Amphetamin thay thế

Amphetamin thay thế là một nhóm các hợp chất dựa trên cấu trúc amphetamin;^[1] nó bao gồm tất cả các hợp chất phái sinh được hình thành bằng cách thay thế một hoặc nhiều nguyên tử hydro trong cấu trúc lõi amphetamin bằng các nhóm thế.^[1][2][3] 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.^[2] Ví dụ về các chất amphetamin thay thế là: amphetamin (chính nó),^[1][2] methamphetamin,^[1] ephedrin,^[1] cathinon,^[1] phentermin,^[1] mephentermin,^[1] bupropion,^[1] methoxyphenamin,^[1] selegilin,^[1] amfepramon,^[1] pyrovaleron,^[1] MDMA (thuốc lắc) và DOM (STP).

Một số dẫn xuất thay thế của amphetamin xảy ra trong tự nhiên, ví dụ như trong lá của cây Ephedra và cây khat.^[1] Chúng đã được sử dụng từ thời cổ đại (ít nhất 1000 năm trước) vì tác dụng dược lý của chúng.^[1] 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 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

Tên hoạt chất	Danh pháp hóa học	# of Subs
Amphetamin	α-Methyl-phenethylamin	0
Methamphetamin	N-Methylamphetamin	1
Ethylamphetamin	N-Ethylamphetamin	1
Propylamphetamin	N-Propylamphetamin	1
Isopropylamphetamin	N-iso-Propylamphetamin	1
Phentermin	α-Methylamphetamin	1
Phenylpropanolamin (PPA)	β-Hydroxyamphetamin, (1R,2S)-	1
Cathine	β-Hydroxyamphetamin, (1S,2S)-	1
Cathinone	β-Ketoamphetamin	1
Ortetamin	2-Methylamphetamin	1
2-Fluoroamphetamin (2-FA)	2-Fluoroamphetamin	1
3-Methylamphetamin (3-MA)	3-Methylamphetamin	1
2-Phenyl-3-aminobutane	2-Phenyl-3-aminobutane	1
3-Fluoroamphetamin (3-FA)	3-Fluoroamphetamin	1
Norfenfluramin	3-Trifluoromethylamphetamin	1
4-Methylamphetamin (4-MA)	4-Methylamphetamin	1
para-Methoxyamphetamin (PMA)	4-Methoxyamphetamin	1
para-Ethoxyamphetamin	4-Ethoxyamphetamin	1
4-Methylthioamphetamin (4-MTA)	4-Methylthioamphetamin	1
Norpholedrine (α-Me-TRA)	4-Hydroxyamphetamin	1
para-Bromoamphetamin (PBA, 4-BA)	4-Bromoamphetamin	1
para-Chloroamphetamin (PCA, 4-CA)	4-Chloroamphetamin	1
para-Fluoroamphetamin (PFA, 4-FA, 4-FMP)	4-Fluoroamphetamin	1
para-Iodoamphetamin (PIA, 4-IA)	4-Iodoamphetamin	1
Clobenzorex	N-(2-chlorobenzyl)-1-phenylpropan-2-amin	1
Dimethylamphetamin	N,N-Dimethylamphetamin	2
Benzphetamin	N-Benzyl-N-methylamphetamin	2
D-Deprenyl	N-Methyl-N-propargylamphetamin, (S)-	2
Selegiline	N-Methyl-N-propargylamphetamin, (R)-	2
Mephentermin	N-Methyl-α-methylamphetamin	2
Phenpentermin	α,β-Dimethylamphetamin	2
Ephedrine	β-Hydroxy-N-methylamphetamin, (1R,2S)-	2
Pseudoephedrine (PSE)	β-Hydroxy-N-methylamphetamin, (1S,2S)-	2
Methcathinone	β-Keto-N-methylamphetamin	2
Ethcathinone	β-Keto-N-ethylamphetamin	2
Clortermin	2-Chloro-α-methylamphetamin	2
Methoxymethylamphetamin (MMA)	3-Methoxy-4-methylamphetamin	2
Fenfluramin	3-Trifluoromethyl-N-ethylamphetamin	2
Dexfenfluramin	3-Trifluoromethyl-N-ethylamphetamin, (S)-	2
4-Methylmethamphetamin (4-MMA)	4-Methyl-N-methylamphetamin	2
para-Methoxymethamphetamin (PMMA)	4-Methoxy-N-methylamphetamin	2
para-Methoxyethylamphetamin (PMEA)	4-Methoxy-N-ethylamphetamin	2
Pholedrine	4-Hydroxy-N-methylamphetamin	2
Chlorphentermin	4-Chloro-α-methylamphetamin	2
para-Fluoromethamphetamin (PFMA, 4-FMA)	4-Fluoro-N-methylamphetamin	2
Xylopropamin	3,4-Dimethylamphetamin	2
α-Methyldopamin (α-Me-DA)	3,4-Dihydroxyamphetamin	2
3,4-Methylenedioxyamphetamin (MDA)	3,4-Methylenedioxyamphetamin	2
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	2,5-dimethoxy-4-methylthioamphetamin	3
Dimethoxybromoamphetamin (DOB)	2,5-Dimethoxy-4-bromoamphetamin	3
Dimethoxychloroamphetamin (DOC)	2,5-Dimethoxy-4-chloroamphetamin	3
Dimethoxyfluoroethylamphetamin (DOEF)	2,5-Dimethoxy-4-fluoroethylamphetamin	3
Dimethoxyethylamphetamin (DOET)	2,5-Dimethoxy-4-ethylamphetamin	3
Dimethoxyfluoroamphetamin (DOF)	2,5-Dimethoxy-4-fluoroamphetamin	3
Dimethoxyiodoamphetamin (DOI)	2,5-Dimethoxy-4-iodoamphetamin	3
Dimethoxymethylamphetamin (DOM)	2,5-Dimethoxy-4-methylamphetamin	3
Dimethoxynitroamphetamin (DON)	2,5-Dimethoxy-4-nitroamphetamin	3
Dimethoxypropylamphetamin (DOPR)	2,5-Dimethoxy-4-propylamphetamin	3
Dimethoxytrifluoromethylamphetamin (DOTFM)	2,5-Dimethoxy-4-trifluoromethylamphetamin	3
Methylenedioxymethamphetamin (MDMA)	3,4-Methylenedioxy-N-methylamphetamin	3
Methylenedioxyethylamphetamin (MDEA)	3,4-Methylenedioxy-N-ethylamphetamin	3
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
Methoxymethylenedioxyamphetamin (MMDA)	3-Methoxy-4,5-methylenedioxyamphetamin	3
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

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. ^ Glennon RA (2013). “Phenylisopropylamine stimulants: amphetamine-related agents”. Trong Lemke TL, Williams DA, Roche VF, Zito W (biên tập). Foye's principles of medicinal chemistry (ấn bản 7). Philadelphia, USA: Wolters Kluwer Health/Lippincott Williams & Wilkins. tr. 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 (tháng 3 năm 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.