Structural Formula Vector Image
Title: g-Hydroxybutyrate
CAS Registry Number: 591-81-1
CAS Name: 4-Hydroxybutanoic acid
Additional Names: g-hydroxybutyric acid; 4-hydroxybutyrate; gamma-hydroxybutyrate; GHB
Molecular Formula: C4H8O3
Molecular Weight: 104.10
Percent Composition: C 46.15%, H 7.75%, O 46.11%
Line Formula: HOCH2CH2CH2COOH
Literature References: Endogenous constituent of mammalian brain; thought to function as a neurotransmitter or neuromodulator. Biosynthesized from g-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).
Derivative Type: Sodium salt
CAS Registry Number: 502-85-2
Additional Names: g-OH; sodium oxybate; sodium g-oxybutyrate
Manufacturers' Codes: Wy-3478; NSC-84223
Trademarks: Somsanit (Kler); Gamma-OH (Clintec Nutrition); Xyrem (Orphan Med.)
Molecular Formula: C4H8NaO3
Molecular Weight: 127.09
Percent Composition: C 37.80%, H 6.34%, Na 18.09%, O 37.77%
Properties: Crystals from alcohol. Highly sol in aq solns. LD50 in male, female rats (mg/kg): 2,000, 1,650 i.p. (Bruguerolle).
Toxicity data: 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.
Therap-Cat: Anesthetic (intravenous). In treatment of narcolepsy; in treatment of alcoholism.

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