Author Topic: a procedure applicable to elemicin / myristicin?  (Read 26864 times)

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a procedure applicable to elemicin / myristicin?
« on: October 28, 2004, 06:37:00 PM »
from Organic Syntheses, Volume 75, page 106. 
Submitted by Carsten Behrens and Leo A. Paquette.
Checked by Kei Manabe and Kenji Koga.

Five point zero grams (26.7 mmol) of N-benzylazetidine-2,3-dione [an alkene alternatively also named N-benzyl-3-(E/Z)-ethylideneazetidine-2-one] was dissolved in 150 mL of methanol and 100 mL of water contained in a 500 mL one-necked, round-bottomed flask.  Next, 14.3 g (67 mmol) of sodium metaperiodate was introduced, followed by approximately 40 mg of osmium tetraoxide. 

The reaction mixture was stirred vigorously for 12 hours under a nitrogen atmosphere, treated with 6 grams of Celite, and agitated for an additional hour prior to filtration.  The filtrate was then concentrated to 1/3 of its original volume under reduced pressure and then extracted with two 200 mL portions of ethyl acetate.  The combined organic phases were washed with brine, dried, and concentrated to leave a dark brown oil. 

Finally, the oil was flushed through a short pad of silica gel (8 cm x 8 cm) using 900 mL of dichloromethane as the eluant.  The pure fractions were pooled and evaporated to give a clear pale yellow oil, which crystallized on prolonged standing at 5 degrees Celsius. 

The yield of N-benzylazetidine-2,3-dione was 3.12 to 3.64 grams (66.7 to 77.9% of theoretical maximum).

* * *

Though some tinkering / improvisation may obviously have to be done, I believe that the above method may prove useful in making the corresponding substituted phenylacetaldehydes of elemicin and myristicin. 

From them can be made mescaline or lophophine (Shulgin's name for the 2 carbon homologue of MMDA) via reductive amination with ammonium acetate and sodium cyanoborohydride, for example.

Has anyone had any success in isolating myristicin from nutmeg oil or elemicin from the oil of elemi via fractional distillation or other purifying technique? 

I know Shulgin mentioned obtaining myristicin from the "careful fractional distillation" of 10 pounds of commercially available oil of nutmeg somewhere in PiHKAL, but I don't believe he mentioned at what temperature or pressure he did that by.  Also, is mescaline really all that it is rumored to be, or is it a mild experience when compared to the gentle, energetic euphoria of MDMA ("ecstasy") or the mind-bending trippiness, anxiety producing, and sometimes visuals-producing LSD ("acid")?


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effects of mescaline
« Reply #1 on: October 28, 2004, 10:10:00 PM »
swim has experienced mescaline in cactus form twice
it has the clear-mindedness of mdma, with visuals like lsd.  you dont have to be "trippin balls" to get great hallucinations, just a great body feeling and great conversation.  mescaline is definitely what its cracked up to be