2,5-Dimethoxy-4-amylamphetamine
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Names | |
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IUPAC name
2-(2,5-Dimethoxy-4-pentyl-phenyl)-1-methyl-ethylamine
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Other names
2,5-Dimethoxy-4-amyl-amphetamine;
2,5-Dimethoxy-4-amyl-1-ethyl-(alpha-methyl)amine |
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Identifiers | |
63779-90-8 ![]() |
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Abbreviations | DOAM |
ChEMBL | ChEMBL161416 ![]() |
ChemSpider | 10440619 ![]() |
Jmol 3D model | Interactive image Interactive image |
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Properties | |
C16H27NO2 | |
Molar mass | 265.39 g/mol |
Vapor pressure | {{{value}}} |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references | |
Dimethoxy-4-amylamphetamine (DOAM) is a lesser-known psychedelic drug and a substituted amphetamine. DOAM was first synthesized by Alexander Shulgin. In his book PiHKAL (Phenethylamines i Have Known And Loved), the minimum dosage is listed as 10 mg, and the duration is unknown. DOAM produces a bare threshold and tenseness. As the 4-alkyl chain length is increased from shorter homologues such as DOM, DOET and DOPR which are all potent hallucinogens, the 5-HT2 binding affinity increases, rising to a maximum with the 4-(n-hexyl) derivative before falling again with even longer chains, but compounds with chain length longer than n-propyl, or with other bulky groups such as isopropyl, t-butyl or γ-phenylpropyl at the 4- position, fail to substitute for hallucinogens in animals or produce hallucinogenic effects in humans, suggesting these have low efficacy and are thus antagonists or weak partial agonists at the 5-HT2A receptor.[1][2][3]
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