CHEBI:182764 - anisatin

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ChEBI Name anisatin
ChEBI ID CHEBI:182764
Definition A sesquiterpene lactone with formula C15H20O8. It is a neurotoxic natural product found in plants of the family Illiciaceae.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter MetaboLights
Secondary ChEBI IDs CHEBI:2733
Supplier Information No supplier information found for this compound.
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Wikipedia License
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 C15H20O8
Net Charge 0
Average Mass 328.317
Monoisotopic Mass 328.11582
InChI InChI=1S/C15H20O8/c1-6-3-7(16)15(21)13(6)4-8(23-10(18)9(13)17)12(2,20)14(15)5-22-11(14)19/h6-9,16-17,20-21H,3-5H2,1-2H3/t6-,7-,8-,9+,12+,13+,14+,15-/m1/s1
InChIKey GEVWHIDSUOMVRI-QWNPAUMXSA-N
SMILES C[C@@H]1C[C@@H](O)[C@]2(O)[C@]3(COC3=O)[C@@](C)(O)[C@H]3C[C@@]12[C@@H](O)C(=O)O3
Metabolite of Species Details
Illicium religiosum (IPNI:554536-1) Found in seed (BTO:0001226). See: DOI
Illicium fargesii (NCBI:txid124774) Found in pericarp (BTO:0001017). See: PubMed
Illicium anisatum (NCBI:txid12479) Found in seed (BTO:0001226). See: PubMed
Illicium oligandrum (NCBI:txid145286) Found in pericarp (BTO:0001017). See: PubMed
Roles Classification
Biological Role(s): GABA antagonist
A compound that inhibits the action of gamma-aminobutyric acid.
neurotoxin
A poison that interferes with the functions of the nervous system.
plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
Application(s): GABA antagonist
A compound that inhibits the action of gamma-aminobutyric acid.
phytogenic insecticide
An insecticide compound naturally occurring in plants.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing anisatin (CHEBI:182764) has role GABA antagonist (CHEBI:65259)
anisatin (CHEBI:182764) has role neurotoxin (CHEBI:50910)
anisatin (CHEBI:182764) has role phytogenic insecticide (CHEBI:22917)
anisatin (CHEBI:182764) has role plant metabolite (CHEBI:76924)
anisatin (CHEBI:182764) is a bridged compound (CHEBI:35990)
anisatin (CHEBI:182764) is a organic heterotetracyclic compound (CHEBI:38163)
anisatin (CHEBI:182764) is a secondary alcohol (CHEBI:35681)
anisatin (CHEBI:182764) is a sesquiterpene lactone (CHEBI:37667)
anisatin (CHEBI:182764) is a spiro compound (CHEBI:33599)
anisatin (CHEBI:182764) is a tertiary alcohol (CHEBI:26878)
anisatin (CHEBI:182764) is a tetrol (CHEBI:33573)
IUPAC Name
(1R,3'S,4R,5R,6aR,7R,9R,9aS)-1,5,6a,7-tetrahydroxy-5,9-dimethylhexahydrospiro[4,9a-methanocyclopenta[d]oxocine-6,3'-oxetane]-2,2'(1H)-dione
Synonyms Sources
(−)-anisatin ChEBI
(1R,3'S,4R,5R,6aR,7R,9R,9aS)-hexahydro-1,5,6a,7-tetrahydroxy-5,9-dimethylspiro[4H-4,9a-methanocyclopent[d]oxocin-6(2H),3'-oxetane]-2,2'-dione ChEBI
Anisatin KEGG COMPOUND
Manual Xrefs Databases
Anisatin Wikipedia
C00003212 KNApSAcK
C09294 KEGG COMPOUND
FDB005800 FooDB
HMDB0302686 HMDB
View more database links
Registry Number Type Source
5230-87-5 CAS Registry Number KEGG COMPOUND
Citations Types Sources
10413298 PubMed citation Europe PMC
10434749 PubMed citation Europe PMC
10455311 PubMed citation Europe PMC
11430054 PubMed citation Europe PMC
18670129 PubMed citation Europe PMC
19159273 PubMed citation Europe PMC
22369157 PubMed citation Europe PMC
22484123 PubMed citation Europe PMC
23802692 PubMed citation Europe PMC
23932223 PubMed citation Europe PMC
25133938 PubMed citation Europe PMC
26361344 PubMed citation Europe PMC
33426076 PubMed citation Europe PMC
37467672 PubMed citation Europe PMC
6292798 PubMed citation Europe PMC
6307484 PubMed citation Europe PMC
6974321 PubMed citation Europe PMC
7284788 PubMed citation Europe PMC
Last Modified
01 September 2023