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

FLEA
Clinical data
Other names3,4-Methylenedioxy-N-hydroxy-N-methylamphetamine; 3,4-Methylenedioxy-N-methyl-N-hydroxyamphetamine; MDMOH; MDHMA; N-Hydroxy-MDMA; FLEA
Routes of
administration		Oral[1]
Drug classEntactogen
ATC code
  • None
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
CompTox Dashboard (EPA)
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.[1] It is the N-hydroxy homologue of MDMA ("Ecstasy"), and the N-methyl homologue of MDOH.[1]

Use and effects

In his book PiHKAL (Phenethylamines I Have Known and Loved), Alexander Shulgin lists FLEA's dose as 100 to 160 mg orally and its duration as 4 to 8 hours.[1] He describes FLEA as producing 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

Chemistry

Synthesis

The chemical synthesis of FLEA has been described.[1]

Analogues

Analogues of FLEA include MDMA and MDOH (N-hydroxy-MDA), among others.[1]

Society and culture

Names

Alexander Shulgin explained the reasoning for naming the compound "FLEA" in his book PiHKAL (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.

Canada

FLEA is a controlled substance in Canada under phenethylamine blanket-ban language.[2]

United Kingdom

This substance is a Class A drug in the Drugs controlled by the UK Misuse of Drugs Act.[3]

United States

FLEA is not an explicitly controlled substance in the United States.[4] However, it could be considered a controlled substance under the Federal Analogue Act if intended for human consumption.

See also

References

  1. ^ a b c d e f g h i j Shulgin A, Shulgin A (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628.
  2. ^ "Controlled Drugs and Substances Act". Department of Justice Canada. Retrieved 19 January 2026.
  3. ^ "UK Misuse of Drugs act 2001 Amendment summary". Isomer Design. Archived from the original on 22 October 2017. Retrieved 12 March 2014.
  4. ^ Orange Book: List of Controlled Substances and Regulated Chemicals (January 2026) (PDF), United States: U.S. Department of Justice: Drug Enforcement Administration (DEA): Diversion Control Division, January 2026
This article is issued from Wikipedia. The text is available under Creative Commons Attribution-Share Alike 4.0 unless otherwise noted. Additional terms may apply for the media files.