Methylenedioxyhydroxyamphetamine

3,4-Methylenedioxy-N-hydroxyamphetamine
Clinical data

ATC code	none
Legal status
Legal status	CA: Schedule I DE: Anlage I (Controlled) UK: Class A US: Schedule I
Identifiers
IUPAC name 1-(1,3-Benzodioxol-5-yl)-N-hydroxypropan-2-amine
CAS Number	74698-47-8
PubChem CID	98528
ChemSpider	88979
Chemical and physical data
Formula	C₁₀H₁₃NO₃
Molar mass	195.22 g/mol
3D model (Jmol)	Interactive image
SMILES CC(CC1=CC2=C(C=C1)OCO2)NO

3,4-Methylenedioxy-N-hydroxyamphetamine (MDOH, MDH, N-hydroxytenamphetamine) is an entactogen, psychedelic, and stimulant of the phenethylamine and amphetamine chemical classes. It is the N-hydroxy homologue of MDA, and the N-desmethyl homologue of MDHMA. MDOH was first synthesized and assayed by Alexander Shulgin. In his book PiHKAL (Phenethylamines i Have Known And Loved), Shulgin listed the dosage range as 100–160 mg, and the duration as approximately 3–6 hours. He describes MDOH as being very psychedelic and producing increased pleasure in beauty and nature. He also mentioned several negative side effects also seen with MDMA ("Ecstasy") such as difficulty urinating and internal dryness.

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