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Chemical Compound Review

3,4-methylenedioxyamphetamine     1-benzo[1,3]dioxol-5- ylpropan-2-amine

Synonyms: Love, Tenamfetamina, Tenamfetamine, Tenamfetaminum, CHEMBL6731, ...
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Disease relevance of 3,4-methylenedioxyamphetamine

  • However, when the animals were rendered hypercapnic, CBF was significantly higher in MDA-treated rats than in normal controls, for example, increasing from 356 +/- 22 ml 100 g-1 min-1 in frontal cortex of hypercapnic controls to 700 +/- 81 ml 100 g-1 min-1 in MDA-pretreated rats with similar levels of hypercapnia [1].
  • In group-housed animals, caffeine (10 mg/kg) enhanced the acute toxicity of MDMA (15 mg/kg) and MDA (7.5 mg/kg), resulting in an exaggerated hyperthermic response (+2 degrees C for 5 h following MDMA and +1.5 degrees C for 3 h following MDA) when compared to MDMA (+1 degree C for 3 h) and MDA (+1 degree C for 1 h) alone [2].
  • The pressor response produced by MDA was accompanied by bradycardia [3].
  • All three amphetamine derivatives caused an initial hypothermic response; however, MDA also produced a subsequent hyperthermia, and the speed of recovery from hypothermia was MDA>MDMA>MDEA [3].
  • Severe and malignant hyperthermia is a frequently reported factor in emergency department (ED) visits and fatalities in which use of amphetamine drugs, such as (+/-)3,4-methylenedioxymethamphetamine (MDMA), (+/-)3,4-methylenedioxyamphetamine (MDA) and (+)methamphetamine (METH), is confirmed [4].

Psychiatry related information on 3,4-methylenedioxyamphetamine


High impact information on 3,4-methylenedioxyamphetamine

  • Via large-scale, random screening of a portion of the receptorome, we have discovered that the amphetamine derivative 3,4-methylenedioxymethamphetamine (MDMA, "Ecstasy") and its N-demethylated metabolite 3,4-methylenedioxyamphetamine (MDA) each preferentially bind to and activate human recombinant 5-HT2B receptors [8].
  • In all animals treated with MDA, there was a significant decrease in serotonin uptake sites throughout the brain, falling from 223 +/- 20 to 40 +/- 16 fmol/mg tissue in parietal cortex, for example, although the raphe nuclei themselves were unaffected (300 +/- 20 fmol/mg tissue in controls and 291 +/- 18 in MDA-treated rats) [1].
  • The results suggested that one or more constitutive isoforms (probably unknown) of cytochrome P450 present in rabbit liver microsomes are primarily responsible for MDA demethylenation but that CYP3A6 contributes slightly [9].
  • Rats trained to discriminate (+/-) 2,5-dimethoxy-4-methylphenylisopropylamine (DOM) (1.0 mg/kg) from saline, using a standard two-lever operant task, were challenged with various doses of 3,4-methylenedioxyphenylisopropylamine (MDA) and several related agents [10].
  • CONCLUSIONS: This gas chromatography-mass spectrometry assay provides adequate sensitivity and performance characteristics for the simultaneous quantification of MDEA, MDMA, and its metabolites HMMA, MDA, and HMA in human urine [11].

Chemical compound and disease context of 3,4-methylenedioxyamphetamine


Biological context of 3,4-methylenedioxyamphetamine


Anatomical context of 3,4-methylenedioxyamphetamine


Associations of 3,4-methylenedioxyamphetamine with other chemical compounds


Gene context of 3,4-methylenedioxyamphetamine


Analytical, diagnostic and therapeutic context of 3,4-methylenedioxyamphetamine


  1. Enhanced cerebrovascular responsiveness to hypercapnia following depletion of central serotonergic terminals. Kelly, P.A., Ritchie, I.M., McBean, D.E., Sharkey, J., Olverman, H.J. J. Cereb. Blood Flow Metab. (1995) [Pubmed]
  2. Caffeine promotes hyperthermia and serotonergic loss following co-administration of the substituted amphetamines, MDMA ("Ecstasy") and MDA ("Love"). McNamara, R., Kerans, A., O'Neill, B., Harkin, A. Neuropharmacology (2006) [Pubmed]
  3. Effects of MDMA, MDA and MDEA on blood pressure, heart rate, locomotor activity and body temperature in the rat involve alpha-adrenoceptors. Bexis, S., Docherty, J.R. Br. J. Pharmacol. (2006) [Pubmed]
  4. Effects of (+/-)3,4-methylenedioxymethamphetamine, (+/-)3,4-methylenedioxyamphetamine and methamphetamine on temperature and activity in rhesus macaques. Crean, R.D., Davis, S.A., Von Huben, S.N., Lay, C.C., Katner, S.N., Taffe, M.A. Neuroscience (2006) [Pubmed]
  5. The effects of MDMA and other methylenedioxy-substituted phenylalkylamines on the structure of rat locomotor activity. Paulus, M.P., Geyer, M.A. Neuropsychopharmacology (1992) [Pubmed]
  6. MDA-assisted psychotherapy with neurotic outpatients: a pilot study. Yensen, R., Di Leo, F.B., Rhead, J.C., Richards, W.A., Soskin, R.A., Turek, B., Kurland, A.A. J. Nerv. Ment. Dis. (1976) [Pubmed]
  7. MDMA and serotonin: based on two cases. Garcia Cabeza, I., Zabala, A., Soto-Montenegro, M.L., Arango, C. Actas españolas de psiquiatría. (2005) [Pubmed]
  8. 3,4-methylenedioxymethamphetamine (MDMA, "Ecstasy") induces fenfluramine-like proliferative actions on human cardiac valvular interstitial cells in vitro. Setola, V., Hufeisen, S.J., Grande-Allen, K.J., Vesely, I., Glennon, R.A., Blough, B., Rothman, R.B., Roth, B.L. Mol. Pharmacol. (2003) [Pubmed]
  9. Regiochemical differences in cytochrome P450 isozymes responsible for the oxidation of methylenedioxyphenyl groups by rabbit liver. Kumagai, Y., Lin, L.Y., Philpot, R.M., Yamada, H., Oguri, K., Yoshimura, H., Cho, A.K. Mol. Pharmacol. (1992) [Pubmed]
  10. Discriminative stimulus properties of MDA analogs. Glennon, R.A., Young, R., Rosecrans, J.A., Anderson, G.M. Biol. Psychiatry (1982) [Pubmed]
  11. Sensitive gas chromatography-mass spectrometry method for simultaneous measurement of MDEA, MDMA, and metabolites HMA, MDA, and HMMA in human urine. Pirnay, S.O., Abraham, T.T., Huestis, M.A. Clin. Chem. (2006) [Pubmed]
  12. (+/-)3,4-Methylenedioxyamphetamine elicits action potential bursts in a central snail neuron. Tsai, M.C., Chen, Y.H. Exp. Neurol. (2007) [Pubmed]
  13. The hyperthermic and neurotoxic effects of 'Ecstasy' (MDMA) and 3,4 methylenedioxyamphetamine (MDA) in the Dark Agouti (DA) rat, a model of the CYP2D6 poor metabolizer phenotype. Colado, M.I., Williams, J.L., Green, A.R. Br. J. Pharmacol. (1995) [Pubmed]
  14. Development and validation of a high-performance liquid chromatography-mass spectrometry assay for determination of amphetamine, methamphetamine, and methylenedioxy derivatives in meconium. Pichini, S., Pacifici, R., Pellegrini, M., Marchei, E., Lozano, J., Murillo, J., Vall, O., García-Algar, O. Anal. Chem. (2004) [Pubmed]
  15. Serotonergic neurotoxic metabolites of ecstasy identified in rat brain. Jones, D.C., Duvauchelle, C., Ikegami, A., Olsen, C.M., Lau, S.S., de la Torre, R., Monks, T.J. J. Pharmacol. Exp. Ther. (2005) [Pubmed]
  16. Centrally active N-substituted analogs of 3,4-methylenedioxyphenylisopropylamine (3,4-methylenedioxyamphetamine). Braun, U., Shulgin, A.T., Braun, G. Journal of pharmaceutical sciences. (1980) [Pubmed]
  17. MDMA administration to pregnant Sprague-Dawley rats results in its passage to the fetal compartment. Campbell, N.G., Koprich, J.B., Kanaan, N.M., Lipton, J.W. Neurotoxicology and teratology. (2006) [Pubmed]
  18. Enhanced learning following a single, acute dose of MDA. Romano, A.G., Harvey, J.A. Pharmacol. Biochem. Behav. (1993) [Pubmed]
  19. Metabolism is required for the expression of ecstasy-induced cardiotoxicity in vitro. Carvalho, M., Remião, F., Milhazes, N., Borges, F., Fernandes, E., Monteiro, M.d.o. .C., Gonçalves, M.J., Seabra, V., Amado, F., Carvalho, F., Bastos, M.L. Chem. Res. Toxicol. (2004) [Pubmed]
  20. Effect of the R(-) and S(+) isomers of MDA and MDMA on phosphatidyl inositol turnover in cultured cells expressing 5-HT2A or 5-HT2C receptors. Nash, J.F., Roth, B.L., Brodkin, J.D., Nichols, D.E., Gudelsky, G.A. Neurosci. Lett. (1994) [Pubmed]
  21. alpha-Methyldopamine, a key intermediate in the metabolic disposition of 3,4-methylenedioxyamphetamine in vivo in dog and monkey. Midha, K.K., Hubbard, J.W., Bailey, K., Cooper, J.K. Drug Metab. Dispos. (1978) [Pubmed]
  22. Behavioral effects of N-ethyl-3,4-methylenedioxyamphetamine (MDE; "EVE"). Boja, J.W., Schechter, M.D. Pharmacol. Biochem. Behav. (1987) [Pubmed]
  23. Detection of amphetamines in fingernails: an alternative to hair analysis. Cirimele, V., Kintz, P., Mangin, P. Arch. Toxicol. (1995) [Pubmed]
  24. Choroid plexus epithelial cells in primary culture: a model of 5HT1C receptor activation by hallucinogenic drugs. Sanders-Bush, E., Breeding, M. Psychopharmacology (Berl.) (1991) [Pubmed]
  25. Selection and Optimization of Hydrolysis Conditions for the Quantification of Urinary Metabolites of MDMA. Pirnay, S.O., Abraham, T.T., Lowe, R.H., Huestis, M.A. Journal of analytical toxicology (2006) [Pubmed]
  26. Adam and Eve make love. Analysis of the enantiomers of 3,4-methylenedioxy-N-ethylamphetamine (MDE, "Eve") and its metabolite 3,4-methylenedioxyamphetamine (MDA) in rat brain. Tucker, G. Human & experimental toxicology. (1996) [Pubmed]
  27. Analysis of 3,4-methylenedioxymethamphetamine (MDMA) and its metabolites in plasma and urine by HPLC-DAD and GC-MS. Helmlin, H.J., Bracher, K., Bourquin, D., Vonlanthen, D., Brenneisen, R. Journal of analytical toxicology. (1996) [Pubmed]
  28. Stereospecific analysis and enantiomeric disposition of 3, 4-methylenedioxymethamphetamine (Ecstasy) in humans. Fallon, J.K., Kicman, A.T., Henry, J.A., Milligan, P.J., Cowan, D.A., Hutt, A.J. Clin. Chem. (1999) [Pubmed]
  29. Determination of paramethoxyamphetamine and other amphetamine-related designer drugs by liquid chromatography/sonic spray ionization mass spectrometry. Mortier, K.A., Dams, R., Lambert, W.E., De Letter, E.A., Van Calenbergh, S., De Leenheer, A.P. Rapid Commun. Mass Spectrom. (2002) [Pubmed]
  30. Microdialysis studies on 3,4-methylenedioxyamphetamine and structurally related analogues. Nash, J.F., Nichols, D.E. Eur. J. Pharmacol. (1991) [Pubmed]
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