آمفتامین استخلافی

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

آمفتامین‌های استخلافی دسته ای از ترکیبات شیمیایی هستند که ساختار هسته اصلی آن بر اساس ساختار آمفتامین بنا شده‌است.[۱] 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.[۲][۳][۴][۵] ترکیبات موجود در این دسته انواع مختلفی از زیردسته‌های دارویی را شامل می‌شوند، از جمله محرک‌ها، empathogenها، توهم‌زاها و غیره.[۶] نمونه‌های آمفتامین استخلافی عبارت است از: آمفتامین (ترکیب هسته سازنده)،[۷][۸]مت‌آمفتامین،[۹] افدرین،[۱۰] کاتینون،[۱۱] فنترمین،[۱۲] مفنترمین،[۱۳] بوپروپیون،[۱۴] متوکسی فنامین،[۱۵] سلژیلین،[۱۶] آمفپرامون،[۱۷] پیرووالرون،[۱۸] MDMA (اکستازی) و DOM (STP).

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
اورتتامین2-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
نورفولدرین (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
کوربادرین (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 (eds.). 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 (به انگلیسی). 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 (eds.). 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 (eds.). 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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