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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-13 11:48:34 UTC
Update Date2022-03-07 02:57:14 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
Data?1563863715
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 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
Description 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
Not AvailableNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP1.64Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+140.29231661259
DarkChem[M-H]-137.0331661259
DeepCCS[M+H]+138.71830932474
DeepCCS[M-H]-135.90830932474
DeepCCS[M-2H]-172.38530932474
DeepCCS[M+Na]+147.92430932474
AllCCS[M+H]+139.532859911
AllCCS[M+H-H2O]+135.132859911
AllCCS[M+NH4]+143.632859911
AllCCS[M+Na]+144.832859911
AllCCS[M-H]-141.432859911
AllCCS[M+Na-2H]-142.032859911
AllCCS[M+HCOO]-142.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3,4-MethylenedioxyamphetamineCC(N)CC1=CC2=C(OCO2)C=C12208.2Standard polar33892256
3,4-MethylenedioxyamphetamineCC(N)CC1=CC2=C(OCO2)C=C11505.8Standard non polar33892256
3,4-MethylenedioxyamphetamineCC(N)CC1=CC2=C(OCO2)C=C11480.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
3,4-Methylenedioxyamphetamine,1TMS,isomer #1CC(CC1=CC=C2OCOC2=C1)N[Si](C)(C)C1644.3Semi standard non polar33892256
3,4-Methylenedioxyamphetamine,1TMS,isomer #1CC(CC1=CC=C2OCOC2=C1)N[Si](C)(C)C1639.3Standard non polar33892256
3,4-Methylenedioxyamphetamine,2TMS,isomer #1CC(CC1=CC=C2OCOC2=C1)N([Si](C)(C)C)[Si](C)(C)C1853.0Semi standard non polar33892256
3,4-Methylenedioxyamphetamine,2TMS,isomer #1CC(CC1=CC=C2OCOC2=C1)N([Si](C)(C)C)[Si](C)(C)C1860.6Standard non polar33892256
3,4-Methylenedioxyamphetamine,1TBDMS,isomer #1CC(CC1=CC=C2OCOC2=C1)N[Si](C)(C)C(C)(C)C1887.9Semi standard non polar33892256
3,4-Methylenedioxyamphetamine,1TBDMS,isomer #1CC(CC1=CC=C2OCOC2=C1)N[Si](C)(C)C(C)(C)C1859.3Standard non polar33892256
3,4-Methylenedioxyamphetamine,2TBDMS,isomer #1CC(CC1=CC=C2OCOC2=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2289.7Semi standard non polar33892256
3,4-Methylenedioxyamphetamine,2TBDMS,isomer #1CC(CC1=CC=C2OCOC2=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2331.2Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 3,4-Methylenedioxyamphetamine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9700000000-694a0e98e0007bd9b8832017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3,4-Methylenedioxyamphetamine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - 3,4-Methylenedioxyamphetamine LC-ESI-QFT , positive-QTOFsplash10-03di-0900000000-ceb833ad1eb42d11bf4a2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3,4-Methylenedioxyamphetamine LC-ESI-QFT , positive-QTOFsplash10-03di-0900000000-7795b35d40550ca1ea102017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3,4-Methylenedioxyamphetamine LC-ESI-QFT , positive-QTOFsplash10-03ei-0900000000-510f32fec3a45da3afe82017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3,4-Methylenedioxyamphetamine LC-ESI-QFT , positive-QTOFsplash10-0a5i-0900000000-5ba589950b29c036e6af2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3,4-Methylenedioxyamphetamine LC-ESI-QFT , positive-QTOFsplash10-0a4r-2900000000-7d9cec73d2dd144096d72017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3,4-Methylenedioxyamphetamine LC-ESI-QFT , positive-QTOFsplash10-0a6r-4900000000-56ce80af24db379bcf902017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3,4-Methylenedioxyamphetamine LC-ESI-QFT , positive-QTOFsplash10-0fb9-9500000000-7c78e7d8dc85b9c6aa0d2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3,4-Methylenedioxyamphetamine LC-ESI-QFT , positive-QTOFsplash10-0fba-9200000000-9b312e42e8f1bd38d6872017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3,4-Methylenedioxyamphetamine LC-ESI-QFT , positive-QTOFsplash10-0udi-9100000000-38f4dd19df31aa785f142017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3,4-Methylenedioxyamphetamine 150V, Positive-QTOFsplash10-0fba-9200000000-e71b359c869f7c1b90b32021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3,4-Methylenedioxyamphetamine 120V, Positive-QTOFsplash10-0fb9-9500000000-b52b9c038a0be1fb60fb2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3,4-Methylenedioxyamphetamine 30V, Positive-QTOFsplash10-03di-0900000000-5b4b266fdfaf116d2c112021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3,4-Methylenedioxyamphetamine 15V, Positive-QTOFsplash10-03di-0900000000-90c6f023c050512edfef2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3,4-Methylenedioxyamphetamine 60V, Positive-QTOFsplash10-0a5i-0900000000-c1ffbc132d48fa5323ea2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3,4-Methylenedioxyamphetamine 45V, Positive-QTOFsplash10-03ei-0900000000-0d18c49ffda39eba17192021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3,4-Methylenedioxyamphetamine 75V, Positive-QTOFsplash10-0a4r-2900000000-a27f93991861f1d8e5bf2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3,4-Methylenedioxyamphetamine 90V, Positive-QTOFsplash10-0a6r-4900000000-e8157165c79492e6d9822021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Methylenedioxyamphetamine 10V, Positive-QTOFsplash10-01q9-0900000000-fe189983d8867c5fb48c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Methylenedioxyamphetamine 20V, Positive-QTOFsplash10-03e9-0900000000-a862d6061554e1fa09b22016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Methylenedioxyamphetamine 40V, Positive-QTOFsplash10-0159-4900000000-29f75fdee1c2f4da927b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Methylenedioxyamphetamine 10V, Negative-QTOFsplash10-004i-0900000000-314837a1ce6decec22062016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Methylenedioxyamphetamine 20V, Negative-QTOFsplash10-004i-0900000000-a60d0f65c4417be99e022016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Methylenedioxyamphetamine 40V, Negative-QTOFsplash10-03di-2900000000-d922e1321d8e07817cec2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Methylenedioxyamphetamine 10V, Negative-QTOFsplash10-004r-0900000000-999b93a28fc3d3d7837e2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Methylenedioxyamphetamine 20V, Negative-QTOFsplash10-01t9-0900000000-70f106f29fa8e6b618a32021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
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
FooDB 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
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
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 ]