3,4-Methylenedioxy-N-hydroxyamphetamine

MDOH
Clinical data
Other namesMDOH; MDH; N-Hydroxy-MDA
Routes of
administration		Oral[1]
Drug classSerotonergic psychedelic; Hallucinogen; Entactogen
ATC code
  • None
Legal status
Legal status
Pharmacokinetic data
Duration of action3–6 hours[1]
Identifiers
  • N-[1-(1,3-benzodioxol-5-yl)propan-2-yl]hydroxylamine
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC10H13NO3
Molar mass195.218 g·mol−1
3D model (JSmol)
  • CC(CC1=CC2=C(C=C1)OCO2)NO
  • InChI=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
  • Key: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.[2] It is the N-hydroxy homologue of MDA, and the N-desmethyl homologue of FLEA (MDMOH).[1]

Use and effects

In his book PiHKAL (Phenethylamines I Have Known and Loved), Alexander Shulgin listed the dose range as 100 to 160 mg orally and its duration as approximately 3 to 6 hours.[1] He describes MDOH as being very psychedelic and producing increased pleasure in beauty and nature.[1] Shulgin also mentioned several negative side effects also seen with MDMA ("Ecstasy") such as difficulty urinating and internal dryness.[1] 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.[1]

Interactions

See also: MDMA § Interactions, Psychedelic drug § Interactions, Trip killer § Serotonergic psychedelic antidotes, Trip killer § Antidotes of other hallucinogens, and MDMA/citalopram

Chemistry

Synthesis

The chemical synthesis of MDOH has been described.[1]

Analogues

Analogues of MDOH include MDA and FLEA (MDMOH), among others.[1]

Society and culture

Canada

MDOH is a controlled substance in Canada.[3]

United States

MDOH is a schedule I controlled substance in the United States.[4]

See also

References

  1. ^ a b c d e f g h i Shulgin A, Shulgin A (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628.
  2. ^ de Boer D, Bosman I (April 2004). "A new trend in drugs-of-abuse; the 2C-series of phenethylamine designer drugs". Pharmacy World & Science. 26 (2): 110–113. doi:10.1023/b:phar.0000018600.03664.36. PMID 15085947.
  3. ^ "Controlled Drugs and Substances Act". Department of Justice Canada. Retrieved 19 January 2026.
  4. ^ Orange Book: List of Controlled Substances and Regulated Chemicals (January 2026) (PDF), United States: U.S. Department of Justice: Drug Enforcement Administration (DEA): Diversion Control Division, January 2026
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