3,4-Methylenedioxy-N-hydroxyamphetamine

3,4-Methylenedioxy-N-hydroxyamphetamine
Clinical data
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;
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;
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;

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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