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Gamma Hydroxybutyric Acid

July 24, 2017
Common Name

Gamma Hydroxybutyric Acid Description

Gamma Hydroxybutyric Acid, commonly abbreviated GHB, is a therapeutic drug which is illegal in mlitiple countries. It is currently regliated in the US and sold by Jazz Pharmaceuticals under the name Xyrem. However, it is important to note that GHB is a designated Orphan drug (in 1985). Today Xyrem is a Schedlie III drug. However, GHB remains a Schedlie I drug and the illicit use of Xyrem falls under penalties of Schedlie I. GHB is a naturally occurring substance found in the central nervous system, wine, beef, small citrus fruits and almost all other living creatures in small amounts. It is used illegally under the street names Juice, Liquid Ecstasy or simply G, either as an intoxicant, or as a date rape drug. Xyrem is a central nervous system depressant that reduces excessive daytime sleepiness and cataplexy in patients with narcolepsy. Structure

MOLSDF3D-SDFPDBSMILESInChI View 3D Structure

Synonyms

Value Source 4-HydroxybutanoateChEBI gamma-HydroxybutyrateChEBI GHBChEBI 4-Hydroxybutanoic acidGenerator g HydroxybutyrateGenerator g Hydroxybutyric acidGenerator gamma HydroxybutyrateGenerator γ hydroxybutyrateGenerator γ hydroxybutyric acidGenerator g-HydroxybutyrateGenerator g-Hydroxybutyric acidGenerator gamma-Hydroxybutyric acidGenerator γ-hydroxybutyrateGenerator γ-hydroxybutyric acidGenerator 4-Hydroxy-butanoic acidHMDB 4-Hydroxybutyric acidHMDB JuiceHMDB Liquid ecstasyHMDB Sodium oxybateHMDB 4 Hydroxybutyrate sodiumMeSH Sodium gamma hydroxybutyrateMeSH Sodium gamma-hydroxybutyrateMeSH Oxybutyrate, sodiumMeSH Sodium oxybutyrateMeSH SomsanitMeSH 4-Hydroxybutyrate sodiumMeSH Oxybate sodiumMeSH Oxybate, sodiumMeSH XyremMeSH

Chemical Formlia

C4H7O3 Average Molecliar Weight

103.0966 Monoisotopic Molecliar Weight

103.03951909 IUPAC Name

4-hydroxybutanoate Traditional Name

gamma-hydroxybutyrate CAS Registry Number

591-81-1 SMILES

OCCCC([O-])=O

InChI Identifier

InChI=1S/C4H8O3/c5-3-1-2-4(6)7/h5H,1-3H2,(H,6,7)/p-1

InChI Key

SJZRECIVHVDYJC-UHFFFAOYSA-M Chemical Taxonomy Description

This compound belongs to the class of chemical entities known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group. Kingdom

Chemical entities Super Class

Organic compounds Class

Lipids and lipid-like moleclies Sub Class

Fatty Acyls Direct Parent

Hydroxy fatty acids Alternative Parents

  • Short-chain hydroxy acids and derivatives
  • Straight chain fatty acids
  • Carboxylic acid salts
  • Monocarboxylic acids and derivatives
  • Carboxylic acids
  • Primary alcohols
  • Organic salts
  • Organic oxides
  • Hydrocarbon derivatives
  • Carbonyl compounds
  • Organic anions

    • Substituents

  • Hydroxy fatty acid
  • Short-chain hydroxy acid
  • Straight chain fatty acid
  • Carboxylic acid salt
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Alcohol
  • Carbonyl group
  • Primary alcohol
  • Organooxygen compound
  • Organic salt
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Organic anion
  • Aliphatic acyclic compound

    • Molecliar Framework

    Aliphatic acyclic compounds External Descriptors

  • hydroxy monocarboxylic acid anion (CHEBI:16724 )
  • a small moleclie (4-HYDROXY-BUTYRATE )

    • Ontology Status

    Expected but not Quantified Origin

  • Drug

    • Biofunction

  • Adjuvants, Anesthesia
  • Anesthetics, Intravenous

    • Application

  • Pharmaceutical

    • Cellliar locations

  • Membrane

    • Physical Properties State

    Solid Experimental Properties

    Property Value Reference Melting PointNot AvailableNot Available Boiling PointNot AvailableNot Available Water Solubility7.11e+02 g/LNot Available LogPNot AvailableNot Available

    Predicted Properties

    Property Value Source Water Solubility711.0 mg/mLALOGPS logP-0.6ALOGPS logP-0.51ChemAxon logS0.77ALOGPS pKa (Strongest Acidic)4.44ChemAxon pKa (Strongest Basic)-2.4ChemAxon Physiological Charge-1ChemAxon Hydrogen Acceptor Count3ChemAxon Hydrogen Donor Count1ChemAxon Polar Surface Area60.36 Å2ChemAxon Rotatable Bond Count3ChemAxon Refractivity34.64 m3·mol-1ChemAxon Polarizability9.73 Å3ChemAxon Number of Rings0ChemAxon Bioavailability1ChemAxon Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

    Spectra Spectra

    Not Available Biological Properties Cellliar Locations

  • Membrane

    • Biofluid Locations

  • Blood
  • Urine

    • Tissue Location

    Not Available Pathways

    Not Available Normal Concentrations

    Biofluid Status Value Age Sex Condition Reference Details BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01440

  • 21059682

    • details UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01440

  • 21059682

    • details

    Abnormal Concentrations

    Not Available Associated Disorders and Diseases Disease References

    None Associated OMIM IDs

    None External Links DrugBank ID

    DB01440 DrugBank Metabolite ID

    Not Available Phenol Explorer Compound ID

    Not Available Phenol Explorer Metabolite ID

    Not Available FoodDB ID

    Not Available KNApSAcK ID

    Not Available Chemspider ID

    2300886 KEGG Compound ID

    C00989 BioCyc ID

    Not Available BiGG ID

    Not Available Wikipedia Link

    Gamma-Hydroxybutyric_acid NuGOwiki Link

    HMDB15507 Metagene Link

    HMDB15507 METLIN ID

    Not Available PubChem Compound

    3037032 PDB ID

    Not Available ChEBI ID

    16724

    Product: Tafluprost

    References Synthesis Reference Not Available Material Safety Data Sheet (MSDS) Not Available General References
    1. Hedner T, Hedner J, Iversen K, Wessberg P, Lundborg P: Gammahydroxybutyric acid: central biochemical and behavioral effects in neonatal rats. Pharmacol Biochem Behav. 1985 Aug;23(2):185-9. [PubMed:2997806 ]
    2. van Amsterdam JG, Brunt TM, McMaster MT, Niesink R, van Noorden MS, van den Brink W: [Cognitive impairment due to intensive use and overdoses of gammahydroxybutyric acid (GHB)]. Tijdschr Psychiatr. 2012;54(12):1001-10. [PubMed:23250641 ]
    3. Stock G, Heidt H, Buss J, Schlor KH: Sleep patterns in cat induced by gammahydroxybutyric acid. Electroencephalogr Clin Neurophysiol. 1978 Apr;44(4):523-7. [PubMed:76561 ]
    4. Anden NE, Stock G: Inhibitory effect of gammahydroxybutyric acid and gammaaminobutyric acid on the dopamine cells in the substantia nigra. Naunyn Schmiedebergs Arch Pharmacol. 1973;279(1):89-92. [PubMed:4356204 ]
    5. Gomes C, Flygt C, Henning M, Norin L, Svensson TH, Trolin G: Gammahydroxy butyric acid: cardiovascular effects in the rat. J Neural Transm. 1976;38(2):123-9. [PubMed:1271050 ]
    6. Pedraza C, Garcia FB, Navarro JF: Neurotoxic effects induced by gammahydroxybutyric acid (GHB) in male rats. Int J Neuropsychopharmacol. 2009 Oct;12(9):1165-77. doi: 10.1017/S1461145709000157. Epub 2009 Mar 17. [PubMed:19288974 ]
    7. Hedner T, Lundborg P: Effect of gammahydroxybutyric acid on catecholamine synthesis and utilization in the developing rat brain. J Neural Transm. 1982;54(1-2):19-28. [PubMed:6809892 ]
    8. Hedner T, Lundborg P: Effect of gammahydroxybutyric acid on serotonin synthesis, concentration and metabolism in the developing rat brain. J Neural Transm. 1983;57(1-2):39-48. [PubMed:6194255 ]
    9. Johansson B, Hardebo JE: Cerebrovascular permeability and cerebral blood flow in hypertension induced by gammahydroxybutyric acid. An experimental study in the rat. Acta Neurol Scand. 1982 May;65(5):448-57. [PubMed:7113657 ]
    10. Hedner T, Lundborg P: Neurochemical characteristics of cerebral catecholamine neurons during the postnatal development in the rat. Med Biol. 1981 Aug;59(4):212-23. [PubMed:6803074 ]
    11. Giorgi O, Rubio MC: Decreased 3H-L-quinuclidinyl benzilate binding and muscarine receptor subsensitivity after chronic gamma-butyrolactone treatment. Naunyn Schmiedebergs Arch Pharmacol. 1981 Dec;318(1):14-8. [PubMed:7329448 ]
    12. Anden NE, Wachtel H: Biochemical effects of baclofen (beta-parachlorophenyl-GABA) on the dopamine and the noradrenaline in the rat brain. Acta Pharmacol Toxicol (Copenh). 1977 Feb;40(2):310-20. [PubMed:576560 ]
    13. Stock G: Failure of anticholinergic drugs to antagonize the increase in dopamine seen after gammahydroxybutyric acid and axotomy. J Neural Transm. 1979;44(1-2):137-43. [PubMed:438801 ]
    14. Baumann KW, Kassell NF, Olin J, Yamada T: The effects of gammahydroxybutyric acid on canine cerebral blood flow and metabolism. J Neurosurg. 1982 Aug;57(2):197-202. [PubMed:7086512 ]
    15. Stock G, Magnusson T, Anden NE: Increase in brain dopamine after axotomy or treatment with gammahydroxybutyric acid due to elimination of the nerve impulse flow. Naunyn Schmiedebergs Arch Pharmacol. 1973;278(4):347-61. [PubMed:4269968 ]
    16. Vulliemoz S, Vanini G, Truffert A, Chizzolini C, Seeck M: Epilepsy and cerebellar ataxia associated with anti-glutamic acid decarboxylase antibodies. J Neurol Neurosurg Psychiatry. 2007 Feb;78(2):187-9. [PubMed:17229747 ]
    17. Gessa GL: [Guidelines for the drug therapy of alcoholism]. Recenti Prog Med. 1990 Mar;81(3):171-5. [PubMed:2359869 ]
    18. Anden NE, Magnusson T, Stock G: Effects of drugs influencing monoamine mechanisms on the increase in brain dopamine produced by axotomy or treatment with gammahydroxybutyric acid. Naunyn Schmiedebergs Arch Pharmacol. 1973;278(4):363-72. [PubMed:4269969 ]

    Enzymes

    General function:
    Involved in ion transport
    Specific function:
    GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel
    Gene Name:
    GABRB1
    Uniprot ID:
    P18505
    Molecular weight:
    54234.1
    References
    1. Maitre M, Humbert JP, Kemmel V, Aunis D, Andriamampandry C: [A mechanism for gamma-hydroxybutyrate (GHB) as a drug and a substance of abuse]. Med Sci (Paris). 2005 Mar;21(3):284-9. [PubMed:15745703 ]

    Transporters

    General function:
    Involved in transmembrane transport
    Specific function:
    Proton-linked monocarboxylate transporter. Catalyzes the rapid transport across the plasma membrane of many monocarboxylates such as lactate, pyruvate, branched-chain oxo acids derived from leucine, valine and isoleucine, and the ketone bodies acetoacetate, beta-hydroxybutyrate and acetate
    Gene Name:
    SLC16A3
    Uniprot ID:
    O15427
    Molecular weight:
    49468.9
    References
    1. Manning Fox JE, Meredith D, Halestrap AP: Characterisation of human monocarboxylate transporter 4 substantiates its role in lactic acid efflux from skeletal muscle. J Physiol. 2000 Dec 1;529 Pt 2:285-93. [PubMed:11101640 ]
    General function:
    Involved in transmembrane transport
    Specific function:
    Proton-linked monocarboxylate transporter. Catalyzes the rapid transport across the plasma membrane of many monocarboxylates such as lactate, pyruvate, branched-chain oxo acids derived from leucine, valine and isoleucine, and the ketone bodies acetoacetate, beta-hydroxybutyrate and acetate
    Gene Name:
    SLC16A1
    Uniprot ID:
    P53985
    Molecular weight:
    53957.7
    References
    1. Lin RY, Vera JC, Chaganti RS, Golde DW: Human monocarboxylate transporter 2 (MCT2) is a high affinity pyruvate transporter. J Biol Chem. 1998 Oct 30;273(44):28959-65. [PubMed:9786900 ]
    General function:
    Involved in transmembrane transport
    Specific function:
    Proton-linked monocarboxylate transporter. Catalyzes the rapid transport across the plasma membrane of many monocarboxylates such as lactate, pyruvate, branched-chain oxo acids derived from leucine, valine and isoleucine, and the ketone bodies acetoacetate, beta-hydroxybutyrate and acetate. MCT2 is a high affinity pyruvate transporter
    Gene Name:
    SLC16A7
    Uniprot ID:
    O60669
    Molecular weight:
    52185.7
    References
    1. Lin RY, Vera JC, Chaganti RS, Golde DW: Human monocarboxylate transporter 2 (MCT2) is a high affinity pyruvate transporter. J Biol Chem. 1998 Oct 30;273(44):28959-65. [PubMed:9786900 ]

    PMID: 23747010

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