2,5-Dimethoxy-4-isopropylamphetamine

Psychedelic drug DOiP DOiP structure.svg skin-invert-image 225px Oral Serotonergic psychedelic; Hallucinogen Schedule I NpSG Class A Unknown 42306-96-7 53581-56-9 (hydrochloride salt) correct FDA PF0P8RBU0X 44265275 23108724 DOIP; DOiP; DOiPr; 2,5-Dimethoxy-4-isopropylamphetamine; 4-Isopropyl-2,5-dimethoxyamphetamine 1-[2,5-Dimethoxy-(propan-2-yl)phenyl]propan-2-amine 14 23 1 2 COC1=C(C=C(C(=C1)C(C)C)OC)CC(C)N 1S/C14H23NO2/c1-9(2)12-8-13(16-4)11(6-10(3)15)7-14(12)17-5/h7-10H,6,15H2,1-5H3 UEEAUFJYLUJWQJ-UHFFFAOYAM DOiP, or DOiPr, also known as 2,5-dimethoxy-4-isopropylamphetamine, is a psychedelic drug of the phenethylamine, amphetamine, and DOx families.http://isomerdesign.com/PiHKAL/read.php?domain=pk&id=71 PiHKAL: A Chemical Love Story #71 DOPR Transform Press September 1991 27 June 2015 Shulgin A, Shulgin A 978 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. Shulgin A, Manning T, Daley PF The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds Transform Press Berkeley, CA 1 2011 978-0-9630096-3-0 709667010 Use and effects In his book PiHKAL (Phenethylamines I Have Known and Loved), Alexander Shulgin describes DOiP as being at least an order of magnitude less potent than DOPR, with doses of 20 to 30mg orally required to produce clear changes in mental state. The specific effects of DOiP have not been described. Interactions Psychedelic drug#Interactions Trip killer#Serotonergic psychedelic antidotes Pharmacology Pharmacodynamics The receptor interactions of DOiP have been studied.Interaction of phenylisopropylamines with central 5-HT2 receptors. Analysis by quantitative structure-activity relationships. Probing Bioactive Mechanisms Glennon RA, Seggel MR ACS Symposium Series November 1989 413 264–280 10.1021/bk-1989-0413.ch018 978-0-8412-1702-7Bryan Roth Seggel MR, Yousif MY, Lyon RA, Titeler M, Roth BL, Suba EA, Glennon RA 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 1032–1036 March 1990 2308135 10.1021/jm00165a023 DOiP substitutes for DOM in rodent drug discrimination tests, but it is several-fold less potent than other DOx drugs like DOM, DOET, and DOPR, though it is similar in potency to DOBU. Glennon RA Stimulus properties of hallucinogenic phenalkylamines and related designer drugs: formulation of structure-activity relationships NIDA Res Monogr 94 43–67 1989 2575229 https://archives.nida.nih.gov/sites/default/files/monograph94.pdf#page=54 https://web.archive.org/web/20230511144224/https://archives.nida.nih.gov/sites/default/files/monograph94.pdf#page=54 dead May 11, 2023 Chemistry Synthesis The chemical synthesis of DOiP has been described. Analogues Analogues of DOiP include DOM, DOET, DOPR, DOBU, DOiB, and 2C-iP, among others. History DOiP was first described in the scientific literature by F. Aldous and colleagues in 1974. Aldous FA, Barrass BC, Brewster K, Buxton DA, Green DM, Pinder RM, Rich P, Skeels M, Tutt KJ 6 Structure-activity relationships in psychotomimetic phenylalkylamines Journal of Medicinal Chemistry 17 10 1100–1111 October 1974 4418757 10.1021/jm00256a016 It was not included as an entry and was only briefly mentioned in Alexander Shulgin's 1991 book PiHKAL (Phenethylamines I Have Known and Loved). However, DOiP was subsequently included as an entry in Shulgin's 2011 book The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds. Society and culture Legal status DOiP is a controlled substance in Canada under phenethylamine blanket-ban language.Controlled Drugs and Substances Act Department of Justice Canada https://laws-lois.justice.gc.ca/eng/acts/c-38.8/FullText.html 19 January 2026 See also DOx (psychedelics) References External links DOIP - Isomer Design DOIP - The Shulgin Index The Small & Handy DOiP Thread - Bluelight DOIP 2nd time difficult yet promising - Bluelight Category:Designer drugs Category:DOx (psychedelics) Category:Isopropyl compounds Category:Psychedelic phenethylamines Category:Serotonin receptor agonists