502-85-2

Basic information

• Product Name: SODIUM 4-HYDROXYBUTYRATE
• Synonyms: SODIUM 4-HYDROXYBUTANOATE;SODIUM 4-HYDROXYBUTYRATE;SODIUM OXYBATE;SODIUM OXYBATE SODIUM SALT;SODIUM GAMMA-HYDROXY-N-BUTYRATE;4-hydroxy-butanoicacimonosodiumsalt;4-hydroxy-butyricacisodiumsalt;γ-Hydroxybutyric acid sodium salt
• CAS NO: 502-85-2
• Molecular Formula: C₄H₇O₃*Na
• Molecular Weight: 126.09
• EINECS: 207-953-3
• Product Categories: Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts;Aliphatics;Carboxylic Acids;Agonist;Intermediates & Fine Chemicals;Isotope Labelled Compounds;Pharmaceuticals;TARGOCID
• Mol File: 502-85-2.mol
• Article Data: 17

Chemical Properties

• Melting Point: 145-146°C
• Boiling Point: 295.6°Cat760mmHg
• Flash Point: 9℃
• Appearance: /solid
• Density: g/cm³
• Vapor Pressure: 0.000156mmHg at 25°C
• Storage Temp.: Controlled Substance, -20?C Freezer
• Merck: 13,4840
• CAS DataBase Reference: SODIUM 4-HYDROXYBUTYRATE(CAS DataBase Reference)
• NIST Chemistry Reference: SODIUM 4-HYDROXYBUTYRATE(502-85-2)
• EPA Substance Registry System: SODIUM 4-HYDROXYBUTYRATE(502-85-2)

Safety Data

• Hazard Codes: F,T
• Statements: 11-23/24/25-39/23/24/25
• Safety Statements: 22-24/25-45-36/37-16-7
• RIDADR: UN1230 - class 3 - PG 2 - Methanol, solution
• WGK Germany: 2
• RTECS: ET4750000
• F: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 502-85-2(Hazardous Substances Data)

Usage

Description

SODIUM 4-HYDROXYBUTYRATE, also known as Xyrem or sodium oxybate, is a white crystalline powder that acts as an agonist to both GHB and GABAB neural receptors, exhibiting neurotransmitter-like effects. It is a metabolite of γ-butyrolactone and is endogenously produced in the central nervous system (CNS) in small concentrations. Due to its potential for abuse, it is regulated as a Schedule I compound in the United States.

Uses

Used in Pharmaceutical Industry:
SODIUM 4-HYDROXYBUTYRATE is used as a prescription drug for the treatment of cataplexy in patients with narcolepsy. It is marketed under the brand name Xyrem by Jazz Pharmaceuticals, Inc. (Palo Alto, CA). The drug helps reduce cataplexy attacks and is distributed in accordance with strict FDA regulations.
Used in Anesthetic Applications:
SODIUM 4-HYDROXYBUTYRATE is used as a general anesthetic in the treatment of sleep disorders and clinical depression. However, it has also been identified as a "date rape drug" due to its potential for abuse.
Used in Antimicrobial Applications:
SODIUM 4-HYDROXYBUTYRATE is used as an antibacterial agent in certain applications.
Used in Research and Forensic Applications:
SODIUM 4-HYDROXYBUTYRATE (sodium salt) (exempt preparation) (Item No. 15661) is an analytical reference standard categorized as a CNS depressant. It is provided as a DEA exempt preparation and is intended for research and forensic applications.

Environmental Fate

Xyrem is a water-soluble white to off-white powder, which can be disposed by dumping the oral solution down the sanitary sewer system. This is the preferred method of disposal for drugs which have a high potential for abuse and/or accidental overdose.

Toxicity evaluation

GHB is endogenously present in the brain and at low concentrations binds to GHB receptors that are excitatory. This effect can cause euphoria, making it a drug of abuse at ‘rave’ parties. However, at higher concentrations, Xyrem is a CNS depressant and this is the main mechanism of its toxicity. The negative effects are mediated by the gamma-aminobutyric acid (GABA)B receptors. The maximum stimulation of these receptors by GHB is w69% when compared to the binding of a GABAB receptor agonist. Therefore, the drug appears to be a weak agonist of the GABA-binding site of GABAB receptors. Overdose can lead to respiratory arrest and death. The combined use of other sedative hypnotic agents or alcohol can exacerbate the toxicity of Xyrem.

InChI:InChI=1/C4H8O3.Na/c5-3-1-2-4(6)7;/h5H,1-3H2,(H,6,7);/q;+1/p-1

Upstream product

• 96-48-0 4-butanolide 
• 28341-54-0 4-(4-nitrophenoxy)butanoic acid 

Downstream Products

• 66767-73-5 (6R)-3-(4-hydroxy-butyryloxymethyl)-8-oxo-7t-(2-thiophen-2-yl-acetylamino)-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-3-ene-2c-carboxylic acid benzhydryl ester 
• 26976-72-7 4-acetoxybutyric acid 
• 118715-16-5 4-((tert-butyldiphenylsilyl)oxy)butanoic acid 
• 10385-30-5 4-(benzyloxy)butanoic acid 
• 64300-98-7 benzhydryl 7-(thien-2-ylacetamido)-3-(4-hydroxybutanoyloxymethyl)-2-cephem-4-carboxylate 
• 1353853-23-2 3-(3-hydroxypropyl)-2-methyl-5-(1-methylethyl)cyclohexa-2,5-diene-1,4-dione 
• 1360544-84-8 N-(benzyloxycarbonyl)-N'-(4-hydroxybutanoyl)-1,4-piperazine 
• 452978-63-1 allyl 4-[(4-methoxybenzyl)oxy]-4-oxobutyl succinate 
• 1192596-44-3 4-(5-phenyl-pentyloxy)-butyric acid 
• 125697-62-3 4-Nitrophenyl 4-(4,4'-dimethoxytrityloxy)-butyrate 
• 591-81-1 4-hydroxybutanoic acid 
• 93903-27-6 benzyl 4-(benzyloxy)butanoate 
• 96-48-0 4-butanolide 
• 91970-62-6 benzyl 4-hydroxybutanoate 

Relevant articles and documents

Metallic Nanoparticle-Enabled Sensing of a Drug-of-Abuse: An Attempt at Forensic Application

γ-Hydroxybutyric acid (GHB) functions as a depressant on the central nerve system and serves as a pharmaceutical agent in the treatment of narcolepsy and alcohol withdraw. In recent years, GHB has been misused as a recreational drug due to its ability to induce euphoric feelings. Moreover, it has gained increasing attention as a popular drug of abuse that is frequently related to drug-facilitated sexual assaults. At the moment, detection methods based on chromatography exhibit extraordinary sensitivity for GHB sensing. However, such techniques require complicated sample treatment prior to analysis. Optical sensors provide an alternative approach for rapid and simple analysis of GHB samples. Unfortunately, currently reported probes are mostly based on hydrogen bonding to recognize GHB, and this raises concerns about, for example, the lack of specificity. In this work, we report a bioinspired strategy for selective sensing of GHB. The method is based on specific enzyme recognition to allow highly selective detection of GHB with minimum interference, even in a complex sample matrix (e. g., simulated urine). In addition, the result can be obtained by either quantitative spectroscopy analysis or colorimetric change observed by the naked-eye, thus demonstrating its potential application in drug screening and forensic analysis.

Derivatives of Napabucasin and pharmaceutical application thereof

The invention relates to derivatives of Napabucasin, and a pharmaceutical application thereof. The structure of the derivatives conforms to the general formula (I), and the water solubility of most of the compounds is obviously higher than that of Napabucasin. The compounds and pharmaceutically acceptable salts thereof can be used for preparing antitumor drugs, and the cell inhibition activity of most of the compounds is obviously superior to that of Napabucasin. Meanwhile, experiments show that the compounds have extremely high helicobacter pylori and fungal activity resistance and can be used for preparing drugs for resisting helicobacter pylori and fungal infection.

Synthesis of Thymoquinone-Artemisinin Hybrids: New Potent Antileukemia, Antiviral, and Antimalarial Agents

A series of hybrid compounds based on the natural products artemisinin and thymoquinone was synthesized and investigated for their biological activity against the malaria parasite Plasmodium falciparum 3D7 strain, human cytomegalovirus (HCMV), and two leukemia cell lines (drug-sensitive CCRF-CEM and multidrug-resistant subline CEM/ADR5000). An unprecedented one-pot method of selective formation of C-10α-acetate 14 starting from a 1:1 mixture of C-10α- to C-10β-dihydroartemisinin was developed. The key step of this facile method is a mild decarboxylative activation of malonic acid mediated by DCC/DMAP. Ether-linked thymoquinone-artemisinin hybrids 6a/b stood out as the most active compounds in all categories, while showing no toxic side effects toward healthy human foreskin fibroblasts and thus being selective. They exhibited EC50 values of 0.2 μM against the doxorubicin-sensitive as well as the multidrug-resistant leukemia cells and therefore can be regarded as superior to doxorubicin. Moreover, they showed to be five times more active than the standard drug ganciclovir and nearly eight times more active than artesunic acid against HCMV. In addition, hybrids 6a/b possessed excellent antimalarial activity (EC50 = 5.9/3.7 nM), which was better than that of artesunic acid (EC50 = 8.2 nM) and chloroquine (EC50 = 9.8 nM). Overall, most of the presented thymoquinone-artemisinin-based hybrids exhibit an excellent and broad variety of biological activities (anticancer, antimalarial, and antiviral) combined with a low toxicity/high selectivity profile.