# Meta-DOB

> Mediated Wiki article. Canonical URL: https://mediated.wiki/source/Meta-DOB
> Markdown URL: https://mediated.wiki/source/Meta-DOB.md
> Source: https://en.wikipedia.org/wiki/Meta-DOB
> Source revision: 1340339627
> License: Creative Commons Attribution-ShareAlike 4.0 International (https://creativecommons.org/licenses/by-sa/4.0/)

{{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](/source/Oral_administration)<ref name="PiHKAL" />
| class = [Psychoactive drug](/source/Psychoactive_drug)
| ATC_prefix = None
| ATC_suffix = 

<!-- Legal status -->
| legal_status = 

<!-- Pharmacokinetic data -->
| bioavailability = 
| protein_bound = 
| metabolism = 
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| 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](/source/psychoactive_drug) of the [phenethylamine](/source/substituted_phenethylamine) and [amphetamine](/source/substituted_amphetamine) families related to the [psychedelic drug](/source/psychedelic_drug) [DOB](/source/DOB_(drug)).<ref name="PiHKAL">{{CitePiHKAL}}</ref> It is a [positional isomer](/source/positional_isomer) of DOB in which the [bromine](/source/bromine) atom at the 4 position and the [methoxy group](/source/methoxy_group) at the 5 position have been interchanged.<ref name="PiHKAL" />

In his book ''[PiHKAL](/source/PiHKAL)'' (''Phenethylamines I Have Known and Loved''), [Alexander Shulgin](/source/Alexander_Shulgin) lists meta-DOB's dose range as 50 to 100{{nbsp}}mg [orally](/source/oral_administration) and its [duration](/source/duration_of_action) as 5 to 6{{nbsp}}hours.<ref name="PiHKAL" /> The effects of meta-DOB have been reported to include [MDA](/source/3%2C4-methylenedioxyamphetamine)-like effects, vague uneasiness, possible threshold psychedelic effects, [anxiety](/source/anxiety), [paranoid](/source/paranoia) [fantasies](/source/fantasy_(psychology)), and [toxic](/source/toxicity) signs such as [flushing](/source/flushing_(medical)), [palpitation](/source/palpitation)s, and occasional [nausea](/source/nausea), [vomiting](/source/vomiting), and [diarrhea](/source/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](/source/chemical_synthesis) of meta-DOB has been described.<ref name="PiHKAL" /> A notable [analogue](/source/structural_analog) of meta-DOB is [meta-DOT](/source/meta-DOT).<ref name="PiHKAL" />

Meta-DOB was first described in the [scientific literature](/source/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](/source/Substituted_methoxyphenethylamine)
* [DOx § Related compounds](/source/DOx)

==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

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Adapted from the Wikipedia article [Meta-DOB](https://en.wikipedia.org/wiki/Meta-DOB) by Wikipedia contributors ([contributor history](https://en.wikipedia.org/wiki/Meta-DOB?action=history)). Available under [Creative Commons Attribution-ShareAlike 4.0 International](https://creativecommons.org/licenses/by-sa/4.0/). Changes may have been made.