4-Hydroxybutyric acid

4-Hydroxybutyric acid Structure
CAS No.
591-81-1
Chemical Name:
4-Hydroxybutyric acid
Synonyms
Butanoic acid, 4-hydroxy-;4-hydroxy-butanoic acid;4-HYDROXYBUTYRATE;4-Hydroxybutanoate;C00989;Anetamin;4-Hydroxybutyric;g-Hydroxybutyrate;4-Hydroxybutyric acid;GAMMA-HYDROXYBUTYRICACID
CBNumber:
CB7954553
Molecular Formula:
C4H8O3
Molecular Weight:
104.1
MOL File:
591-81-1.mol
Modify Date:
2023/5/4 15:12:55

4-Hydroxybutyric acid Properties

Melting point 212℃
Boiling point 235.97°C (rough estimate)
Density 1.1405 g/cm3
refractive index 1.4761 (estimate)
pka 4.72(at 25℃)
EPA Substance Registry System Butanoic acid, 4-hydroxy- (591-81-1)

SAFETY

Risk and Safety Statements

Symbol(GHS) 
GHS07,GHS05
Signal word  Danger
Hazard statements  H318-H302-H336
Precautionary statements  P280-P305+P351+P338-P310-P264-P270-P301+P312-P330-P501-P261-P271-P304+P340-P312-P403+P233-P405-P501
Toxicity LD50 oral in mouse: 4800mg/kg

4-Hydroxybutyric acid Chemical Properties,Uses,Production

Description

γ-Hydroxybutyric acid (GHB), also known as 4- hydroxybutanoic acid, is a naturally occurring substance found in the human central nervous system, as well as in wine, beef, small citrus fruits, and almost all animals in small amounts. It is also categorized as an illegal drug in many countries. It is currently regulated in Australia and New Zealand, Canada, most of Europe and in the US. GHB as the sodium salt, known as sodium oxybate (INN) or by the trade name Xyrem, is used to treat cataplexy and excessive daytime sleepiness in patients with narcolepsy.

Uses

Anesthetic (intravenous). In treatment of narcolepsy; in treatment of alcoholism. This is a Schedule III controlled substance.

Definition

ChEBI: 4-Hydroxybutyric acid is a 4-hydroxy monocarboxylic acid that is butyric acid in which one of the hydrogens at position 4 is replaced by a hydroxy group.

Clinical Use

The only common medical applications for GHB today are in the treatment of narcolepsy and more rarely alcoholism.
GHB is the active ingredient in the prescription medication sodium oxybate (Xyrem). Sodium oxybate is approved by the U.S. Food and Drug Administration (FDA) for the treatment of cataplexy associated with narcolepsy and Excessive Daytime Sleepiness (EDS) associated with narcolepsy.

Metabolic pathway

Also note that both of the metabolic breakdown pathways shown for GHB can run in either direction, depending on the concentrations of the substances involved, so the body can make its own GHB either from GABA or from succinic semialdehyde. Under normal physiological conditions, the concentration of GHB in the body is rather low, and the pathways would run in the reverse direction to what is shown here to produce endogenous GHB. However, when GHB is consumed for recreational or health promotion purposes, its concentration in the body is much higher than normal, which changes the enzyme kinetics so that these pathways operate to metabolise GHB rather than producing it.

4-Hydroxybutyric acid Preparation Products And Raw materials

4-Hydroxybutyric 4-Hydroxybutyric acid GAMMA-HYDROXYBUTYRICACID C00989 g-Hydroxybutyrate Anetamin SJZRECIVHVDYJC-UHFFFAOYSA-N Butanoic acid, 4-hydroxy- 4-HYDROXYBUTYRATE 4-hydroxy-butanoic acid 4-Hydroxybutanoate 591-81-1 20-79-2