Page last updated: 2024-12-08

alpha-methylepinine

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

Description

alpha-methylepinine: cpd is not responsible for the neurotoxic effects of MDMA; structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID161126
SCHEMBL ID2738991
MeSH IDM0189692

Synonyms (17)

Synonym
alpha-methylepinine
3,4-dihydroxymethamphetamine
15398-87-5
4-[2-(methylamino)propyl]benzene-1,2-diol
1,2-benzenediol, 4-(2-(methylamino)propyl)-
unii-vfv03wn1vn
vfv03wn1vn ,
NTCPGTZTPGFNOM-UHFFFAOYSA-N
hhma
SCHEMBL2738991
n-methyl-3,4-dihydroxyamphetaminehydrochloride
DTXSID90934885
4-(2-(methylamino)propyl)-1,2-benzenediol
di-oh-ma
ba-2816
.alpha.-methylepinine
PD048740

Research Excerpts

Toxicity

ExcerptReferenceRelevance
"Intracerebroventricular injection of methylenedioxymethamphetamine (MDMA, ecstasy) in rats fails to reproduce long-term toxic effects observed after peripheral administration."( [Metabolites of ecstasy and cytotoxicity effects].
Blanco, M; Felim, A; Fleury, MB; Largeron, M; Monnet, FP; Neudörffer, A, 2009
)
0.35
" MMMA was not toxic in the bacterial assay, indicating that its toxicity is not related to increased oxidative stress."( Synthesis and in vitro cytotoxicity profile of the R-enantiomer of 3,4-dihydroxymethamphetamine (R-(-)-HHMA): comparison with related catecholamines.
Blanco, M; Felim, A; Herrera, G; Largeron, M; Neudörffer, A; O'Connor, JE, 2010
)
0.36
"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

Pharmacokinetics

ExcerptReferenceRelevance
" Curiously, the approximate elimination half-life (t(1/2)) of MDMA at 18 degrees C (136 min) and 31 degrees C (144 min) was increased compared with 24 degrees C (90 min) and is most likely because of volume of distribution changes induced by core temperature alterations."( Ambient temperature effects on 3,4-methylenedioxymethamphetamine-induced thermodysregulation and pharmacokinetics in male monkeys.
Banks, ML; Czoty, PW; Kisor, DF; Nader, MA; Nichols, DE; Sprague, JE, 2007
)
0.34
" At each dose, pharmacokinetic parameters for MDMA and its metabolites 3,4-dihydroxymethamphetamine (HHMA), 4-hydroxy-3-methoxymethamphetamine (HMMA), and 3,4-methylenedioxyamphetamine were determined."( Nonlinear pharmacokinetics of (+/-)3,4-methylenedioxymethamphetamine (MDMA, "Ecstasy") and its major metabolites in squirrel monkeys at plasma concentrations of MDMA that develop after typical psychoactive doses.
Maurer, HH; McCann, UD; Mueller, M; Peters, FT; Ricaurte, GA, 2008
)
0.35

Dosage Studied

ExcerptRelevanceReference
"3,4-Methylenedioxymethamphetamine (MDMA) is a racemic drug of abuse and its R- and S-enantiomers are known to differ in their dose-response curve."( Development and validation of LC-HRMS and GC-NICI-MS methods for stereoselective determination of MDMA and its phase I and II metabolites in human urine.
Huestis, MA; Maurer, HH; Meyer, MR; Schwaninger, AE, 2011
)
0.37
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (27)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's5 (18.52)18.2507
2000's15 (55.56)29.6817
2010's7 (25.93)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 11.14

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 Index11.14 (24.57)
Research Supply Index3.47 (2.92)
Research Growth Index4.60 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (11.14)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials3 (10.71%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other25 (89.29%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]