Substituerede amfetaminer

Optiske isomerer af amfetamin
L-ampfetaminD-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.

Eksempler

Phenethylamin (blå) med markerede substitutionspunkter. Amfetamin and dets substituerede derivater indeholder en CH3-gruppe på alfa-positionen (Rα).
Amfetamin med markerede substitutionspunkter (undtagen N-positionen på NH2-gruppen som er umarkeret.

Amfetaminer er selv en undergruppe af substituerede phenethylamin-forbindelser. Substitution af brintatomer resulterer i en stor klasse af kemiske forbindelser. Typisk reaktioner er substitution med methyl- og nogle gange ethylgrupperamin- og fenylgrupperne:[5][6][7]

StofSubstituenterStruktur
Nαβfenylgruppe
2345
PhenethylaminPhenethylamin
Amfetamin (α-methylphenylethylamine)-CH3Amfetamin
Metamfetamin (N-metylamfetamin)-CH3-CH3Metamfetamin
Fentermin (α-metylamfetamin)-(CH3)2Fentermin
Efedrin-CH3-CH3-OH(+)-Efedrin
Pseudoefedrin-CH3-CH3-OH(+)-Pseudoefedrin
Cathinon-CH3=OCathinon
Metcathinon (efedron)-CH3-CH3=OMetcathinon
MDA (3,4-methylenedioxyamphetamine)-CH3-O-CH2-O-3,4-metylendioksyamfetamin
MDMA (3,4-metylenedioxymethamfetamin)-CH3-CH3-O-CH2-O-3,4-metylenedioxymethamfetamin
MDEA (3,4-metylenedioxy-N-etylamfetamin)-CH2-CH3-CH3-O-CH2-O-Metylenedioxyetylamfetamin
EDMA (3,4-etylenedioxy-N-metylamfetamin)-CH3-CH3-O-CH2-CH2-O-3,4-etylenedioxy-N-metylamfetamin
MBDB (N-metyl-1,3-benzodioxolylbutanamin)-CH3-CH2-CH3-O-CH2-O-N-metyl-1-(3,4-metylenedioxyfenyl)-2-aminobutan
PMA (para-methoxyamfetamin)-CH3-O-CH3para-methoxyamfetamin
PMMA (para-metoxymetamfetamin)-CH3-CH3-O-CH3para-metoxymetamfetamin
4-MTA (4-metylthioamfetamin)-CH3-S-CH34-metylthioamfetamin
3,4-DMA (3,4-dimetoxyamfetamin)-CH3-O-CH3-O-CH3Dimetoxyamfetamin
3,4,5-trimetoxyamfetamin (α-metylmescalin)-CH3-O-CH3-O-CH3-O-CH3Trimetoxyamfetamin
DOM (2,5-dimethoxy-4-metylamfetamin)-CH3-O-CH3-CH3-O-CH32,5-dimethoxy-4-metylamfetamin
DOB (2,5-dimethoxy-4-bromoamfetamin)-CH3-O-CH3-Br-O-CH32,5-dimethoxy-4-bromoamfetamin

Referencer

  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.
  5. ^ Goldfrank, s. 1125-1127
  6. ^ Glennon, s. 184-187
  7. ^ Schatzberg, s. 843

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L-amphetamine (levoamphetamine) 3D structure (methodology)
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2,5-Dimethoxy-4-methylamphetamine; DOM or STP
PMA.svg
2D structure of empathogen drug PMA (paramethoxyamphetamine)
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Dextroamphetamine structure
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Levamphetamine structure
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General structure of phenylethyl amines (a group of compounds)
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Chemical diagram for EDMA (3,4-ethylenedioxy-N-methylamphetamine)
(+)-Pseudoephedrin.svg
Structure of (+)-Pseudoephedrine
MDEA.svg
2D structure of CNS stimulant MDEA
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D-amphetamine (dextroamphetamine) 3D structure (methodology)
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Skeletal formula of phentermine.
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2D structure of CNS stimulant MBDB
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Structure of (+)-Ephedrine
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Skeletal structure of 4-methoxymethamphetamine.
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racemic amphetamine
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2D structure of empathogen drug MDMA (methylenedioxymethamphetamine)
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2D structure of psychedelic amphetamine DOB (R-isomer)
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Chemical structure of 3,4-dimethoxyamphetamine, drawn in ChemDraw by User:Mark PEA.
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2D structure of stimulant drug methamphetamine
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2D structure of CNS stimulant 4-MTA (also called para-methylthioamphetamine)
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2D structure of empathogen drug MDA (3,4-methylenedioxyamphetamine)
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Trimethoxyamphetamine; alpha-Methylmescaline
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Amphetamine structural formula with positions numbered