NAV

Methylenedioxyethamphetamine

Identification

Generic Name
Methylenedioxyethamphetamine
DrugBank Accession Number
DB01566
Background

Not Available

Type
Small Molecule
Groups
Experimental, Illicit
Structure
3D
Similar Structures
Weight
Average: 207.2689
Monoisotopic: 207.125928793
Chemical Formula
C12H17NO2
Synonyms
  • (+/-)-MDE
  • 3,4-methylenedioxy-N-ethylamphetamine
  • MDE
  • n-ethyl MDA
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
Not Available
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
Not Available

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
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AcebutololThe therapeutic efficacy of Acebutolol can be decreased when used in combination with Methylenedioxyethamphetamine.
AcetazolamideAcetazolamide may decrease the excretion rate of Methylenedioxyethamphetamine which could result in a higher serum level.
AcetophenazineAcetophenazine may decrease the stimulatory activities of Methylenedioxyethamphetamine.
AcrivastineMethylenedioxyethamphetamine may decrease the sedative activities of Acrivastine.
AlfentanilMethylenedioxyethamphetamine may increase the analgesic activities of Alfentanil.
Food Interactions
Not Available

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This 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.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Benzodioxoles
Sub Class
Not Available
Direct Parent
Benzodioxoles
Alternative Parents
Aralkylamines / Benzenoids / Oxacyclic compounds / Dialkylamines / Acetals / Organopnictogen compounds / Hydrocarbon derivatives
Substituents
Acetal / Amine / Aralkylamine / Aromatic heteropolycyclic compound / Benzenoid / Benzodioxole / Hydrocarbon derivative / Organic nitrogen compound / Organic oxygen compound / Organonitrogen compound
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
ML1I4KK67B
CAS number
82801-81-8
InChI Key
PVXVWWANJIWJOO-UHFFFAOYSA-N
InChI
InChI=1S/C12H17NO2/c1-3-13-9(2)6-10-4-5-11-12(7-10)15-8-14-11/h4-5,7,9,13H,3,6,8H2,1-2H3
IUPAC Name
[1-(2H-1,3-benzodioxol-5-yl)propan-2-yl](ethyl)amine
SMILES
CCNC(C)CC1=CC2=C(OCO2)C=C1

References

General References
Not Available
PubChem Compound
105039
PubChem Substance
46508229
ChemSpider
94775
ChEBI
132234
ChEMBL
CHEMBL126279
Wikipedia
Methylenedioxyethamphetamine

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility1.46 mg/mLALOGPS
logP2.25ALOGPS
logP2.22Chemaxon
logS-2.2ALOGPS
pKa (Strongest Basic)10.22Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count3Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area30.49 Å2Chemaxon
Rotatable Bond Count4Chemaxon
Refractivity59 m3·mol-1Chemaxon
Polarizability23.46 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleYesChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9688
Caco-2 permeable+0.6126
P-glycoprotein substrateSubstrate0.5652
P-glycoprotein inhibitor INon-inhibitor0.794
P-glycoprotein inhibitor IINon-inhibitor0.9212
Renal organic cation transporterNon-inhibitor0.7516
CYP450 2C9 substrateNon-substrate0.881
CYP450 2D6 substrateNon-substrate0.5632
CYP450 3A4 substrateNon-substrate0.6102
CYP450 1A2 substrateInhibitor0.7531
CYP450 2C9 inhibitorNon-inhibitor0.8018
CYP450 2D6 inhibitorInhibitor0.7922
CYP450 2C19 inhibitorNon-inhibitor0.5247
CYP450 3A4 inhibitorNon-inhibitor0.546
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.5085
Ames testNon AMES toxic0.6861
CarcinogenicityNon-carcinogens0.7729
BiodegradationNot ready biodegradable0.6904
Rat acute toxicity2.6623 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.922
hERG inhibition (predictor II)Non-inhibitor0.6988
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-03di-0930000000-1c409c044a990269552d
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-03di-0910000000-b81cd94455fc636ec752
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-03ei-0900000000-ea619bf2f0ed78a397ce
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0a5i-0900000000-f70ec61288348785c4d5
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0a4r-1900000000-be25351a999d4b8a92aa
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0a70-4900000000-1174b1509d424f5c6980
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-056r-9500000000-0497c4c7b17f4e2e718e
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0fba-9200000000-6e2343d7fe50220fbfcb
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0udi-9100000000-34f0bb3383cddf0aec60
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0bt9-0980000000-0b72f23c6037df74c8c9
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-0290000000-99bee8e078f761359f48
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-03ei-2900000000-6b44973f9d66dcb8eff3
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0ae9-0930000000-ad89dd2849e1e5789994
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-00mo-5900000000-81d84a5fd51400baab8b
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0002-1900000000-dfc8837194e622fac6fe
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-145.44672
predicted
DeepCCS 1.0 (2019)
[M+H]+147.80472
predicted
DeepCCS 1.0 (2019)
[M+Na]+155.97427
predicted
DeepCCS 1.0 (2019)

Drug created at July 31, 2007 13:10 / Updated at June 12, 2020 16:51