3,4-Methylenedioxy-N-hydroxyamphetamine

MDOH
Clinical data
Other names	MDOH; MDH; N-Hydroxy-MDA
Routes of; administration	Oral
Drug class	Serotonergic psychedelic; Hallucinogen; Entactogen
ATC code	None;
Legal status
Legal status	CA: Schedule I; DE: Anlage I (Authorized scientific use only); UK: Class A; US: Schedule I; UN: Psychotropic Schedule I;
Pharmacokinetic data
Duration of action	3–6 hours
Identifiers
	IUPAC name N-[1-(1,3-benzodioxol-5-yl)propan-2-yl]hydroxylamine;
CAS Number	74698-47-8;
PubChem CID	98528;
ChemSpider	88979;
UNII	SJE1T2B1A7;
KEGG	C22807;
CompTox Dashboard (EPA)	DTXSID30860972 ;
Chemical and physical data
Formula	C10H13NO3
Molar mass	195.218 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC(CC1=CC2=C(C=C1)OCO2)NO;
	InChI 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

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

Legal status

Canada

MDOH is a controlled substance in Canada.^[3]

United States

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

References

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.
↑ 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.
↑ "Controlled Drugs and Substances Act". Department of Justice Canada. Retrieved 19 January 2026.
↑ 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

External links

[PiHKAL-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.

[de_Boer_2004-2] 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.

[CDSA-3] "Controlled Drugs and Substances Act". Department of Justice Canada. Retrieved 19 January 2026.

[OrangeBook2026-4] 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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