Methylenedioxyamphetamine

One of the structural features of MDMA that is somewhat unusual is the fact that it is 3,4-disubstituted. Both 3,4-methylenedioxyamphetamine (MDA) (figure 2) and MDMA possess the 3,4-methylenedioxy function, and there apparently are no other active compounds known that fall within the... 

Boja, J.W., and Schechter, M.D. Behavioral effects of N-ethyl-3,4-methylenedioxyamphetamine (MDE Eve ). Pharmacol Biochem Behav 28 153-156, 1987. 

Callahan, P.M., and Appel, J.B. Differences in the stimulus properties of 3,4-methylenedioxyamphetamine (MDA) and N-Methyl-l-(3,4-methylene-dioxyamphetamine) MDMA in animals trained to discriminate hallucinogens from saline. Abstr Soc Neurosci 476.2, 1987. 

Ricaurte, G.A. Fomo, L.S. Wilson, M.A. DeLanney, L.E. Irwin, L. Molliver, M.E. and Langston, J.W. ( )-3,4-methylenedioxyamphetamine selectively damages central serotonergic neurons in nonhuman primates. 

Fitzgerald, R. Blanke, R.V. Namsimhachari, N. Glennon, R.A. and Rosecrans, J.A. Identification of 3,4-methylenedioxyamphetamine (MDA) as a major urinary metabolite of 3,4-methylenedioxymeth-amphetamine (MDMA). Presented at the Committee on Problems of Drug Dependence Meeting, Philadelphia, PA, June 1987. 

Gold, L.H. Koob, G.F. and Geyer, M.A. Stimulant and hallucinogenic behavioral profiles of 3,4-methylenedioxymethamphetamine (MDMA) and N-ethyl-3,4-methylenedioxyamphetamine (MDE) in rats. J Pharmacol Exp Ther 247 547-555, 1988. 

Large doses of the ring-substituted amphetamine derivative ( )3,4-methylenedioxyamphetamine (MDA) repeatedly administered to rats... 

Battaglia, G. Yeh, S.Y. O Heam, E. Molliver. M.E. Kuhar, M.J. and De Souza, E.B. 3,4-Methylenedioxymethamphetamine (MDMA) and 3,4-methylenedioxyamphetamine (MDA) preferentially destroy serotonin terminals in rat brain Quantification of neurodegeneration by measurement of H-paroxetine-labeled serotonin uptake sites. 

Johnson, M. Letter, A.A. Merchant, K. Hanson. G.R. and Gibb, J.W. Effects of 3,4-methylenedioxyamphetamine and 3,4-methylenedioxymeth-amphetamine isomers on central serotonergic, dopaminergic and nigral neurotensin systems of the rat. J Pharmacol Exp Ther 244 977-982,... 

Mamounas, L.A. Mullen, C. O Heam, E. and Molliver, M.E. Morphologically distinct types of serotonergic axon terminals are differentially vulnerable to neurotoxic amphetamine derivatives. Effects of 3,4-methylenedioxyamphetamine (MDA), 3,4-methylenedioxymethampheta-mine (MDMA), and p-chloroamphetamine (PCA). in preparation. 

This volume has focused on several amphetamine analogs in addition to amphetamine and methamphetamine, especially 3,4-methylenedioxymeth-amphetamine (MDMA) and 3,4-methylenedioxyamphetamine (MDA). 

A relatively unique type of reactive metabolite is carbene, i.e., a divalent carbon, which is a proposed intermediate in the oxidation of methylene dioxy-containing compounds. A methylenedioxy group in aromatic compounds is subject to O-dealkylation, e.g., 3,4-methylenedioxyamphetamine, as shown in Figure 8.20. The process generates formic acid and the catechol metabolite as final products. However, in the course of the reaction, a... 

Examples of specific methods important to neurochemists include separation and quantification of R- and S-fluoxetine and R- and S-norfluoxetine in brain tissue and body fluids using derivatization with (—)-(S)-N-(trifluoracetyl)prolyl chloride, a chiral derivatizing agent (Torok-Both et al., 1992 Aspeslet et al., 1994). A similar method has been used to separate the enantiomers of 3,4-methylenedioxyamphetamine (MDA) and 3,4-methylenedioxymethamphetamine (MDMA) (Hegadoren et al., 1993). Eluoxetine and norfluoxetine enantiomers have also been separated on a chiral column in series with a nonchiral column with NPD detections (Ulrich, 2003). Reviews of the analysis of enantiomers of several drugs of abuse are available (Jirovsky et al., 1998 Tao and Zeng, 2002 Liu and Liu, 2002). 

Mancinelli and colleagues (1999) reported the simultaneous determination of 3-4-methylenedioxymethamphetamine (MDMA), N-ethyl-3,4-methylenedioxyamphetamine (MDEA), methylenedioxyamphetamine (MDA), and N-methyl-l-(l,3-benzdioxol-5-yl)-2-butamine (MBDB) by RP-HPLC with fluorometric detection. The method required a 100 pi sample volume of serum, urine, or saliva separation was achieved on a LiChrospher lOORP-18 analytical column using an acetonitrile/water mobile phase (pH 11.4) set at a flow rate of 1 ml/min. The LLOQ and LLOD were 50 and 10 ng/ml respectively. 

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