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 ChemicalBook:CB6851738
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Ozone () (or trioxygen) is an inorganic molecule with the chemical formula O3. It is a pale blue gas with a distinctively pungent smell. It is an allotrope of oxygen that is much less stable than the diatomic allotrope O2, breaking down in the lower atmosphere to O2 (dioxygen). Ozone is formed from dioxygen by the action of ultraviolet (UV) light and electrical discharges within the Earth's atmosphere. It is present in very low concentrations throughout the atmosphere, with its highest concentration high in the ozone layer of the stratosphere, which absorbs most of the Sun's ultraviolet (UV) radiation. Ozone's odor is reminiscent of chlorine, and detectable by many people at concentrations of as little as 0.1 ppm in air. Ozone's O3 structure was determined in 1865. The molecule was later proven to have a bent structure and to be weakly diamagnetic. At standard temperature and pressure, ozone is a pale blue gas that condenses at cryogenic temperatures to a dark blue liquid and finally a violet-black solid. Ozone's instability with regard to more common dioxygen is such that both concentrated gas and liquid ozone may decompose explosively at elevated temperatures, physical shock, or fast warming to the boiling point. It is therefore used commercially only in low concentrations. Ozone is a powerful oxidizing agent (far more so than dioxygen) and has many industrial and consumer applications related to oxidation. This same high oxidizing potential, however, causes ozone to damage mucous and respiratory tissues in animals, and also tissues in plants, above concentrations of about 0.1 ppm. While this makes ozone a potent respiratory hazard and pollutant near ground level, a higher concentration in the ozone layer (from two to eight ppm) is beneficial, preventing damaging UV light from reaching the Earth's surface.
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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 )
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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 Types Sources
15062945 PubMed citation Europe PMC
18570171 PubMed citation Europe PMC
Last Modified
20 June 2016
General Comment
2005-08-19 The active ingredient in the recreational drug ecstasy.