Substituerede amfetaminer

Optiske isomerer af amfetamin

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.

1. ^ ^{a b c d e f g h i j k l m n} Hagel JM, Krizevski R, Marsolais F, Lewinsohn E, Facchini PJ (2012). "Biosynthesis of amphetamine analogs in plants". Trends Plant Sci. 17 (7): 404-412. doi:10.1016/j.tplants.2012.03.004. PMID 22502775. 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.
2. ^ ^{a b c} Glennon RA (2013). "Phenylisopropylamine stimulants: amphetamine-related agents". Foye's principles of medicinal chemistry (7th udgave). Philadelphia, USA: Wolters Kluwer Health/Lippincott Williams & Wilkins. s. 646-648. ISBN 9781609133450. 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).
3. ^ Lillsunde P, Korte T (marts 1991). "Determination of ring- and N-substituted amphetamines as heptafluorobutyryl derivatives". Forensic Sci. Int. 49 (2): 205-213. doi:10.1016/0379-0738(91)90081-s. PMID 1855720.
4. ^ Custodio, Raly James Perez; Botanas, Chrislean Jun; Yoon, Seong Shoon; Peña, June Bryan de la; Peña, Irene Joy dela; Kim, Mikyung; Woo, Taeseon; Seo, Joung-Wook; Jang, Choon-Gon; Kwon, Yong Ho; Kim, Nam Yong (2017-11-01). "Evaluation of the Abuse Potential of Novel Amphetamine Derivatives with Modifications on the Amine (NBNA) and Phenyl (EDA, PMEA, 2-APN) Sites". Biomolecules & Therapeutics (engelsk). 25 (6): 578-585. doi:10.4062/biomolther.2017.141. ISSN 2005-4483. PMC 5685426. PMID 29081089.