sodium 4-hydroxybutanoate

• ChemBase ID: 53620
• Molecular Formular: C4H7NaO3
• Molecular Mass: 126.08635
• Monoisotopic Mass: 126.02928837
• SMILES: C(=O)([O-])CCCO.[Na+]
• Canonical SMILES: OCCCC(=O)[O-].[Na+]
• InChI: InChI=1S/C4H8O3.Na/c5-3-1-2-4(6)7;/h5H,1-3H2,(H,6,7);/q;+1/p-1
• InChIKey: XYGBKMMCQDZQOZ-UHFFFAOYSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium 4-hydroxybutanoate
• IUPAC Traditional name: sodium gamma hydroxybutyric acid
• Synonyms: Sodium 4-hydroxybutanoate; 4-Hydroxybutanoic Acid Sodium Salt; Anetamin Sodium Salt; Xyrem; Oxybate Sodium; NSC 84223; 4-Hydroxybutyric Acid Sodium Salt; γ-Hydroxybutyric acid sodium salt; 4-Hydroxybutyric acid sodium salt; GHB; Sodium 4-hydroxybutyrate; γ-Hydroxybutyric acid sodium salt

Database IDs

• CAS Number: 502-85-2
• EC Number: 207-953-3
• MDL Number: MFCD00004402
• Beilstein Number: 3709170
• PubChem SID: 162058383; 24895583
• PubChem CID: 23663870

CALCULATED PROPERTIES

• Acid pKa: 4.440874
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): -1.608916
• LogD (pH = 7.4): -3.371081
• Log P: -0.5149198
• Molar Refractivity: 34.6374 cm^3
• Polarizability: 9.2274685 Å^3
• Polar Surface Area: 60.36 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Water
• Apperance: White Solid
• Melting Point: 149-151°C

Safety Information

• Storage Condition: Controlled Substance, -20°C Freezer
• Storage Warning: IRRITANT
• RTECS: ET4750000
• German water hazard class: 2
• TSCA Listed: false
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Drug Control: USDEA Schedule I; Home Office Schedule 4.1; stupéfiant; kontrollierte Droge in Deutschland; regulated under CDSA - not available from Sigma-Aldrich Canada

DETAILS

Sigma Aldrich - H3635

Biochem/physiol Actions
Endogenous GABA analog that induces absence-like seizures. It blocks dopamine release by blocking impulse flow in dopaminergic neurons.

Toronto Research Chemicals - H833015

An agonist to both GHB and GABAB neural receptors, exhibiting neurotransmitter-like effects. It has been used as a general anesthetic in treatment for sleep disorders and clinical depression, but also has been identified as a “date rape drug”.

REFERENCES

• Mamelak, M., et al.: Prog. Neurobiol., 89, 193 (2009)
• Zhang, L., et al.: App. Microbiol. Biotechnol., 84, 909 (2009)
• Pedraza, C., Int. J. Neuropsychopharmacol., 12, 1165 (2009)
• McGonigle, I., et al.: Biochem., 49, 2897 (2009)