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

3,4-Methylenedioxy-N-hydroxy-N-methylamphetamine, also known as MDMOH, MDHMA, or FLEA, is an entactogen, psychedelic, and stimulant of the phenethylamine, amphetamine, and MDxx families. It is the N-hydroxy homologue of MDMA ("Ecstasy"), and the N-methyl homologue of MDOH.

FLEA

Clinical data
Other names	3,4-Methylenedioxy-N-hydroxy-N-methylamphetamine; 3,4-Methylenedioxy-N-methyl-N-hydroxyamphetamine; MDMOH; MDHMA; N-Hydroxy-MDMA; FLEA
Legal status
Legal status	DE: Anlage I (Authorized scientific use only) UK: Class A
Pharmacokinetic data
Duration of action	4–8 hours[1]
Identifiers
IUPAC name 1-(1,3-benzodioxol-5-yl)-N-hydroxy-N-methylpropan-2-amine
CAS Number	214414-88-7
PubChem CID	44350092
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
InChI InChI=1S/C11H15NO3/c1-8(12(2)13)5-9-3-4-10-11(6-9)15-7-14-10/h3-4,6,8,13H,5,7H2,1-2H3 Key:ORADFQZOLNHWRQ-UHFFFAOYSA-N

Use and effects

In his book PiHKAL (Phenethylamines I Have Known and Loved), Alexander Shulgin listed the dose range as 100–160 mg, and the duration as approximately 4–8 hours.^[1] He describes FLEA as causing entactogenic and open MDMA-like effects, easing communication, and increasing appreciation of the senses.^[1] He has noted that the properties and effects of the closely related drug 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, Trip killer § Antidotes of other hallucinogens, and MDMA/citalopram

Society and culture

Names

Alexander Shulgin explained the reasoning for naming the compound "FLEA" in his book PiHKAL.^[1]

Legal status

United Kingdom

This substance is a Class A drug in the Drugs controlled by the UK Misuse of Drugs Act.^[2]

See also

• Substituted methylenedioxyphenethylamine
• MDOH
• HOT-x (psychedelics)