CHEBI:85014 - 2,5-hexanedione

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ChEBI Name 2,5-hexanedione
ChEBI ID CHEBI:85014
Definition A diketone that is hexane substituted by oxo groups at positions 2 and 5. It is a toxic metabolite of hexane and of 2-hexanone
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Stan Laulederkind
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 C6H10O2
Net Charge 0
Average Mass 114.14240
Monoisotopic Mass 114.06808
InChI InChI=1S/C6H10O2/c1-5(7)3-4-6(2)8/h3-4H2,1-2H3
InChIKey OJVAMHKKJGICOG-UHFFFAOYSA-N
SMILES CC(=O)CCC(C)=O
Roles Classification
Biological Role(s): human xenobiotic metabolite
Any human metabolite produced by metabolism of a xenobiotic compound in humans.
neurotoxin
A poison that interferes with the functions of the nervous system.
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ChEBI Ontology
Outgoing 2,5-hexanedione (CHEBI:85014) has parent hydride hexane (CHEBI:29021)
2,5-hexanedione (CHEBI:85014) has role human xenobiotic metabolite (CHEBI:76967)
2,5-hexanedione (CHEBI:85014) has role neurotoxin (CHEBI:50910)
2,5-hexanedione (CHEBI:85014) is a diketone (CHEBI:46640)
2,5-hexanedione (CHEBI:85014) is a methyl ketone (CHEBI:51867)
IUPAC Name
hexane-2,5-dione
Synonyms Sources
1,2-Diacetylethane ChemIDplus
2,5-Diketohexane ChemIDplus
2,5-Hexadione ChemIDplus
2,5-hexanedione UniProt
Acetonyl acetone ChemIDplus
acetonylacetone SUBMITTER
α,β-diacetylethane NIST Chemistry WebBook
alpha,beta-Diacetylethane ChemIDplus
CH3COCH2CH2COCH3 NIST Chemistry WebBook
hexane-2,5-dione SUBMITTER
NSC 7621 NIST Chemistry WebBook
Manual Xrefs Databases
CPD-15521 MetaCyc
Hexane-2,5-dione Wikipedia
View more database links
Registry Numbers Types Sources
110-13-4 CAS Registry Number ChemIDplus
110-13-4 CAS Registry Number NIST Chemistry WebBook
506525 Reaxys Registry Number Reaxys
Citations Types Sources
1781736 PubMed citation Europe PMC
24634916 PubMed citation Europe PMC
25549948 PubMed citation SUBMITTER
Last Modified
03 August 2021