3,4-Methylenedioxy-N-hydroxy-N-methylamphetamine

3,4-Methylenedioxy-N-hydroxy-N-methylamphetamine
Legal status
Legal status	DE: Anlage I (Authorized scientific use only); UK: Class A;
Identifiers
	IUPAC name 1-(1,3-Benzodioxol-5-yl)-N-hydroxy-N-methylpropan-2-amine;
CAS Number	214414-88-7;
ChemSpider	21106310;
UNII	E2816HU3KT;
KEGG	C22806;
CompTox Dashboard (EPA)	DTXSID90658377 ;
Chemical and physical data
Formula	C11H15NO3
Molar mass	209.245 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C1=C2C(=CC=C1CC(C)N(C)O)OCO2;

3,4-Methylenedioxy-N-hydroxy-N-methylamphetamine (MDHMA; FLEA) is an entactogen, psychedelic, and stimulant of the phenethylamine and amphetamine chemical classes. It is the N-hydroxy homologue of MDMA ("Ecstasy"), and the N-methyl homologue of MDOH. MDHMA was first synthesized and assayed by Alexander Shulgin.^[1] In his book PiHKAL (Phenethylamines i Have Known And Loved), Shulgin listed the dosage range as 100–160 mg, and the duration as approximately 4–8 hours.^[1] He describes MDHMA as causing entactogenic and open MDMA-like effects, easing communication, and increasing appreciation of the senses.^[1]

^ ^a ^b ^c Shulgin A, Shulgin A (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628.

[CitePiHKAL-1] Shulgin A, Shulgin A (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628.

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