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; 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.^[13]^[14] It is also used illicitly for performance enhancement, date rape, and recreation.^[15]

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.^[16]

Succinic semialdehyde dehydrogenase deficiency causes GHB to accumulate in the blood.

^ "Pingers, pingas, pingaz: how drug slang affects the way we use and understand drugs". The Conversation. 8 January 2020. Archived from the original on 15 January 2021. Retrieved 13 May 2023.
^ "GHB/GBL "G"". Archived from the original on 24 May 2024. Retrieved 24 May 2024.
^ Tay, E., Lo, W. K. W., & Murnion, B. (2022). Current Insights on the Impact of Gamma-Hydroxybutyrate (GHB) Abuse. Substance Abuse and Rehabilitation, 13, 13–23. doi:10.2147/SAR.S315720
^ "Therapeutic Goods (Poisons Standard—June 2024) Instrument 2024". 30 May 2024.
^ Anvisa (31 March 2023). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 4 April 2023). Archived from the original on 3 August 2023. Retrieved 16 August 2023.
^ Cite error: The named reference Xyrem FDA label was invoked but never defined (see the help page).
^ Cite error: The named reference Lumryz FDA label was invoked but never defined (see the help page).
^ Cite error: The named reference Xywav FDA label was invoked but never defined (see the help page).
^ "What is GHB?" (PDF). U.S. Drug Enforcement Administration. Archived (PDF) from the original on 17 October 2020. Retrieved 6 March 2022.
^ Cite error: The named reference DEA was invoked but never defined (see the help page).
^ Riviello RJ (2010). Manual of forensic emergency medicine : a guide for clinicians. Sudbury, MA: Jones and Bartlett Publishers. p. 42. ISBN 978-0763744625.
^ ^a ^b Cite error: The named reference auto was invoked but never defined (see the help page).
^ "Sodium Oxybate: MedlinePlus Drug Information". Nlm.nih.gov. 28 July 2010. Archived from the original on 11 April 2010. Retrieved 1 August 2010.
^ Benzer TI, Cameron S (8 January 2007). VanDeVoort JT, Benitez JG (eds.). "Toxicity, Gamma-Hydroxybutyrate". eMedicine. Archived from the original on 28 November 2021. Retrieved 16 January 2007.
^ Cite error: The named reference dea-daterape was invoked but never defined (see the help page).
^ Weil A, Winifred R (1993). "Depressants". From Chocolate to Morphine (2nd ed.). Boston/New York: Houghton Mifflin Company. p. 77. ISBN 978-0-395-66079-9.

[1] "Pingers, pingas, pingaz: how drug slang affects the way we use and understand drugs". The Conversation. 8 January 2020. Archived from the original on 15 January 2021. Retrieved 13 May 2023.

[2] "GHB/GBL "G"". Archived from the original on 24 May 2024. Retrieved 24 May 2024.

[3] Tay, E., Lo, W. K. W., & Murnion, B. (2022). Current Insights on the Impact of Gamma-Hydroxybutyrate (GHB) Abuse. Substance Abuse and Rehabilitation, 13, 13–23. doi:10.2147/SAR.S315720

[4] "Therapeutic Goods (Poisons Standard—June 2024) Instrument 2024". 30 May 2024.

[5] Anvisa (31 March 2023). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 4 April 2023). Archived from the original on 3 August 2023. Retrieved 16 August 2023.

[Xyrem_FDA_label-6] Cite error: The named reference Xyrem FDA label was invoked but never defined (see the help page).

[Lumryz_FDA_label-7] Cite error: The named reference Lumryz FDA label was invoked but never defined (see the help page).

[Xywav_FDA_label-8] Cite error: The named reference Xywav FDA label was invoked but never defined (see the help page).

[9] "What is GHB?" (PDF). U.S. Drug Enforcement Administration. Archived (PDF) from the original on 17 October 2020. Retrieved 6 March 2022.

[DEA-10] Cite error: The named reference DEA was invoked but never defined (see the help page).

[11] Riviello RJ (2010). Manual of forensic emergency medicine : a guide for clinicians. Sudbury, MA: Jones and Bartlett Publishers. p. 42. ISBN 978-0763744625.

[auto-12] Cite error: The named reference auto was invoked but never defined (see the help page).

[13] "Sodium Oxybate: MedlinePlus Drug Information". Nlm.nih.gov. 28 July 2010. Archived from the original on 11 April 2010. Retrieved 1 August 2010.

[emedicineonGHB-14] Benzer TI, Cameron S (8 January 2007). VanDeVoort JT, Benitez JG (eds.). "Toxicity, Gamma-Hydroxybutyrate". eMedicine. Archived from the original on 28 November 2021. Retrieved 16 January 2007.

[dea-daterape-15] Cite error: The named reference dea-daterape was invoked but never defined (see the help page).

[Choc_to_Morph-16] Weil A, Winifred R (1993). "Depressants". From Chocolate to Morphine (2nd ed.). Boston/New York: Houghton Mifflin Company. p. 77. ISBN 978-0-395-66079-9.

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