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

{{Short description|Chemical compound}}

{{Drugbox

| drug_name = FLEA

| IUPAC_name = 1-(1,3-Benzodioxol-5-yl)-N-hydroxy-N-methylpropan-2-amine

| image = FLEA.svg

| width = 200px

| tradename =

| pregnancy_category =

| legal_UK = Class A

| legal_DE = Anlage I

| routes_of_administration =

| bioavailability =

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| CAS_number = 214414-88-7

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = E2816HU3KT

| ATC_prefix =

| ATC_suffix =

| PubChem = 44350092

| KEGG = C22806

| DrugBank =

| ChemSpiderID = 21106310

| synonyms = 3,4-Methylenedioxy-N-hydroxy-N-methylamphetamine; 3,4-Methylenedioxy-N-methyl-N-hydroxyamphetamine; MDMOH; MDHMA; N-Hydroxy-MDMA

| C=11 | H=15 | N=1 | O=3

| SMILES = C1=C2C(=CC=C1CC(C)N(C)O)OCO2

| Jmol =

| StdInChI = 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

| StdInChI_comment =

| StdInChIKey = ORADFQZOLNHWRQ-UHFFFAOYSA-N

}}

FLEA, also known as 3,4-methylenedioxy-N-hydroxy-N-methylamphetamine (MDMOH or MDHMA), 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 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 4–8 hours.{{CitePiHKAL|name-list-style = vanc }} He describes FLEA as causing entactogenic and open MDMA-like effects, easing communication, and increasing appreciation of the senses. Shulgin explained the reasoning for naming the compound "FLEA" in PiHKAL.