Substituerede amfetaminer
 |  |
 |  |
| 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.
Eksempler
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 ethylgrupper på amin- og fenylgrupperne:[5][6][7]
| Stof | Substituenter | Struktur | ||||||
|---|---|---|---|---|---|---|---|---|
| N | α | β | fenylgruppe | |||||
| 2 | 3 | 4 | 5 | |||||
| Phenethylamin |  | |||||||
| Amfetamin (α-methylphenylethylamine) | -CH3 |  | ||||||
| Metamfetamin (N-metylamfetamin) | -CH3 | -CH3 |  | |||||
| Fentermin (α-metylamfetamin) | -(CH3)2 |  | ||||||
| Efedrin | -CH3 | -CH3 | -OH | -Ephedrin.svg){kind=small} | ||||
| Pseudoefedrin | -CH3 | -CH3 | -OH | -Pseudoephedrin.svg){kind=small} | ||||
| Cathinon | -CH3 | =O |  | |||||
| Metcathinon (efedron) | -CH3 | -CH3 | =O |  | ||||
| MDA (3,4-methylenedioxyamphetamine) | -CH3 | -O-CH2-O- |  | |||||
| MDMA (3,4-metylenedioxymethamfetamin) | -CH3 | -CH3 | -O-CH2-O- | .svg){kind=small} | ||||
| MDEA (3,4-metylenedioxy-N-etylamfetamin) | -CH2-CH3 | -CH3 | -O-CH2-O- |  | ||||
| EDMA (3,4-etylenedioxy-N-metylamfetamin) | -CH3 | -CH3 | -O-CH2-CH2-O- |  | ||||
| MBDB (N-metyl-1,3-benzodioxolylbutanamin) | -CH3 | -CH2-CH3 | -O-CH2-O- |  | ||||
| PMA (para-methoxyamfetamin) | -CH3 | -O-CH3 |  | |||||
| PMMA (para-metoxymetamfetamin) | -CH3 | -CH3 | -O-CH3 |  | ||||
| 4-MTA (4-metylthioamfetamin) | -CH3 | -S-CH3 |  | |||||
| 3,4-DMA (3,4-dimetoxyamfetamin) | -CH3 | -O-CH3 | -O-CH3 |  | ||||
| 3,4,5-trimetoxyamfetamin (α-metylmescalin) | -CH3 | -O-CH3 | -O-CH3 | -O-CH3 |  | |||
| DOM (2,5-dimethoxy-4-metylamfetamin) | -CH3 | -O-CH3 | -CH3 | -O-CH3 |  | |||
| DOB (2,5-dimethoxy-4-bromoamfetamin) | -CH3 | -O-CH3 | -Br | -O-CH3 |  | |||
Referencer
- ^ 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. - ^ 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).
- ^ 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.
- ^ 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.
- ^ Goldfrank, s. 1125-1127
- ^ Glennon, s. 184-187
- ^ Schatzberg, s. 843
Bibliografi
- Ghodse, Hamid (2002). Drugs and Addictive Behaviour. A Guide to Treatment. 3rd Edition. Cambridge University Press. s. 501. ISBN 978-0-511-05844-8.
- Glennon, Richard A. (2008). "Neurobiology of Hallucinogens". The American Psychiatric Publishing textbook of substance abuse treatment. American Psychiatric Publishing. ISBN 978-1-58562-276-4.
- Goldfrank, Lewis R. & Flomenbaum, Neal (2006). Goldfrank's Toxicologic Emergencies, 8th Edition. McGraw Hill. ISBN 978-0-07-147914-1.
- Katzung, Bertram G. (2009). Basic & clinical pharmacology. 11th edition. McGraw-Hill Medical. ISBN 978-0-07-160405-5. (Webside ikke længere tilgængelig)
- Ledgard, Jared (2007). A Laboratory History of Narcotics. Volume 1. Amphetamines and Derivatives. Jared Ledgard. s. 268. ISBN 978-0-615-15694-1.
- Schatzberg, Alan F. & Nemeroff, Charles B. (2009). The American Psychiatric Publishing Textbook of Psychopharmacology. The American Psychiatric Publishing. ISBN 978-1-58562-309-9.
- Snow, Otto (2002). Amphetamine syntheses. Thoth Press. ISBN 978-0-9663128-3-6.
- Veselovskaya NV, Kovalenko AE (2000). Drugs. Properties, effects, pharmacokinetics, metabolism. MA: Triada-X. ISBN 978-5-94497-029-9.
 | Infoboks uden skabelon Denne artikel har en infoboks dannet af en tabel eller tilsvarende. |
|
Medier brugt på denne side
List-Icon.svg
Forfatter/Opretter: Tango Project], Gnome, og VisualEditor team, Licens: GPL
Icon used to indicate a list
Forfatter/Opretter: Tango Project], Gnome, og VisualEditor team, Licens: GPL
Icon used to indicate a list
2,5-Dimethoxy-4-methylamphetamine.svg
2,5-Dimethoxy-4-methylamphetamine; DOM or STP
2,5-Dimethoxy-4-methylamphetamine; DOM or STP
PMA.svg
2D structure of empathogen drug PMA (paramethoxyamphetamine)
2D structure of empathogen drug PMA (paramethoxyamphetamine)
D-amphetamine.svg
Dextroamphetamine structure
Dextroamphetamine structure
L-amphetamine.svg
Levamphetamine structure
Levamphetamine structure
Phenylethyl Amine General Formula V1.svg
Forfatter/Opretter: Jü, Licens: CC BY-SA 4.0
General structure of phenylethyl amines (a group of compounds)
Forfatter/Opretter: Jü, Licens: CC BY-SA 4.0
General structure of phenylethyl amines (a group of compounds)
EDMA.svg
Chemical diagram for EDMA (3,4-ethylenedioxy-N-methylamphetamine)
Chemical diagram for EDMA (3,4-ethylenedioxy-N-methylamphetamine)
(+)-Pseudoephedrin.svg
Structure of (+)-Pseudoephedrine
Structure of (+)-Pseudoephedrine
MDEA.svg
2D structure of CNS stimulant MDEA
2D structure of CNS stimulant MDEA
Phenethylamine2DCSD.svg
Structure of
Structure of
MBDB.svg
2D structure of CNS stimulant MBDB
2D structure of CNS stimulant MBDB
(+)-Ephedrin.svg
Structure of (+)-Ephedrine
Structure of (+)-Ephedrine
4-Methoxymethamphetamine.svg
Forfatter/Opretter: JaGa, Licens: CC BY-SA 3.0
Skeletal structure of 4-methoxymethamphetamine.
Forfatter/Opretter: JaGa, Licens: CC BY-SA 3.0
Skeletal structure of 4-methoxymethamphetamine.
Racemic amphetamine 2.svg
racemic amphetamine
racemic amphetamine
MDMA (simple).svg
2D structure of empathogen drug MDMA (methylenedioxymethamphetamine)
2D structure of empathogen drug MDMA (methylenedioxymethamphetamine)
R-DOB.svg
2D structure of psychedelic amphetamine DOB (R-isomer)
2D structure of psychedelic amphetamine DOB (R-isomer)
Methcathinone skeletal.svg
Skeletal formula of methcathinone. Created using ACD/ChemSketch 10.0 and Inkscape.
Skeletal formula of methcathinone. Created using ACD/ChemSketch 10.0 and Inkscape.
Methamphetamine.svg
2D structure of stimulant drug methamphetamine
2D structure of stimulant drug methamphetamine
4-methylthioamphetamine.svg
2D structure of CNS stimulant 4-MTA (also called para-methylthioamphetamine)
2D structure of CNS stimulant 4-MTA (also called para-methylthioamphetamine)
MDA-2D-skeletal.svg
2D structure of empathogen drug MDA (3,4-methylenedioxyamphetamine)
2D structure of empathogen drug MDA (3,4-methylenedioxyamphetamine)
Trimethoxyamphetamine structure.svg
Trimethoxyamphetamine; alpha-Methylmescaline
Trimethoxyamphetamine; alpha-Methylmescaline
Amphetamine numbered.svg
Amphetamine structural formula with positions numbered
Amphetamine structural formula with positions numbered