{{Infobox drug | verifiedrevid = 415699222 | drug_name = | image = Meta-DOB.svg | image_class = skin-invert-image | width = 225px | caption =
<!-- Clinical data --> | pronounce = | tradename = | Drugs.com = | MedlinePlus = | licence_CA = | licence_EU = | DailyMedID = | licence_US = | pregnancy_AU = | pregnancy_category = | dependency_liability = | addiction_liability = | routes_of_administration = Oral<ref name="PiHKAL" /> | class = Psychoactive drug | ATC_prefix = None | ATC_suffix =
<!-- Legal status --> | legal_status =
<!-- Pharmacokinetic data --> | bioavailability = | protein_bound = | metabolism = | metabolites = | onset = | elimination_half-life = | duration_of_action = 5–6 hours<ref name="PiHKAL" /> | excretion =
<!-- Identifiers --> | CAS_number_Ref = {{cascite|correct|??}} | CAS_number = 60917-67-1 | CAS_supplemental = | PubChem = 143750 | PubChemSubstance = | IUPHAR_ligand = | DrugBank = | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 126826 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = SY5NJH58HC | KEGG = | ChEBI = | ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL = 33867 | NIAID_ChemDB = | PDB_ligand = | synonyms = 5-Bromo-2,4-dimethoxyamphetamine; 2,4-Dimethoxy-5-bromoamphetamine; 5-Bromo-TMA-2
<!-- Chemical data --> | IUPAC_name = 1-(5-bromo-2,4-dimethoxyphenyl)propan-2-amine | C=11 | H=16 | Br=1 | N=1 | O=2 | SMILES = Brc1cc(c(OC)cc1OC)CC(N)C | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 1S/C11H16BrNO2/c1-7(13)4-8-5-9(12)11(15-3)6-10(8)14-2/h5-7H,4,13H2,1-3H3 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = YFSLPSITQIUFQK-UHFFFAOYSA-N }}
'''Meta-DOB''', also known as '''5-bromo-2,4-dimethoxyamphetamine''', is a psychoactive drug of the phenethylamine and amphetamine families related to the psychedelic drug DOB.<ref name="PiHKAL">{{CitePiHKAL}}</ref> It is a positional isomer of DOB in which the bromine atom at the 4 position and the methoxy group at the 5 position have been interchanged.<ref name="PiHKAL" />
In his book ''PiHKAL'' (''Phenethylamines I Have Known and Loved''), Alexander Shulgin lists meta-DOB's dose range as 50 to 100{{nbsp}}mg orally and its duration as 5 to 6{{nbsp}}hours.<ref name="PiHKAL" /> The effects of meta-DOB have been reported to include MDA-like effects, vague uneasiness, possible threshold psychedelic effects, anxiety, paranoid fantasies, and toxic signs such as flushing, palpitations, and occasional nausea, vomiting, and diarrhea.<ref name="PiHKAL" /><ref name="SepúlvedaValenzuelaCassels1972" /> It has been said that any possible psychedelic effects of meta-DOB seem to have been blurred by its more obvious toxic effects.<ref name="PiHKAL" />
The chemical synthesis of meta-DOB has been described.<ref name="PiHKAL" /> A notable analogue of meta-DOB is meta-DOT.<ref name="PiHKAL" />
Meta-DOB was first described in the scientific literature by Silvia Sepúlveda and colleagues by 1972.<ref name="SepúlvedaValenzuelaCassels1972">{{cite journal | vauthors = Sepúlveda S, Valenzuela R, Cassels BK | title = Potential psychotomimetics. New bromoalkoxyamphetamines | journal = J Med Chem | volume = 15 | issue = 4 | pages = 413–415 | date = April 1972 | pmid = 5019563 | doi = 10.1021/jm00274a022 | url = }}</ref> Subsequently, it was described in greater detail by Shulgin in ''PiHKAL'' in 1991.<ref name="PiHKAL" />
==See also== * Substituted methoxyphenethylamine * DOx § Related compounds
==References== {{Reflist}}
==External links== * [https://isomerdesign.com/pihkal/explore/124 Meta-DOB - Isomer Design] * [http://www.erowid.org/library/books_online/pihkal/pihkal124.shtml Meta-DOB - PiHKAL - Erowid] * [https://isomerdesign.com/pihkal/read/pk/124 Meta-DOB - PiHKAL - Isomer Design]
{{Phenethylamines}}
Category:Methoxyphenethylamines Category:Organobromides Category:Phenol ethers Category:PiHKAL Category:Substituted amphetamines