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Wierd opiate

haribo1

haribo1

Ex-Bluelighter
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Nov 29, 2006
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wierd.jpg


This one is 50x morphine, but who the hell would go to all the trouble!
 
You certainly enjoy your opiates don't you? Their chemical structures that is. ;)
 
there is a function in chemdraw called clean up structure, check it out ;)

not trying to be an ass, just could look better :)

if you had the chirality right, that hydroxyl hydrogen in that proximity to the amide might show up around 13 in the chemical shift for an NMR due to the funky sharing between the two oxygens

ps-if chirality isn't an issue, that puppy is pretty easy to make, and you can have some of the chlorinated aromatic left over for the k synth ;)
 
^Everyone needs a hobby.... Yours it seems, is collecting US quarters...
 
if you don't have acces to books or full journal articles, where do you always find these god-like looking structures?

are such books/articles available in libraries of large universities??
 
I attended a U-of-WI that wasn't @Madison, and our library (yes, only one) had a few books that had some obscure chems in them.

Took a lot of time to track down structures, though.

I'm sure if you had time and patience, you could always request books be sent to you via ILL or your state UNI-trading system.
 
ha, now i remember why this opiate looks kinda familiar to me (at least the ortho-substitutions). it reminds me of viminol, which could, with some imagination, be viewed as a derivative of the thread-compound
 
Have you been reading "Opiod Analgesics: Chemistry and Receptors" by any chance?

If not check it out, useful info on this compound and others!
 
is viminol scheduled? It was apparently marketed, but I can't find much about it. I can't even find the structure, though?
 
pretty interesting

Pharmacol Biochem Behav. 1984 Jan;20(1):59-62.Links
The discriminative stimulus properties of the R2 isomer of viminol.Shook JE, Kallman MJ, Dewey WL.
Viminol is a pyrrylethanolamine derivative which exists naturally as a racemic mixture containing six different stereoisomers. Viminol has been reported to exert both potent analgesic activity and minimal dependence liability. The analgesic component of racemic viminol has been attributed to the R2 isomer, while the antagonistic S2 isomer appears to be responsible for minimizing the dependence liability of the racemate. We tested the R2 isomer of viminol in rats trained to discriminate 3 mg/kg morphine sulfate from saline on a VI-15 sec schedule for sweetened milk reinforcement. The R2 isomer resulted in dose dependent morphine-like responding, with complete generalization to the 2.5 mg/kg dose of R2 viminol. The morphine-like discriminative stimulus properties of R2 viminol were reversed by naloxone in a dose-dependent fashion, with total blockade by 0.1 mg/kg naloxone. R2 viminol, like morphine, also had a biphasic effect on response rate with low doses increasing and high doses suppressing response rates. R2 viminol had a overall shorter time course than that reported for morphine, and its different physiological and behavioral effects may not occur simultaneously. These data suggest that R2 viminol exerts a subjective effect similar to that of morphine and supports the hypothesis that R2 viminol has opiate activity despite its lack of structural relationship to the opiate series.

PMID: 6546450 [PubMed - indexed for MEDLINE]
 
Oh, it's one of those with one isomer being an antagonist and the other an agonist. Well, that's better than one being a partial agonist and the other a sigma agonist (or an NMDA antagonist).

The antagonism much be fairly weak, or there wouldn't be any analgesia, I suppose.
 
emerald2303 said:
What is this Viminol? Is it available in the US?
Click to expand...

Apparently it is to vimto what cocaine is to coca cola.... :)
google is your friend.

Viminol (Merck Index, XI Ed., No. 9885, pages 1569-70) is the common name of the compound 1-(2-chlorobenzyl)-2-[(1-hydroxy-2-di-sec.butylamino)]-ethyl pyrrole.

The compound has three asymmetric carbon atoms but it exists only in the form of 6 stereoisomers because of the presence of two equivalent sec.butyl groups on the amino nitrogen.

Viminol is a strong analgesic drug used in the treatment of pain of different origin and it is commercialized as a mixture of stereoisomers with the registered trademark Dividol TM (Zambon Group S.p.A.) in the form of 4-hydroxybenzoic acid salt.
Click to expand...
 
According to chemdraw, this is the structure:
Viminol.gif​
I see somebody already posted a link, but its nice to have an image for quick reference. Grayte...
 
Removing the Cl would alter the pharmacodynamic properties of the compound - it is in the position it is for a reason. Concerning lipophilicity, there are other parts of the structure that contributes much more to lipophilicity than the chlorine.
 
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