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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.[citation needed]
It has been suggested that DOB is a prodrug metabolized in the lungs.[2][7]
Excessively high doses of this hallucinogen may cause diffuse arterial spasm.[8] The vasospasm responded readily to intra-arterial and intravenous vasodilators, such as tolazoline.
Listed as a Schedule 1 as it is an analogue of amphetamine.[10]
Australia
DOB is considered a Schedule 9 prohibited substance in Australia under the Poisons Standard (February 2017).[11] A Schedule 9 substance is a substance which may be abused or misused, the manufacture, possession, sale or use of which should be prohibited by law except when required for medical or scientific research, or for analytical, teaching or training purposes with approval of Commonwealth and/or State or Territory Health Authorities.[11]
Russia
Schedule I, possession of at least 10mg is a criminal offence.[12]
^Shulgin, A.T.; Sargent, T.; Naranjo, C. (1971). "4-Bromo-2,5-Dimethoxyphenylisopropylamine, a New Centrally Active Amphetamine Analog". Pharmacology. 5 (2): 103–107. doi:10.1159/000136181. PMID5570923. S2CID46844380.
^Parrish, Jason C.; Braden, Michael R.; Gundy, Emily; Nichols, David E. (2005-12-01). "Differential phospholipase C activation by phenylalkylamine serotonin 5-HT2A receptor agonists". Journal of Neurochemistry. 95 (6): 1575–1584. doi:10.1111/j.1471-4159.2005.03477.x. ISSN1471-4159. PMID16277614. S2CID24005602.
^Bowen, J. Scott, MD; Davis, Gary B., MD; Kearney, Thomas E., PharmD (1983-03-18). "Diffuse Vascular Spasm Associated With 4-Bromo-2,5-Dimethoxyamphetamine Ingestion". JAMA: The Journal of the American Medical Association. 249 (11): 1477–1479. doi:10.1001/jama.1983.03330350053028.{{cite journal}}: CS1 maint: multiple names: authors list (link)
‡ References for synthetic TAAR1 agonists can be found at TAAR1 or in the associated compound articles. For TAAR2 and TAAR5 agonists and inverse agonists, see TAAR for references.