xyrem); UN: Psychotropic Schedule II; EU: List I (Netherlands);
Pharmacokinetic data
Bioavailability	25% (oral)
Metabolism	95%, mainly liver, also in blood and tissues
Onset of action	Within 5–15 minutes
Elimination half-life	30–60 minutes
Excretion	5%, kidney
Identifiers
	IUPAC name 4-hydroxybutanoic acid;
CAS Number	591-81-1 ;
PubChem CID	3037032;
IUPHAR/BPS	4711;
DrugBank	DB01440 ;
ChemSpider	9984 ;
UNII	30IW36W5B2;
KEGG	C00989 ;
ChEBI	CHEBI:30830 ;
ChEMBL	ChEMBL1342 ;
CompTox Dashboard (EPA)	DTXSID2074740 ;
ECHA InfoCard	100.218.519
Chemical and physical data
Formula	C4H8O3
Molar mass	104.105 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C(O)CCCO;
	InChI InChI=1S/C4H8O3/c5-3-1-2-4(6)7/h5H,1-3H2,(H,6,7) ; Key:SJZRECIVHVDYJC-UHFFFAOYSA-N ;
	(verify)

gamma-Hydroxybutyric acid (or γ-hydroxybutyric acid (GHB), also known as 4-hydroxybutanoic acid) is a naturally occurring neurotransmitter and a depressant drug. It is a precursor to GABA, glutamate, and glycine in certain brain areas. It acts on the GHB receptor and is a weak agonist at the GABA_B receptor. GHB has been used in the medical setting as a general anesthetic and as treatment for cataplexy, narcolepsy, and alcoholism. The substance is also used illicitly for various reasons, including as a performance-enhancing drug, date rape drug, and as a recreational drug.

It is commonly used in the form of a salt, such as sodium γ-hydroxybutyrate (NaGHB, sodium oxybate, or Xyrem) or potassium γ-hydroxybutyrate (KGHB, 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.

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