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L-ampfetamin | D-ampfetamin |
Substituerede amfetaminer eller amfetaminer er en klasse af kemiske stoffer baseret på amfetamins struktur.[1] Den omfatter alle derivater som er dannet ved at erstatte eller substituere et eller flere brintatomer i amfetamin med substituenter.[1][2][3][4] Forbindelserne i denne gruppe spænder over en række farmakologiske midler, herunder stimulanter, empatogener og hallucinogener og andre.[2] Eksempler på substituerede amfetaminer er amfetamin,[1][2] metamfetamin,[1] efedrin,[1] cathinon,[1] fentermin,[1] mefentermin,[1] bupropion,[1] methoxyfenamin,[1] selegilin,[1] amfepramon,[1] pyrovaleron,[1] MDMA (ecstasy) og DOM (STP).
Nogle af amfetamins substituerede derivater forekommer i naturen, for eksempel i bladene på ledris- og khat-planter, som har været brugt af mennesker i mere end 1000 år for deres farmakologiske virkninger.[1] Amfetamin blev først fremstillet i slutningen af det 19. århundrede. I 1930'erne fandt amfetamin og nogle af dets derivater brug som anti-kongestanter i symptomatisk behandling af forkølelse og også lejlighedsvis som psykoaktive midler. Deres virkninger på centralnervesystemet er forskelligartede, men kan opsummeres ved tre overlappende typer aktivitet: psykoanaleptisk, hallucinogen og empatogen. Forskellige substituerede amfetaminer kan forårsage disse virkninger enten separat eller i kombination.
Substituted amphetamines, which are also called phenylpropylamino alkaloids, are a diverse group of nitrogen-containing compounds that feature a phenethylamine backbone with a methyl group at the α-position relative to the nitrogen (Figure 1). Countless variation in functional group substitutions has yielded a collection of synthetic drugs with diverse pharmacological properties as stimulants, empathogens and hallucinogens [3]. ... Beyond (1R,2S)-ephedrine and (1S,2S)-pseudoephedrine, myriad other substituted amphetamines have important pharmaceutical applications. The stereochemistry at the α-carbon is often a key determinant of pharmacological activity, with (S)-enantiomers being more potent. For example, (S)-amphetamine, commonly known as d-amphetamine or dextroamphetamine, displays five times greater psychostimulant activity compared with its (R)-isomer [78]. Most such molecules are produced exclusively through chemical syntheses and many are prescribed widely in modern medicine. For example, (S)-amphetamine (Figure 4b), a key ingredient in Adderall and Dexedrine, is used to treat attention deficit hyperactivity disorder (ADHD) [79]. ...
[Figure 4](b) Examples of synthetic, pharmaceutically important substituted amphetamines.
The simplest unsubstituted phenylisopropylamine, 1-phenyl-2-aminopropane, or amphetamine, serves as a common structural template for hallucinogens and psychostimulants. Amphetamine produces central stimulant, anorectic, and sympathomimetic actions, and it is the prototype member of this class (39).
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