2,5-Dimethoxy-4-hydroxyamphetamine

vanc 6 DOOH DOOH structure.svg skin-invert-image 225px 2,5-dimethoxy-4-hydroxyamphetamine.png bg-transparent 185px None Generally not controlled 44265202 23108622 8352 DOOH; 2,5-Dimethoxy-4-hydroxyamphetamine; 4-Hydroxy-2,5-dimethoxyamphetamine 4-(2-aminopropyl)-2,5-dimethoxyphenol 11 17 1 3 CC(CC1=CC(=C(C=C1OC)O)OC)N 1S/C11H17NO3/c1-7(12)4-8-5-11(15-3)9(13)6-10(8)14-2/h5-7,13H,4,12H2,1-3H3 XZYTWVYCADLTTI-UHFFFAOYSA-N DOOH, also known as 2,5-dimethoxy-4-hydroxyamphetamine, is a chemical compound of the phenethylamine, amphetamine, and DOx families related to the psychedelic drug DOM. Trachsel D, Lehmann D, Enzensperger C 2013 Phenethylamine: von der Struktur zur Funktion de Nachtschatten-Verlag 1 978-3-03788-700-4 https://books.google.com/books?id=-Us1kgEACAAJ 13 November 2025 https://web.archive.org/web/20251113135159/https://books.google.com/books?id=-Us1kgEACAAJ Phenethylamines: From Structure to Function Solothurn Nachtschatten-Science 858805226 23 March 2026 bot: unknown Shulgin A, Manning T, Daley PF 2011 The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds Transform Press 1 978-0-9630096-3-0 Berkeley Runyon SP, Mosier PD, Roth BL, Glennon RA, Westkaemper RB Potential modes of interaction of 9-aminomethyl-9,10-dihydroanthracene (AMDA) derivatives with the 5-HT2A receptor: a ligand structure-affinity relationship, receptor mutagenesis and receptor modeling investigation Journal of Medicinal Chemistry 51 21 6808–6828 November 2008 18847250 3088499 10.1021/jm800771x Compounds 2a-e and 2g have also been previously reported in the literature, and their syntheses are discussed elsewhere.11-13 [...] Table 1. Effects of Aromatic Substitution on 5-HT2A Receptor Affinity [...] The effects of 4-position substitution on the affinities of 1-(2,5-dimethoxy)-2-aminopropanes (DOX; 2a-e) are qualitatively similar in that each of these, with the exception of the hydroxy substituent (2g, Ki > 50000 nM), retains or enhances affinity. However, in the DOX series, the range of affinity enhancement is much greater (2d, Ki ) 2.5 nM; 2a, Ki ) 5200 nM) than for the AMDA series with a maximum range of about 2000-fold, excluding the 4-hydroxy compound (2g) that shows no measurable affinity. Glennon RA, Seggel MR 1989 Interaction of Phenylisopropylamines with Central 5-HT2 Receptors Probing Bioactive Mechanisms 413 264–280 978-0-8412-1702-7 10.1021/bk-1989-0413.ch018 ACS Symposium Series 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 In contrast to DOM and other DOx drugs, DOOH appears to be inactive. Pharmacology Pharmacodynamics DOOH showed no affinity for the serotonin 5-HT2A receptor (Ki = >50,000nM). This was in notable contrast to closely related compounds like DOM (the 4-methyl analogue) and TMA-2 (the 4-methoxy analogue) (Ki = 100nM and 1,250nM, respectively). Hence, DOOH showed more than 40- to 500-fold lower affinity for the receptor than these analogues. Chemistry Synthesis The chemical synthesis of DOOH has been described. History DOOH was first described in the scientific literature by George Anderson and colleagues by 1978. Anderson GM, Castagnoli N, Kollman PA Quantitative structure-activity relationships in the 2,4,5-ring substituted phenylisopropylamines NIDA Research Monograph 22 199–217 1978 101881 Subsequently, its pharmacology was described by Richard Glennon and colleagues in 1989 and 1990. See also DOx (psychedelics) References External links DOOH - Isomer Design Category:DOx (psychedelics) Category:Hydroxyarenes