3,4-Methylenedioxy-N-hydroxyamphetamine

3,4-Methylenedioxy-N-hydroxyamphetamine (MDOH, MDH), also known as N-hydroxy-MDA, is an entactogen, psychedelic, and stimulant of the phenethylamine and amphetamine chemical classes.^[2] It is the N-hydroxy homologue of MDA, and the N-desmethyl homologue of MDHMA.^[1]

MDOH

Clinical data
Other names	MDOH; MDH; N-Hydroxy-MDA
Routes of administration	Oral[1]
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[1]
Identifiers
IUPAC name 1-(1,3-Benzodioxol-5-yl)-N-hydroxypropan-2-amine
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

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

See also

• Substituted methylenedioxyphenethylamine
• FLEA (MDMOH)
• HOT-x (psychedelics)
• N-Hydroxy-DOM
• N-Hydroxy-AMT