2,5-Dimethoxy-4-isopropylamphetamine (also known asDOiP andDOiPr) is apsychedelicdrug of thephenethylamine,amphetamine, andDOx families.[1][2][3][4] It was firstsynthesized byAlexander Shulgin, and was described in his bookPiHKAL (Phenethylamines I Have Known and Loved).[1] He described DOiPR as being at least an order of magnitude weaker thanDOPR, with doses of 20 to 30mgorally required to produce valid changes in mental state.[1] Very little data exists about the pharmacological properties, metabolism, and toxicity of DOiP. DOiP substitutes forDOM in rodentdrug discrimination tests, but it is several-fold lesspotent than other DOx drugs likeDOM,DOET, and DOPR, though it is similar in potency toDOBU.[5] It is acontrolled substance inCanada under phenethylamine blanket-ban language.[6]
^abcdeShulgin A, Shulgin A (September 1991)."PiHKAL: A Chemical Love Story #71 DOPR". Transform Press. p. 978. Retrieved27 June 2015.But this is all with the n-propyl compound. There is a rich collection of misinformation and potential discovery that is associated with the isopropyl isomer. This structural isomer, 2,5-dimethoxyl-4-isopropylamphetamine is properly called DOIP for des-oxy-isopropyl. It has been synthesized and explored in animals and, to a modest extent, in man. The synthesis has proceeded from 2,5-dimethoxyacetophenone by the addition of a methyl group to the carbonyl followed by reduction to the hydrocarbon. Aldehyde formation, nitropropene synthesis with nitroethane, and lithium aluminum hydride reduction are uneventful, providing the hydrochloride salt DOIP, which has a mp of 183–184 °C as an analytical sample. Animal tests (such as rabbit hyperthermia assays), have indicated that the isopropyl compound DOIP is less potent than the propyl prototype, DOPR, by between one and two orders of magnitude. In man, a dose of four milligrams, a rousing dose of DOPR, is without any effects. At 10 milligrams, there is some disturbance but substantially no effects. I have been told that with doses in the 20 to 30 milligram range there are valid changes in mental state, but I have not been told the nature of these changes.
^Glennon RA, Seggel MR (November 1989). "Interaction of phenylisopropylamines with central 5-HT2 receptors. Analysis by quantitative structure-activity relationships.".Probing Bioactive Mechanisms. ACS Symposium Series. Vol. 413. pp. 264–280.doi:10.1021/bk-1989-0413.ch018.ISBN978-0-8412-1702-7.
^Seggel MR, Yousif MY, Lyon RA, Titeler M,Roth BL, Suba EA, Glennon RA (March 1990). "A structure-affinity study of the binding of 4-substituted analogues of 1-(2,5-dimethoxyphenyl)-2-aminopropane at 5-HT2 serotonin receptors".Journal of Medicinal Chemistry.33 (3):1032–6.doi:10.1021/jm00165a023.PMID2308135.
^Aldous FA, Barrass BC, Brewster K, Buxton DA, Green DM, Pinder RM, et al. (October 1974). "Structure-activity relationships in psychotomimetic phenylalkylamines".Journal of Medicinal Chemistry.17 (10):1100–11.doi:10.1021/jm00256a016.PMID4418757.
