2,5-Dimethoxy-3-bromoamphetamine

vanc 6 3-DOB 3-DOB.svg skin-invert-image 225px None Psychoactive drug; Serotonin receptor modulator 106791-38-2 None 12626552 23115301 16883 3-Br-2,5-DMA; 3-DOB; iso-DOB; SL-7161; 2,5-Dimethoxy-3-bromoamphetamine; 3-Bromo-2,5-dimethoxyamphetamine 1 11 16 1 2 COc1cc(CC(N)C)c(c(c1)Br)OC InChI=1S/C11H16BrNO2/c1-7(13)4-8-5-9(14-2)6-10(12)11(8)15-3/h5-7H,4,13H2,1-3H3 HCZXNFSMGJKVHO-UHFFFAOYSA-N 2,5-Dimethoxy-3-bromoamphetamine, also known as 3-Br-2,5-DMA, 3-DOB, or iso-DOB, is a psychoactive compound belonging to the family of substituted phenеthylamines and amphetamine derivatives. It is a positional isomer of 4-bromo-2,5-dimethoxyamphetamine (DOB; 4-Br-2,5-DMA) and a derivative of 2,5-dimethoxyamphetamine (2,5-DMA; DOH) where the hydrogen atom in the 3 position of the benzene ring is replaced by bromine. 3-Br-2,5-DMA exhibits agonistic activity against serotonin 5-HT2 and 5-HT3 receptors. Merahi N, Laguzzi R Cardiovascular effects of 5HT2 and 5HT3 receptor stimulation in the nucleus tractus solitarius of spontaneously hypertensive rats Brain Research 669 1 130–134 January 1995 7712156 10.1016/0006-8993(94)01202-s Merahi N, Orer HS, Laguzzi R 5-HT2 receptors in the nucleus tractus solitarius: characterisation and role in cardiovascular regulation in the rat Brain Research 575 1 74–78 March 1992 1504784 10.1016/0006-8993(92)90425-9 In The Shulgin Index, 3-Br-2,5-DMA was referred to as "3-DOB" 3-DOB explore PiHKAL·info https://isomerdesign.com/pihkal/explore/7060 2026-02-22 isomerdesign.com Pharmacology Pharmacodynamics 3-Br-2,5-DMA demonstrated weak or even low psychoactivity, unlike its isomers, and did not have a significant effect on the activity of neurons in the locus coeruleus. Despite the structural difference, it is precisely because of the positional difference from other isomers that this substance exhibits a low psychoactive effect, 3-Br-2,5-DMA It did not cause any behavioral changes or hallucinogenic effects, it is noted that this substance is of "inactive". Rasmussen K, Glennon RA, Aghajanian GK Phenethylamine hallucinogens in the locus coeruleus: potency of action correlates with rank order of 5-HT2 binding affinity European Journal of Pharmacology 132 1 79–82 December 1986 3816969 10.1016/0014-2999(86)90014-2 free 3-Br-2,5-DMA binds to serotonin receptors approximately 50 to 60times weaker than DOB. Glennon RA, Liebowitz SM, Anderson GM Serotonin receptor affinities of psychoactive phenalkylamine analogues Journal of Medicinal Chemistry 23 3 294–299 March 1980 7365744 10.1021/jm00177a017 Chemistry Synthesis 3-Br-2,5-DMA can be successfully obtained from nitropropene. Synthesis of the 3-Br-2,5-DMA requires the use of aluminum hydride (AlH3) instead of the standard lithium aluminum hydride, since the latter causes a dehalogenation side reaction leading to the elimination of a bromine atom. History 3-DOB was first described in the scientific literature by Richard Glennon and colleagues by 1980. See also Substituted methoxyphenethylamine DOx § Related compounds References External links 3-DOB - Isomer Design Category:Bromobenzene derivatives Category:Methoxyphenethylamines Category:Serotonin receptor modulators Category:Substituted amphetamines