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3,4-Methylenedioxy-N-hydroxyamphetamine

Psychedelic and entactogen

Field	Value
drug_name	MDOH
image	MDOH_structure.svg
image_class	skin-invert-image
width	250px
routes_of_administration	Oral
class	Serotonergic psychedelic; Hallucinogen; Entactogen
ATC_prefix	None
legal_CA	Schedule I
legal_UK	Class A
legal_DE	Anlage I
legal_US	Schedule I
legal_UN	P I
duration_of_action	3–6 hours
CAS_number	74698-47-8
UNII_Ref
UNII	SJE1T2B1A7
PubChem	98528
KEGG	C22807
ChemSpiderID	88979
synonyms	MDOH; MDH; N-Hydroxy-MDA
IUPAC_name	1-(1,3-Benzodioxol-5-yl)-N-hydroxypropan-2-amine
C	10	H=13	N=1	O=3
SMILES	CC(CC1=CC2=C(C=C1)OCO2)NO

| elimination_half-life =

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. It is the N-hydroxy homologue of MDA, and the N-desmethyl homologue of FLEA (MDMOH).

Use and effects

In his book PiHKAL (Phenethylamines I Have Known and Loved), Alexander Shulgin listed the dose range as 100 to 160mg orally and its duration as approximately 3 to 6hours. He describes MDOH as being very psychedelic and producing increased pleasure in beauty and nature. Shulgin also mentioned several negative side effects also seen with MDMA ("Ecstasy") such as difficulty urinating and internal dryness. 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.

Interactions

Chemistry

Synthesis

The chemical synthesis of MDOH has been described.

Analogues

Analogues of MDOH include MDA and FLEA (MDMOH), among others.

Society and culture

Legal status

Canada

MDOH is a controlled substance in Canada.

United States

MDOH is a schedule I controlled substance in the United States.

References

(April 2004). "A new trend in drugs-of-abuse; the 2C-series of phenethylamine designer drugs". Pharmacy World & Science.
{{CitePiHKAL
"Controlled Drugs and Substances Act".
(January 2026). "Orange Book: List of Controlled Substances and Regulated Chemicals (January 2026)". U.S. [[Department of Justice]]: [[Drug Enforcement Administration]] (DEA): Diversion Control Division.

Info: Wikipedia Source

This article was imported from Wikipedia and is available under the Creative Commons Attribution-ShareAlike 4.0 License. Content has been adapted to SurfDoc format. Original contributors can be found on the article history page.

designer-prodrugs entactogens human-drug-metabolites hydroxylamines methylenedioxyphenethylamines pihkal psychedelic-phenethylamines recreational-drug-metabolites serotonin-norepinephrine-dopamine-releasing-agents substituted-amphetamines

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