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

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FLEA
File:FLEA.svg
Clinical data
Other names3,4-Methylenedioxy-N-hydroxy-N-methylamphetamine; 3,4-Methylenedioxy-N-methyl-N-hydroxyamphetamine; MDMOH; MDHMA; N-Hydroxy-MDMA; FLEA
Legal status
Legal status
Pharmacokinetic data
Duration of action4–8 hours[1]
Identifiers
  • 1-(1,3-benzodioxol-5-yl)-N-hydroxy-N-methylpropan-2-amine
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
E number{{#property:P628}}
CompTox Dashboard (EPA)
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Chemical and physical data
FormulaC11H15NO3
Molar mass209.245 g·mol−1
3D model (JSmol)
  • C1=C2C(=CC=C1CC(C)N(C)O)OCO2
  • 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

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.

Use and effects

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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

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See also: MDMA § Interactions, Trip killer § Antidotes of other hallucinogens, and MDMA/citalopram

Society and culture

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Names

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

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United Kingdom

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

See also

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References

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