آمفتامین استخلافی

آمفتامین‌های استخلافی دسته ای از ترکیبات شیمیایی هستند که ساختار هسته اصلی آن بر اساس ساختار آمفتامین بنا شده‌است.[1] این ترکیبات شامل تمام ترکیبات مشتق شده از آمفتامین به وسیله جابجایی یا جانشینی یک یا چند اتم هیدروژن در ساختار هسته آمفتامین با یک استخلاف است.[2][3][4][5] ترکیبات موجود در این دسته انواع مختلفی از زیردسته‌های دارویی را شامل می‌شوند، از جمله محرک‌ها، empathogenها، توهم‌زاها و غیره.[6] نمونه‌های آمفتامین استخلافی عبارت است از: آمفتامین (ترکیب هسته سازنده)،[7][8]مت‌آمفتامین،[9] افدرین،[10] کاتینون،[11] فنترمین،[12] مفنترمین،[13] بوپروپیون،[14] متوکسی فنامین،[15] سلژیلین،[16] آمفپرامون،[17] پیرووالرون،[18] MDMA (اکستازی) و DOM (STP).

آمفتامین استخلافی
کلاس دارویی
ساختار آمفتامین
شناسه‌های دسته‌بندی
طبقه‌بندی شیمیاییمشتقات استخلافی آمفتامین
در ویکی‌داده
ایزومرهای نوری آمفتامین
ال-آمفتامیندی-آمفتامین

فهرست برخی از آمفتامین‌های استخلافی
نام ژنریک یا غیررسمی نام شیمیایی # تعداد استخلاف‌ها
آمفتامینα-Methyl-phenethylamine۰
مت‌آمفتامینN-Methylamphetamine۱
EthylamphetamineN-Ethylamphetamine۱
پروپیل آمفتامینN-Propylamphetamine۱
IsopropylamphetamineN-iso-Propylamphetamine۱
Phentermineα-Methylamphetamine۱
فنیل پروپانول آمین (PPA)β-Hydroxyamphetamine, (1R,2S)-۱
کاتین (شیمی)β-Hydroxyamphetamine, (1S,2S)-۱
کاتینونβ-Ketoamphetamine۱
Ortetamine2-Methylamphetamine۱
2-Fluoroamphetamine (2-FA)2-Fluoroamphetamine۱
3-Methylamphetamine (3-MA)3-Methylamphetamine۱
2-Phenyl-3-aminobutane2-Phenyl-3-aminobutane۱
3-Fluoroamphetamine (3-FA)3-Fluoroamphetamine۱
نورفن‌فلورآمین3-Trifluoromethylamphetamine۱
4-Methylamphetamine (4-MA)4-Methylamphetamine۱
para-Methoxyamphetamine (PMA)4-Methoxyamphetamine۱
para-Ethoxyamphetamine4-Ethoxyamphetamine۱
4-Methylthioamphetamine (4-MTA)4-Methylthioamphetamine۱
Norpholedrine (α-Me-TRA)4-Hydroxyamphetamine۱
para-Bromoamphetamine (PBA, 4-BA)4-Bromoamphetamine۱
para-Chloroamphetamine (PCA, 4-CA)4-Chloroamphetamine۱
para-Fluoroamphetamine (PFA, 4-FA, 4-FMP)4-Fluoroamphetamine۱
para-Iodoamphetamine (PIA, 4-IA)4-Iodoamphetamine۱
ClobenzorexN-(2-chlorobenzyl)-1-phenylpropan-2-amine۱
DimethylamphetamineN,N-Dimethylamphetamine۲
BenzphetamineN-Benzyl-N-methylamphetamine۲
D-DeprenylN-Methyl-N-propargylamphetamine, (S)-۲
سلژیلینN-Methyl-N-propargylamphetamine, (R)-۲
مفنترمینN-Methyl-α-methylamphetamine۲
Phenpentermineα,β-Dimethylamphetamine۲
افدرینβ-Hydroxy-N-methylamphetamine, (1R,2S)-۲
سودوافدرین (PSE)β-Hydroxy-N-methylamphetamine, (1S,2S)-۲
Methcathinoneβ-Keto-N-methylamphetamine۲
Ethcathinoneβ-Keto-N-ethylamphetamine۲
کلورترمین2-Chloro-α-methylamphetamine۲
Methoxymethylamphetamine (MMA)3-Methoxy-4-methylamphetamine۲
فنفلورامین3-Trifluoromethyl-N-ethylamphetamine۲
Dexfenfluramine3-Trifluoromethyl-N-ethylamphetamine, (S)-۲
4-Methylmethamphetamine (4-MMA)4-Methyl-N-methylamphetamine۲
para-Methoxymethamphetamine (PMMA)4-Methoxy-N-methylamphetamine۲
para-Methoxyethylamphetamine (PMEA)4-Methoxy-N-ethylamphetamine۲
فولدرین4-Hydroxy-N-methylamphetamine۲
Chlorphentermine4-Chloro-α-methylamphetamine۲
para-Fluoromethamphetamine (PFMA, 4-FMA)4-Fluoro-N-methylamphetamine۲
زیلوپروپامین3,4-Dimethylamphetamine۲
α-Methyldopamine (α-Me-DA)3,4-Dihydroxyamphetamine۲
3,4-Methylenedioxyamphetamine (MDA)3,4-Methylenedioxyamphetamine۲
Dimethoxyamphetamine (DMA)X,X-Dimethoxyamphetamine۲
6-APB6-(2-aminopropyl)benzofuran۲
Nordefrin (α-Me-NE)β,3,4-Trihydroxyamphetamine, (R)-۳
Oxilofrineβ,4-Dihydroxy-N-methylamphetamine۳
Aleph2,5-dimethoxy-4-methylthioamphetamine۳
دی‌اوبی (روانگردان) (DOB)2,5-Dimethoxy-4-bromoamphetamine۳
Dimethoxychloroamphetamine (DOC)2,5-Dimethoxy-4-chloroamphetamine۳
دی‌اوئی‌اف (روانگردان) (DOEF)2,5-Dimethoxy-4-fluoroethylamphetamine۳
Dimethoxyethylamphetamine (DOET)2,5-Dimethoxy-4-ethylamphetamine۳
Dimethoxyfluoroamphetamine (DOF)2,5-Dimethoxy-4-fluoroamphetamine۳
دی‌اوآی (روانگردان) (DOI)2,5-Dimethoxy-4-iodoamphetamine۳
دی‌اوام (روانگردان) (DOM)2,5-Dimethoxy-4-methylamphetamine۳
دی‌اوان (روانگردان) (DON)2,5-Dimethoxy-4-nitroamphetamine۳
Dimethoxypropylamphetamine (DOPR)2,5-Dimethoxy-4-propylamphetamine۳
Dimethoxytrifluoromethylamphetamine (DOTFM)2,5-Dimethoxy-4-trifluoromethylamphetamine۳
Methylenedioxymethamphetamine (اکستازی)3,4-Methylenedioxy-N-methylamphetamine۳
Methylenedioxyethylamphetamine (MDEA)3,4-Methylenedioxy-N-ethylamphetamine۳
Methylenedioxyhydroxyamphetamine (MDOH)3,4-Methylenedioxy-N-hydroxyamphetamine۳
2-Methyl-MDA3,4-Methylenedioxy-2-methylamphetamine۳
5-Methyl-MDA4,5-Methylenedioxy-3-methylamphetamine۳
Methoxymethylenedioxyamphetamine (MMDA)3-Methoxy-4,5-methylenedioxyamphetamine۳
Trimethoxyamphetamine (TMA)X,X,X-Trimethoxyamphetamine۳
Dimethylcathinoneβ-Keto-N,N-dimethylamphetamine۳
Diethylcathinoneβ-Keto-N,N-diethylamphetamine۳
بوپروپیونβ-Keto-3-chloro-N-tert-butylamphetamine۳
مفدرون (4-MMC)β-Keto-4-methyl-N-methylamphetamine۳
Methedrone (PMMC)β-Keto-4-methoxy-N-methylamphetamine۳
Brephedrone (4-BMC)β-Keto-4-bromo-N-methylamphetamine۳
Flephedrone (4-FMC)β-Keto-4-fluoro-N-methylamphetamine۳

منابع
  1. 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. 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.
  3. Glennon RA (2013). "Phenylisopropylamine stimulants: amphetamine-related agents". In Lemke TL, Williams DA, Roche VF, Zito W. Foye's principles of medicinal chemistry (7th ed.). Philadelphia, USA: Wolters Kluwer Health/Lippincott Williams & Wilkins. pp. 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).
  4. Lillsunde P, Korte T (March 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.
  5. 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. 25 (6): 578–585. doi:10.4062/biomolther.2017.141. ISSN 2005-4483. PMC 5685426. PMID 29081089.
  6. Glennon RA (2013). "Phenylisopropylamine stimulants: amphetamine-related agents". In Lemke TL, Williams DA, Roche VF, Zito W. Foye's principles of medicinal chemistry (7th ed.). Philadelphia, USA: Wolters Kluwer Health/Lippincott Williams & Wilkins. pp. 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).
  7. 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.
  8. Glennon RA (2013). "Phenylisopropylamine stimulants: amphetamine-related agents". In Lemke TL, Williams DA, Roche VF, Zito W. Foye's principles of medicinal chemistry (7th ed.). Philadelphia, USA: Wolters Kluwer Health/Lippincott Williams & Wilkins. pp. 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).
  9. 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.
  10. 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.
  11. 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.
  12. 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.
  13. 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.
  14. 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.
  15. 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.
  16. 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.
  17. 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.
  18. 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.

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