3,4-Methylenedioxy-methamphetamine MDMA

Ricaurte GA, McCann UD, Szabo Z, et al Toxicodynamics and long-term toxicity of the recreational drug 3,4-methylenedioxy-methamphetamine (MDMA, Ecstasy ). Toxicol Lett 112-113 143-146, 2000 Robinson TN, Killen JD, Taylor CB, et al Perspectives on adolescent substance use a defined population study. JAMA 258 2072-2076, 1987 Rubinstein JS Abuse of antiparkinson drugs feigning of extrapyramidal symptoms to obtain trihexyphenidyl. JAMA 239 2365, 1978 Rumack BH (ed) LSD, in Poisindex, Vol 54. Denver, CO, Micromedex, 1987 Rusyniak DE, Banks ML, Mills EM, et al Dantrolene use in 3,4-methylenedioxymethamphetamine ( ecstasy )-medicated hyperthermia (letter). Anesthesiology 10 263, 2004... 

Lamb, R.J., and Griffiths, R.R. Self-injection of 7,1-3,4-methylenedioxy-methamphetamine (MDMA) in the baboon. Psychopharmacology 91 268-272, 1987. 

Wang, S.S. Ricauite, G.A. and Peroutka, S.J. [ H]3,4-methylenedioxy-methamphetamine (MDMA) interactions with brain membranes and glass fiber filter paper. Eur J Pharmacol 138 439-443, 1977. 

The analogs of current concern include 3,4-methylenedioxy-amphetamine (MDA) and 3,4-methylenedioxy-methamphetamine (MDMA, ecstasy, Adam, X, Stacy). 

Helmlin, H.J., Bracher, K., Salamone, S.J., and Brenneisen, R., Analysis of 3,4-methylenedioxy-methamphetamine (MDMA) and its metabolites in human plasma and urine, Society of Forensic Toxicologists, Inc., Phoenix, AZ, October 1993 [Abstract]. 

Rudnick G, Wall SC (1992) The molecular mechanism of ecstasy [3,4-methylenedioxy-methamphetamine (MDMA)] serotonin transporters are targets for MDMA-induced serotonin release. Proc Natl Acad Sci USA 89 1817-1821. 

Methylenedioxy-methamphetamine MDMA, ecstasy, Adam Sympathomimetic hyperthermia, seizures, cerebral hemorrhage, and arrhythmias reported hyponatremia. 

Complications of drug analysis were successfully resolved by the combination of TLC with MALDI-MS. TLC combined with MALDI-MS was used for analysis of psychotropic drugs (3,4-methylenedioxy methamphetamine, 4-hydroxy-3-methoxy methamphetamine, 3,4-methylenedioxy amphetamine, methamphetamine, p-hydroxy methamphetamine, amphetamine, ketamine, caffeine, chlorpromazine, triazolam, and morphine) in biological samples [42]. This technique was able to analyze 3,4-methylenedioxy methamphetamine (MDMA) and its metabolites in urine samples without sample dilution, and the detection limit of the MDMA spot was 0.05 ng/ spot. Crecelius and coworkers described the use of TLC with MALDI-MS/MS for the structural analysis of small drug molecules [43]. This method was successfully applied to analyze two representatives of nonsteroidal antiinflammatory drugs (tenoxi-cam and piroxicam), and pharmaceutically active compound UK-137,457 and one of its related substances UK-124,912. The feasibility of UTLC-atmospheric pressure (AP)-MALDI-MS was described for the analysis of small molecules (triazole, midazolam, verapamil, and metaprolol) [44]. The authors compared the selectivity and sensitivity between UTLC- and HPTLC-AP-MALDI-MS. It was observed that UTLC plates provided 10-100 times better sensitivity in MALDI analysis than the conventional... 

Banta-Green, C. J., J. A. Field, A. C. Chiaia, D. L. Sudakin, L. Power, and L. de Montigny. 2009. The spatial epidemiology of cocaine, methamphetamine and 3,4-methylenedioxy methamphetamine (MDMA) use a demonstration using a population measure of community drug load derived from municipal w slsv/aisr. Addiction 104 1874-1880. 

Fig. 3 Concentrations reported for amphetamine-like compounds in surface water of different European and American countries. AM amphetamine MDA 3,4-methylenedioxy amphetamine MDMA 3,4-methylenedioxy methamphetamine (ecstasy) MA methamphetamine N/A Values not availabe, not measured...

MAOIs, monoamine oxidase inhibitors MDMA, methylenedioxy-methamphetamine (ecstasy) SSRIs, selective serotonin reuptake inhibitors. Serotonin Syndrome and Similar Syndromes... 

Several people have asked me what I thought about the potential activity of a compound with a methyl group added to DMMDA. One of these possibilities would be the N-methylated derivative, 2,5-dimethoxy-N-methyl-3,4-methylene-dioxyamphetamine, or METHYL-DMMDA (or DMMDMA for the dimethoxy-methylenedioxy-methamphetamine nomenclature). It is a MDMA analogue, and is described in the recipe for METHYL-MMDA-2. 

DMMDMA for the dimethoxy-methylenedioxy-methamphetamine nomenclature). It is a MDMA analogue, and is described in the recipe for METHYL-MMDA-2. 

FIG U RE 11.1 Effect of supporting gas atmosphere on collision cross section of six amphetamines in four gases. Although the core ion (MH ) is the same in each gas, adducts and associations are influenced distinctly by each gas. Differences in cross section will lead to differences in mobility. The substances are as follows AM, amphetamine MA, methamphetamine EA, ethylamphetamine MDA, 3,4-methylenedioxy amphetamine MDMA, 3,4-methylenedioxy methamphetamine and MDEA, 3,4-methylenedioxy ethylamphetamine. (From Matz et al.. Investigation of drift gas selectivity inhigh resolution ion mobility spectrometry with mass spectrometry detection, J. Am. Soc. Mass Spectrom. 2002, 300-307. With permission.)... 

Amphetamine, methamphetamine, MDA (3,4-methylenedioxyamphetamine), and MDMA (3,4-methylenedioxy methamphetamine) are examples that have similar structures to catecholamines, as shown in Fig. 17.10. The strnctnral similarity snggests that they may interfere with catecholamines pathways. Amphetamine is known to bind to and block the re-nptake mechanism (i.e., reabsorb the nenrorans-mitter such as dopamine back into the presynaptic cell) and increase the level of the nenrotransmitter in the synapse. Methamphetamine seems to have a similar effect bnt even stronger than that of amphetamine. 

The drugs 3,4-methylenedioxymethamphetamine (MDMA) and 3,4-methyl-enedioxyamphetamine (MDA) are ring-substituted derivatives of methamphetamine and amphetamine, respectively. These methylenedioxy-substituted amphetamines have been reported to exhibit both stimulant and psychotomimetic properties (Anderson et al. 1978 Braun et al. 1980 ... 

As shown in table 6, we have compared the affinities of a series of methylenedioxy derivatives with those of the parent compounds (amphetamine and methamphetamine) at some of the recognition sites in brain at which MDMA exhibited the highest affinities. These comparative studies indicate that addition of the methylenedioxy subshtuent in the 3,4 position inereases their affinity at serotonin uptake, 5-HT2 serotonin, and M-1 muscarinic receptors, while the unsubstituted parent compounds appear to be more potent at Ct2-iadrenergic receptors. 

Amphetamine group— amphetamine, methamphetamine, methylenedioxyam-phetamine (MDA), methylenedioxymethylamphetamine (MDMA), methylenedioxy-ethylamphetamine (MDME or MDE)... 

The deficits in TPH activity and content of 5-HT and 5-HIAA normally seen in MDMA-treated rats were attenuated by concurrent administration of MT these deficits returned when L-dopa was administered concurrently with MT and MDMA. Prior treatment with 6-OHDA (described above) selectively attenuated the serotonergic deficits in the neostriatum while no protection by 6-OHDA occurred in the hippocampus or cerebral cortex. Prior depletion of DA with reserpine attenuated the neurotoxicity of MDMA. From these experiments the authors concluded that DA and/or its metabolites play a key role not only in the neurotoxicity observed with methamphetamine, but also with its methylenedioxy analogs. 

ATS include the amphetamine-group substances, consisting of methamphetamine and amphetamine, and the ecstasy-group substances, consisting mainly of 3,4-methylenedioxymethamphetamine (ecstasy or MDMA), 3,4-methylene-dioxyamphetamine (MDA), 3,4-methylenedioxy-A-ethylamphetamine (MDEA), and A-methyl-l-(3,4 methylenedioxyphenyl)-2-butanamine (MBDB)(UNODC, 2009). 

Amphetamine and related substances show symphaticomimetic and CNS stimulant activity. Amphetamines are indirect monoamine agonists and interact with the membrane transporters involved in neurotransmitter reuptake and vesicular storage systems. Therefore, they stimulate the release of norepinephrine, dopamine, and serotonin from presynaptic terminals in the CNS and at the peripheral level (De La Torre et al., 2004). Methamphetamine and the methylenedioxy derivatives (MDA, MDMA, MDEA, MBDB) can inhibit the activity of enzymes of dopamine or serotonin biosynthesis (De La Torre et al., 2004). 

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