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Either your web browser doesn't support Javascript or it is currently turned off. In the latter case, please turn on Javascript support in your web browser and reload this page. Refer to the copyright information in the article for licensing details. Free full text in Europe PMC. Amphetamine and its derivatives exhibit a wide range of pharmacological activities, including psychostimulant, hallucinogenic, entactogenic, anorectic, or antidepressant effects. The mechanisms of action underlying these effects are usually related to the ability of the different amphetamines to interact with diverse monoamine transporters or receptors. Moreover, many of these compounds are also potent and selective monoamine oxidase inhibitors. Furthermore, we discuss how monoamine oxidase inhibition might influence the pharmacology of these compounds. Nowadays, AMPH is indicated for the treatment of attention deficit hyperactivity disorder Heal et al. Its psychostimulant effects are usually related to its catecholamine-releasing properties, which arise from its ability to compete with dopamine DA and norepinephrine NE for uptake into the nerve terminals, and to induce reverse transport via the corresponding transporter DAT and NET, respectively. Nevertheless, its polypharmacological profile involves actions upon other monoaminergic targets such as the serotonin 5-HT transporter SERT , the vesicular monoamine transporter and monoamine oxidase MAO Sulzer et al. A remarkable characteristic of AMPH is that subtle structural variations can produce drastic changes in its pharmacodynamics, and lead to compounds that interact differentially with several biogenic amine target proteins. Consequently, the AMPH skeleton has served as a privileged scaffold for the design and synthesis of hundreds of derivatives with many different and often useful activities, but also conveying misuse potential Biel and Bopp, ; Nichols, ; Glennon, ; Rothman and Baumann, ; Welter-Luedeke and Maurer, Thus, the diversity of mechanisms of action of AMPH derivatives determines a many-colored palette of pharmacological activities in humans, including psychostimulant, entactogenic, psychedelic, anorectic, nootropic, and antidepressant effects. It is noteworthy that the structural changes also modify toxicological properties and abuse liability of AMPH derivatives Fleckenstein et al. MAO monoamine oxygen oxidoreductase deaminating flavin-containing ; EC 1. Both isozymes are outer mitochondrial membrane-bound flavoproteins, with the FAD cofactor covalently bound to the enzyme. The metabolic reaction involves the generation of an imine intermediate and the reduction of the flavin cofactor, which is reoxidized by molecular oxygen producing hydrogen peroxide. The imine intermediate is hydrolyzed, in a non-enzymatic process, generating ammonia and the corresponding aldehyde Shih et al. Although both isoforms have similar catalytic activities, they differ in their molecular genetics, physiological roles, tissue distribution, substrate preference, and inhibitor selectivity Reyes-Parada et al. MAO-A preferentially metabolizes 5-HT and is irreversibly inhibited by nanomolar concentrations of clorgyline, whereas MAO-B preferentially catalyzes the oxidative deamination of phenethylamine and benzylamine and is irreversibly inhibited by nanomolar concentrations of l -deprenyl. DA and NE are non-selective substrates of both isoforms Youdim et al. MAO inhibitors MAOI are currently used in the treatment of diverse neuropsychiatric and neurological disorders, including depression and Parkinson's disease Cesura and Pletscher, ; Youdim et al. In , Binda and colleagues Binda et al. Subsequent structures of this enzyme Binda et al. The availability of MAO crystal structures has allowed a quicker pace in the rational design of novel MAOIs and in the understanding of catalytic and inhibitory mechanisms. In all cases, for the sake of clarity, only the most relevant residues are shown. Docking conditions were as in Fierro et al. Since the first pharmacological study more than 50 years ago proving the existence of the two enzyme isoforms Johnston, , hundreds of AMPH derivatives have been tested as MAOIs. Tables 1 — 5 summarize the effects of a subset of these compounds. It should be noted that, as expected for results obtained from different laboratories over a long period of time, the methodological approaches used to assess MAO inhibition are diverse. Thus, a variety of biochemical assays to follow MAO activities e. IC 50 , K i , tissue sources e. Therefore, although we made an effort to consider results obtained under relatively similar conditions for comparative analysis, the reader should bear in mind this limitation when evaluating the data presented below. When not indicated, the compound is the racemic mixture. NT, Not tested. Ar, Aromatic ring. Thus, in the vast majority of the cases in which a relevant inhibitory activity was detected, this effect shows a clear selectivity towards MAO-A e. Mantle et al. Even though no crystal structure of MAO-A in complex with AMPH derivatives has been reported yet, docking simulations have shed light on the molecular mechanism underlying both the MAO-A inhibitory activity and the selectivity exhibited by these compounds Vallejos et al. Figure 2 summarizes our current view in this regard. Thus, when a substrate, in this case 5-HT, is docked at the catalytic site, it locates in a pose where the amino group is in close proximity to the isoalloxazine ring of the FAD cofactor Figure 2A. Indeed, such a binding mode provides a rationale for the observed inhibitory activity, since while blocking the access of any substrate to the active site, AMPH derivatives could avoid deamination by adopting a pose where the amino group is remote from the influence of the flavin ring. Edwards, ; Yu, ; Fagervall et al. Figure 3. Although stereospecific abstraction of the pro- R -hydrogen has been demonstrated with several substrates Yu et al. Moreover, cyclization of the side chain to generate 2-aminoindan or 2-aminotetraline analogues results in a marked decrease of the affinity of these compounds for MAOs Feenstra et al. Such reductions of inhibitory activity would presumably reflect impediments to binding in the enzyme's active site. When not indicated the compound is the racemic mixture. This suggests that stereoselectivity may not be as influential in the pharmacodynamics of these compounds as has been shown to be for the effects of AMPH derivatives upon other monoaminergic target proteins such as monoamine transporters or 5-HT receptors Nichols, ; Nichols, Given the notoriety that the recreational use of cathinone derivatives has reached in the last few years Simmler et al. Nevertheless, Osorio-Olivares et al. Nevertheless, some of these compounds showed an interesting MAO-B inhibiting activity Table 3 , which suggests that selectivity can be effectively modulated by side-chain substituents. In addition, enlargement of the amine substituent to N -ethyl, N - n -propyl, or N -allyl seems to cause a further decrease in MAO-A affinity, correlated with the length of the substituent Kilpatrick et al. Furthermore, tertiary amines i. Even though some aliphatic MAO substrates and inhibitors have been identified Yu et al. Accordingly, a handful of QSAR studies have shown that electronic features of the benzene ring e. In this respect, the presence of a single substituent with electron-donor properties e. The importance of the electron-donor character of the substituent at the para position is substantiated by the significant decrease of potency observed when the p -methylthio group is replaced by electron-withdrawing moieties such as p -methylsulfoxy or p -methylsulfonyl i. It has been suggested Fierro et al. Longer chains, however, might oblige the compound to adopt a more folded conformation, which would disfavor their interaction with the residues at the binding site. In contrast, the presence of substituents at the ortho or meta positions in para -unsubstituted compounds had no effect or led to a decrease of the potency as MAOI-A as compared with AMPH Green and el Hait, ; Scorza et al. Moreover, the addition of bulky groups adjacent to the para -substituted position induces a decrease in potency. Thus, the presence of one or two substituents at the meta position s of PMA produce compounds that are respectively fold less potent or completely inactive Scorza et al. Nonetheless, the introduction of substituents at more distant positions has less detrimental effects on potency, and even in some cases a marked increase of activity and selectivity has been reported. IC 50 values are from Scorza et al. NE, No effect. This could have been anticipated considering that: a the structure of 5-HT, one of the natural substrates of MAO-A, contains an indolyl moiety instead a simple benzene ring and; b the electron-richness of the aromatic ring seems to be an important molecular determinant for MAO-A affinity Vallejos et al. Both electronic and steric factors have been invoked to explain the higher activity of AMPH derivatives containing aromatic rings larger than benzene Vallejos et al. In addition, docking simulations have shown that AMPH derivatives containing large aromatic rings, can establish interactions not only with the aromatic residues forming the so-called aromatic cage i. Y and Y , but also with aminoacids located more distantly, such as F, Y69, and F Vallejos et al. Therefore, the higher potency of AMPH derivatives containing condensed aromatic systems could be explained by an increased probability of establishing dispersive short length interactions and also a greater number of interactions. This is likely due to the structural similarity of this type of compounds with physiological substrates, which allows AMPH derivatives to occupy, and consequently block the access of any substrate into the active site of the enzyme. Although not extensively studied, in general the introduction of diverse substituents on either the amino group or the side chain of the basic AMPH skeleton leads to compounds with lower affinity as compared with the parent counterparts. Besides, as aromatic interactions in the active site of the enzyme seem to be critical for inhibition, substituents at this portion of the AMPH structure greatly modulate its potency. In general, electron-donor substituents at the para position of the aromatic ring generate potent MAOI-A, while substituents adjacent to this position decrease activity. Even though MAO inhibition has been demonstrated for several AMPH derivatives, this is often considered not relevant for their global effect, since their affinity for MAO is usually weak compared to affinity for their main pharmacological targets i. This is most likely true in the case of compounds such as the anti-obesity agents phentermine and fenfluramine Kilpatrick et al. However, in the case of monoamine releasing agents such as PMA or MTA, their potency upon their main protein targets i. Thus, one may assume that the cases of severe toxicity reported after recreational use of these drugs e. Elliott, ; De Letter et al. In this sense, accumulation and pronounced inhibition of MAO in monoaminergic neurons has been consistently reported for amiflamine and its analogues Ask et al. Thus, for example, considering the high overlap between depression and drug abuse Markou et al. Thus, these and other examples highlight the notion that MAOI properties should be considered when assessing the overall pharmacology of AMPH derivatives. This calls for a broader exploration of the chemical space around the parent scaffold in the search of compounds with novel properties, in which MAOI properties might or might not be pursued. Regarding the mechanism of enzyme inhibition, insofar as a crystal structure of MAO in complex with some AMPH derivative is not available, molecular simulation appears as one of the most reliable tools to study this issue. Nevertheless, most of current information has been obtained through docking studies, without resorting to molecular dynamics simulations that consume much more computer time, and therefore models generated still require a further validation. Hence, inferences regarding possible effects in humans should be most cautious when data are obtained initially in animal models. Moreover, in comparison to recent characterizations of the monoamine transporter and receptor interactions of amphetamines Simmler et al. Therefore, comparative analyses should be done cautiously when considering results obtained under different experimental conditions. Beyond these considerations, in our view it is clear that AMPH derivatives can act as MAOI and that this activity should be taken into account when analyzing the overall pharmacodynamics of these structurally versatile compounds. All authors equally contributed to the writing of this manuscript. The authors declare that the research was conducted in the absence of any commercial or financial relationships that could be construed as a potential conflict of interest. The authors are grateful to all the colleagues who have contributed over the years to the studies carried out in our laboratories on the MAOI properties of AMPH derivatives. We also thank Dr. This characteristic leads to an irreversible mode of inhibition and generates completely different structure-activity relationships. These have been analyzed elsewhere e. Magyar, ; Yoshida et al. Molecules , 28 16 , 09 Aug Molecules , 28 1 , 24 Dec Int J Mol Sci , 23 12 , 12 Jun Int J Mol Sci , 22 21 , 05 Nov Fitzgerald PJ. Int J Mol Sci , 22 19 , 02 Oct This data has been text mined from the article, or deposited into data resources. Europe PMC requires Javascript to function effectively. Search life-sciences literature 44,, articles, preprints and more Search Advanced search. This website requires cookies, and the limited processing of your personal data in order to function. By using the site you are agreeing to this as outlined in our privacy notice and cookie policy. Reyes-Parada M 1 ,. Iturriaga-Vasquez P 2 ,. Cassels BK 3. Affiliations 1. Authors Reyes-Parada M 1. Authors Iturriaga-Vasquez P 2. Authors Cassels BK 3. Share this article Share with email Share with twitter Share with linkedin Share with facebook. Abstract Amphetamine and its derivatives exhibit a wide range of pharmacological activities, including psychostimulant, hallucinogenic, entactogenic, anorectic, or antidepressant effects. Free full text. Front Pharmacol. Published online Jan PMID: Cassels 4. Bruce K. Author information Article notes Copyright and License information Disclaimer. Liechti, University Hospital of Basel, Switzerland. This article was submitted to Neuropharmacology, a section of the journal Frontiers in Pharmacology. Received Sep 14; Accepted Dec 9. The use, distribution or reproduction in other forums is permitted, provided the original author s and the copyright owner s are credited and that the original publication in this journal is cited, in accordance with accepted academic practice. No use, distribution or reproduction is permitted which does not comply with these terms. This article has been cited by other articles in PMC. Go to:. Keywords: monoamine oxidase, amphetamine derivatives, serotonin syndrome, serotonin transporter, dopamine transporter, norepinephrine transporter, monoamine oxidase-A. Open in a separate window. Figure 1. Figure 2. Figure 4. Figure 5. Figure 6. Figure 7. Figure 8. Figure 9. Figure Neurotoxicology of Synthetic Cathinone Analogs. Inhibition of brain type A monoamine oxidase and 5-hydroxytryptamine uptake by two amphetamine metabolites, p-hydroxyamphetamine and p-hydroxynorephedrine. Inhibition of 5-hydroxytryptamine accumulation and deamination by substituted phenylalkylamines in hypothalamic synaptosomes from normal and reserpine-pretreated rats. Naunyn Schmiedebergs Arch. Selective inhibition of the A form of monoamine oxidase by 4-dimethylamino-alpha-methylphenylalkylamine derivatives in the rat. Neuropharmacology 21 , — Selective inhibition of monoamine oxidase in monoaminergic neurons in the rat brain. Naunyn-Schmiedebergs Arch. Inhibition of monoamine oxidase in 5-hydroxytryptaminergic neurones by substituted p-aminophenylalkylamines. Selective inhibition of monoamine oxidase by p-aminosubstituted phenylalkylamines in catecholaminergic neurones. Neuropharmacology 25 , 33— Mitochondria: key players in the neurotoxic effects of amphetamines. Iversen L. New York, NY: Stimulants. Plenum; , 1— Structure of human monoamine oxidase B, a drug target for the treatment of neurological disorders. Insights into the mode of inhibition of human mitochondrial monoamine oxidase B from high-resolution crystal structures. Crystal structures of monoamine oxidase B in complex with four inhibitors of the N-propargylamino-indan class. Structural properties of human monoamine oxidases A, and B. Neurobiological mechanisms in addictive and psychiatric disorders. North Am. 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