File:4-Hydroxybutansäure_-_4-Hydroxybutanoic_acid.svg · Wikimedia Commons · See Wikimedia Commons
4-hydroxybutyric acid
Sign in to saveAlso known as Alcover®, GHB, WY-3478, Xyrem®, 4HB, γ-hydroxybutyrate, gamma-hydroxybutyric acid, 4-hydroxy-butyric acid
chemical compound
Key facts
- 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 )
- Bioavailability
- 25% (oral)
- Metabolism
- 95–98%, mainly liver , also in blood and tissues
- Metabolites
- Succinic semialdehyde , Succinic acid
- Onset of action
- Within 5–15 minutes
- Elimination half life
- 30–60 minutes
- Excretion
- 1–5%, kidney
- Cas number
- 591-81-1
- Drugbank
- DB01440
- Unii
- 30IW36W5B2
- Kegg
- C00989
- Chebi
- CHEBI:30830
- Chembl
- ChEMBL1342
- Comptox dashboard u s environmental prot
- DTXSID2074740
via Wikipedia infobox
Chemical data
- Formula
- C4H8O3
- Molecular weight
- 104.1 g/mol
- IUPAC name
- 4-hydroxybutanoic acid
- SMILES
- C(CC(=O)O)CO
- InChIKey
- SJZRECIVHVDYJC-UHFFFAOYSA-N
- XLogP
- -0.6
- Polar surface area
- 57.5 Ų
- H-bond donors
- 2
- H-bond acceptors
- 3
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Approved
- Molecule type
- Small molecule
- First approval
- 2002
- Admin. routes
- oral
via ChEMBL · EBI
Wikidata facts
- Mass
- 104.047344
- Has use
- medication
Show 8 more facts
- Commons category
- GHB
- chemical formula
- C₄H₈O₃
- canonical SMILES
- C(CC(=O)O)CO
- medical condition treated
- narcolepsy
- found in taxon
- Caenorhabditis elegans
- melting point
- 16.5
- pKa
- 4.71
- subject has role
- depressant
Sources (6)
via Wikidata · CC0
~30 min read
Encyclopedic overview
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 GABAB 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.
Excerpted from Wikipedia’s “4-hydroxybutyric acid” article, available under the CC BY-SA 4.0 licence.