dormouse (Member)
04-19-00 13:24
No 122736
      oxazoline-based rigid bodied analogs of X -drone 342  Bookmark   

Author  Topic:   oxazoline-based rigid bodied analogs of X 
drone 342
Member   posted 10-13-98 11:45 AM          
Several rigid-bodied MDA and MDMA analogs have already been investigated, incuding the indane-based derivative. So what of an oxazoline-based anolog, or any number of other variations like a morpholine or piperidine derivatives? Has anybody looked into their synthesis?
I know the topic came up before where aromatic aldehydes, when treated with yeast, form hydroxy acetones, perfectly suitable for reductive amination into phenylpropanonamine and ephedrine derivatives, but it was stated that substitution on the phenyl ring reduced the yields of this bioological conversion. Does anybody care to give references for that?

A possible way around this would be to use the pure enzyme (alpha decarboxylase), rather than the whole organism; this enzyme is commercially available in large quantities (used occasionally in brewing). Any thoughts?

The reason I bring this up is that it would make an excellent springboard for further chemical shennanigans -- 3,4-methylenedioxycathinones, methylenedioxy-4-methylaminorex analogs, and a slew of other goodies.

-drone #342

Member   posted 10-15-98 09:56 AM          
That MD-aminoxazoline can be synthesized in two ways from the aminoalcohol:
1)reaction with a halogencyan, BrCN/ClCN
2)reaction with an isocyanate (forming the substituted urea), then cyclisation with a halogenating agent, e.g. SOCL2.
I've been scanning some relevant articles on this topic very recently. They're from the Arch. Pharm. and Eur. JMC. If you're interested I can mail them to ya. Lr/
Administrator   posted 10-15-98 01:29 PM          
I'm VERY interested.
Member   posted 10-16-98 10:22 AM          
I'll send the articles to you, Rhodium, so everybody can enjoy them! They're written in German, so I don't hope this will give problems. Expect to find the first one in your mailbox soon! Lr/
Administrator   posted 10-16-98 11:20 AM          
Thank you! German is all right with me.
Member   posted 10-30-98 02:23 PM          
For your information the MD version of aminorex (or methyl-aminorex) have been tested for anorexigenic effects on rats up to 150 mg / kg with no concluent results. So, I would not expect them to be active as emphatogenes.
(See Poos et al. ref. given in the Merck under aminorex; synthesis...)