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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-13 11:48:34 UTC

Update Date

2022-03-07 02:57:14 UTC

HMDB ID

HMDB0041931

Secondary Accession Numbers

HMDB41931

Metabolite Identification

Common Name

3,4-Methylenedioxyamphetamine

Description

An 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

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1509                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      12.033   0.762   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      12.033  -1.717   0.000  0.00  0.00           O+0
HETATM    3  N   UNK     0       3.907   1.063   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       6.574   1.063   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.241   0.293   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.908   0.293   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.242   1.063   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.576   0.293   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.908  -1.247   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.576  -1.247   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.241  -1.247   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.242  -2.017   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      12.932  -0.477   0.000  0.00  0.00           C+0
CONECT    1    8   13                                                       
CONECT    2   10   13                                                       
CONECT    3    5                                                            
CONECT    4    5    6                                                       
CONECT    5    3    4   11                                                  
CONECT    6    4    7    9                                                  
CONECT    7    6    8                                                       
CONECT    8    1    7   10                                                  
CONECT    9    6   12                                                       
CONECT   10    2    8   12                                                  
CONECT   11    5                                                            
CONECT   12    9   10                                                       
CONECT   13    1    2                                                       
MASTER        0    0    0    0    0    0    0    0   13    0   28    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(RS)-3,4-(Methylenedioxy)methamphetamine	HMDB
1-(1,3-Benzodioxol-5-yl)-N-methyl-2-propanamine	HMDB
1-(1,3-Benzodioxol-5-yl)-N-methylpropan-2-amine	HMDB
3,4-Methylenedioxymethamphetamine	HMDB
DL-(3,4-Methylenedioxy)methamphetamine	HMDB
MDMA	HMDB
N,alpha-Dimethyl-1,3-benzodioxole-5-ethanamine	HMDB
N-Methyl-3,4-methylenedioxyamphetamine	HMDB
3,4 Methylenedioxyamphetamine	HMDB
3,4-Methylenedioxyamphetamine	MeSH

Chemical Formula

C₁₀H₁₃NO₂

Average Molecular Weight

179.2157

Monoisotopic Molecular Weight

179.094628665

IUPAC Name

1-(2H-1,3-benzodioxol-5-yl)propan-2-amine

Traditional Name

3,4-methylenedioxyamphetamine

CAS Registry Number

4764-17-4

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 Key

NGBBVGZWCFBOGO-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.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzodioxoles

Sub Class

Not Available

Direct Parent

Benzodioxoles

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 Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	1.64	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	2.83 g/L	ALOGPS
logP	1.15	ALOGPS
logP	1.43	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Basic)	10.01	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	44.48 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	49.47 m³·mol⁻¹	ChemAxon
Polarizability	19.51 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	140.292	31661259
DarkChem	[M-H]-	137.03	31661259
DeepCCS	[M+H]+	138.718	30932474
DeepCCS	[M-H]-	135.908	30932474
DeepCCS	[M-2H]-	172.385	30932474
DeepCCS	[M+Na]+	147.924	30932474
AllCCS	[M+H]+	139.5	32859911
AllCCS	[M+H-H2O]+	135.1	32859911
AllCCS	[M+NH4]+	143.6	32859911
AllCCS	[M+Na]+	144.8	32859911
AllCCS	[M-H]-	141.4	32859911
AllCCS	[M+Na-2H]-	142.0	32859911
AllCCS	[M+HCOO]-	142.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3,4-Methylenedioxyamphetamine	CC(N)CC1=CC2=C(OCO2)C=C1	2208.2	Standard polar	33892256
3,4-Methylenedioxyamphetamine	CC(N)CC1=CC2=C(OCO2)C=C1	1505.8	Standard non polar	33892256
3,4-Methylenedioxyamphetamine	CC(N)CC1=CC2=C(OCO2)C=C1	1480.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3,4-Methylenedioxyamphetamine,1TMS,isomer #1	CC(CC1=CC=C2OCOC2=C1)N[Si](C)(C)C	1644.3	Semi standard non polar	33892256
3,4-Methylenedioxyamphetamine,1TMS,isomer #1	CC(CC1=CC=C2OCOC2=C1)N[Si](C)(C)C	1639.3	Standard non polar	33892256
3,4-Methylenedioxyamphetamine,2TMS,isomer #1	CC(CC1=CC=C2OCOC2=C1)N([Si](C)(C)C)[Si](C)(C)C	1853.0	Semi standard non polar	33892256
3,4-Methylenedioxyamphetamine,2TMS,isomer #1	CC(CC1=CC=C2OCOC2=C1)N([Si](C)(C)C)[Si](C)(C)C	1860.6	Standard non polar	33892256
3,4-Methylenedioxyamphetamine,1TBDMS,isomer #1	CC(CC1=CC=C2OCOC2=C1)N[Si](C)(C)C(C)(C)C	1887.9	Semi standard non polar	33892256
3,4-Methylenedioxyamphetamine,1TBDMS,isomer #1	CC(CC1=CC=C2OCOC2=C1)N[Si](C)(C)C(C)(C)C	1859.3	Standard non polar	33892256
3,4-Methylenedioxyamphetamine,2TBDMS,isomer #1	CC(CC1=CC=C2OCOC2=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2289.7	Semi standard non polar	33892256
3,4-Methylenedioxyamphetamine,2TBDMS,isomer #1	CC(CC1=CC=C2OCOC2=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2331.2	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 3,4-Methylenedioxyamphetamine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9700000000-694a0e98e0007bd9b883	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,4-Methylenedioxyamphetamine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,4-Methylenedioxyamphetamine LC-ESI-QFT , positive-QTOF	splash10-03di-0900000000-ceb833ad1eb42d11bf4a	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,4-Methylenedioxyamphetamine LC-ESI-QFT , positive-QTOF	splash10-03di-0900000000-7795b35d40550ca1ea10	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,4-Methylenedioxyamphetamine LC-ESI-QFT , positive-QTOF	splash10-03ei-0900000000-510f32fec3a45da3afe8	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,4-Methylenedioxyamphetamine LC-ESI-QFT , positive-QTOF	splash10-0a5i-0900000000-5ba589950b29c036e6af	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,4-Methylenedioxyamphetamine LC-ESI-QFT , positive-QTOF	splash10-0a4r-2900000000-7d9cec73d2dd144096d7	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,4-Methylenedioxyamphetamine LC-ESI-QFT , positive-QTOF	splash10-0a6r-4900000000-56ce80af24db379bcf90	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,4-Methylenedioxyamphetamine LC-ESI-QFT , positive-QTOF	splash10-0fb9-9500000000-7c78e7d8dc85b9c6aa0d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,4-Methylenedioxyamphetamine LC-ESI-QFT , positive-QTOF	splash10-0fba-9200000000-9b312e42e8f1bd38d687	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,4-Methylenedioxyamphetamine LC-ESI-QFT , positive-QTOF	splash10-0udi-9100000000-38f4dd19df31aa785f14	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,4-Methylenedioxyamphetamine 150V, Positive-QTOF	splash10-0fba-9200000000-e71b359c869f7c1b90b3	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,4-Methylenedioxyamphetamine 120V, Positive-QTOF	splash10-0fb9-9500000000-b52b9c038a0be1fb60fb	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,4-Methylenedioxyamphetamine 30V, Positive-QTOF	splash10-03di-0900000000-5b4b266fdfaf116d2c11	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,4-Methylenedioxyamphetamine 15V, Positive-QTOF	splash10-03di-0900000000-90c6f023c050512edfef	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,4-Methylenedioxyamphetamine 60V, Positive-QTOF	splash10-0a5i-0900000000-c1ffbc132d48fa5323ea	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,4-Methylenedioxyamphetamine 45V, Positive-QTOF	splash10-03ei-0900000000-0d18c49ffda39eba1719	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,4-Methylenedioxyamphetamine 75V, Positive-QTOF	splash10-0a4r-2900000000-a27f93991861f1d8e5bf	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,4-Methylenedioxyamphetamine 90V, Positive-QTOF	splash10-0a6r-4900000000-e8157165c79492e6d982	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Methylenedioxyamphetamine 10V, Positive-QTOF	splash10-01q9-0900000000-fe189983d8867c5fb48c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Methylenedioxyamphetamine 20V, Positive-QTOF	splash10-03e9-0900000000-a862d6061554e1fa09b2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Methylenedioxyamphetamine 40V, Positive-QTOF	splash10-0159-4900000000-29f75fdee1c2f4da927b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Methylenedioxyamphetamine 10V, Negative-QTOF	splash10-004i-0900000000-314837a1ce6decec2206	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Methylenedioxyamphetamine 20V, Negative-QTOF	splash10-004i-0900000000-a60d0f65c4417be99e02	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Methylenedioxyamphetamine 40V, Negative-QTOF	splash10-03di-2900000000-d922e1321d8e07817cec	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Methylenedioxyamphetamine 10V, Negative-QTOF	splash10-004r-0900000000-999b93a28fc3d3d7837e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Methylenedioxyamphetamine 20V, Negative-QTOF	splash10-01t9-0900000000-70f106f29fa8e6b618a3	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01509

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

1555

KEGG Compound ID

C07577

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

3,4-Methylenedioxyamphetamine

METLIN ID

Not Available

PubChem Compound

1614

PDB ID

Not Available

ChEBI ID

1391

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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 ]

Showing metabocard for 3,4-Methylenedioxyamphetamine (HMDB0041931)

MOL for HMDB0041931 (3,4-Methylenedioxyamphetamine)

3D MOL for HMDB0041931 (3,4-Methylenedioxyamphetamine)

3D SDF for HMDB0041931 (3,4-Methylenedioxyamphetamine)

3D-SDF for HMDB0041931 (3,4-Methylenedioxyamphetamine)

PDB for HMDB0041931 (3,4-Methylenedioxyamphetamine)

3D PDB for HMDB0041931 (3,4-Methylenedioxyamphetamine)

SMILES for HMDB0041931 (3,4-Methylenedioxyamphetamine)

INCHI for HMDB0041931 (3,4-Methylenedioxyamphetamine)

Structure for HMDB0041931 (3,4-Methylenedioxyamphetamine)

3D Structure for HMDB0041931 (3,4-Methylenedioxyamphetamine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra