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[[Tập tin:Amphetaminsulfat-d-l-10mg.jpg|nhỏ|Lọ Amphetamin sulfat]]
'''Amphetamin''' '''thay thế''' là một nhóm các hợp chất dựa trên cấu trúc [[amphetamin]];<ref name="Amphetamine - a substituted amphetamine" /> nó bao gồm tất cả các hợp chất phái sinh được hình thành bằng cách [[Phản ứng thế|thay thế]] một hoặc nhiều [[nguyên tử hydro]] trong cấu trúc lõi amphetamin bằng các [[nhóm thế]].<ref name="Amphetamine - a substituted amphetamine">{{Chú thích tạp chí|vauthors=Hagel JM, Krizevski R, Marsolais F, Lewinsohn E, Facchini PJ|date=2012|title=Biosynthesis of amphetamine analogs in plants|journal=Trends Plant Sci.|volume=17|issue=7|pages=404–412|doi=10.1016/j.tplants.2012.03.004|pmid=22502775|quote=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 (1''R'',2''S'')-ephedrine and (1''S'',2''S'')-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.}}</ref><ref name="Substituted amphetamines">{{Chú thích sách|title=Foye's principles of medicinal chemistry|last=Glennon RA|date=2013|publisher=Wolters Kluwer Health/Lippincott Williams & Wilkins|isbn=9781609133450|veditors=Lemke TL, Williams DA, Roche VF, Zito W|edition=7th|location=Philadelphia, USA|pages=646–648|chapter=Phenylisopropylamine stimulants: amphetamine-related agents|quote=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).|access-date =|chapter-url=https://books.google.com/books?id=Sd6ot9ul-bUC&pg=PA646&q=substituted%20derivatives%20substituents%20amphetamine%20substitution#v=onepage}}</ref><ref name="pmid1855720">{{Chú thích tạp chí|vauthors=Lillsunde P, Korte T|date=March 1991|title=Determination of ring- and N-substituted amphetamines as heptafluorobutyryl derivatives|url=https://archive.org/details/sim_forensic-science-international_1991-03_49_2/page/205|journal=Forensic Sci. Int.|volume=49|issue=2|pages=205–213|doi=10.1016/0379-0738(91)90081-s|pmid=1855720}}</ref> Các hợp chất trong lớp này bao gồm nhiều loại phân loại dược lý, bao gồm các [[chất kích thích]], chất thấu cảm và [[chất ảo giác]], và những loại khác.<ref name="Substituted amphetamines" /> Ví dụ về các chất amphetamin thay thế là: amphetamin (chính nó),<ref name="Amphetamine - a substituted amphetamine" /><ref name="Substituted amphetamines" /> [[Ma túy đá|methamphetamin]],<ref name="Amphetamine - a substituted amphetamine" /> [[ephedrine|ephedrin]],<ref name="Amphetamine - a substituted amphetamine" /> [[cathinone|cathinon]],<ref name="Amphetamine - a substituted amphetamine" /> [[phentermine|phentermin]],<ref name="Amphetamine - a substituted amphetamine" /> [[mephentermine|mephentermin]],<ref name="Amphetamine - a substituted amphetamine" /> [[bupropion]],<ref name="Amphetamine - a substituted amphetamine" /> [[methoxyphenamine|methoxyphenamin]],<ref name="Amphetamine - a substituted amphetamine" /> [[selegiline|selegilin]],<ref name="Amphetamine - a substituted amphetamine" /> [[amfepramone|amfepramon]],<ref name="Amphetamine - a substituted amphetamine" /> [[pyrovalerone|pyrovaleron]],<ref name="Amphetamine - a substituted amphetamine" /> [[Thuốc lắc|MDMA]] (thuốc lắc) và [[2,5-dimethoxy-4-methylamphetamine|DOM]] (STP).

Một số dẫn xuất thay thế của amphetamin xảy ra trong tự nhiên, ví dụ như trong lá của cây ''[[Chi Ma hoàng|Ephedra]]'' và [[Lá khát|cây khat]].<ref name="Amphetamine - a substituted amphetamine"/> Chúng đã được sử dụng từ thời cổ đại (ít nhất 1000 năm trước) vì tác dụng dược lý của chúng.<ref name="Amphetamine - a substituted amphetamine" /> Amphetamin được sản xuất lần đầu tiên vào cuối thế kỷ 19. Vào những năm 1930, [[amphetamin]] và một số hợp chất dẫn xuất của nó được sử dụng làm [[thuốc thông mũi]] trong [[điều trị triệu chứng]] [[cảm lạnh]] và đôi khi là tác nhân tâm thần. Ảnh hưởng của chúng trên [[Hệ thần kinh trung ương|hệ thống thần kinh trung ương]] rất đa dạng, nhưng có thể được tóm tắt bằng ba loại tác động chồng chéo: kích thích thần kinh, gây [[ảo giác]] và tạo cảm giác thấu cảm. Các loại thuốc kích thích thay thế khác nhau có thể gây ra các tác động này một cách riêng biệt hoặc kết hợp.
==Danh sách các hợp chất được thay thế của amphetamin==
{| class="wikitable sortable"
! Tên hoạt chất
! Danh pháp hóa học
! # of Subs
|-
| [[Amphetamine|Amphetamin]] || α-Methyl-phenethylamin || 0
|-
| [[Methamphetamine|Methamphetamin]] || ''N''-Methylamphetamin || 1
|-
| [[Etilamfetamine|Ethylamphetamin]] || ''N''-Ethylamphetamin || 1
|-
| [[Propylamphetamine|Propylamphetamin]] || ''N''-Propylamphetamin || 1
|-
| [[Isopropylamphetamine|Isopropylamphetamin]] || ''N''-''iso''-Propylamphetamin || 1
|-
| [[Phentermine|Phentermin]] || α-Methylamphetamin || 1
|-
| [[Phenylpropanolamine|Phenylpropanolamin]] (PPA) || β-Hydroxyamphetamin, (1''R'',2''S'')- || 1
|-
| [[Cathine]] || β-Hydroxyamphetamin, (1''S'',2''S'')- || 1
|-
| [[Cathinone]] || β-Ketoamphetamin || 1
|-
| [[Ortetamine|Ortetamin]] || 2-Methylamphetamin || 1
|-
| [[2-Fluoroamphetamine|2-Fluoroamphetamin]] (2-FA) || 2-Fluoroamphetamin || 1
|-
| [[3-Methylamphetamine|3-Methylamphetamin]] (3-MA) || 3-Methylamphetamin || 1
|-
| [[2-Phenyl-3-aminobutane]] || 2-Phenyl-3-aminobutane || 1
|-
| [[3-Fluoroamphetamine|3-Fluoroamphetamin]] (3-FA) || 3-Fluoroamphetamin || 1
|-
| [[Norfenfluramine|Norfenfluramin]] || 3-Trifluoromethylamphetamin || 1
|-
| [[4-Methylamphetamine|4-Methylamphetamin]] (4-MA) || 4-Methylamphetamin || 1
|-
| [[para-Methoxyamphetamine|''para''-Methoxyamphetamin]] (PMA) || 4-Methoxyamphetamin || 1
|-
| [[para-Ethoxyamphetamine|''para''-Ethoxyamphetamin]] || 4-Ethoxyamphetamin || 1
|-
| [[4-Methylthioamphetamine|4-Methylthioamphetamin]] (4-MTA) || 4-Methylthioamphetamin || 1
|-
| [[Norpholedrine]] (α-Me-TRA) || 4-Hydroxyamphetamin || 1
|-
| [[para-Bromoamphetamine|''para''-Bromoamphetamin]] (PBA, 4-BA) || 4-Bromoamphetamin || 1
|-
| [[para-Chloroamphetamine|''para''-Chloroamphetamin]] (PCA, 4-CA) || 4-Chloroamphetamin || 1
|-
| [[para-Fluoroamphetamine|''para''-Fluoroamphetamin]] (PFA, 4-FA, 4-FMP) || 4-Fluoroamphetamin || 1
|-
| [[para-Iodoamphetamine|''para''-Iodoamphetamin]] (PIA, 4-IA) || 4-Iodoamphetamin || 1
|-
| [[Clobenzorex]] || ''N''-(2-chlorobenzyl)-1-phenylpropan-2-amin || 1
|-
| [[Dimethylamphetamine|Dimethylamphetamin]] || ''N'',''N''-Dimethylamphetamin || 2
|-
| [[Benzphetamine|Benzphetamin]] || ''N''-Benzyl-''N''-methylamphetamin || 2
|-
| [[D-Deprenyl|D-Deprenyl]] || ''N''-Methyl-''N''-propargylamphetamin, (''S'')- || 2
|-
| [[Selegiline]] || ''N''-Methyl-''N''-propargylamphetamin, (''R'')- || 2
|-
| [[Mephentermine|Mephentermin]] || ''N''-Methyl-α-methylamphetamin || 2
|-
| [[Phenpentermine|Phenpentermin]] || α,β-Dimethylamphetamin || 2
|-
| [[Ephedrine]] || β-Hydroxy-''N''-methylamphetamin, (1''R'',2''S'')- || 2
|-
| [[Pseudoephedrine]] (PSE) || β-Hydroxy-''N''-methylamphetamin, (1''S'',2''S'')- || 2
|-
| [[Methcathinone]] || β-Keto-''N''-methylamphetamin || 2
|-
| [[Ethcathinone]] || β-Keto-''N''-ethylamphetamin || 2
|-
| [[Clortermine|Clortermin]] || 2-Chloro-α-methylamphetamin || 2
|-
| [[Methoxymethylamphetamine|Methoxymethylamphetamin]] (MMA) || 3-Methoxy-4-methylamphetamin || 2
|-
| [[Fenfluramine|Fenfluramin]] || 3-Trifluoromethyl-''N''-ethylamphetamin || 2
|-
| [[Dexfenfluramine|Dexfenfluramin]] || 3-Trifluoromethyl-''N''-ethylamphetamin, (''S'')- || 2
|-
| [[4-Methylmethamphetamine|4-Methylmethamphetamin]] (4-MMA) || 4-Methyl-''N''-methylamphetamin || 2
|-
| [[Para-methoxymethamphetamine|''para''-Methoxymethamphetamin]] (PMMA) || 4-Methoxy-''N''-methylamphetamin || 2
|-
| [[para-Methoxyethylamphetamine|''para''-Methoxyethylamphetamin]] (PMEA) || 4-Methoxy-''N''-ethylamphetamin || 2
|-
| [[Pholedrine]] || 4-Hydroxy-''N''-methylamphetamin || 2
|-
| [[Chlorphentermine|Chlorphentermin]] || 4-Chloro-α-methylamphetamin || 2
|-
| [[para-Fluoromethamphetamine|''para''-Fluoromethamphetamin]] (PFMA, 4-FMA) || 4-Fluoro-''N''-methylamphetamin || 2
|-
| [[Xylopropamine|Xylopropamin]] || 3,4-Dimethylamphetamin || 2
|-
| [[α-Methyldopamine|α-Methyldopamin]] (α-Me-DA) || 3,4-Dihydroxyamphetamin || 2
|-
| [[3,4-Methylenedioxyamphetamine|3,4-Methylenedioxyamphetamin]] (MDA) || 3,4-Methylenedioxyamphetamin || 2
|-
| [[Dimethoxyamphetamine|Dimethoxyamphetamin]] (DMA) || X,X-Dimethoxyamphetamin || 2
|-
| [[6-APB]] || 6-(2-aminopropyl)benzofuran || 2
|-
| [[Nordefrin]] (α-Me-NE) || β,3,4-Trihydroxyamphetamin, (''R'')- || 3
|-
| [[Oxilofrine]] || β,4-Dihydroxy-''N''-methylamphetamin || 3
|-
| [[Aleph (psychedelic)|Aleph]] || 2,5-dimethoxy-4-methylthioamphetamin || 3
|-
| [[Dimethoxybromoamphetamine|Dimethoxybromoamphetamin]] (DOB) || 2,5-Dimethoxy-4-bromoamphetamin || 3
|-
| [[Dimethoxychloroamphetamine|Dimethoxychloroamphetamin]] (DOC) || 2,5-Dimethoxy-4-chloroamphetamin || 3
|-
| [[Dimethoxyfluoroethylamphetamine|Dimethoxyfluoroethylamphetamin]] (DOEF) || 2,5-Dimethoxy-4-fluoroethylamphetamin || 3
|-
| [[Dimethoxyethylamphetamine|Dimethoxyethylamphetamin]] (DOET) || 2,5-Dimethoxy-4-ethylamphetamin || 3
|-
| [[Dimethoxyfluoroamphetamine|Dimethoxyfluoroamphetamin]] (DOF) || 2,5-Dimethoxy-4-fluoroamphetamin || 3
|-
| [[Dimethoxyiodoamphetamine|Dimethoxyiodoamphetamin]] (DOI) || 2,5-Dimethoxy-4-iodoamphetamin || 3
|-
| [[Dimethoxymethylamphetamine|Dimethoxymethylamphetamin]] (DOM) || 2,5-Dimethoxy-4-methylamphetamin || 3
|-
| [[Dimethoxynitroamphetamine|Dimethoxynitroamphetamin]] (DON) || 2,5-Dimethoxy-4-nitroamphetamin || 3
|-
| [[Dimethoxypropylamphetamine|Dimethoxypropylamphetamin]] (DOPR) || 2,5-Dimethoxy-4-propylamphetamin || 3
|-
| [[Dimethoxytrifluoromethylamphetamine|Dimethoxytrifluoromethylamphetamin]] (DOTFM) || 2,5-Dimethoxy-4-trifluoromethylamphetamin || 3
|-
| Methylenedioxymethamphetamin ([[MDMA]]) || 3,4-Methylenedioxy-''N''-methylamphetamin || 3
|-
| [[Methylenedioxyethylamphetamine|Methylenedioxyethylamphetamin]] (MDEA) || 3,4-Methylenedioxy-''N''-ethylamphetamin || 3
|-
| [[Methylenedioxyhydroxyamphetamine|Methylenedioxyhydroxyamphetamin]] (MDOH) || 3,4-Methylenedioxy-''N''-hydroxyamphetamin || 3
|-
| [[2-Methyl-MDA]] || 3,4-Methylenedioxy-2-methylamphetamin || 3
|-
| [[5-Methyl-MDA]] || 4,5-Methylenedioxy-3-methylamphetamin || 3
|-
| [[Methoxymethylenedioxyamphetamine|Methoxymethylenedioxyamphetamin]] (MMDA) || 3-Methoxy-4,5-methylenedioxyamphetamin || 3
|-
| [[Trimethoxyamphetamine|Trimethoxyamphetamin]] (TMA) || X,X,X-Trimethoxyamphetamin || 3
|-
| [[Dimethylcathinone]] || β-Keto-''N'',''N''-dimethylamphetamin || 3
|-
| [[Diethylcathinone]] || β-Keto-''N'',''N''-diethylamphetamin || 3
|-
| [[Bupropion]] || β-Keto-3-chloro-''N''-''tert''-butylamphetamin || 3
|-
| [[Mephedrone]] (4-MMC) || β-Keto-4-methyl-''N''-methylamphetamin || 3
|-
| [[Methedrone]] (PMMC) || β-Keto-4-methoxy-''N''-methylamphetamin || 3
|-
| [[Brephedrone]] (4-BMC) || β-Keto-4-bromo-''N''-methylamphetamin || 3
|-
| [[Flephedrone]] (4-FMC) || β-Keto-4-fluoro-''N''-methylamphetamin || 3
|-
|}
==Tham khảo==
{{tham khảo}}

[[Thể loại:Amphetamin]]

Amphetamin thay thế - Lịch sử thay đổi

imported>DaoTrungHai: /* growthexperiments-addimage-summary-summary: 1 */