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| Other names | 3,4-Methylenedioxy-N-hydroxy-N-methylamphetamine; 3,4-Methylenedioxy-N-methyl-N-hydroxyamphetamine; MDMOH; MDHMA;N-Hydroxy-MDMA; FLEA |
| Routes of administration | Oral[1] |
| Drug class | Entactogen |
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| Duration of action | 4–8 hours[1] |
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| Formula | C11H15NO3 |
| Molar mass | 209.245 g·mol−1 |
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3,4-Methylenedioxy-N-hydroxy-N-methylamphetamine, also known asMDMOH,MDHMA, orFLEA, is anentactogen,psychedelic, andstimulant of thephenethylamine,amphetamine, andMDxx families.[1] It is theN-hydroxyhomologue ofMDMA ("Ecstasy"), and theN-methyl homologue ofMDOH.[1]
In his bookPiHKAL (Phenethylamines I Have Known and Loved),Alexander Shulgin listed the dose range as 100 to 160 mgorally, and theduration as approximately 4 to 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]
Thechemical synthesis of FLEA has been described.[1]
Analogues of FLEA includeMDMA andMDOH (N-hydroxy-MDA), among others.[1]
Alexander Shulgin explained the reasoning for naming the compound "FLEA" in his bookPiHKAL (Phenethylamines I Have Known and Loved):[1]
Of course, I was asked, why call it FLEA? The origin was in a classic bit of poetry. A commonly used code name for MDMA was ADAM, and I had tried making several modest modifications of the MDMA structure in the search for another compound that would maintain its particular music without the annoying tooth-grinding and occasional nystagmus, or eye-wiggle, that some users have mentioned. One of these was the 6-methyl homologue which was, with some perverse logic, called MADAM. And, following this pattern, the 6-fluoroanalogue was to be FLADAM. So, with the N-hydroxy analogue, what about HADAM? Which brought to mind the classic description of Adam's earliest complaint, an infestation of fleas.The poem was short and direct. "Adam had 'em." So, in place of HAD 'EM, the term FLEA jumped into being.
FLEA is acontrolled substance inCanada under phenethylamine blanket-ban language.[2]
This substance is a Class A drug in theDrugs controlled by the UK Misuse of Drugs Act.[3]
FLEA is not an explicitlycontrolled substance in theUnited States.[4] However, it could be considered a controlled substance under theFederal Analogue Act if intended for human consumption.
