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phenmetrizine analogue

M

mysticmusic

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Joined
Sep 3, 2011
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69
Does anyone have any pharmacological data on 3-methyl-2-phenyl-1,3-oxazolidine, it's basically the phenmetrizine molecule with a carbon and it's connected hydrogens removed from the morphiline ring.
It is commercially available, but I can't find any data regarding it's activity. Considering it's structure I'd be more surprised if it were inactive than active.
The source I found didn't specify chirality or exactly which salt or if a base, no doubt relevant questions.
Anyway, any data would be appreciated, thanks!
 
As far as I know, binding data on this series of compounds is quite limited, but the chemistry is there for production of phenmetrizine analogues. So we're going to see a lot of novel monoaminergic releasers coming out with relatively unknown SAR pretty soon.

ebola
 
I probably wrote the chemical incorrectly. I believe (4R, 5S)4-methyl-5-phenyl-1,3-oxazolidine is the correct name.
The oxygen and nitrogen are the same structurally relative to the phenyl and methyl as with phenmetrizine.
The HCL salt could be very interesting, or maybe it's toxic, removing a carbon and it's hydrogens can make a big difference or not. I'd like to know in this case.
 
WAIT, DID SOMEONE SAY PHENMETRAZINE ANALOGS? 8o
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I found what looks like a french patent on some other phenmetrazine analogs, but I can't parlez vous my francais well enough to make heads or tails of it: http://www.freepatentsonline.com/EP0139590.pdf

I did make one very interesting discovery though, Phenmetrazine functions partially as a prodrug to Fenmetramide, a muscle relaxant and tranquilizer (with stimulant properties?): http://www-06.all-portland.net/bst/002/0877/0020877.pdf (The Metabolism of Phenmetrazine in Man and Laboratory Animals)

Original US patent on the series: http://www.google.com/patents/US3308121

So it is conceivable that some of Phenmetrazine's "magical smoothness" is due to ~29% of it being converted into Fenmetramide. Which of course begs the question, what is the binding profile of Fenmetramide, or even Phenmetrazine for that matter? What exactly are we after with analogs here?

I'd be very interested in learning the monoamine transporter binding profiles, especially VMAT as compared to other stims (is my general hypothesis on low VMAT binding for smoother stims true here).

Why was Fenmetramide never marketed?

Has Anyone Really Been Far Even as Decided to Use Even Go Want to do Look More Like Phenmetrazine? =D

I kid, I kid. But seriously, looking at Fenmetramide might be a good direction to take this in. I'd imagine OP's compound does not metabolize the same way, and hence does not produce a Fenmetramide analog.

On a somewhat unrelated note, I ran across this paper looking for more info on OP's compound: http://pubs.rsc.org/en/content/articlelanding/1985/p1/p19850002361#!divAbstract
Fascinating (non-recreational, but possible meth adjuvant) parent drug: http://en.wikipedia.org/wiki/Edaravone
 
Thanks Tweex, the links are appreciated!
I think if more people had experience with phenmetrazine, the analogues would generate a great deal more interest. I personally know of no more euphoric substance; even if phenmetrazine analogue x only possesses half the euphoric properties of phenmetrazine, it would surpass almost everything presently available.
 
Fenmetramide kind of reminds me of an odd barbiturate analogue. Could be an active cns depressant.
 
Preludin gave us the Beatles. Do you guys not realize things would still in Black and White if not for this drug?

Edit: Hmmm says here...Fenbutrazate (INN), also known as phenbutrazate (BAN), is a psychostimulant used as an appetite suppressant under the trade names Cafilon, Filon, and Sabacid in Europe, Japan, and Hong Kong.[1][2] It is a derivative of phenmetrazine and may function as a prodrug to it similarly to phendimetrazine.[3] It is not known to be a controlled substance anywhere in the world yet.
 
my favorite quote from the article Yaesutom posted is

"these designer drugs cover every category of intoxication imaginable, and their effects resemble the full range of banned drugs, from the mellowness of marijuana to the extremes of cocaine"

I thought this was funny because all the coke analogs (dimethocaine) are mild but all the cannabinoids (am and jwh series) are found by many to be too intense.
 
Dimethocaine is no cocaine analogue, unlike beta-cit and the like, which are not mild.
 
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