CHEBI:30830 - 4-hydroxybutyric acid

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name 4-hydroxybutyric acid
ChEBI ID CHEBI:30830
Definition A 4-hydroxy monocarboxylic acid that is butyric acid in which one of the hydrogens at position 4 is replaced by a hydroxy group.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:386065, CHEBI:1860, CHEBI:20402
Supplier Information No supplier information found for this compound.
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3,4-Methylenedioxymethamphetamine (MDMA), commonly known as ecstasy (tablet form), and molly (crystal form), is an empathogen–entactogenic drug with stimulant and minor psychedelic properties. In studies, it has been used alongside psychotherapy in the treatment of post-traumatic stress disorder (PTSD) and social anxiety in autism spectrum disorder. The purported pharmacological effects that may be prosocial include altered sensations, increased energy, empathy, and pleasure. When taken by mouth, effects begin in 30 to 45 minutes and last three to six hours. MDMA was first synthesized in 1912 by Merck chemist Anton Köllisch. It was used to enhance psychotherapy beginning in the 1970s and became popular as a street drug in the 1980s. MDMA is commonly associated with dance parties, raves, and electronic dance music. Tablets sold as ecstasy may be mixed with other substances such as ephedrine, amphetamine, and methamphetamine. In 2016, about 21 million people between the ages of 15 and 64 used ecstasy (0.3% of the world population). This was broadly similar to the percentage of people who use cocaine or amphetamines, but lower than for cannabis or opioids. In the United States, as of 2017, about 7% of people have used MDMA at some point in their lives and 0.9% have used it in the last year. The lethal risk from one dose of MDMA is estimated to be from 1 death in 20,000 instances to 1 death in 50,000 instances. Short-term adverse effects include grinding of the teeth, blurred vision, sweating, and a rapid heartbeat, and extended use can also lead to addiction, memory problems, paranoia, and difficulty sleeping. Deaths have been reported due to increased body temperature and dehydration. Following use, people often feel depressed and tired, although this effect does not appear in clinical use, suggesting that it is not a direct result of MDMA administration. MDMA acts primarily by increasing the release of the neurotransmitters serotonin, dopamine, and norepinephrine in parts of the brain. It belongs to the substituted amphetamine classes of drugs. MDMA is structurally similar to mescaline (a psychedelic), methamphetamine (a stimulant), as well as endogenous monoamine neurotransmitters such as serotonin, norepinephrine, and dopamine. MDMA has limited approved medical uses in a small number of countries, but is illegal in most jurisdictions. In the United States, the Food and Drug Administration (FDA) is evaluating the drug for clinical use as of 2021. Canada has allowed limited distribution of MDMA upon application to and approval by Health Canada. In Australia, it may be prescribed in the treatment of PTSD by specifically authorised psychiatrists.
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Formula C4H8O3
Net Charge 0
Average Mass 104.10452
Monoisotopic Mass 104.04734
InChI InChI=1S/C4H8O3/c5-3-1-2-4(6)7/h5H,1-3H2,(H,6,7)
InChIKey SJZRECIVHVDYJC-UHFFFAOYSA-N
SMILES OCCCC(O)=O
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): GHB receptor agonist
A drug that binds to and activates gamma-hydroxybutyric acid receptors.
neurotoxin
A poison that interferes with the functions of the nervous system.
Application(s): general anaesthetic
Substance that produces loss of consciousness.
GHB receptor agonist
A drug that binds to and activates gamma-hydroxybutyric acid receptors.
sedative
A central nervous system depressant used to induce drowsiness or sleep or to reduce psychological excitement or anxiety.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 4-hydroxybutyric acid (CHEBI:30830) has functional parent butyric acid (CHEBI:30772)
4-hydroxybutyric acid (CHEBI:30830) has role general anaesthetic (CHEBI:38869)
4-hydroxybutyric acid (CHEBI:30830) has role GHB receptor agonist (CHEBI:53353)
4-hydroxybutyric acid (CHEBI:30830) has role neurotoxin (CHEBI:50910)
4-hydroxybutyric acid (CHEBI:30830) has role sedative (CHEBI:35717)
4-hydroxybutyric acid (CHEBI:30830) is a 4-hydroxy monocarboxylic acid (CHEBI:35970)
4-hydroxybutyric acid (CHEBI:30830) is a hydroxybutyric acid (CHEBI:24684)
4-hydroxybutyric acid (CHEBI:30830) is conjugate acid of 4-hydroxybutyrate (CHEBI:16724)
Incoming 4-hydroxybutyryl-CoA (CHEBI:28522) has functional parent 4-hydroxybutyric acid (CHEBI:30830)
mono(3-carboxypropyl) phthalate (CHEBI:132872) has functional parent 4-hydroxybutyric acid (CHEBI:30830)
4-hydroxybutyrate (CHEBI:16724) is conjugate base of 4-hydroxybutyric acid (CHEBI:30830)
IUPAC Name
4-hydroxybutanoic acid
Synonyms Sources
3-carboxypropoxy acid ChEBI
4-hydroxy-butyric acid LIPID MAPS
4-Hydroxyalkanoic acid KEGG COMPOUND
4-Hydroxybutanoate KEGG COMPOUND
4-Hydroxybutanoic acid KEGG COMPOUND
4-Hydroxybutyric acid KEGG COMPOUND
4-Hydroxycarboxylic acid KEGG COMPOUND
Gamma Hydroxybutyric Acid DrugBank
gamma-Hydroxybutyric acid DrugBank
γ-hydroxybutyric acid ChEBI
GHB DrugBank
oxy-n-butyric acid ChEBI
Xyrem DrugBank
Manual Xrefs Databases
C00989 KEGG COMPOUND
C01991 KEGG COMPOUND
DB01440 DrugBank
LMFA01050006 LIPID MAPS
Oxybate Wikipedia
View more database links
Registry Numbers Types Sources
1720582 Reaxys Registry Number Reaxys
591-81-1 CAS Registry Number KEGG COMPOUND
591-81-1 CAS Registry Number ChemIDplus
591-81-1 CAS Registry Number DrugBank
591-81-1 CAS Registry Number NIST Chemistry WebBook
Citations Types Sources
15927467 PubMed citation ChEMBL
3361576 PubMed citation ChEMBL
Last Modified
20 August 2024
General Comment
2010-12-30 4-hydroxybutyric acid finds application as a central nervous system depressant that reduces excessive daytime sleepiness and cataplexy in patients with narcolepsy.