2,5-Dimethoxy-4-benzylamphetamine

DOBz DOBz structure.svg skin-invert-image 250px Serotonin 5-HT2 receptor modulator None 125903-73-3 24039384 23108642 274589 DOBz; DOBZ; DOBN; DOBn; 4-Benzyl-2,5-dimethoxyamphetamine; 2,5-Dimethoxy-4-benzylamphetamine 1-(4-benzyl-2,5-dimethoxyphenyl)propan-2-amine 18 23 1 2 CC(CC1=C(C=C(C(=C1)OC)CC2=CC=CC=C2)OC)N 1S/C18H23NO2/c1-13(19)9-15-11-18(21-3)16(12-17(15)20-2)10-14-7-5-4-6-8-14/h4-8,11-13H,9-10,19H2,1-3H3 FQARCNZVKSYIGI-UHFFFAOYSA-N 2,5-Dimethoxy-4-benzylamphetamine (DOBz or DOBN) is a serotonin 5-HT2 receptor modulator of the amphetamine and DOx families. Nelson DL, Lucaites VL, Wainscott DB, Glennon RA Comparisons of hallucinogenic phenylisopropylamine binding affinities at cloned human 5-HT2A, -HT(2B) and 5-HT2C receptors Naunyn Schmiedebergs Arch Pharmacol 359 1 1–6 January 1999 9933142 10.1007/pl00005315 https://citeseerx.ist.psu.edu/document?repid=rep1&type=pdf&doi=598855ff348176de6e6aae050cf17401bab3faeb subscription Blaazer AR, Smid P, Kruse CG Structure-activity relationships of phenylalkylamines as agonist ligands for 5-HT(2A) receptors ChemMedChem 3 9 1299–1309 September 2008 18666267 10.1002/cmdc.200800133 Studies on the homologation of phenylisopropylamines at the 4-position found a decrease of in vivo hallucinogenic potency beyond n-propyl.[163] Yet later work using [3 H]ketanserin as a radioligand for 5-HT2 receptors in rat brain homogenate revealed significantly increased binding affinities with the more lipophilic derivatives; n-hexyl and n-octyl derivatives showed the highest binding affinity. After in vitro testing, these derivatives were found to act as 5-HT2 receptor antagonists.[67] Using [125I]DOI labeled human receptor data, the highest binding affinity at 5-HT2A receptors was found for the 4-nhexyl analogue DOHx (21, Ki=0.1 nm), followed by the 4- benzyl analogue DOBz (22, Ki=0.4 nm), DOB (16, Ki=0.6 nm), DOI (17, Ki=0.7 nm), and the 4-n-propyl analogue DOPR (23, Ki=0.9 nm).[63] Duan W, Cao D, Wang S, Cheng J Serotonin 2A Receptor (5-HT2AR) Agonists: Psychedelics and Non-Hallucinogenic Analogues as Emerging Antidepressants Chem Rev 124 1 124–163 January 2024 38033123 10.1021/acs.chemrev.3c00375 https://bitnest.netfirms.com/external/10.1021/acs.chemrev.3c00375 Replacing the halogen on the 4-position with a methyl group led to significantly reduced activity (91, DOM, Ki = 100 nM), but the activity could be restored with longer linear alkyl chains and the benzyl group, such as compounds DOPR (92, Ki = 0.9 nM), DOHx (93, Ki = 0.1 nM), and DOBz (94, Ki = 0.4 nM).172 Interestingly, these DOXs compounds also exhibited some selectivity against the 5- HT2BR and 5-HT2CR.172 subscription It is the DOx derivative with a benzyl ring at the 4 position. The drug's affinities (Ki) for the human serotonin 5-HT2 receptors have been found to be 0.40nM for the serotonin 5-HT2A receptor, 24.5 to 35.0nM for the serotonin 5-HT2B receptor, and 1.0nM for the serotonin 5-HT2C receptor. Its affinities for the serotonin 5-HT2 receptors are very similar to those of DOB. The drug has been assessed and found to act as a silent antagonist of the serotonin 5-HT2B receptor (Emax maximal efficacy = 0%). Hemanth P, Nistala P, Nguyen VT, Eltit JM, Glennon RA, Dukat M Binding and functional structure-activity similarities of 4-substituted 2,5-dimethoxyphenyl isopropylamine analogues at 5-HT2A and 5-HT2B serotonin receptors Front Pharmacol 14 1101290 2023 36762110 9902381 10.3389/fphar.2023.1101290 free In rodent drug discrimination tests, DOBz neither antagonized nor generalized to the stimulus of DOM. 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 May 11, 2023 Higher doses produced behavioral disruption however. DOBz was first described in the scientific literature by Richard Glennon and colleagues in 1989. Glennon RA, Seggel MR Interaction of Phenylisopropylamines with Central 5-HT2 Receptors: Analysis by Quantitative Structure—Activity Relationships Probing Bioactive Mechanisms American Chemical Society Washington, DC 413 14 November 1989 978-0-8412-1702-7 10.1021/bk-1989-0413.ch018 264–280 https://bitnest.netfirms.com/external/10.1021/bk-1989-0413.ch018 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 J Med Chem 33 3 1032–1036 March 1990 2308135 10.1021/jm00165a023 https://www.erowid.org/archive/rhodium/pdf/glennon.sar.4-subst.pea.pdf It 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) 2C-Ph 4-PhPr-2,5-DMA 2C-T-27 Benzscaline (BZ) 3C-BZ Phescaline References External links DOBZ - Isomer Design Category:5-HT2B antagonists Category:DOx (psychedelics) Category:Serotonin receptor modulators