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Synthesis of DMMDA-2, 6-Br-DMMDA-2 and DMMDMA-2

By Antibody2
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500mls of dillapiole [1] was refluxed with 10g of 85% KOH under medium vacuum for 11 hours, then transferred to a vacuum distillation rig and 450ml of iso-dillapiole was recovered at bp 145-146C/6mmHg, it was recrystallized from an equivalent volume of boiling petroleum ether, yeilding 410g of clear 1-2 cm long prisms with a mp of 38C [2].


337g 85% HCOOH is added to 206g H2O2 with stirring, the mixture then added dropwise to a stirred mixture of 300g isodillapiole, 811ml of DCM and 68g NaHCO3, which was stirred under light reflux for 24 hours, then allows to settle. The DCM layer was isolated and stripped of solvent on the water bath. The residue was stirred with 189g H2SO4 diluted to 15% with dH2O for 2hours at 80C. The organic layer was removed, and the acid layer extracted with 100ml DCM. The pooled organic layers was washed with a NaHCO3 solution followed by water and distilled [3] at at 151-156C/6mmHg to yield 230g of ketone [4].

2,3-Dimethoxy-4,5-Methylenedioxy-Methamphetamine HCl (DMMDMA-2)

14g of Al (Heavy duty Reynolds) was amalgamated in 400mls MeOH and 50mg Hg2Cl2 by heating to reflux. The flask was fitted with a reflux condenser and was then transferred to a cold stirrer, 18.3g ketone and 13.7g MeNO2 in 50mls MeOH were then added dropwise over 15 minutes [5]. The rxn was allopwed to stir overnight. 500mls 50% NaOH was slowly added, then extracted with 400mls toluene followed by a 150ml extraction. Pooled extracts, and washed twice with H2O and once with brine, dried through MgSO4, and gassed yeilding 15.5g of DMMDMA-2 [6] with a melting point of 147-148C [2].

Oxime of 2,3-Dimethoxy-4,5-Methylenedioxy-Phenyl-2-Propanone

195g NaOAc.3H2O was dissolved in 140mls dH2O with stirring, followed by addition of 725mls MeOH, 230g of the phenylacetone and 83g NH2OH.HCl, the stirred suspension was heated to reflux for 1.5hrs on water bath then 350mls of cold dH2O was slowly poured down the condenser and rxn was allowed to cool to RT with vigourous stirring and then refrigerated and the precipitate vac filtered after 2-3 hours. The mass of the crude oxime was greater than the input of precursor ketone. Recrystallization of 55g crude from 100mls IPA yeilded 20g of white needles with a mp of 107-108C [2,7].

2,3-Dimethoxy-4,5-Methylenedioxy-Amphetamine HCl (DMMDA-2) [8]

7g of oxime was dissolved in 150mls dry THF and poured over activated 10g HD reynolds Al [9] followed by 18g GAA. It was allowed to react with mag stirring at RT overnight. In morning rxn was basified with 50% NaOH, and top THF layer was seperated, and stripped of solvent under low vac. The residue was dissolved in a portion of 2M HCl with much shaking. This was basified and extracted with 150mls toluene, which was also stripped of solvent under low vac on a water bath. The residue being taken up in 50mls acetone, and gassed with dry HCl yeilding 3.75g of the title compound with a mp of 178-180C.

2,3-MeO-4,5-MD-6-Br-Amphetamine HCl (6-Bromo-DMMDA-2)

1.6g DMMDA-2.SO4 (5mmol)is dissolved in 150mls H2O. Then slowly basified with 25% NaOH. Xtract 3x 75mls DCM. Solvent stripped on water bath and residue was dissolved in 10ml HOAc and placed in an ice bath. 0.3ml Br2 dissolved in 4mls HOAc is added dropwise with stirring. Solution turns bright orange/gold. Ice bath is removed when rxn begins to freeze. Rxn allowed to stir for 2.5 hours during which time colour fades from bright orange to a golden to a yellow and then a light ochre precipitation turns entire rxn into a beige suspension, requiring a 5mls HOAc dilution.

Option 1) Rxn is extended with 150mls dH2O, and washed 1x with DCM, then basified with 25% NaOH and Xtracted 3x 75mls DCM. Xtracts pooled washed with a portion of H2o followed by brine, driied through MgSO4, and the striiped of solvent. The dark amber residue was dissolved in 10mls HOAc (the freebase was not soluble in acetone), the acetate salt visible in suspension. 31% HCl is dripped through MgSO4 into the amine solution until precipitation of white crystals stops. Mixture is refridgerated and then vac filtered yeilding 0.5g of the hydrochloride salt.

Option 2) Skip the extension & concentrate on water bath, with med vac, cool to crystallize and elute repeatedly with acetone until washs were clear. YIELD: 1.1g 6Br-DMMDA-2.HBr (2.7mmol)


  1. The dillapiole used was the residue of Indian Dill Seed Oil (Anethum sowa robx.) after d-Carvone had been removed for the flavouring industry. It was represented as being 90% dillapiole and was used as is, with no further purification.
  2. Melting point apparatus in all experiments was a -15C-260C immersion thermometer taped to a 20ml test tube containing 1 mg of product. These were placed in a 100ml beaker filled with safflower oil and slowly heated on hotplate until product had melted.
  3. Smaller batchs of ketone had much lower yeilds (ca 50%) due to polymerization during distillation. Smoke entering the reciver was witnessed with oil bath temperatures as low as 190C. 185C was the highest bath temperature that did not result in massive polymerization. Bisulfite purification with amounts less than 100mls might be prudent.
  4. Ketone reacted quantitativly with sodium metabisulfite. ketone tested via bisulfite adduct requiring addition of EtOH, refrigeration and titration to crystallize.
  5. This addition rate caused several runaways, requiring rxn to be cooled in ice water periodically.
  6. Crystals are extremely fine, and take some time to properly crystallize, initially the gassed solution appears as though there was H2O in the gas, the cloudiness disappears as amine crystallizes, leaving a water clear solution.
  7. Oxime that was produced in rxns lacking the H2O quench at the end, yeilded, white needles with the same MP.
  8. Attempts to optimize this rxn have failed, one attempt to reduce at reflux temp failed entirely as did a rxn using Al sheet.
  9. Prepared by amalgamation using Hg2Cl2 in refluxing 50%H20/MEOH, followed by MeOH wash and a THF wash.

Appendix 1: Molecular weights

For all the bees who hate calculations, here are the molecular weights for most of the dillapiole derivatives you will encounter.

  1. dillapiole - 222.24
  2. isodillapiole - 222.24
  3. isodillapiole epoxide - 238.24
  4. isodillapiole glycol - 256.26
  5. isodillapiole ketone (DMMDP2P-2) - 238.24
  6. isodillapiole ketoxime - 253.26
  7. isodillapiole pseudonitrosite - 298.25
  8. isodillapiole nitropropene - 267.24
  9. isodillapiole amine (DMMDA-2) - 239.27
  10. isodillapiole amine hydrochloride (DMMDA-2.HCl) - 275.73
  11. isodillapiole methylamine (DMMDMA-2) - 253.20
  12. isodillapiole methylamine hydrochloride (DMMDMA-2.HCl) - 289.66

Appendix 2: Bioassays


A bioassay was attempted last nite, before making the last couple posts, a wee taste test was done make sure that characteristic amphetamine taste was present, so as not to make a fool of myself, it was definately present, although distinct from dmmda there was some common ground in the taste. A much drier taste.

Anyways licked the finger eneough to be worried that a small dose 30mgs had been consumed, wasn't really meant to be bioassay, but on the way out the door, put another 60-70mgs in a a baggie just in case the 30mgs kicks in so there is enoeugh to evaluate the trip. Well sitting bored at this agm start getting these warm muscle sensations, a bit like the onset of mdma the 1st time, excited we make a trip to the washroom and eat the maybe another 50mgs. go back and half an hour latter squirming in my seat, a really strong body stone starts tro set in, I find myself cracking huge grins and feeling a lot of empathy for those at the meeting. Yet tyhere is no impairment thinking or external sensory. this feeling slowly tapers off after 3 hours the meeting lasted, and while receeding hit baseline and then bounced back up a few times breifly. At home later that evening a 50mg line was snorted, with no tangible effect.

At the height of this trip though, i was for 10-15 minutes concerned i had eaten way too much. All in all a slightly erratic trip. I would reccommend a much larger dose another time 120-180mgs. But keep in mind your lift off may be turbulent and alarming.


120mgs were consumed, 45 minutes later, no activity is as yet apparent, an additional 120mgs were consumed. maybe 15 minutes later, we decide to smoke a joint. It kicked in while smoking the joint and then slowly tapered off over the next 2 hours, and was again re-activated by smoking another joint, with the effects disappearing with the pot buzz. It is for me a very mild drug, pleasant, a slight euphoria was apparent, this stuff would be good for doing at work or in church maybe. There was no impairment of motor function or thought processes, just a mild buzz. This compound might be best described in the words Shulgin used to describe butylamines, he refered to them as emphogens. It may be that psychadelic activity is beyond the scope of this drug, or perhaps much larger doses 450-600mgs would be required for recreational use. One pitfall to be aware of, is that doses greater than 400mgs daily, are likely to cause the amphetamine psychosis that Shulgin cautions of in his PMA write-up.


40mgs - No discernable activity

90mgs - At 1.5 hours i find myself wondering how i am managing so well with some drudgery i would normally find it hard to stick to. I finished more than i set out to do. At 2 hours +1 here getting abit of that expanding head tiype sensation and hints of breathlessness, but pleasant as is the mild buzz that is becoming more and more apparent, kind of a glowing satisfaction, with heitened awareness of white noise. 2.5 hours, +2 there is a lightness to my movement. Am in a warm space like being in bed on a cold morning, mellow and everything has sugar coating. 4 hours its pretty much gone now, didn't even notice it slipping away.