Drug info - FLEA (N-hydroxy-MDMA) Drug Info

Discussion in 'Phenethylamines' started by Alfa, Feb 28, 2004.

  1. Alfa

    Alfa Productive Insomniac Staff Member Administrator

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    Please post info about FLEA here.

    Please post information about:
    • Names / synonyms
    • Molecule
    • Dose
    • Duration
    • Legal status
    • Reported incidents/fatalities
    • Since when has this research chemical been available
    • Stability
    • if this compound detectable in drug tests & for how long
    • Reaction to Marquis or other tests.
    • Tolerance & Cross-tolerance
    • Appearance (visual, smell, taste, crystal/powder)
    • Forms commonly available & routes used with each.
    • Common Effects: Main (During & after), Side (long & short term)
    • Any known drug & food interactions

    Names: FLEA

    Experiences with FLEA should be discussed here: FLEA experiences
    These documents about FLEA are in the file archive
    FLEA pics
    Research Chemicals Index – Piperazines
    Research Chemicals Index - Phenethylamines
    Research Chemicals Index - Tryptamines


    [​IMG]

    _________________________________________________________________________________

    Pihkal Entry #81
    FLEA



    N-HYDROXY-N-METHYL-3,4-METHYLENEDIOXYAMPHETAMINE

    SYNTHESIS: (from 3,4-methylenedioxyphenylacetone) A solution of 2.1 g N-methylhydroxylamine hydrochloride and 4.4 g 3,4-methylenedioxyphenylacetone in 5.5 mL MeOH was added to a suspension of 4.5 g NaHCO3 in 30 mL boiling MeOH. There was added about 5 mL H2O (which gave a clear solution) followed by another 50 mL H2O which produced a pale yellow color. To this solution of the unisolated nitrone there was added 1.7 g sodium cyanoborohydride, which generated a goodly amount of foaming. There was HCl added as needed to maintain the pH at about neutrality. The reaction appeared to have stopped after a day or two, so all was poured into 500 mL H2O, acidified with HCl, and washed with 2x75 mL CH2Cl2. The addition of base brought the pH >9, and this was then extracted with 3x75 mL CH2Cl2. Removal of the solvent from the pooled extracts gave a residue of 1.65 g of crude N-hydroxy-N-methyl-3,4-methylenedioxyamphetamine. Efforts to obtain solid seed samples of the salts with hydrochloric acid, perchloric acid, sulfuric acid, phosphoric acid, and with a number of organic acids, all failed. The salt formation from this free-base will be discussed below.

    (from MDOH) A solution of 0.75 g crystalline free-base MDOH in a few mL MeOH was treated with a solution of 0.4 g sodium cyanoborohydride in 10 mL MeOH, and there was then added 2 mL of 35% formaldehyde. The stirred reaction mixture was kept at a neutral pH with the occasional addition of HCl. After several days (when additional acid was no longer required) the excess solvent was removed under vacuum, and the residue poured into dilute H2SO4. This was washed with 2x75 mL CH2Cl2 and then, following the addition of base, this was extracted with 3x75 mL CH2Cl2. Removal of the solvent from the pooled extracts gave a viscous oil residue of 0.53 g. The free-base product from these preparations was distilled at 110-120 °C at 0.2 mm/Hg to give the N-hydroxy-N-methyl product as a white oil. An alternate methylation procedure used a solution of MDOH in a 4:1 MeOH/acetic acid solution containing formaldehyde which was reduced with sodium borohydride at dry ice temperatures. Its work-up is identical to that involving sodium cyanoborohydride.

    The distilled product was dissolved in an equal volume of MeOH, and treated with a half-equivalent of oxalic acid dihydrate, dissolved in 10 volumes of MeOH. This combination gave the slow deposition of crystals of the full oxalate salt (one acid, two bases) as a white crystalline product. The mp of the crude salt was in the 130-150 °C range, and after recrystallization from CH3CN, N-hydroxy-N-methyl-3,4-methylenedioxyamphetamine oxalate (FLEA) had a mp of 146-147 °C.

    DOSAGE: 100 - 160 mg.

    DURATION: 4 - 8 h.

    QUALITATIVE COMMENTS: (with 90 mg) The material tastes terrible, like grapefruit juice that has stayed in the can too long. There was no nausea, no feeling of difficulty in swallowing at any time during the day. I felt a dry mouth and was thirsty--sipped water throughout the day. At the beginning of the experiment, there was a glimmer of the MDMA warmth, but later I felt separated and a bit isolated. I was just floating around, seeing the beauty of colors and objects in the house and outdoors and listening first to this conversation, then to that one. All senses seemed enhanced. I found the material pleasant. I was happy with the amount I took but would not be afraid to take more or to take a supplement. I found it similar to, but not the same as, MDMA.

    (with 110 mg) We found this very similar to MDMA, but perhaps slightly slower. I plateau'd at 2:30 hours and had a very gradual descent. My friend had a marvelous and private 'cone of silence' that was to him unique to MDMA or to 2C-T-8. Teeth problems were minor, and the descent from the top of the experience showed less interactive, and more contemplative action, than with MDMA. Very similar to MDMA, but with its own character.

    (with 110 mg) The onset was at about a half-hour. The come-on was more gradual and much easier than with MDMA, and it seemed to be more head than body oriented. I had about two hours of very complex and personal self-evaluation, and I am not at peace in putting all of it down here in writing. Overall I like it, and I would be interested to see if there's a difference in conjunction with MDMA. Thanks very much.

    (with 110 mg + 35 mg) I saw my onset at 20 minutes, and it was subtle, and very pleasant, and had a mild amphetamine-like elevation for me (body lightness, cognitive functions seemed clear and clean, heightened visual awareness and with some enhancement of color). It seemed as if I were on the fringe of LSD-like visual changes, but that never materialized. The affect was very good, communicative, friendly, accepting, but without the profound emotional bonding of MDMA. The following day felt very much like a post-LSD day; we felt great. The body was light, energy good, emotions high, several insights throughout the day, interactions clear and open--a magnificent gift of a day. I started a menstrual period the day of the experience and it lasted 6 to 7 days; all of this was a couple of weeks early. I have a very favorable impression of FLEA although the body penalty seems high.

    EXTENSIONS AND COMMENTARY: Most people who were involved with the evaluation of FLEA quite logically compared it with MDMA, as it was presented as being a very close analogue which might share some of the latter's properties. And to a large measure, the comparison was favorable. The dosages are almost identical, the chronological course of action is almost identical, and there are distinct similarities in the effects that are produced. If there is a consensus of similarities and differences it would be that it is not quite as enabling in allowing a closeness to be established with others. And perhaps there is more of a move towards introspection. And perhaps a slightly increased degree of discoordination in the thought processes. But also, part of this same consensus was that, were MDMA unknown, this material would have played its role completely.

    And from the scientific point of view, it lends more weight to a hypothesis that just might be a tremendous research tool in pharmacology. I first observed the intimate connection between an amine and a hydroxylamine with the discovery that N-hydroxy-MDA (MDOH) was equipotent and of virtually identical activity to the non-hydroxylated counterpart (MDA). And I have speculated in the recipe for MDOH about the possible biological interconversions of these kinds of compounds. And here, the simple addition of a hydroxyl group to the amine nitrogen atom of MDMA produces a new drug that is in most of its properties identical to MDMA. The concept has been extended to 2C-T-2, 2C-T-7, and 2C-T-17, where each of these three active compounds was structurally modified in exactly this way, by the addition of a hydroxyl group to the amine nitrogen atom. The results, HOT-2, HOT-7 and HOT-17 were themselves all active, and compared very closely with their non-hydroxylated prototypes.

    Just how general might this concept be, that an N-hydroxyl analog of an active amine shall be of similar action and duration as the parent drug? What if it really were a generality! What havoc it would wreak in the pharmaceutical industry! If I could patent the concept, then I would be able to make parallel best sellers to all of the primary and secondary amines out there in the industry. Perhaps 90% of all the commercially available drugs that are concerned with the human mental state are amines. And a goodly number of these are primary or secondary amines. And each and every one of these could be converted to its N-hydroxyl analogue, effectively by-passing the patent protection that the originating corporation so carefully crafted. An example, just for fun. A run-away best seller right now is an antidepressant called fluoxetine, with the trade name Prozac. I will make a small wager that if I were to synthesize and taste N-hydroxy-N-methyl-3-phenyl-3-((a,a,a-trifluoro-p-tolyl)oxy)propylamine, I would find it to be an active antidepressant. Remember, Mr. Eli Lilly and Company; you read about it first, right here!

    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.
     

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  2. Sick Jack

    Sick Jack Newbie

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    The only thing that I know about this compound, is that it's really expensive to produce, that's the reason why you will barely find this product on the market...
     
  3. ibbjamin

    ibbjamin Newbie

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    is this illegal, or just not commercially produced because of high cost?
     
  4. Alfa

    Alfa Productive Insomniac Staff Member Administrator

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    The costs are very high, unless a new route of synthesis is found. I think FLEA will prove to be a very interesting compound if production costs are low enough for people to make.
     
  5. Barron

    Barron Silver Member

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    Nobody has tried it since the last post?
     
  6. Sick Jack

    Sick Jack Newbie

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    The manager of a Research Chemical firm said once on his firm's forum that the syntheses of FLEA is really expensive.

    But I remember that Alfa wrote on this forum that there is new routes of synthesis for this compound and it could eventually become more available.

    The problem in this case will be that as usual dutch smartshops will launch big operations with this stuff, as with methylone, and make it illegal as usual once again......... [​IMG]
     
  7. Barron

    Barron Silver Member

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    According to a chem supplier, there could have some contamination (on synthesis, degradation over time, and during testing like HPLC) of MDMA, which would be reason for not having this product available soon. Has anybody heard about such issue?
     
  8. radiometer

    radiometer bananadine addict Platinum Member & Advisor

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  9. nanobrain

    nanobrain Platinum Member

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    so the pesky FLEA is bound to be contaminated w/MDMA making it illegal purty much everywhere...
     
  10. gn2osis

    gn2osis Iridium Member

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    Sounds like two names run together:



    3,4-Methylenedioxyamphetamine = MDA



    2-Benzo[1,3]dioxol-5-yl-1-methyl-ethylamine = MDA again? ... not quite to standard, but I think it must mean MDA



    *
     
    Last edited by a moderator: Apr 22, 2008
  11. Barron

    Barron Silver Member

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    Couldn't we have another reaction for FLEA than with N-hydroxy-DOB because of the difference of the structure (that would prevent the degradaction ofFLEAinto MDMA)? If not, do you think that an appropriate storage of the product preventingany contact with the atmosphere, or the adding of another group to stabilizethe n-hydroxy group,would be sufficient to avoid such degradation?
     
  12. Jaw Clenching

    Jaw Clenching Silver Member

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    I wonder why N-hydroxy-3,4-methylenedioxyamphetamine is scheduled in the US but not N-hydroxy-N-methyl-3,4-methylenedioxyamphetamine?
     
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  13. radiometer

    radiometer bananadine addict Platinum Member & Advisor

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    Re: Flea

    Oh Flea, won't you ever fly this-a-way?? I'll even let you bite my cats.

    Closely related, a little birdy did come by and tweet to me that MDOH has been spotted by various well connected terrestrials.
     
  14. Desertfox

    Desertfox Palladium Member

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    Re: Flea

    I am fancys this. He wonders why this has not been discussed further. I know there has to be some swimmer out there who has tried it. Please share your experiences with this compound or alt. synthesis.
     
  15. gammabetalactone

    gammabetalactone Silver Member

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    Re: Flea

    gammabetalactone added 1 Minutes and 49 Seconds later...

    I did wonder why the only UK legal drug in PIKHAL (referring to MDOH BTW) (well bar PEA) never seemed to be available from vendors. Are all these n-hydroxy analogues unstable?
     
    Last edited: Oct 3, 2010
  16. fatal

    fatal Silver Member

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    Re: Flea

    I believe that the hydroxy compounds such as FLEA, MDOH, and HOT-7 are subject to a degree of instability much in the same way 4hydroxy tryptamines are not very stable unless well stored. The problem being legally speaking that if you had a batch that had any degraded product in it (MDMA for example, in this case) that the whole bunch of it then becomes an admixture containing MDMA and is therefore considered to be all MDMA with X% purity. Say if 0.1% degraded during shipment and you had 10 grams. You would be charged for possessing 10 grams of MDMA mixture at 0.1% purity. The same problem applies to 4-ACO-DMT which breaks down to psilocin(4-ho-DMT) which is illegal in many countries.

    Interestingly one precursor to FLEA is MDOH which can contain a large amount of MDA as an impurity if not done properly. Seems to just degrade directly to MDA at 100C, at least during distillation. MDA and the oxime analogue of the ketone(Methylone = ketone of MDA etc. right?). Would that ketoxime possibly be active?

    :joint:
     
    Last edited: Oct 4, 2010
  17. Alfa

    Alfa Productive Insomniac Staff Member Administrator

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    Re: anyone heard of anyone trying FLEA?

    MDOH and HOT-7 are very pleasurable compounds, so I would expect FLEA to be very nice as well.
     
  18. keepinitreal

    keepinitreal Newbie

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    Re: anyone heard of anyone trying FLEA?

    im curious as to whether anyone has had the the oppurtunity to hear of a story of somebody/something trying it? how was it in comparison to methylone, mdai, mephedrone, and mdma?

    afoaf is looking to find a chemical that is very similar if not the same effects as mdma in effects and dosage ranges. so hoping to get as much information about experiences with this chem so afoaf can be confident this is the chemical to be looking for. would also like to point out that this chemical is legal in the u.s. making it a desirable candidate.
     
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  19. Phenoxide

    Phenoxide Super Moderator

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    This is worth re-iterating and I would think is a major reason for this substance being so rare. As fatal mentions above, Shulgin notes in the PiHKAL entry on MDOH that during the preparation of the N-hydroxyamphetamines a substantial amount of the material loses the hydroxyl group (e.g. MDOH decomposes to MDA) if the preparative conditions are not carefully controlled. If the same pattern holds true for FLEA then is a genuine risk of MDMA contamination.

    Even if the reaction conditions are well managed and the product is chromatographically purified afterwards, a very minor MDMA contaminant might persist. Further degradation over time may exacerbate this problem. The instruments used to perform chemical analysis are now so sensitive that even a very minor contaminant can be detected, and would flag the batch as a controlled substance.

    Additionally it's likely to be subject to the US Federal Analog Act and analogue laws in some states under certain circumstances.

    An interesting substance no doubt, but its instability makes it a legal headache.
     
  20. radiometer

    radiometer bananadine addict Platinum Member & Advisor

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    Re: anyone heard of anyone trying FLEA?

    Try a search for posts by member "Pinkavvy." Some FLEA was apparently going around on the Pacific NW festival circuit several years back and he posted about it. Sorry if you can't find them, it is possible that said posts were made in the restricted access forums.
     
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