{"Abbreviation":["GHB"],"Absorption, Distribution and Excretion":"Animal studies indicate that metabolism is the major elimination pathway for sodium oxybate, producing carbon dioxide and water via the tricarboxylic acid (Krebs) cycle and secondarily by beta-oxidation. Succinic acid enters the Krebs cycle where it is metabolized to carbon dioxide and water. Fecal and renal excretion is negligible. 5% renal elimination.","Aliases":["4-Hydroxybutyric Acid","4-Hydroxybutanoic acid","4-Hydroxybutyric acid","γ-Hydroxybutyric acid","591-81-1","4-hydroxy-butyric acid","Anetamin","4-hydroxy-butanoic acid","oxy-n-butyric acid","Butyric acid, 4-hydroxy-","3-carboxypropoxy acid","4-Hydroxyalkanoic acid","γ-Hydroxybutanoic acid","Dtxsid2074740","30IW36W5B2","Chebi:30830","Dtxcid9042548","Butanoic acid, 4-hydroxy-","γ-Hydroxybutyrate","Oxybate","γ Hydroxybutyric Acid","GHB","4-Hydroxycarboxylic acid","Somsanit","γ Hydroxybutyrate","γ-hydroxybutyrate","γ OH","Gam-OH","CHEMBL1342","Sodium γ-oxybutyrate","4-OHB","Sodium γ-hydroxybutyrate","4 HB","4-Hydroxybuttersaeure","EB 27","γ-OH","WY 3478","Butyric acid, 4-hydroxy-, monosodium salt","Butyric acid, 4-hydroxy-, sodium salt","4-Hydroxyacid","γ-Hydroxybutyrate sodium","γ-Hydroxy sodium butyrate","Hydroxybutyric acid monosodium salt","γ-hydroxy butyrate","γ-Hydroxybutyric acid, sodium salt","Ncgc00247714-01","SHB","γ-Hydroxybutyric acid monosodium salt","Brn 1720582","Alcover","Unii-30iw36w5b2","52352-27-9","HSDB 6927","Hydroxybutyric acid-",".γ.-Hydroxy butyrate","4-Hydroxybutanoic acid #","Schembl10786","Schembl66852","4-03-00-00774","Schembl147664","Schembl336775","GTPL4711","Schembl2836855","Schembl4198312","Schembl5668142","DEA No. 2010","Aa3e2af0-ab7a-4a1e-a391-199c049d7162","Schembl10606860","Bdbm50023575","Lmfa01050006","Pdsp1_000342","Pdsp2_000340","DB01440","Sbi-0206686.p002","NS00002886","C00989","C01991","Q207920","Brd-k82166906-236-02-8"],"Biological Half-Life":"30 to 60 minutes","Boiling Point":"180 °C","CAS":"591-81-1","Chemical Classes":"Other Carboxylic Acid Derivatives","ChemicalClasses":["carboxylic acid"],"Chirality":"achiral","Color/Form":"Viscid yellow mass","Drug Classes":["Breast Feeding","Lactation","Milk, Human","Anesthetics","Hypnotics and Sedatives","GABA Modulators"],"Drug Indication":"Gamma-hydroxybutyric acid  is a central nervous system depressant indicated for the treatment of cataplexy or excessive daytime sleepiness (EDS) in patients aged 7 years and older with narcolepsy, as well as idiopathic hypersomnia (IH) in adults","Drug Warnings":"Central nervous system depressant with abuse potential. Should not be used with alcohol or other CNS depressants.  Sodium oxybate is GHB, a known drug of abuse. Abuse has been associated with some important central nervous system (CNS) adverse events (including death). Even at recommended doses, use has been associated with confusion, depression and other neuropsychiatric events. Reports of respiratory depression occurred in clinical trials. Almost all of the patients who received sodium oxybate during clinical trials were receiving CNS stimulants.  Important CNS adverse events associated with abuse of GHB include seizure, respiratory depression and profound decreases in level of consciousness, with instances of coma and death. For events that occurred outside of clinical trials, in people taking GHB for recreational purposes, the circumstances surrounding the events are often unclear (e.g., dose of GHB taken, the nature and amount of alcohol or any concomitant drugs). /Sodium oxybate/","Esters":[],"European Community (EC) Number":"691-053-4","FDA Pharmacological Classification":"30IW36W5B2","Formating":["gamma-hydroxybutyric acid"],"HMDB ID":"HMDB0000710","Health Effects":"Chronically high levels of 4-hydroxybutyric acid are associated with the inborn errors of metabolism called: 4-Hydroxybutyric Aciduria/Succinic Semialdehyde Dehydrogenase Deficiency.","HeavyAtomCount":7,"Human Drugs":"Breast Feeding; Lactation; Milk, Human; Anesthetics; Hypnotics and Sedatives; GABA Modulators","IUPACName":"4-hydroxybutanoic acid","InChI":"InChI=1S/C4H8O3/c5-3-1-2-4(6)7/h5H,1-3H2,(H,6,7)","InChIKey":"SJZRECIVHVDYJC-UHFFFAOYSA-N","Interactions":"Potential pharmacologic interaction (additive sedative effects). Sodium oxybate is contraindicated in patients receiving sedative-hypnotic agents. Sodium oxybate should not be used concomitantly with alcohol or other CNS depressants. /Sodium oxybate/","Mechanism of Action":"GHB is present at much higher concentrations in the brain, where it activates GABA-B receptors to exert its sedative effects. With high affinity, GHB binds to excitatory GHB receptors that are densely expressed throughout the brain, including the cotex and hippocampus. There is some evidence in research that upon activation of GHB receptors in some brain areas, the excitatory neurotransmitter glutamate is released. GHB stimulates dopamin release at low concentrations by acting on the GHB receptor, and the release of dopamine occurs in a biphasic manner. At higher concentrations, GHB inhibits dopamine release by acting on the GABA-B receptors, which is followed by GHB receptor signaling and increased release of dopamine. This explains the paradoxical mix of sedative and stimulatory properties of GHB, as well as the so-called \"rebound\" effect, experienced by individuals using GHB as a sleeping agent, wherein they awake suddenly after several hours of GHB-induced deep sleep. It is proposed that overtime, the level of GHB in the brain decreases below the threshold for significant GABA-B receptor activation, leading to preferential activation of GHB receptor over GABA-B receptors and enhanced wakefulness.","Melting Point":"48-50 °C","Metabolism/Metabolites":"gamma-Hydroxybutyrate (chemical formula HOOC-CH2-CH2- CH2OH) is a four-carbon molecule that is found naturally in the central nervous system and, in higher concentrations, in peripheral tissues. It has a structure much like gamma-aminobutyric acid (GABA), which is better understood than GHB and acts as an inhibitory neurotransmitter in vivo. gamma-Aminobutyric acid is catabolized by transamination to succinate semialdehyde, which is then oxidized to succinate. Brain tissue is capable of reducing succinate semialdehyde to GHB. Concentrations of both GHB and GHB-oxidizing enzymes are 15 to 20 times higher in kidney, heart, skeletal muscle, and brown fat than in the central nervous system.","MolecularFormula":"C\u003csub\u003e4\u003c/sub\u003eH\u003csub\u003e8\u003c/sub\u003eO\u003csub\u003e3\u003c/sub\u003e","MolecularWeight":"104.10 g/mol","Non-Human Toxicity Values":"LD50 Rat (male) ip 2000 mg/kg /sodium salt/","Pharmacodynamics":"GHB predominantly works at two distinct binding sites in the central nervous system: it works as an agonist at the newly-characterized excitatory GHB receptor, while acting as a weak agonist at the inhibitory GABAB receptor. Since it is a naturally occurring substance, its physiological action is similar to that of some endogenous neurotransmitters in mammalian brain. GHB is probably synthesized from GABA in GABAergic neurons, and released when the neurons fire.","Physical Description":"Solid","PubChemId":10413,"RefChem":"912580","RefCount":2,"RefCur":"","References":[{"Name":"Wikipedia","Urls":[{"Link":"https://en.wikipedia.org/wiki/Gamma-Hydroxybutyric acid","Name":"γ-Hydroxybutyric acid","Sub":false}]},{"Name":"Wikidata","Urls":[{"Link":"https://www.wikidata.org/wiki/Q207920","Name":"γ-Hydroxybutyric acid","Sub":false}]},{"Name":"DrugBank","Urls":[{"Link":"https://go.drugbank.com/DB01440","Name":"γ-Hydroxybutyric acid","Sub":false}]},{"Name":"PubChem","Urls":[{"Link":"https://pubchem.ncbi.nlm.nih.gov/compound/10413","Name":"γ-Hydroxybutyric acid","Sub":false}]},{"Name":"Common Chemistry","Urls":[{"Link":"https://commonchemistry.cas.org/detail?cas_rn=591-81-1","Name":"γ-Hydroxybutyric acid","Sub":false}]},{"Name":"HMDB","Urls":[{"Link":"https://hmdb.ca/metabolites/HMDB0000710","Name":"γ-Hydroxybutyric acid","Sub":false}]},{"Name":"KEGG","Urls":[{"Link":"https://www.kegg.jp/entry/C00989","Name":"γ-Hydroxybutyric acid","Sub":false}]},{"Name":"UNII","Urls":[{"Link":"https://gsrs.ncats.nih.gov/ginas/app/ui/substances/30IW36W5B2","Name":"γ-Hydroxybutyric acid","Sub":false}]},{"Name":"EPA DSSTox","Urls":[{"Link":"https://comptox.epa.gov/dashboard/chemical/details/DTXSID2074740","Name":"γ-Hydroxybutyric acid","Sub":false}]}],"Refs":["National Center for Biotechnology Information. PubChem Compound Summary for CID 10413, 4-Hydroxybutyric Acid. Accessed February 11, 2026. \u003ca href=https://pubchem.ncbi.nlm.nih.gov/compound/10413\u003ehttps://pubchem.ncbi.nlm.nih.gov/compound/10413\u003c/a\u003e"],"SMILES":"C(CC(=O)O)CO","SaltData":[],"Salts":[],"Solubility":"Very soluble in water, alcohol and ether.","StereoisomerData":[],"Stereoisomers":[],"Structure":"\u003csvg xmlns=\"http://www.w3.org/2000/svg\" preserveAspectRatio=\"none\" style=\"display:block\" viewBox=\"0 0 53.845 67.122\"\u003e\u003crect width=\"100%\" height=\"100%\" fill=\"#fff\"/\u003e\u003cdesc\u003eGenerated by the Chemistry Development Kit (http://github.com/cdk)\u003c/desc\u003e\u003cg fill=\"#ff0d0d\" stroke=\"#000\" stroke-linecap=\"round\" stroke-linejoin=\"round\" stroke-width=\".7\"\u003e\u003cpath fill=\"#fff\" stroke=\"none\" d=\"M0 0h54v68H0z\"/\u003e\u003cg class=\"mol\"\u003e\u003cpath d=\"M33.522 41.181v-15.24M33.522 25.941l-13.198-7.62\" class=\"bond\"/\u003e\u003cg class=\"bond\"\u003e\u003cpath d=\"M19.104 19.025V7.002M21.543 19.025V7.002\"/\u003e\u003cpath stroke=\"#ff0d0d\" d=\"M19.104 7.002v6.011M21.543 7.002v6.011\" class=\"hi\"/\u003e\u003c/g\u003e\u003cpath d=\"m20.324 18.321-9.92 5.727M33.522 41.181l13.198 7.62M46.72 48.801V60.12\" class=\"bond\"/\u003e\u003cpath stroke=\"none\" d=\"M22.583 3.078q0 .756-.256 1.328-.256.565-.756.881-.5.315-1.244.315-.756 0-1.262-.315-.506-.316-.757-.887-.244-.572-.244-1.334 0-.75.244-1.309.251-.566.757-.881T20.339.56q.732 0 1.232.316.5.309.756.875.256.565.256 1.327m-3.864 0q0 .923.387 1.459.393.53 1.221.53.839 0 1.22-.53.387-.536.387-1.459 0-.929-.387-1.452-.381-.524-1.208-.524-.834 0-1.227.524-.393.523-.393 1.452\" class=\"atom\"/\u003e\u003cg stroke=\"none\" class=\"atom\"\u003e\u003cpath d=\"M9.385 25.938q0 .756-.256 1.328-.256.565-.756.881-.5.315-1.245.315-.756 0-1.262-.315-.506-.316-.756-.887-.244-.572-.244-1.334 0-.75.244-1.309.25-.566.756-.881t1.274-.316q.733 0 1.233.316.5.309.756.875.256.565.256 1.327m-3.864 0q0 .923.387 1.459.393.53 1.22.53.84 0 1.221-.53.387-.536.387-1.459 0-.929-.387-1.452-.381-.524-1.209-.524-.833 0-1.226.524-.393.523-.393 1.452M4.305 28.391h-.62v-2.286H1.173v2.286H.56v-4.9h.613v2.072h2.512v-2.072h.62z\"/\u003e\u003c/g\u003e\u003cg stroke=\"none\" class=\"atom\"\u003e\u003cpath d=\"M48.979 64.038q0 .756-.256 1.328-.256.565-.756.881-.5.315-1.244.315-.756 0-1.262-.315-.506-.316-.756-.887-.244-.572-.244-1.334 0-.75.244-1.309.25-.566.756-.881t1.274-.316q.732 0 1.232.316.5.309.756.875.256.565.256 1.327m-3.863 0q0 .923.387 1.459.393.53 1.22.53.839 0 1.22-.53.387-.536.387-1.459 0-.929-.387-1.452-.381-.524-1.208-.524-.833 0-1.226.524-.393.523-.393 1.452M53.285 66.491h-.619v-2.286h-2.512v2.286h-.613v-4.9h.613v2.072h2.512v-2.072h.619z\"/\u003e\u003c/g\u003e\u003cpath stroke=\"#ff0d0d\" d=\"m10.404 24.048 4.96-2.864M10.404 24.048l4.96-2.864M46.72 60.12v-5.66\" class=\"hi\"/\u003e\u003c/g\u003e\u003c/g\u003e\u003c/svg\u003e","Therapeutic Uses":"Xyrem (sodium oxybate) oral solution is indicated for the treatment of excessive daytime sleepiness and cataplexy in patients with narcolepsy. /Sodium oxybate/","Title":"γ-Hydroxybutyric acid","UNII":"30IW36W5B2","Wikidata":"Q207920","Wikipedia":"Gamma-Hydroxybutyric acid","XLogP":-0.6}