Page last updated: 2024-11-07

3,4-methylenedioxyethamphetamine

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

3,4-methylenedioxyethamphetamine: legal replacement for MDMA; RN given for (+-)-isomer; structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

1-(1,3-benzodioxol-5-yl)-N-ethylpropan-2-amine : A secondary amino compound that is N-ethylisopropylamine in which a hydrogen of one of the isopropyl methyl groups has been replaced by a 3,4-methylenedioxyphenyl group. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID105039
CHEMBL ID126279
CHEBI ID132234
SCHEMBL ID715096
MeSH IDM0147289

Synonyms (46)

Synonym
n-ethyl-3,4-methylenedioxyamphetamine
mde (+-)
eve (amphetamine)
mdea
1,3-benzodioxole-5-ethanamine, n-ethyl-alpha-methyl-
n-ethyl-mda
1,3-benzodioxole-5-ethanamine, n-ethyl-alpha-methyl-, (+-)-
n-mde
3,4-methylenedioxyethamphetamine
MDE ,
3,4-methylenedioxy-n-ethylamphetamine
DB01566
n-ethyl mda
methylenedioxyethamphetamine
(+/-)-mde
CHEBI:132234
1-(1,3-benzodioxol-5-yl)-n-ethylpropan-2-amine
CHEMBL126279
NCGC00247723-01
(r,s)-n-ethyl-3,4-methylenedioxyamphetamine
82801-81-8
n-ethyl-alpha-methyl-3,4-(methylenedioxy)phenethylamine
M055000000
14089-52-2
(+-)-n-ethyl-3,4-methylenedioxyamphetamine
dea no. 7404
unii-ml1i4kk67b
(+-)-mde
ml1i4kk67b ,
(+/-)-n-ethyl-3,4-methylenedioxyamphetamine
mde [mi]
mde (psychedelic)
1,3-benzodioxole-5-ethanamine, n-ethyl-.alpha.-methyl-
SCHEMBL715096
methylenedioxyamphetamine, n-ethyl
n-ethyl-.alpha.-methyl-1,3-benzodioxole-5-ethanamine
1-(1,3-benzodioxol-5-yl)-n-ethyl-2-propanamine
(+/-)-3,4-methylenedioxyethylamphetamine
rac-mdea (rac-3,4-methylenedioxy-n-ethylamphetamine) 1.0 mg/ml in methanol
1-(benzo[d][1,3]dioxol-5-yl)-n-ethylpropan-2-amine
3,4-methylenedioxyethamphetamine (mdea)
FT-0708631
DTXSID70860971
Q223011
[1-(2h-1,3-benzodioxol-5-yl)propan-2-yl](ethyl)amine
n-ethyl-1-[(1,3-benzodioxole-5-yl)methyl]ethanamine

Research Excerpts

Toxicity

ExcerptReferenceRelevance
"XTC and other amphetamines are considered to be safe by the majority of partying young people who are unaware of (or unwilling to know about) the acute and chronic toxicity of these substances, and these drugs are widespread, illicit stimulants."( Amphetamine toxicity in the emergency department.
Bronselaer, K; De Feyter, K; De Munnynck, K; Sabbe, M; Smets, G; Van de Voorde, W, 2005
)
0.33
"3,4-Methylenedioxymethamphetamine (MDMA)'s O-demethylenated metabolite, 3,4-dihydroxymethamphetamine (HHMA), has been hypothesized to serve as a precursor for the formation of toxic catechol-thioether metabolites (e."( Inhibition of 3,4-methylenedioxymethamphetamine metabolism leads to marked decrease in 3,4-dihydroxymethamphetamine formation but no change in serotonin neurotoxicity: implications for mechanisms of neurotoxicity.
Maldonado Adrian, C; McCann, UD; Mueller, M; Ricaurte, GA; Yuan, J, 2011
)
0.37

Dosage Studied

ExcerptRelevanceReference
"0 mg/kg MDA in both components of the multiple schedule, but did not affect the MDMA dose-response curve."( Behavioral effects of (+-) 3,4-methylenedioxyamphetamine (MDA) and (+-) 3,4-methylenedioxymethamphetamine (MDMA) in the pigeon: interactions with noradrenergic and serotonergic systems.
Barrett, JE; Hoffmann, SM; Nader, MA, 1989
)
0.28
" The statistical distribution of the drug concentrations compared with the self-reported consumption behaviour of the users may possibly lead to a better understanding of the relationship between drug dosage and corresponding concentrations in hair."( Concentrations of delta 9-tetrahydrocannabinol, cocaine and 6-monoacetylmorphine in hair of drug abusers.
Kauert, G; Röhrich, J, 1996
)
0.29
"Surveys into the pharmacological constituents of ecstasy tablets, dosage levels, and empirical reports of their perceived purity, provide the main data for this review."( Is ecstasy MDMA? A review of the proportion of ecstasy tablets containing MDMA, their dosage levels, and the changing perceptions of purity.
Parrott, AC, 2004
)
0.32
" Dosage levels of tablets are also highly variable, with low dose tablet often encountered during the mid-1990s, and high dose tablets now seen more frequently."( Is ecstasy MDMA? A review of the proportion of ecstasy tablets containing MDMA, their dosage levels, and the changing perceptions of purity.
Parrott, AC, 2004
)
0.32
" For future research, challenge studies in animals using dosing regimens adapted to human consumption patterns are needed."( The Neuropsychopharmacology and Toxicology of 3,4-methylenedioxy-N-ethyl-amphetamine (MDEA).
Freudenmann, RW; Spitzer, M, 2004
)
0.32
" Mentions on medical death certificates, last year's ecstasy use, number of drug offenders, seizures, prices and dosage levels figures were used for this descriptive and correlational study."( Ecstasy (MDMA, MDA, MDEA, MBDB) consumption, seizures, related offences, prices, dosage levels and deaths in the UK (1994-2003).
Corkery, J; Deluca, P; Ghodse, AH; Oyefeso, A; Schifano, F, 2006
)
0.33
"The purpose of the current study was to extend previous results on the acute effects of MDMA on behavioral thermoregulation to a repeated dosing regime, simulating regular weekend use of ecstasy, on measures of thermoregulation and heart rate (HR)."( The effect of long-term repeated exposure to 3,4-methylenedioxymethamphetamine on cardiovascular and thermoregulatory changes.
Irvine, RJ; Jaehne, EJ; Salem, A, 2008
)
0.35
" HR responses to MDMA over 6 weeks at both TAs progressively decreased with repeated dosing (P<0."( The effect of long-term repeated exposure to 3,4-methylenedioxymethamphetamine on cardiovascular and thermoregulatory changes.
Irvine, RJ; Jaehne, EJ; Salem, A, 2008
)
0.35
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (2)

ClassDescription
benzodioxoles
secondary amino compoundA compound formally derived from ammonia by replacing two hydrogen atoms by organyl groups.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (1)

Other Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Cytochrome P450 2D6Homo sapiens (human)Km3.65001.10003.72868.2000AID254565; AID256544; AID256545; AID256546
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (16)

Processvia Protein(s)Taxonomy
xenobiotic metabolic processCytochrome P450 2D6Homo sapiens (human)
steroid metabolic processCytochrome P450 2D6Homo sapiens (human)
cholesterol metabolic processCytochrome P450 2D6Homo sapiens (human)
estrogen metabolic processCytochrome P450 2D6Homo sapiens (human)
coumarin metabolic processCytochrome P450 2D6Homo sapiens (human)
alkaloid metabolic processCytochrome P450 2D6Homo sapiens (human)
alkaloid catabolic processCytochrome P450 2D6Homo sapiens (human)
monoterpenoid metabolic processCytochrome P450 2D6Homo sapiens (human)
isoquinoline alkaloid metabolic processCytochrome P450 2D6Homo sapiens (human)
xenobiotic catabolic processCytochrome P450 2D6Homo sapiens (human)
retinol metabolic processCytochrome P450 2D6Homo sapiens (human)
long-chain fatty acid biosynthetic processCytochrome P450 2D6Homo sapiens (human)
negative regulation of bindingCytochrome P450 2D6Homo sapiens (human)
oxidative demethylationCytochrome P450 2D6Homo sapiens (human)
negative regulation of cellular organofluorine metabolic processCytochrome P450 2D6Homo sapiens (human)
arachidonic acid metabolic processCytochrome P450 2D6Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (8)

Processvia Protein(s)Taxonomy
monooxygenase activityCytochrome P450 2D6Homo sapiens (human)
iron ion bindingCytochrome P450 2D6Homo sapiens (human)
oxidoreductase activityCytochrome P450 2D6Homo sapiens (human)
oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygenCytochrome P450 2D6Homo sapiens (human)
heme bindingCytochrome P450 2D6Homo sapiens (human)
anandamide 8,9 epoxidase activityCytochrome P450 2D6Homo sapiens (human)
anandamide 11,12 epoxidase activityCytochrome P450 2D6Homo sapiens (human)
anandamide 14,15 epoxidase activityCytochrome P450 2D6Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (5)

Processvia Protein(s)Taxonomy
mitochondrionCytochrome P450 2D6Homo sapiens (human)
endoplasmic reticulumCytochrome P450 2D6Homo sapiens (human)
endoplasmic reticulum membraneCytochrome P450 2D6Homo sapiens (human)
cytoplasmCytochrome P450 2D6Homo sapiens (human)
intracellular membrane-bounded organelleCytochrome P450 2D6Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (9)

Assay IDTitleYearJournalArticle
AID255155Vmax for oxidation to 3,4-OH-MA by cytochrome P450 2D6 (wild type pSP19T7LT); expressed in 10E5 fluorescence units min-1 nmol-1 CYP2005Journal of medicinal chemistry, Sep-22, Volume: 48, Issue:19
Metabolic regio- and stereoselectivity of cytochrome P450 2D6 towards 3,4-methylenedioxy-N-alkylamphetamines: in silico predictions and experimental validation.
AID256554Vmax for oxidation to N-OH-MDMA by cytochrome P450 2D6 (Phe120Ala mutant); expressed in 10E5 fluorescence units min-1 nmol-1 CYP2005Journal of medicinal chemistry, Sep-22, Volume: 48, Issue:19
Metabolic regio- and stereoselectivity of cytochrome P450 2D6 towards 3,4-methylenedioxy-N-alkylamphetamines: in silico predictions and experimental validation.
AID256545Michaelis-Menten constant for oxidation to 3,4-OH-MA by cytochrome P450 2D6 (Phe120Ala mutant)2005Journal of medicinal chemistry, Sep-22, Volume: 48, Issue:19
Metabolic regio- and stereoselectivity of cytochrome P450 2D6 towards 3,4-methylenedioxy-N-alkylamphetamines: in silico predictions and experimental validation.
AID256553Vmax for oxidation to 3,4-OH-MA by cytochrome P450 2D6 (Phe120Ala mutant); expressed in 10E5 fluorescence units min-1 nmol-1 CYP2005Journal of medicinal chemistry, Sep-22, Volume: 48, Issue:19
Metabolic regio- and stereoselectivity of cytochrome P450 2D6 towards 3,4-methylenedioxy-N-alkylamphetamines: in silico predictions and experimental validation.
AID256552Vmax for oxidation to MDA by cytochrome P450 2D6 (Phe120Ala mutant)2005Journal of medicinal chemistry, Sep-22, Volume: 48, Issue:19
Metabolic regio- and stereoselectivity of cytochrome P450 2D6 towards 3,4-methylenedioxy-N-alkylamphetamines: in silico predictions and experimental validation.
AID254565Michaelis-Menten constant for oxidation to 3,4-OH-MA by cytochrome P450 2D6 (wild type pSP19T7LT)2005Journal of medicinal chemistry, Sep-22, Volume: 48, Issue:19
Metabolic regio- and stereoselectivity of cytochrome P450 2D6 towards 3,4-methylenedioxy-N-alkylamphetamines: in silico predictions and experimental validation.
AID256546Michaelis-Menten constant for oxidation to N-OH-MDMA by cytochrome P450 2D6 (Phe120Ala mutant)2005Journal of medicinal chemistry, Sep-22, Volume: 48, Issue:19
Metabolic regio- and stereoselectivity of cytochrome P450 2D6 towards 3,4-methylenedioxy-N-alkylamphetamines: in silico predictions and experimental validation.
AID256544Michaelis-Menten constant for oxidation to MDA by cytochrome P450 2D6 (Phe120Ala mutant)2005Journal of medicinal chemistry, Sep-22, Volume: 48, Issue:19
Metabolic regio- and stereoselectivity of cytochrome P450 2D6 towards 3,4-methylenedioxy-N-alkylamphetamines: in silico predictions and experimental validation.
AID91217Compound tested for hallucinogenic activity in humans was reported; Value reported in (A)= Mescaline units1998Journal of medicinal chemistry, Sep-24, Volume: 41, Issue:20
The frontier orbital phase angles: novel QSAR descriptors for benzene derivatives, applied to phenylalkylamine hallucinogens.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (158)

TimeframeStudies, This Drug (%)All Drugs %
pre-199015 (9.49)18.7374
1990's64 (40.51)18.2507
2000's50 (31.65)29.6817
2010's20 (12.66)24.3611
2020's9 (5.70)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 9.76

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index9.76 (24.57)
Research Supply Index5.20 (2.92)
Research Growth Index4.96 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (9.76)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials10 (5.88%)5.53%
Reviews11 (6.47%)6.00%
Case Studies21 (12.35%)4.05%
Observational0 (0.00%)0.25%
Other128 (75.29%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]