3.4- methylene-dioxyamphetamine

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. 

Kamien, J.B. Johanson, C.E. Schuster, C.R. and Woolverton, W.L. The effects of ( )methylenedioxymethamphetamine and ( )methylene-dioxyamphetamine in monkeys trained to discriminate (-l-)amphetamine from saline. Drug Alcohol Depend 18 139-147, 1986. 

Battaglia, G. Yeh, S.Y. O Heam Kuhar, M.J. Molliver, M.E. and De Souza, E.B. 3,4-Methylenedioxymethamphetamine and 3,4-methylene-dioxyamphetamine destroy serotonin terminals in rat brain Quantification of neurodegeneration by measurement of [ HJparoxetine-labeled serotonin uptake sites. J Pharmacol Exp Ther 242 911-916, 1987. 

This chapter discusses the responses of these extrapyramidal neuropeptide systems to the amphetamine analogs methamphetamine (METH), methylene dioxyamphetamine (MDA), and methylenedioxymethamphetamine (MDMA). These dmgs were selected for this study because they represent somewhat diverse mechanisms of action. While all three agents are able to enhance extrapyramidal serotonergic activity (Schmidt et al. 1987). only METH has been characterized as a substantial stimulant of the DA system. The effects of MDA and MDMA on extrapyramidal DA systems have not been well elucidated. Thus, evaluating and comparing the responses of the SP, NT, and Dyn extrapyramidal systems to these dmgs will help to determine the nature of the DA responses to METH, MDA, and MDMA administrations. 

Ricaurte GA, Markowska AL, Wenk GL, et al 3,4-Methylene dioxyamphetamine, serotonin and memory. J Pharmacol Exp Ther 266 1097-1105, 1993... 

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. 

In addition, other drugs that do not act as primary hallucinogens, such as methylene-dioxyamphetamine derivatives (e.g., 3,4-dimethylene-dioxymethamphetamine, Ecstasy ) and cocaine pose a health risk. The acute intoxication is associated with a misperception of reality, a period of exhaustion follows. After prolonged use, dependence develops associated with intellectual degradation and physical decay. Withdrawal therapy is very dif cult. Marihuana frequently serves as an entry-level recreational substance for hard drugs. 

Hensley D, Cody JT. Simultaneous determination of amphetamine, methamphetamine, methylene-dioxyamphetamine (MDA), methylenedioxymethamphetamine (MDMA), and methylenedioxyethylam-phetamine (MDEA) enantiomers by GC-MS. J Anal Toxicol 1999 23 518-523. 

Mcl nna, D.J. etal. i99r. 3,4-Methylene-dioxyamphetamine (mda) analogues exhibit differential effects on synaptosomal release of H-dopamine and H-5-hydrox-ytryptamine Pharmacology Biochemistry and Behavior 505-512. 

Maurer, M. ayahtmsca psychonaut)—225 Mayan Indians of C. Am.—125,277,351,382 Maypure Indians of South America-165 Mazan Indians of South America-199 Mazatec Indians of Mexico-76,126,194,213, 284,307,313.315-6,381-4 MDA(3,4-Methylene-DioxyAmphetamine)-54,90-2,154,188,441 MDDM (AjA -dimethyl-MDA)—91 MDE (iV-ethyl-MDA)—gi MDip (Ai-isopropyl-MDA)-9i MDMA (Af-methyl-MDA)-68,9i-2,244,442 MDPR (Ai-propyl-MDA)-9i mead (metheglin)—157,307 mellitoxin (hyenanchin, hyaenanchin)-398 Mendez, E.-284... 

Hyperthermic patients are usually obtunded, agitated or thrashing about, diaphoretic, and hyperreflexic. Untreated, hyperthermia may result in hypotension, coagulopathy, rhabdomyolysis, and hepatic and other organ failure (see p 21). Hyperthermia has been associated with LSD, methylene dioxyamphetamine (MDA), MDMA, and paramethoxyamphetamine (PMA). 

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). 

We report a vibrational spectroscopic study of several yS-methyl-y nitrostyrene derivatives that are important intermediates in the synthesis of illicit amphetamine-like drugs, such as 3,4-methylenedioxymethamphetamine ( ecstasy or MDMA), 3,4-methylene-dioxyamphetamine (MDA), 4-methyl-thioamphetamine (MTA) and 4-methoxyamphetamine (PMA). A complete vibrational analysis of these systems was carried out by Raman spectroscopy and DFT calculations (103), The corresponding Raman spectra evidenced distinctive features for each of the >5-nitrostyrene precursors investigated (Figure 7), allowing their ready identification in the final product (104),... 

The stereoselective synthesis of (5)-3,4-methylene dioxyamphetamines (5)-36, which are controversially discussed as psychoactive compounds [63], is another interesting example... 

---