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MDPV chirality

General alcazar said:
Has anyone looked at the ratio of enantiomers or what each individual enantiomer's effects are.
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I have no idea if this has any implications for MDPV but I didn't even notice this was mentioned in the following paper because I was too busy looking at O-2484 at the time...

Peter C. Meltzer,,, David Butler,, Jeffrey R. Deschamps, and, Bertha K. Madras
Journal of Medicinal Chemistry 2006 49 (4), 1420-1432

Abstract

Dopamine, serotonin, and norepinephrine are essential for neurotransmission in the mammalian system. These three neurotransmitters have been the focus of considerable research because the modulation of their production and their interaction at monoamine receptors has profound effects upon a multitude of pharmacological outcomes. Our interest has focused on neurotransmitter reuptake mechanisms in a search for medications for cocaine abuse. Herein we describe the synthesis and biological evaluation of an array of 2-aminopentanophenones. This array has yielded selective inhibitors of the dopamine and norepinephrine transporters with little effect upon serotonin trafficking. A subset of compounds had no significant affinity at 5HT1A, 5HT1B, 5HT1C, D1, D2, or D3 receptors. The lead compound, racemic 1-(4-methylphenyl)-2-pyrrolidin-1-yl-pentan-1-one 4a, was resolved into its enantiomers and the S isomer was found to be the most biologically active enantiomer. Among the most potent of these DAT/NET selective compounds are the 1-(3,4-dichlorophenyl)- (4u) and the 1-naphthyl- (4t) 2-pyrrolidin-1-yl-pentan-1-one analogues.
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here's the article (shoula done a google search)
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC2602954/
And here's the answer to my question :

"The resolution of racemic 1-(4-methylphenyl)-2-pyrrolidin-1-yl-pentan-1-one 4a was accomplished by recrystallization from CH2Cl2/hexane of the diastereomeric salts obtained upon reaction with dibenzoyl-D-tartaric acid in refluxing ethanol.
This provided the (2R)-pyrovalerone dibenzoyl-D-tartrate salt. The purity was determined by 1H-NMR spectroscopy. The diastereomeric salt mixture showed two sets of triplets at δ = 0.73 and 0.69 ppm (CDCl3). These correspond to the ω-methyl protons of the pyrovalerone moieties of the (2S)-pyrovalerone dibenzoyl-D-tartrate and (2R)-pyrovalerone dibenzoyl-D-tartrate salts respectively. After four recrystallizations, the triplet at 0.73 ppm was no longer visible. The absence of the triplet attests to the diastereomeric purity of the compound, and this can be assumed to be >95% d.e. on the basis of the limits of sensitivity of the NMR experiment. "

I don't have the resources to do this but it would be at least of academic interest for someone to try. Perhaps there was some inadvertent selection for one stereoisomer during purification steps of the original batch of material, maybe when trying to rid it of the pyrrolidine impurity ? Just a guess - i'm not a chemist, just a degenerate....
 
Wouldn't it just mean that weight for weight the resulting product would be twice as potent?

The paper above was published in 2006 and is a decent list of alternatives to the methylenedioxyphenyl analogue that might have been a better logistical/economical prospect for whoever is/was mass producing the stuff after the initial batches of MDPV proved a success...
 
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