Somantadine

[Jamshyd]

I was going through the science dept. library at my university today and passed by a book of several volumes titled "Organic Chemistry of Drug Synthesis". For some reason, my hand fell on Vol.4, and... lo and behold! turns out this volume is all about drugs that you and I care about! (I checked the other volumes and they talked mostly about uninteresting things like corticosteroids and prostaglandins). But anyways...

My eyes fell upon this very interesting structure (reproduced below). The book calls it "Somantadine" and describes a pretty loose synth (though it is the express intention of the book to be written for graduate organic chem. students). A google search shows several foreign chemical catalogues listing it, but a search on pubmed yeilds nothing.

What is interesting about this compound is that it is an Amantadine/Amphetamine hybrid. I am wondering what everyone thinks about it, and whether anyone has any info on it...

 

[johanneschimpo]

Wow. Very interesting. I'm going to google it myself, see what I can find and see what others on this board have to say as well.

Edit: From the few things I can find (barring medical journals) it seems to not be recreational. Apparently it targets coreceptor binding and fusion proteins in viral molecules (whatever the FUCK that means ???)

 

[kaoskid]

amantadine does the same thing. (i'd be willing to bet that memantine does as well)

 

[Smyth]

Interesting how there are two alpha-methyl groups and yet the molecule is still active. Can this be transferred over into regular PEA chemistry or not? If one is good then two is better, right? or wrong! Surely somebody must have explored this by now.

http://en.wikipedia.org/wiki/Phentermine

Ah I realize that is phentermine for you, tried and trusted. Also a couple of compounds in the PIHKAL archives have this.

 

[Jamshyd]

Yes, I do realize that the 2 methyl groups are more akin to phentermine than plain old amphetamine. However, I thought I'd transfere the figure from the book as accurately as possible.

Lets assume that this thing had only one methyl group (and lets assume isomeric equivalency, or whatever you chemists call this). Then it would be closer to plain amphetamine, though I do not think anyone has synthesized it (and I certainly have not encountered it anywhere).

I made a collection of Amantadine and analogues for comparative purposes (see below). Compounds 1, 2, and 4 are currently in medical use. All of them are anti-viral. I could not find any literature about memantine being specifically tested as anti-viral, though literature about amantadine-derrivatives seems to implicitly take for granted that Memantine is anti-viral. Compound 3 is, to my knowledge, not currently used medically, however it is cited in studies for anti-viral activity.

Compound 5 is of course our Somantadine.

Compounds 6 and 7 are theoretical (hence the asterisk) since I have not been able to locate them mentioned anywhere (and I did try an IUPAC name search). I am using the word "amphetadine" arbitrarily to make life easier. Notice thatn #7 is the DOM equivalent (or at least, an audacious attempt at it!).

 

[Smyth]

The cyclohexane ring derivative on amphetamine has already been covered several months back (almost a year ago now). It is in inhaler products. It is still active yet rather impotent and lacking the euphoria of aromatic congers. I think the idea of a 3,4-MD-analog became extinct due to diminished interest and the issue of isomerisim.

 

[Jamshyd]

Interesting (I assume you are talking about propylhexedrine).

Though keep in mind that this is not cyclohexane, it is adamantane.