SteveZissou
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Furane based MTP analogues
Hello there! Long time lurker and first time poster, glad to be a part of a community of such intelligent and free-thinking folks like yourselves!
I did a quick search of ACS literature and some Googling and I couldn't find anything about this anywhere. My idea is very simple, I just want to take
the structure of methiopropamine and replace the sulfur with an oxygen, the precursors for this are cheap and readily available and I'd just like to
know what can be speculated on the activity of this compound.
The 3d structure would remain unchanged, the hybridization of oxygen would be similar, and therefore I expect structure activity relationships to
remain essentially the same.
I haven't looked into the synthesis all that much but off the top of my head by using furfural as a starting point one could nitroaldol to the
nitropropene, reduce with Al/Ga (not in literature but it works and I'll do a write up of a procedure I performed on a nitrostyrene with this if
anyone would like, should work for the propene) then go to the formyl, reduce, and bada-bing you've got your compound.
The lack of literature on this compound worries me, I do have access to an IR so I know what I'm making though. Ring strain on the furfural's ether
also gives me some worries, not sure if any of my proposed reactions would crack that baby.
I also know that MTP has considerable toxicity, this may transfer over.
tl;dr - Replace sulfur with oxygen in methiopropamine. Discuss.
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Dr.Bob
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If you research their medicinal chemistry, you would find that a thiophene and a benzene ring are quite similar in their properties, since a S atom
(being quite large) and an C=C double bond are similar in size and character. That is why thiophene and benzene are very similar in their chemistry,
BP and reactivity. However, furan is much smaller than benzene, has some differences in chemistry, and does not act as much like a benzene as
thiophene does. So I would be careful when experimenting with things.
And while Woodward did an amazing job using UV and IR, I would not ever consider doing even animal testing of an unknown compound without more data,
such as a good NMR and LC-MS of a compound. I understand that some people are willing to ingest anything that they can buy, make, or steal, but
having seen how hard it is to make compounds pure under the best conditions, I would never trust something that has not been tested well. I don't
even like cheap generics from China, having seen the crap in some of them. So please be careful with what you experiment with.
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SteveZissou
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Thanks for the excellent reply Bob!
I did consider the size differences as a potential problem, but did not know how much of a difference there was.
Upon further research I found a good article that compares the sizes of furan and thiophene:
http://deepblue.lib.umich.edu/bitstream/handle/2027.42/38279...
The furan and thiophene rings have a difference in circumference of about 0.4 Angstroms; neglibile compared to benzene and thiophene which have a
difference of 1.8 Angstroms yet MTP retains much of the action of it's amphetamine analogue. I was under the assumption that the aromaticity and
propylamine sidechain played a bigger role in the structure-activity relationship.
Safety is a concern, but I have a good idea of what I'm doing and I'll be starting with sub mg doses if I decide to proceed and do a bioassay. At the
moment this is pure speculation. And good god I wish I could afford a half decent LC-MS or NMR, I was lucky enough to get an affordable dated IR spec
used.
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paw_20
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Al/Ga reduction does work? I had been wondering if it would some months ago after reading the papers on it has a hydrogen 'storage' medium for a fuel
cell, but it seemed that some of their graphs were showing rather small amounts of hydrogen on a molar basis being release even after a couple of
hours. This specifically was the purdue paper comparing Al/Ga vs. an alloy they had developed of Al/Ga/In/Sn
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SteveZissou
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Yeah, I did manage to get it to work. I found smaller yields than would have been expected out of Hg/Al but not by much, I think the key to the
process is making the alloy into pellets and slowing adding these to the rxn vessel. Two things:
1. Zn/HCl gives me better yields for nitrostyrenes but has a little more work-up due to the ZnO
2. Gallium is highly recoverable but is a royal pain in the ass to get out of the vessel; it wets everything
I'll have to post up something next time I do a reduction, not having to deal with mercury is a major plus.
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