Homomyristicylamine; a worthy target?

[Fatass]

While just browsing the net, I came across this link from Lycaeum:

http://leda.lycaeum.org/?ID=16291

It is a collection of three papers by Shulgin on the topic of Mescaline.  One paragraph caught my attention:

A fourth compound is homomyristicylamine (lophophine, 9) which also has never been observed in the peyote plant, but which presents an obvious theoretical potential as a biosynthetic precursor of the tetrahydroisoquinoline alkaloids such as lophophorine and anhalonine. This compound is active in man at dosage levels of 150 to 200 mg, about twice the potency of mescaline (18). The quali- tative description of its action is quite similar to that of mescaline, in that there is a peaceful elevation of mood, the generation of an euphoric state, and the enhancement of visual perception especially in the color sense. There are dis- similarities, particularly in that there is little if any nausea and there is no visual distortion. These latter differences disappear at dosages of 300 mg and there is the generation of eyes-closed imagery similar to that observed with mescaline.

The compound is basically 3,4-methylenedioxy-5-methoxyphenthylamine.  The benifits of this substance are the reduced nausea and the increase in potency.

Of course, the precursor, 3,4-methylenedixoy-5-methoxybenzaldehyde is likely a not very incriminating compound to purchase (relative to the trimethoxy analogue).

So all in all, anyone have any experience with this compound?

[yellium]

YM pikhal #95?

[Aurelius]

Are all watched.  Especially since it's a benzaldehyde.  I wouldn't count on easily obtaining the stuff w/o owning/working for a legit lab.

[Vitus_Verdegast]

Maybe you should try methylenation of 5-hydroxyvanillin ?

https://www.thevespiary.org/rhodium/Rhodium/chemistry/mmda.mescaline.html

[hypo]

which would be my first try.

[GC_MS]

or oxidation of myristicin, which would be my first try.

[...]

The third route, that which starts with myristicin, appeared to be the only practical synthesis of the title compound. Base-catalyzed isomerization to isomyristicin places the double bond in a position appropriate to an aldehydic end product. KMnO4 has been employed in a number of procedures to provide the final aldehyde, but there is concurrent formation of the corresponding benzoic acid. Hydrogen peroxide with a vanadium catalyst precludes acid formation but still provides only modest yields. It has only been through ozonolysis that sizable quantities of 4 have been prepared but here minor variations in the reaction conditions seriously affect the yields realized.

[...]

Myristicinaldehyde

An intimate mixture of 50 g 2 (1-(3-methoxy-4,5-methylenedioxyphenyl)-2-nitropropene) and 26 g DL-&alfa;-methylbenzylamine was heated on the steam bath until solution was effected and the evolution of nitroethane was complete. The intermediate Schiff base 3 was hydrolyzed without isolation by the addition of dilute hydrochloric acid and continued heating. At 60 to 80° there was an abrupt solidification of the myristicinaldehyde that had formed and further heating was unnecessary. The aldehyde is removed by filtration of the cooled reaction mixture and could be purified either by crystallization from water, or better by exhaustive extraction of this crude solid product with boiling hexane. The yield thus obtained is 36.9 g (97% of theory and 79% overall from isomyristicin) of a cream-colored solid with mp 128-129°.
Complete integrity of the ether orientation was established by the reconversion of 4 (myristicinaldehyde) to 2 with nitroethane as has been described for the trimethoxy counterpart.

[...]

note: 2 was prepared from isomyristicin using tetranitromethane.

reference: A Shulgin. Can J Chem 46 (1968) 75

[cattleprodder]

myristicin (KMnO4 under the right conditions) --> vicinal diol (HIO4) -->  NaBH3CN + ammonium acetate --> lophophine

These reaction specifics still need looking up, however.