4815. γ-Hydroxybutyrate

Nomenclature

CAS number: 591-81-1
4-Hydroxybutanoic acid; γ-hydroxybutyric acid; 4-hydroxybutyrate; gamma-hydroxybutyrate; GHB.
C4H8O3; mol wt 104.10.
C 46.15%, H 7.75%, O 46.11%.

Description and references

Endogenous constituent of mammalian brain; thought to function as a neurotransmitter or neuromodulator. Biosynthesized from γ-aminobutyric acid, q.v.; freely crosses the blood-brain barrier. Prepn of salts: A. Saytzeff, Ann. 171, 258 (1874); C. S. Marvel, E. R. Birkhimer, J. Am. Chem. Soc. 51, 260 (1929). Acute toxicity: B. Bruguerolle et al., Therapie 32, 375 (1977). GC-MS determn in biological fluids: S. D. Ferrara et al., J. Pharm. Biomed. Anal. 11, 483 (1993). Clinical pharmacokinetics: idem et al., Br. J. Clin. Pharmacol. 34, 231 (1992). Clinical studies in narcolepsy: L. Scrima et al., Sleep 13, 479 (1990); in opiate withdrawal: L. Gallimberti et al., Neuropsychopharmacology 9, 77 (1993). Review of efficacy in alcoholism: G. Biggio et al., Adv. Biochem. Psychopharmacol. 47, 281-288 (1992). Review of potential role as neurotransmittor: G. Tunnicliff, Gen. Pharmacol. 23, 1027-1034 (1992); of neuropharmacology and abuse potential: R. Bernasconi et al., Trends Pharmacol. Sci. 20, 135-141 (1999); of clinical experience in narcolepsy: M. J. Thorpy, Expert Opin. Pharmacother. 6, 329-335 (2005).

Chemical structure

Derivative

Sodium salt.

Nomenclature

CAS number: 502-85-2
γ-OH; sodium oxybate; sodium γ-oxybutyrate; Wy-3478; NSC-84223; Somsanit (Khler); Gamma-OH (Clintec Nutrition); Xyrem (Orphan Med.).
C4H7NaO3; mol wt 126.09.
C 38.10%, H 5.60%, Na 18.23%, O 38.07%.

Properties

Crystals from alcohol. Highly sol in aq solns. LD50 in male, female rats (mg/kg): 2,000, 1,650 i.p. (Bruguerolle).

Note

This is a controlled substance (depressant): 21 CFR, 1308.11.

Therapeutic Category

Anesthetic (intravenous). In treatment of narcolepsy; in treatment of alcoholism.

Keywords

Sodium Oxybate: Anesthetic (Intravenous)