HA-966 (3-amino-1-hydroxypyrrolid-2-one) is a potent GBL-like sedative

[Holy_cow]

http://www.pubmedcentral.nih.gov/picrender.fcgi?artid=53260&blobtype=pdf

 

[LabRatNW]

Well it seems that one isomer is, and the other isn't. Its strange how the two have completely different effects.

 

[wungchow]

Interesting structure - I wonder if it undergoes oxidative deamination in vivo?

 

[Hammilton]

I wish there was useful information in that study. I mean, it's interesting and all, but I'm way more interested in knowing which receptors the sedative enantiomer binds to. I wonder if this would have GABA-A receptor affinity (at the GABA site, this is). Muscimol and gaboxadol aren't incredibly far off, but I think you need 4-methylamino not 3-amino with that basic structure. There is a good paper that looked at a variety of GABA-A agonists and determined the structural features neccessary. As I recall, they all exhibit keto-enol tautomerism.

 

[Hammilton]

Where did I infer? I didn't, and I doubt it is, without knowing about receptor affinity.