Amphetamines ring-substituted

Fenfluramine, like MDMA and MDA, is a ring-substituted amphetamine derivative that has been found to meet all the criteria for neurotoxicity. 

Table 2 summarizes results of neurotoxicity studies that have utilized the same regimen of drug injections (twice daily for 4 days) and survival times (2 weeks). In addition, the ability of these drugs to suppress milk intake in rats is also presented. It is clear that ring-substituted amphetamines are more potent in terms of absolute dose required to reduce amine content than is the parent compound amphetamine. With regard to relative potency, METH is toxic to DA and 5-HT neurons at doses that are more than tenfold higher than doses that produce anorexia, whereas fenfluramine,... 

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

Note The microfiche I got this formula from was so abused that I could not read the instmctions for making the precursors. It may be interesting to see what effects this bromination will have on 3,4-methylenedioxyamphetamine and other ring substituted amphetamines. 

In discussing MDA and MMDA, psychiatrist Claudio Naranjo points out that a tiny percentage of the population is intensely sensitive to one-ring substituted amphetamines. Such persons may exhibit extreme reactions including sweating and hypertension as sometimes occurs with other amphetamine-like compounds. His recommendation is that an initial experience be of a low dosage. 

MDA-like compounds—such as the TMAs, DOB, DOET, DOM, MMDA, PBR, TMPEA, DMPEA, DMA, PMA and MED A—have molecular structures that resemble mescaline, dopamine and amphetamine. Moreover, the effects are often experienced as being like an interplay between mescaline and amphetamine—one or the other tendency predominating according to the structure of the particular compound. Thus this cluster often has been referred to as "psychedelic amphetamines. (A chemist would probably designate them as "alpha-methyl phenethylamines, "indolealkylamines or "one-ring substituted amphetamines. )... 

This is prepared by dissolving 5 ml of 40% formaldehyde in 100 ml of concentrated sulfuric acid. The reagent is then added directly to the test substrate. A purple-olive coloration is produced with opiates, and yellow-orange with amphetamine, methylamphetamine, psilocybin and psilocin, among others. A grey-purple colour reaction is obtained with ring-substituted amphetamines. 

Pierce, P.A. andS.J, Peroutkai9S8. Ring-substituted amphetamine interactions with neurotransmitter receptor binding sites in human cortex Neuroscience Letters 95(1-2) 208-212. 

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 ... 

Ring-substituted psychoactive derivatives of amphetamine exhibited high affinities for a number of serotonin recognition sites. Derivatives of... 

The following table lists common names, position of ring substitution, and approximate activity of the amphetamine derivatives for some readily available allyl and propenyl benzenes (see J. Chromatography 30,54(1967) for further information on these compounds). Activity is relative to mescaline which equals 1 (an activity of 12 means a dose of about 25 mg). Parentheses indicate a methylenedioxy bridge other substituents are methoxy groups. 

Add 0.44 moles ring substituted phenylacetate, 100 g acetic anhydride and 30 g sodium acetate and heat at 145-150° for 18 hours to get ca. 0.4 moles of the methyl-phenylacetate (I). Add (I) and formamide (or N-methyl-formamide for the N-methyl cpd.), heat 4-5 hours at 180-195°, cool and extract with CHC13. Evaporate in vacuum, dissolve residue in 40% sulfuric acid and heat at 90-125° for 5-6 hours. Neutralize and add solid NaOH to precipitate about 50% amphetamine. Treat with 10% sulfuric acid to get the sulfate. 

The meta-orientation of the two methoxyl groups does, however, greatly increase the susceptibility of the aromatic ring to electrophilic attack. This is one of the three possible meta-dimethoxy substituted amphetamines, and it is the best studied one in the pursuit of potential radio-halogen substituted brain blood-flow agents. This strategy is discussed under 1DNNA the other two meta-compounds are discussed under 3,4-DMA. 

The essential oil that corresponds to DMMDA is, of course, apiole from the Oil of Parsley, which again ties together the spice world and the amphetamine world. And there is isoapiole, also a natural thing. This pair represents the ring-substitution pattern of one of the ten essential oils and DMMDA is one of the ten essential amphetamines. 

Gordon Alles, a pharmacologist associated with the Medical School of the University of California in Los Angeles and the initial sponsor of Edward Anderson s peyote studies, was very interested in this area of chemistry and eventually synthesized a number of psychoactive compounds that have chemical structures similar to that of mescaline. The best known of these are amphetamine and MDA. His discoveries inspired further investigations that led to the creation of quite a number of "one-ring substituted phenyl-isopropylamines, which look much like mescaline on the molecular level but so far rarely have been found in the natural world. Many of these compounds will be discussed in Chapter Five. 

In addition, while in some GC-MS systems it is possible to obtain a molecular ion and individual fragments for amphetamine (Figure 2.2) under the majority of conditions, amphetamines without ring substitutions fragment in a very similar... 

Several presumptive tests are available for barbiturates and benzodiazepines. These are not as general as those used for other drug classes (for example, the Marquis test for opiates and amphetamines (including ring-substituted species)), but have the disadvantage that they do not discriminate between the drugs within the specific class. These tests are described in the following sections. 

Aromatic Ring Substitution. Simple ring substituents can change the targets of the amphetamines from one monoamine uptake carrier to another. The dopamine and norepinephrine uptake carrier proteins have the most stringent structural demands, and any... 

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