4-Hydroxybutanoate
Grundinformationen
- CAS
1320-61-2- Standard-SMILES
O=C([O-])CCCO- InChIKey
SJZRECIVHVDYJC-UHFFFAOYSA-M- Summenformel
- C4H7O3-
- Durchschnittliche Molmasse
- 103,1 g/mol
- Monoisotopische Masse
- 103,03951908
Überblick
4-hydroxybutyrate is a 4-hydroxy monocarboxylic acid anion resulting from the removal of a proton from the carboxy group of 4-hydroxybutyric acid. It has a role as an intravenous anaesthetic and an anaesthesia adjuvant. It is a 4-hydroxy monocarboxylic acid anion, a short-chain fatty acid anion and a hydroxy fatty acid anion. It is functionally related to a butyrate. It is a conjugate base of a 4-hydroxybutyric acid.
Namen und Bezeichner
- Bevorzugter Name
- 4-Hydroxybutanoate
- IUPAC
- 4-hydroxybutanoate
Namen und Synonyme
4-Hydroxybutanoate4-hydroxybutyrateHydroxybutyrateg-hydroxybutyric acid1320-61-2CHEBI:16724DTXSID10157296Butyric acid, hydroxy-, ion(1-)Butanoic acid, hydroxy-, ion(1-)RefChem:524018Butyric acid, hydroxy, ion(1)DTXCID3079787
Weitere Namen anzeigen
Butanoic acid, hydroxy, ion(1)691-053-4Gamma Hydroxy butyrate4-HBSJZRECIVHVDYJC-UHFFFAOYSA-MAKOS024437936PD009490AB01563260_01
Datenbank-Bezeichner
- CAS
1320-61-2、591-81-1- PubChem CID
- 3037032
- DTXSID
DTXSID10157296- ChEBI
CHEBI:16724- EC Number
- 691-053-4
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 0
- Polarare Oberfläche (TPSA)
- 60,4 Ų
- H-Brücken-Donoren
- 1
- H-Brücken-Akzeptoren
- 3
- Frei drehbare Bindungen
- 2
- Schwere Atome
- 7
- Formalladung
- -1
- Komplexität
- 54,4
Experimentelle und physikochemische Eigenschaften
Chemical ClassesOther Classes -> Organic Acids
DrugsDEA Schedule I Controlled Substance -> Depressants
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
GHS-Klassifizierung
GHS Classification
This chemical does not meet GHS hazard criteria for 100% (2 of 2) of all reports.
Not Classified
Aggregated GHS information provided per 2 reports by companies from 1 notifications to the ECHA C&L Inventory.
Gefahrenhinweise
Regulatory InformationDEA schedule I controlled substance
Hazards SummarySee Butyric acid.
Hazard Classes and CategoriesNot Classified
Toxikologische Informationen
Health EffectsChronically high levels of 4-hydroxybutyric acid are associated with the inborn errors of metabolism called: 4-Hydroxybutyric Aciduria/Succinic Semialdehyde Dehydrogenase Deficiency.
Toxicity Summary
GHB reaches much higher concentrations in the brain and activates GABAB receptors, which are primarily responsible for its sedative effects. GHB receptors are densely expressed in many areas of the brain, including the cortex and hippocampus, and these are the receptors that GHB displays the highest affinity for. There has been somewhat limited research into the GHB receptor; however, there is evidence that activation of the GHB receptor in some brain areas results in the release of glutamate, the principal excitatory neurotransmitter. Activation of both the GHB receptor and GABA(B) is responsible for the addictive profile of GHB. GHB's effect on dopamine release is biphasic,[19] low concentrations stimulate dopamine release via the GHB receptor.[20] Higher concentrations inhibit dopamine release via GABA(B) receptors as do other GABA(B) agonists such as baclofen and phenibut.[21] After an initial phase of inhibition, dopamine release is then increased via the GHB receptor. 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. That is to say that, over time, the concentration of GHB in the system decreases below the threshold for significant GABAB receptor activation and activates predominantly the GHB receptor, leading to wakefulness.
Chemie und Industrie
Pharmakologische Informationen
Metabolism/Metabolites
Route of Elimination: 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. Half Life: 30 to 60 minutes
Verwendung und Herstellung
UsesUsed as a general anesthetic, to treat conditions such as insomnia, clinical depression, narcolepsy, and alcoholism, and to improve athletic performance.
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