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591-81-1 molecular structure
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4-hydroxybutanoic acid

ChemBase ID: 1247
Molecular Formular: C4H8O3
Molecular Mass: 104.10452
Monoisotopic Mass: 104.04734412
SMILES and InChIs

SMILES:
OCCCC(=O)O
Canonical SMILES:
OCCCC(=O)O
InChI:
InChI=1S/C4H8O3/c5-3-1-2-4(6)7/h5H,1-3H2,(H,6,7)
InChIKey:
SJZRECIVHVDYJC-UHFFFAOYSA-N

Cite this record

CBID:1247 http://www.chembase.cn/molecule-1247.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
4-hydroxybutanoic acid
IUPAC Traditional name
gamma-hydroxybutyric acid
hydroxybutyric acid
Brand Name
Xyrem
Synonyms
gamma-Hydroxybutyric acid
4-hydroxybutanoic acid
GHB
4-hydroxybutanoate
4-Hydroxybutyric acid
4-Hydroxy-butanoic acid
Juice
Liquid Ecstasy
Sodium oxybate
Gamma Hydroxybutyric Acid
γ-Hydroxybutyric acid
γ-Hydroxybutyrate
GHB
Gamma-Hydroxybutyric acid
CAS Number
591-81-1
PubChem SID
46507548
160964707
PubChem CID
3037032
10413
CHEBI ID
30830
ATC CODE
N01AX11
N07XX04
CHEMBL
1342
Chemspider ID
9984
DrugBank ID
DB01440
KEGG ID
C00989
Unique Ingredient Identifier
30IW36W5B2
Wikipedia Title
Gamma-Hydroxybutyric_acid

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID Price

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 4.440874  H Acceptors
H Donor LogD (pH = 5.5) -1.608916 
LogD (pH = 7.4) -3.371081  Log P -0.5149198 
Molar Refractivity 23.8003 cm3 Polarizability 9.344846 Å3
Polar Surface Area 57.53 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P -0.6  LOG S 0.77 
Solubility (Water) 7.11e+02 g/l 

PROPERTIES

PROPERTIES

Pharmacology Properties Bioassay(PubChem)
Admin Routes
Usually oral; intravenous expand Show data source
Bioavailability
25% (oral) expand Show data source
Excretion
5%, renal expand Show data source
Half Life
30–60 minutes expand Show data source
Metabolism
95%, mainly Hepatic, also in blood and tissues expand Show data source
Legal Status
Class B (NZ), Schedule I and III (US) expand Show data source
Class C (UK) expand Show data source
S9 (Australia) expand Show data source
Schedule III (Canada) expand Show data source
Pregnancy Category
B expand Show data source

DETAILS

DETAILS

DrugBank DrugBank Wikipedia Wikipedia
DrugBank - DB01440 external link
Item Information
Drug Groups illicit; approved
Description Gamma Hydroxybutyric Acid, commonly abbreviated GHB, is a therapeutic drug which is illegal in multiple countries. It is currently regulated 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 Schedule III drug;
however GHB remains a Schedule I drug and the illicit use of Xyrem falls under penalties of Schedule 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.
Indication Used as a general anesthetic, to treat conditions such as insomnia, clinical depression, narcolepsy, and alcoholism, and to improve athletic performance.
Pharmacology GHB has at least two distinct binding sites in the central nervous system. GHB is an agonist at the newly-characterized GHB receptor, which is excitatory, and it is a weak agonist at the GABAB receptor, which is inhibitory. GHB is a naturally-occurring substance that acts in a similar fashion to some neurotransmitters in the mammalian brain. GHB is probably synthesized from GABA in GABAergic neurons, and released when the neurons fire.
Toxicity At higher doses, GHB may induce nausea, dizziness, drowsiness, agitation, visual disturbances, depressed breathing, amnesia, unconsciousness, and death.
Affected Organisms
Humans and other mammals
Half Life 30 to 60 minutes
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.
Distribution * 190 to 384 mL/kg
Clearance * apparent oral cl=9.1 mL/min/kg [healthy adults receiving a single oral dose of 25 mg/kg]
* 4.5 mL/min/kg [cirrhotic patients without ascites receiving a single oral dose of 25 mg/kg]
* 4.1 mL/min/kg [cirrhotic patients with ascites receiving a single oral dose of 25 mg/kg]
External Links
Wikipedia

REFERENCES

REFERENCES

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PATENTS

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