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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-13 11:48:34 UTC
Update Date2017-12-07 04:29:38 UTC
HMDB IDHMDB0041931
Secondary Accession Numbers
  • HMDB41931
Metabolite Identification
Common Name3,4-Methylenedioxyamphetamine
DescriptionAn amphetamine derivative that inhibits uptake of catecholamine neurotransmitters. It is a hallucinogen. It is less toxic than its methylated derivative but in sufficient doses may still destroy serotonergic neurons and has been used for that purpose experimentally. [PubChem]; In 1970, the Controlled Substances Act was enacted in the United States, placing MDA into Schedule I. It is similarly controlled in other nations. In Canada MDA is a Schedule III drug. Internationally, MDA is a Schedule I drug under the Convention on Psychotropic Substances. Many similar unscheduled MDxx chemicals can be prosecuted under the Federal Analog Act. MDA (3,4-methylenedioxyamphetamine), also known as tenamfetamine (INN), is a psychedelic and entactogenic drug of the phenethylamine and amphetamine chemical classes. It is mainly used as a recreational drug, an entheogen, and a tool in use to supplement various types of practices for transcendence, including in meditation, psychonautics, and as an agent in psychedelic psychotherapy. It was first synthesized by G. Mannish and W. Jacobson in 1910. There are about 20 different synthetic routes described in the literature for its preparation.
Structure
Thumb
Synonyms
ValueSource
(RS)-3,4-(Methylenedioxy)methamphetamineHMDB
1-(1,3-Benzodioxol-5-yl)-N-methyl-2-propanamineHMDB
1-(1,3-Benzodioxol-5-yl)-N-methylpropan-2-amineHMDB
3,4-MethylenedioxymethamphetamineHMDB
DL-(3,4-Methylenedioxy)methamphetamineHMDB
MDMAHMDB
N,alpha-Dimethyl-1,3-benzodioxole-5-ethanamineHMDB
N-Methyl-3,4-methylenedioxyamphetamineHMDB
3,4 MethylenedioxyamphetamineMeSH
Chemical FormulaC10H13NO2
Average Molecular Weight179.2157
Monoisotopic Molecular Weight179.094628665
IUPAC Name1-(2H-1,3-benzodioxol-5-yl)propan-2-amine
Traditional Name3,4-methylenedioxyamphetamine
CAS Registry Number4764-17-4
SMILES
CC(N)CC1=CC2=C(OCO2)C=C1
InChI Identifier
InChI=1S/C10H13NO2/c1-7(11)4-8-2-3-9-10(5-8)13-6-12-9/h2-3,5,7H,4,6,11H2,1H3
InChI KeyNGBBVGZWCFBOGO-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as benzodioxoles. These are organic compounds containing a benzene ring fused to either isomers of dioxole. Dioxole is a five-membered unsaturated ring of two oxygen atoms and three carbon atoms.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzodioxoles
Sub ClassNot Available
Direct ParentBenzodioxoles
Alternative Parents
Substituents
  • Benzodioxole
  • Aralkylamine
  • Benzenoid
  • Oxacycle
  • Acetal
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Role

Industrial application:

Biological role:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP1.64Not Available
Predicted Properties
PropertyValueSource
Water Solubility2.83 g/LALOGPS
logP1.15ALOGPS
logP1.43ChemAxon
logS-1.8ALOGPS
pKa (Strongest Basic)10.01ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area44.48 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity49.47 m³·mol⁻¹ChemAxon
Polarizability19.51 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9700000000-694a0e98e0007bd9b883View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-03di-0900000000-ceb833ad1eb42d11bf4aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-03di-0900000000-7795b35d40550ca1ea10View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-03ei-0900000000-510f32fec3a45da3afe8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0a5i-0900000000-5ba589950b29c036e6afView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0a4r-2900000000-7d9cec73d2dd144096d7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0a6r-4900000000-56ce80af24db379bcf90View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0fb9-9500000000-7c78e7d8dc85b9c6aa0dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0fba-9200000000-9b312e42e8f1bd38d687View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0udi-9100000000-38f4dd19df31aa785f14View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01q9-0900000000-fe189983d8867c5fb48cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03e9-0900000000-a862d6061554e1fa09b2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0159-4900000000-29f75fdee1c2f4da927bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0900000000-314837a1ce6decec2206View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0900000000-a60d0f65c4417be99e02View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03di-2900000000-d922e1321d8e07817cecView in MoNA
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01509
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID1555
KEGG Compound IDC07577
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link3,4-Methylenedioxyamphetamine
METLIN IDNot Available
PubChem Compound1614
PDB IDNot Available
ChEBI ID1391
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Aalberg L, Clark CR, Deruiter J: Chromatographic and mass spectral studies on isobaric and isomeric substances related to 3,4-methylenedioxymethamphetamine. J Chromatogr Sci. 2004 Oct;42(9):464-9. [PubMed:15693185 ]