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Analogs of .alpha.-methylphenethylamine (amphetamine). I. Synthesis and pharmacological activity of some methoxy and/or methyl analogs

Cite this: J. Med. Chem. 1970, 13, 1, 26–30
Publication Date (Print):January 1, 1970
https://doi.org/10.1021/jm00295a007
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    Cited By

    This article is cited by 37 publications.

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    2. Lee A. Flippin,, Jacob Berger,, Jason S. Parnes, and, Mark S. Gudiksen. Effect of the Substitution Pattern on Reactions of Methoxylated Araldehyde 2,4-Dimethylpent-3-ylimines with Organolithium Reagents. The Journal of Organic Chemistry 1996, 61 (14) , 4812-4815. https://doi.org/10.1021/jo9602175
    3. David E. Nichols. Entactogens: How the Name for a Novel Class of Psychoactive Agents Originated. Frontiers in Psychiatry 2022, 13 https://doi.org/10.3389/fpsyt.2022.863088
    4. Beng T Ho, Jen-Tzaw Huang. Effects of mescaline and 2, 5-dimethoxy-4-methylphenethylamine on sleeping time in mice. Journal of Pharmacy and Pharmacology 2011, 22 (12) , 949-951. https://doi.org/10.1111/j.2042-7158.1970.tb08483.x
    5. Ya‐Zhu Xu, Huei‐Ru Lin, Chang‐Ahai Lua, Chinpiao Chen. Synthesis of Deuterium Labeled (±)‐2,5‐Dimethoxyamphetamine (DMA), (±)‐4‐Bromo‐2,5‐Dimethoxyamphetamine (DOB), and (±)‐4‐Methoxyamphetamine (PMA) as Internal Standards for Quantitative Analyses by GC‐MS. Journal of the Chinese Chemical Society 2007, 54 (2) , 493-502. https://doi.org/10.1002/jccs.200700070
    6. Carla Macedo, Paula Sério Branco, Luísa Maria Ferreira, Ana Maria Lobo, João Paulo Capela, Eduarda Fernandes, Maria de Lourdes Bastos, Felix Carvalho. Synthesis and Cyclic Voltammetry Studies of 3,4-Methylenedioxymethamphetamine (MDMA) Human Metabolites. JOURNAL OF HEALTH SCIENCE 2007, 53 (1) , 31-42. https://doi.org/10.1248/jhs.53.31
    7. . 2,5‐Dimethoxy‐4‐Methylamphetamine Hydrochloride 15589‐00‐1. 2004https://doi.org/10.1002/0471701343.sdp09536
    8. . 1‐(2,5‐Dimethoxyphenyl)‐2‐Aminopropane 24973‐25‐9. 2004https://doi.org/10.1002/0471701343.sdp09545
    9. . 3,4,5‐Trimethoxyamphetamine Hydrochloride 5688‐80‐2. 2004https://doi.org/10.1002/0471701343.sdp24894
    10. . Mescaline 54‐04‐6. 2004https://doi.org/10.1002/0471701343.sdp16195
    11. Jared M. Wagner, Charles J. McElhinny, Anita H. Lewin, F.Ivy Carroll. Stereospecific synthesis of amphetamines. Tetrahedron: Asymmetry 2003, 14 (15) , 2119-2125. https://doi.org/10.1016/S0957-4166(03)00438-5
    12. Sally Freeman, John F. Alder. Arylethylamine psychotropic recreational drugs: a chemical perspective. European Journal of Medicinal Chemistry 2002, 37 (7) , 527-539. https://doi.org/10.1016/S0223-5234(02)01382-X
    13. Karel Valter, Philippe Arrizabalaga. Substance Number 1 in Chapter 2.1.1. 1998, 15-16. https://doi.org/10.1016/B978-044420525-4/50056-5
    14. Karel Valter, Philippe Arrizabalaga. Subtance Number in Chapter 2.1.4. 1998, 57-58. https://doi.org/10.1016/B978-044420525-4/50062-0
    15. Karel Valter, Philippe Arrizabalaga. Substance Number 8 in Chapter 2.1.2. 1998, 38. https://doi.org/10.1016/B978-044420525-4/50108-X
    16. Karel Valter, Philippe Arrizabalaga. Substance Number 2 in Chapter 2.1.4. 1998, 59. https://doi.org/10.1016/B978-044420525-4/50123-6
    17. Karel Valter, Philippe Arrizabalaga. Substance Number 3 in Chapter 2.1.4. 1998, 60. https://doi.org/10.1016/B978-044420525-4/50124-8
    18. Karel Valter, Philippe Arrizabalaga. Substance Number 7 in Chapter 2.1.4. 1998, 66. https://doi.org/10.1016/B978-044420525-4/50128-5
    19. Karel Valter, Philippe Arrizabalaga. Substance Number 8 in Chapter 2.1.4. 1998, 67. https://doi.org/10.1016/B978-044420525-4/50129-7
    20. George W. Kabalka, Rajender S. Varma. Reduction of Nitro and Nitroso Compounds. 1991, 363-379. https://doi.org/10.1016/B978-0-08-052349-1.00231-6
    21. TAD Cason. An Evaluation of the Potential for Clandestine Manufacture of 3,4-Methylenedioxyamphetamine (MDA) Analogs and Homologs. Journal of Forensic Sciences 1990, 35 (3) , 675-697. https://doi.org/10.1520/JFS12874J
    22. George W. Kabalka, Guindi M.H. Laila, Rajender S. Varma. Selected reductions of conjugated nitroalkenes. Tetrahedron 1990, 46 (21) , 7443-7457. https://doi.org/10.1016/S0040-4020(01)89059-1
    23. Jaroslav Málek. Reductions by Metal Alkoxyaluminum Hydrides. Part II . Carboxylic Acids and Derivatives, Nitrogen Compounds, and Sulfur Compounds. 1988, 249-590. https://doi.org/10.1002/0471264180.or036.03
    24. George W. Kabalka, Rajender S. Varma. SYNTHESES AND SELECTED REDUCTIONS OF CONJUGATED NITROALKENES. A REVIEW. Organic Preparations and Procedures International 1987, 19 (4-5) , 283-328. https://doi.org/10.1080/00304948709356200
    25. Rajender S. Varma, George W. Kabalka. A Simple Route to Alkylamines Via the Reduction of Nitroalkenes. Synthetic Communications 1985, 15 (9) , 843-847. https://doi.org/10.1080/00397918508063880
    26. John Avolio, Robert Rothchild. Optical Purity Determination, Conformer Populations, and 1 H NMR Spectral Simplification with Lanthanide Shift Reagents. Part VII: 3,4-Methylenedioxyamphetamine (MDA). Applied Spectroscopy 1985, 39 (4) , 604-610. https://doi.org/10.1366/0003702854250239
    27. M. Soubel Mourad, Rajender S. Varma, George W. Kabalka. A Convenient Reduction of α,β-Unsaturated Nitroalkenes to Alkylamines Using Boron Hydrides. Synthetic Communications 1984, 14 (12) , 1099-1104. https://doi.org/10.1080/00397918408059641
    28. Richard A. Glennon, Richard Young. Comparison of behavioral properties of di- and tri-methoxyphenylisopropylamines. Pharmacology Biochemistry and Behavior 1982, 17 (4) , 603-607. https://doi.org/10.1016/0091-3057(82)90330-6
    29. David E. Nichols. Structure-Activity Relationships of Phenethylamine Hallucinogens. Journal of Pharmaceutical Sciences 1981, 70 (8) , 839-849. https://doi.org/10.1002/jps.2600700802
    30. Gisela Braun, Alexander T. Shulgin, Thornton Sargent. Synthesis of 123 I‐labelled 4‐iodo‐2, 5‐dimethoxyphenylisopropylamine. Journal of Labelled Compounds and Radiopharmaceuticals 1978, 14 (5) , 767-773. https://doi.org/10.1002/jlcr.2580140515
    31. Alexander T. Shulgin. Psychotomimetic Drugs: Structure-Activity Relationships. 1978, 243-333. https://doi.org/10.1007/978-1-4757-0510-2_6
    32. E. Campaigne, Yasuo Abe. Benzo[ b ] thiophene derivatives. XXII. Synthesis of the isomeric 5‐methyl‐6‐methoxy‐ and 5‐methoxy‐6‐methylbenzo[ b ] thiophene‐2‐carboxylic acids. Journal of Heterocyclic Chemistry 1975, 12 (5) , 889-892. https://doi.org/10.1002/jhet.5570120515
    33. Dieter Seebach, Herbert F. Leitz, Volker Ehrig. Michael ‐Additionen von Lithiumenolaten und schwefelsubstituierten Lithiumorganylen an Nitroolefine. Chemische Berichte 1975, 108 (6) , 1924-1945. https://doi.org/10.1002/cber.19751080615
    34. P.H. Morgan, A.H. Beckett. Synthesis of some N-oxygenated products of 3,4-dimethoxyampetamine and its N-alkyl derivatives. Tetrahedron 1975, 31 (20) , 2595-2601. https://doi.org/10.1016/0040-4020(75)80276-6
    35. Karl A. Nieforth. Psychotomimetic Phenethylamines. Journal of Pharmaceutical Sciences 1971, 60 (5) , 655-665. https://doi.org/10.1002/jps.2600600502
    36. . Preparation of Aldehydes. 1971, 132-176. https://doi.org/10.1002/9780470125946.ch4
    37. B. T. HO, W. M. MCISAAC, R. AN, L. W. TANSEY, K. E. WALKER, L. F. ENGLERT, M. B. NOEL. ChemInform Abstract: ANALOGA DES ALPHA‐METHYLPHENAETHYLAMINS (AMPHETAMIN) 1. MITT. SYNTH. UND PHARMAKOLOGISCHE AKTIVITAET EINIGER METHOXY‐ UND/ODER METHYLANALOGA. Chemischer Informationsdienst. Organische Chemie 1970, 1 (17) https://doi.org/10.1002/chin.197017199

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