4- Hydroxybutyrate, sodium

OFFICIAL NAMES Gamma-hydroxybutyrate (GHB), 4-hydroxy butyrate, gamma hydrate, gamma-hydroxybutyrate sodium, gamma hydroxybutyric acid, gamma-OH, sodium oxy-bate, sodium oxybutyrate... 

SYNS GAMMA OH 7-HYDROXYBUTYR.ATE SODIUM SALT SODIUM-y-HYDROXYBUTYRATE SODIUM-4-HYDROXYBLTVRATE SODIUM OXYBATE SOMSANIT WY-3478... 

HYDROXYBUTYRALDEHYDE see. AAH750 P-HYDROXYBUTYRALDEHYDE see YAH750 Y-HYDROXYBUTYRATE sodium salt see HJS500 Y-HYDROXYBUTYRIC acid CYCUC ester see BOVOOO... 

Gamma-hydroxybutyrate, sodium salt CASRN 502-85-2 C4H7Na03 MW 126.09 Prescription drug formulations sodium oxybate (generic name) Gamma OH (France) Somsanit (Germany) Alcover (Italy) and Xyrem (United States) ... 

Preparation of L-(-)-y-Benzyloxycarbonylamino-a-Hydroxybutyric Acid L-(-)-7-amino-o-hydroxybutyric acid (7.4 g, 0,062 mol) was added to a solution of 5.2 grams (0.13 mol) of sodium hydroxide in 50 ml of water. To the stirred soiution was added dropwise at 0 -5°C over a period of 0.5 hour, 11.7 grams (0.06B mol) of carbobenzoxy chloride and the mixture was stirred for another hour at the same temperature. The reaction mixture was washed with 50 ml of ether, adjusted to pH 2 with dilute hydrochloric acid and extracted with four BO ml portions of ether. The ethereai extracts were combined, washed with a small amount of saturated sodium chloride solution, dried with anhydrous sodium sulfate and filtered. The filtrate was evaporated in vacuo and the resulting residue was crystallized from benzene to give 11.6 grams (74%) of colorless plates MP 78.5° to 79.5°C. 

Dantrolene sodium L-(-) - y-Amino-a-hydroxybutyric acid Amikacin... 

The synthesis of the pyridine acid 3 is outlined in Scheme 9.3. The 2-chloro-5-trifluoromethylpyridine was coupled with hydroxybutyric acid in the presence of an excess of sodium hydride to afford acid 3 in around 35% yield after necessary purification. 

After completion of the reaction (1 hour), the solution was neutralized with dilute hydrochloric acid and the solvent removed in vacuo. The residue was diluted with ethyl acetate and the organic solution was washed with saturated aqueous sodium chloride. The organic layer was dried over magnesium sulfate, concentrated under reduced pressure and distilled to afford tert-butyl 3-hydroxybutyrate (80 %). 

In 23-cpoxybutyric acid sodium borohydride opened the epoxide ring without affecting the carboxyl. Varying ratios of 2- and 3-hydroxybutyric acid were obtained depending on the reaction conditions. Sodium borohydride in alkaline solution gave 18% of a- and 82% of -hydroxybutyric acid while in the presence of lithium bromide the two isomers were obtained in 60 40 percentage ratio [1000]. 

OFFICIAL NAMES Gamma butyrolactone (GBL), dihydro-2(3H)-furanone, 4-butanolide, 2(3H)-furanone dihydro, tetrahy-dro-2-furanone, butyrolactone gamma, gamma hydroxybutyric acid (GHB), 1,4 butanediol (BD tetramethylene glycol Sucol B), sodium oxybate (Xyrem)... 

Isobutylene Glycol and a-Hydroxybutyric Acid.37 To 16.3 g. of a-hydroxyisobutyraldehyde is added dropwise 40 cc. of 10% aqueous sodium hydroxide. The resulting solution is warmed on the water bath to complete the reaction, cooled, and extracted with ether. Bemoval of the ether leaves the glycol as a honey-colored oil which is purified by distillation (b.p. 177-179°). 

M /l-1 lydroxybutyrate—Dissolve 1.3 g of (i-hydroxybutyric acid in 25 ml of distilled water by gradual addition of 12.5 ml of 1 N NaOH (final pH should be in the range from 6 to 8) dilute to a final volume of 50 ml with distilled water. Alternatively use the sodium salt of /3-hydroxybutyrate (1.575 g) and adjust the pH with HC1. Refrigerate. Stable for 1 week. 

Narcolepsy is a rare disease characterized by excessive daytime sleepiness. It has a prevalence of 0.05% in the general population and affects an estimated 140,000 people in the United States. In 2002, the FDA approved sodium oxybate (Xyrem ) for the treatment of cataplexy in patients with narcolepsy. The active ingredient in this drug is gamma hydroxybutyrate, or GHB. The development and marketing of sodium oxybate was permitted after a revision of the Date Rape Prevention Act of 2000 (see Chapter 5) that allowed GHB to be legally administered for medical purposes. 

Drakontides, A. B., J. A. Schneider, and W. H. Funderburk. Some Effects of Sodium Gamma-hydroxybutyrate on the Central Nervous System. Journal of Pharmacology and Experimental Therapeutics 135 (1962) 275-284 Tunnicliff, G. Significance of Gamma-hydroxybutyric Acid in the Brain. General Pharmacology 23 (1992) 1027-1034. 

An Open Multicentric Study Evaluating 4-hydroxybutyric Acid Sodium Salt in the Medium-term Treatment of 179 Alcohol Dependent Subjects. GHB Study Group. Alcohol and Alcoholism 31... 

Addolorato, G., E. Castelli, G. F. Stefanini, G. Casella, F. Caputo, L. Marsigli, M. Bernardi, and G. Gasbarrini. An Open Multicentric Study Evaluating 4-hydroxybutyric Acid Sodium Salt in the Medium-term Treatment of 179 Alcohol Dependent Subjects. GHB Study GroupJ Alcohol and... 

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