CHEBI:1391 - 3,4-methylenedioxymethamphetamine

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ChEBI Name 3,4-methylenedioxymethamphetamine
ChEBI ID CHEBI:1391
Definition A member of the class of benzodioxoles that is 1,3-benzodioxole substituted by a 2-(methylamino)propyl group at position 5.
Stars This entity has been manually annotated by the ChEBI Team.
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 C11H15NO2
Net Charge 0
Average Mass 193.24234
Monoisotopic Mass 193.11028
InChI InChI=1S/C11H15NO2/c1-8(12-2)5-9-3-4-10-11(6-9)14-7-13-10/h3-4,6,8,12H,5,7H2,1-2H3
InChIKey SHXWCVYOXRDMCX-UHFFFAOYSA-N
SMILES CNC(C)Cc1ccc2OCOc2c1
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Biological Role(s): neurotoxin
A poison that interferes with the functions of the nervous system.
Application(s): central nervous system stimulant
Any drug that enhances the activity of the central nervous system.
(via amphetamines )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 3,4-methylenedioxymethamphetamine (CHEBI:1391) has role neurotoxin (CHEBI:50910)
3,4-methylenedioxymethamphetamine (CHEBI:1391) is a amphetamines (CHEBI:35338)
3,4-methylenedioxymethamphetamine (CHEBI:1391) is a benzodioxoles (CHEBI:38298)
IUPAC Name
1-(1,3-benzodioxol-5-yl)-N-methylpropan-2-amine
Synonyms Sources
(RS)-3,4-(methylenedioxy)methamphetamine ChemIDplus
1-(1,3-Benzodioxol-5-yl)-N-methyl-2-propanamine NIST Chemistry WebBook
3,4-Methylenedioxymethamphetamine KEGG COMPOUND
DL-(3,4-Methylenedioxy)methamphetamine ChemIDplus
ecstasy
Note: (2016-06-20) The name "ecstasy" is no longer used only for MDMA, but for the whole group of ring-substituted amphetamines (RSAs) including MDA, MDMA, MDEA and MBDB, as they are chemically and pharmacologically nearly identical; moreover, many ecstasy pills contain mixtures of the RSAs.
ChEBI
MDMA KEGG COMPOUND
MDMA ChemIDplus
N,α-dimethyl-1,3-benzodioxole-5-ethanamine NIST Chemistry WebBook
N-Methyl-3,4-methylenedioxyamphetamine KEGG COMPOUND
Manual Xrefs Databases
C07577 KEGG COMPOUND
DB01454 DrugBank
HMDB0041931 HMDB
MDMA Wikipedia
View more database links
Registry Numbers Types Sources
158675 Reaxys Registry Number Reaxys
42542-10-9 CAS Registry Number KEGG COMPOUND
42542-10-9 CAS Registry Number ChemIDplus
Citations
Beuerle JR, Barrueto F (2008)
Neurogenic bladder and chronic urinary retention associated with MDMA abuse.
Journal of medical toxicology : official journal of the American College of Medical Toxicology 4, 106-108 [PubMed:18570171]
[show Abstract]
De Letter EA, Bouche MP, Van Bocxlaer JF, Lambert WE, Piette MH (2004)
Interpretation of a 3,4-methylenedioxymethamphetamine (MDMA) blood level: discussion by means of a distribution study in two fatalities.
Forensic science international 141, 85-90 [PubMed:15062945]
[show Abstract]
Last Modified
20 June 2016
General Comment
2005-08-19 The active ingredient in the recreational drug ecstasy.