{{Infobox drug | verifiedrevid = 415838126 | drug_name = | image = Methyl-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 = Serotonin receptor modulator; Psychoactive drug | ATC_prefix = None | ATC_suffix =
<!-- Legal status --> | legal_status =
<!-- Pharmacokinetic data --> | bioavailability = | protein_bound = | metabolism = | metabolites = | onset = 1.3 hours<ref name="PiHKAL" /> | elimination_half-life = | duration_of_action = "Probably rather long"<ref name="PiHKAL" /> | excretion =
<!-- Identifiers --> | CAS_number_Ref = {{cascite|correct|CAS}} | CAS_number = 155638-80-5 | CAS_supplemental = | PubChem = 10085486 | PubChemSubstance = | IUPHAR_ligand = | DrugBank = | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 8261023 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = WW3LF52S82 | KEGG = | ChEBI = | ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL = 351858 | NIAID_ChemDB = | PDB_ligand = | synonyms = ''N''-Methyl-DOB; ''N''-Me-DOB; 4-Bromo-2,5-dimethoxy-''N''-methylamphetamine; MDOB; M-154
<!-- Chemical data --> | IUPAC_name = 1-(4-bromo-2,5-dimethoxyphenyl)-''N''-methylpropan-2-amine | C=12 | H=18 | Br=1 | N=1 | O=2 | SMILES = Brc1cc(OC)c(cc1OC)CC(NC)C | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 1S/C12H18BrNO2/c1-8(14-2)5-9-6-12(16-4)10(13)7-11(9)15-3/h6-8,14H,5H2,1-4H3 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = GURVSGCCXMIFMQ-UHFFFAOYSA-N }}
'''Methyl-DOB''', or '''''N''-methyl-DOB''', also known as '''4-bromo-2,5-dimethoxy-''N''-methylamphetamine''', '''MDOB''', or '''M-154''', is a psychoactive drug of the phenethylamine, amphetamine, and DOx families.<ref name="PiHKAL">{{CitePiHKAL}} http://www.erowid.org/library/books_online/pihkal/pihkal127.shtml</ref> It is the ''N''-methyl derivative of the psychedelic drug DOB.<ref name="PiHKAL" />
==Use and effects== In his book ''PiHKAL'' (''Phenethylamines I Have Known and Loved''), Alexander Shulgin lists methyl-DOB's dose as greater than 8{{nbsp}}mg orally and its duration as "probably rather long".<ref name="PiHKAL" /> Its onset was about 1.3{{nbsp}}hours.<ref name="PiHKAL" /> Analogously to the case of other ''N''-methylated phenethylamines, the potency of methyl-DOB is dramatically reduced compared to DOB, which has a listed dose of 1 to 3{{nbsp}}mg orally.<ref name="PiHKAL" />
At tested doses of 8 to 10{{nbsp}}mg orally, the effects of methyl-DOB have been reported to include lightheadedness, spaciness, physical effects or body load, tight and rubby teeth, tenseness, exaggerated reflexes, pupil dilation, and next-day hangover.<ref name="PiHKAL" /> No clear psychoactive or hallucinogenic effects were described.<ref name="PiHKAL" /> The drug may also potentiate other psychedelic drugs like even on the next day however, with a "severe response" to a low 5{{nbsp}}mg dose of psilocybin 24{{nbsp}}hours later occurring in one instance.<ref name="PiHKAL" />
==Interactions== {{See also|Psychedelic drug#Interactions|Trip killer#Serotonergic psychedelic antidotes}}
==Pharmacology== ===Pharmacodynamics=== Methyl-DOB shows affinity for the serotonin 5-HT<sub>2A</sub> and 5-HT<sub>2C</sub> receptors (K<sub>i</sub> = 79–80{{nbsp}}nM and 98{{nbsp}}nM, respectively).<ref name="GlennonRaghupathiBartyzel1992">{{cite journal | vauthors = Glennon RA, Raghupathi R, Bartyzel P, Teitler M, Leonhardt S | title = Binding of phenylalkylamine derivatives at 5-HT1C and 5-HT2 serotonin receptors: evidence for a lack of selectivity | journal = J Med Chem | volume = 35 | issue = 4 | pages = 734–740 | date = February 1992 | pmid = 1542100 | doi = 10.1021/jm00082a014 | url = }}</ref><ref name="GlennonTitelerSeggel1987">{{cite journal | vauthors = Glennon RA, Titeler M, Seggel MR, Lyon RA | title = N-methyl derivatives of the 5-HT2 agonist 1-(4-bromo-2,5-dimethoxyphenyl)-2-aminopropane | journal = J Med Chem | volume = 30 | issue = 5 | pages = 930–932 | date = May 1987 | pmid = 3572981 | doi = 10.1021/jm00388a032 | url = }}</ref> Its affinities for serotonin 5-HT<sub>2</sub> receptors were 1.4- to 9.7-fold lower than those of DOB depending on the receptor and radioligand.<ref name="GlennonRaghupathiBartyzel1992" /><ref name="GlennonTitelerSeggel1987" /> Methyl-DOB substituted for (''R'')-DOB in rodent drug discrimination tests, but was approximately 16-fold less potent in comparison.<ref name="GlennonTitelerSeggel1987" />
==Chemistry== ===Synthesis=== The chemical synthesis of methyl-DOB has been described.<ref name="PiHKAL" />
===Analogues=== Analogues of methyl-DOB include ''N''-methyl-DOI, IDNNA (''N'',''N''-dimethyl-DOI), ''N''-methyl-2C-B, Beatrice (''N''-methyl-DOM), ''N''-methyl-DOET, ''N''-methyl-TMA-2, and methyl-TMA (''N''-methyl-TMA), among others.<ref name="PiHKAL" />
==History== Methyl-DOB was first described in the scientific literature by Richard Glennon and colleagues by 1987.<ref name="GlennonTitelerSeggel1987" /> Subsequently, it was described in greater detail by Alexander Shulgin in his book ''PiHKAL'' (''Phenethylamines I Have Known and Loved'') in 1991.<ref name="PiHKAL" />
==Society and culture== ===Legal status=== Methyl-DOB is a controlled substance in Canada under phenethylamine blanket-ban language.<ref name="CDSA">{{cite web | title=Controlled Drugs and Substances Act | website=Department of Justice Canada | url=https://laws-lois.justice.gc.ca/eng/acts/c-38.8/FullText.html | access-date=19 January 2026}}</ref>
==See also== * DOx (psychedelics)
==References== {{Reflist}}
==External links== * [https://isomerdesign.com/pihkal/explore/127 Methyl-DOB - Isomer Design] * [http://www.erowid.org/library/books_online/pihkal/pihkal127.shtml Methyl-DOB - PiHKAL - Erowid] * [http://pihkal.info/read.php?domain=pk&id=127 Methyl-DOB - PiHKAL - Isomer Design]
{{Serotonin receptor modulators}} {{Phenethylamines}}
Category:DOx (psychedelics) Category:Methamphetamines Category:PiHKAL Category:Serotonin receptor modulators