2,5-dimethoxy-4-amylamphetamine 2,5-dimethoxy-4-amylamphetamine 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 partial agonists at the 5-ht2a receptor. 2,5-dimethoxy-4-amylamphetamine names preferred iupac name 1-(2,5-dimethoxy-4-pentylphenyl)propan-2-amine other names 2,5-dimethoxy-4-amyl-amphetamine;2,5-dimethoxy-4-amyl-1-ethyl-(alpha-methyl)amine identifiers cas number 63779-90-8 y 3d model (jsmol) interactive imageinteractive image abbreviations doam chembl chembl161416 y chemspider 10440619 y pubchem cid 12262512 unii n80ewl36cb y comptox dashboard (epa) dtxsid50482958 inchi inchi=1s/c16h27no2/c1-5-6-7-8-13-10-16(19-4)14(9-12(2)17)11-15(13)18-3/h10-12h,5-9,17h2,1-4h3 ykey: vljorlcvoauukm-uhfffaoysa-n yinchi=1/c16h27no2/c1-5-6-7-8-13-10-16(19-4)14(9-12(2)17)11-15(13)18-3/h10-12h,5-9,17h2,1-4h3key: vljorlcvoauukm-uhfffaoyan smiles cccccc1=cc(oc)=c(cc(c)n)c=c1occoc1cc(ccccc)c(cc1cc(c)n)oc properties chemical formula c16h27no2 molar mass 265.39 g/mol except where otherwise noted, data are given for materials in their standard state (at 25 °c , 100 kpa). n verify (what is yn ?) infobox references