Γ-Hydroxybutyric acid

γ-Hydroxybutyric acid
Clinical data
Other names	GHB; Liquid ecstasy; γ-hydroxybutyrate; Fishies; G;
Addiction; liability	High
Routes of; administration	By mouth, intravenous
Drug class	GABA analogue, GHB receptor agonists—GABA receptor agonist; Psycholeptic; Depressant;; Hypnotic; Sedative
ATC code	N01AX11 (WHO) N07XX04 (WHO);
Legal status
Legal status	AU: S9 (Prohibited substance) / S8 as sodium oxybate; 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	95–98%, mainly liver, also in blood and tissues
Onset of action	Within 5–15 minutes
Elimination half-life	30–60 minutes
Excretion	1–5%, 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)

γ-Hydroxybutyric acid, also known as gamma-hydroxybutyric acid, GHB, or 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 medicine as a general anesthetic and as treatment for cataplexy, narcolepsy, and alcoholism. It is also used illicitly for performance enhancement, date rape, and recreation.

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 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 causes GHB to accumulate in the blood.

Clinical data


Other names	GHB Liquid ecstasy γ-hydroxybutyrate Fishies G
Addiction liability	High
Routes of administration	By mouth, intravenous
Drug class	GABA analogue, GHB receptor agonists—GABA receptor agonist; Psycholeptic; Depressant; Hypnotic Sedative
ATC code	N01AX11 (WHO) N07XX04 (WHO)
Legal status
Legal status	AU: S9 (Prohibited substance) / S8 as sodium oxybate 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	95–98%, mainly liver, also in blood and tissues
Onset of action	Within 5–15 minutes
Elimination half-life	30–60 minutes
Excretion	1–5%, kidney
Identifiers
IUPAC name 4-hydroxybutanoic acid
CAS Number	591-81-1^Y
PubChem CID	3037032
IUPHAR/BPS	4711
DrugBank	DB01440^Y
ChemSpider	9984^Y
UNII	30IW36W5B2
KEGG	C00989^Y
ChEBI	CHEBI:30830^Y
ChEMBL	ChEMBL1342^Y
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)^Y Key:SJZRECIVHVDYJC-UHFFFAOYSA-N^Y
(verify)