{{Short description|Psychedelic and entactogen}} {{DISPLAYTITLE:3,4-Methylenedioxy-''N''-hydroxyamphetamine}} {{Infobox drug | drug_name = MDOH | image = MDOH_structure.svg | image_class = skin-invert-image | width = 250px | image2 = MDOH ball-and-stick structure.png | image_class2 = bg-transparent | width2 = 225px
<!-- Clinical data --> | tradename = | pregnancy_category = | routes_of_administration = Oral<ref name="PiHKAL" /> | class = Serotonergic psychedelic; Hallucinogen; Entactogen | ATC_prefix = None | ATC_suffix =
<!-- Legal status --> | legal_CA = Schedule I | legal_UK = Class A | legal_DE = Anlage I | legal_US = Schedule I | legal_UN = P I
<!-- Pharmacokinetic data --> | bioavailability = | protein_bound = | metabolism = | onset = | elimination_half-life = | duration_of_action = 3–6 hours<ref name="PiHKAL" /> | excretion =
<!-- Identifiers --> | CAS_number = 74698-47-8 | PubChem = 98528 | DrugBank = | ChemSpiderID = 88979 | KEGG = C22807 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = SJE1T2B1A7 | synonyms = MDOH; MDH; ''N''-Hydroxy-MDA
<!-- Chemical data --> | IUPAC_name = ''N''-[1-(1,3-benzodioxol-5-yl)propan-2-yl]hydroxylamine | C=10 | H=13 | N=1 | O=3 | SMILES = CC(CC1=CC2=C(C=C1)OCO2)NO | StdInChI = 1S/C10H13NO3/c1-7(11-12)4-8-2-3-9-10(5-8)14-6-13-9/h2-3,5,7,11-12H,4,6H2,1H3 | StdInChIKey = FNDCTJYFKOQGTL-UHFFFAOYSA-N }}
'''3,4-Methylenedioxy-''N''-hydroxyamphetamine''' ('''MDOH''', '''MDH'''), also known as '''''N''-hydroxy-MDA''', is an entactogen, psychedelic, and stimulant of the phenethylamine, amphetamine, and MDxx families.<ref name="de_Boer_2004">{{cite journal | vauthors = de Boer D, Bosman I | title = A new trend in drugs-of-abuse; the 2C-series of phenethylamine designer drugs | journal = Pharmacy World & Science | volume = 26 | issue = 2 | pages = 110–113 | date = April 2004 | pmid = 15085947 | doi = 10.1023/b:phar.0000018600.03664.36 }}</ref> It is the ''N''-hydroxy homologue of MDA, and the ''N''-desmethyl homologue of FLEA (MDMOH).<ref name="PiHKAL">{{CitePiHKAL|name-list-style = vanc }}</ref>
==Use and effects== In his book ''PiHKAL'' (''Phenethylamines I Have Known and Loved''), Alexander Shulgin listed the dose range as 100 to 160{{nbsp}}mg orally and its duration as approximately 3 to 6{{nbsp}}hours.<ref name = "PiHKAL" /> He describes MDOH as being very psychedelic and producing increased pleasure in beauty and nature.<ref name = "PiHKAL" /> Shulgin also mentioned several negative side effects also seen with MDMA ("Ecstasy") such as difficulty urinating and internal dryness.<ref name="PiHKAL" /> He has noted that the properties and effects of MDOH are very similar or near-identical to those of MDA and that MDOH might be converted into MDA in the body.<ref name="PiHKAL" />
==Interactions== {{See also|MDMA#Interactions|Psychedelic drug#Interactions|Trip killer#Serotonergic psychedelic antidotes|Trip killer#Antidotes of other hallucinogens|MDMA/citalopram}}
==Chemistry== ===Synthesis=== The chemical synthesis of MDOH has been described.<ref name="PiHKAL" />
===Analogues=== Analogues of MDOH include MDA and FLEA (MDMOH), among others.<ref name="PiHKAL" />
==Society and culture== ===Legal status=== ====Canada==== MDOH is a controlled substance in Canada.<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>
====United States==== MDOH is a schedule I controlled substance in the United States.<ref name="OrangeBook2026">{{citation | title = Orange Book: List of Controlled Substances and Regulated Chemicals (January 2026) | date = January 2026 | publisher = U.S. Department of Justice: Drug Enforcement Administration (DEA): Diversion Control Division | location = United States | url = https://www.deadiversion.usdoj.gov/schedules/orangebook/orangebook.pdf}}</ref>
==See also== * Substituted methylenedioxyphenethylamine * HOT-x (psychedelics) * ''N''-Hydroxyamphetamine * ''N''-Hydroxy-DOM * ''N''-Hydroxy-AMT
==References== {{Reflist}}
==External links== * [https://isomerdesign.com/pihkal/explore/114 MDOH - Isomer Design] * [http://www.erowid.org/library/books_online/pihkal/pihkal114.shtml MDOH - PiHKAL - Erowid] * [http://pihkal.info/read.php?domain=pk&id=114 MDOH - PiHKAL - Isomer Design]
{{Entactogens}} {{Psychedelics}} {{Stimulants}} {{Monoamine releasing agents}} {{Phenethylamines}}
{{DEFAULTSORT:Methylenedioxy-N-hydroxyamphetamine, 3,4-}}
Category:Designer prodrugs Category:Entactogens Category:Methylenedioxyamphetamines Category:N-Hydroxyphenethylamines Category:PiHKAL Category:Psychedelic drug metabolites Category:Psychedelic phenethylamines Category:Serotonin-norepinephrine-dopamine releasing agents