This article will be permanently flagged as inappropriate and made unaccessible to everyone. Are you certain this article is inappropriate? Excessive Violence Sexual Content Political / Social
Email Address:
Article Id: WHEBN0000690940 Reproduction Date:
Dimethoxybromoamphetamine (DOB), also known as brolamfetamine ([1] and bromo-DMA, is a psychedelic drug and substituted amphetamine of the phenethylamine class of compounds. DOB was first synthesized by Alexander Shulgin in 1967.[2][3] Its synthesis and effects are documented in Shulgin's book PiHKAL: A Chemical Love Story.
The full name of the chemical is 2,5-dimethoxy-4-bromoamphetamine. DOB has a stereocenter and R-(–)-DOB is the eutomer. This is an important finding as it is suggestive that it is targeting different receptors relative to most other phenethylamines (e.g. MDMA) where the R-isomer serves as the distomer. The toxicity of DOB is not fully known, although high doses may cause serious vasoconstriction of the extremities. DOB is one of the most potent compounds in PiHKAL; while the active dose is similar to that of DOI, another psychedelic amphetamine, DOB has been shown to have a higher efficacy in triggering downstream effects mediated by 5-HT2 receptors,[4] making it likely to be slightly more dangerous than DOI in overdose, due to greater vasoconstrictive action. Omission of the amphetamine related α-methyl leads to 2C-B, a compound that possesses a lower affinity for the 5-HT2A receptor and is a weaker receptor agonist which results in drastically reduced vasoconstriction.
DOB is a 5-HT2A, 5-HT2B, and 5-HT2C receptor partial agonist.[5] Its psychedelic effects are mediated by its agonistic properties at the 5-HT2A receptor. Due to its selectivity, DOB is often used in scientific research when studying the 5-HT2 receptor subfamily. It is an agonist of human TAAR1.[6]
It has been suggested that DOB is a prodrug metabolized in the lungs.[2][7]
DOB is a Schedule I drug under the Convention on Psychotropic Substances.[8]
Listed as a Schedule 1 as it is an analogue of amphetamine.[9]
Entactogens: Lophophine
Methamphetamine, Amphetamine, Migraine, Ergotamine, Norepinephrine
5-Carboxamidotryptamine, 5-Methoxytryptamine, Metitepine, Lysergic acid diethylamide, Methysergide
Methamphetamine, Addiction, Norepinephrine, Gene expression, PubChem
5-Carboxamidotryptamine, Metitepine, Lysergic acid diethylamide, Bromocriptine, Methysergide
Ergoline, Serotonin, Amphetamine, Lysergic acid diethylamide, 5-Methoxytryptamine
Serotonin, Ergoline, Lysergic acid diethylamide, Amphetamine, 5-Methoxytryptamine
Stimulant, Amphetamine, Methamphetamine, Lysergic acid diethylamide, Entactogen