Human Metabolome Database: Showing metabocard for 3,4-Methylenedioxyamphetamine (HMDB0041931)

You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.

Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

4.0

Status

Expected but not Quantified

Creation Date

2012-09-13 11:48:34 UTC

Update Date

2019-07-23 06:35:15 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 SDF PDB SMILES InChI

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

Role

Industrial application:

Drug

Pharmaceutical industry:

Pharmaceutical

Biological role:

Nutrient

Physical Properties

State

Not Available

Experimental 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

Predicted 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

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9700000000-694a0e98e0007bd9b883	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-03di-0900000000-ceb833ad1eb42d11bf4a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-03di-0900000000-7795b35d40550ca1ea10	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-03ei-0900000000-510f32fec3a45da3afe8	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-0a5i-0900000000-5ba589950b29c036e6af	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-0a4r-2900000000-7d9cec73d2dd144096d7	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-0a6r-4900000000-56ce80af24db379bcf90	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-0fb9-9500000000-7c78e7d8dc85b9c6aa0d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-0fba-9200000000-9b312e42e8f1bd38d687	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-0udi-9100000000-38f4dd19df31aa785f14	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-01q9-0900000000-fe189983d8867c5fb48c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03e9-0900000000-a862d6061554e1fa09b2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0159-4900000000-29f75fdee1c2f4da927b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0900000000-314837a1ce6decec2206	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-0900000000-a60d0f65c4417be99e02	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-03di-2900000000-d922e1321d8e07817cec	Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/Pathwhiz	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

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)

Structure for HMDB0041931 (3,4-Methylenedioxyamphetamine)