3,4-Methylenedioxy-N-hydroxyamphetamine

MDOH
Clinical data
Other namesMDOH; MDH; N-Hydroxy-MDA
Routes of
administration		Oral
Drug classSerotonergic psychedelic; Hallucinogen; Entactogen
ATC code
  • None
Legal status
Legal status
Pharmacokinetic data
Duration of action3–6 hours
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. 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 160 mg orally and its duration as approximately 3 to 6 hours. 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

Canada

MDOH is a controlled substance in Canada.

United States

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

See also

References

  1. 1 2 3 4 5 6 7 8 9 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