N-Acyl-Dopamines as Novel CB1 Ligands

[Ham-milton]

I've been trying to post this thread for 4 or 5 days now, so hopefully it'll work.

It won't let me post a link for some reason, so I've copied the abstract into here. The full text version is available for free online, however. I can't get into the .pdf, though, so my question may be answered in there and I'm just not able to get into it.

basically, "does anyone think that these might have recreational value? I would think that these would be weak agonists, and possibly weak partial agonists, the general requirement for recreational cannabinoids to be good. Or would they have too much adrenergic activity?"

Biochem J. 2000 November 1; 351(Pt 3): 817–824.

here's the link to the astract. It won't let me copy that in here either.

 

[LuxEtVeritas]

i had taken a good hard look at these a long while back and was sitting on the fence [as to possibility of true worthwhile effect] and wanted to but never did the synth though still think about it now and again

obviously AA-DA looks to have potential but does it go beyond analgesia and sedation...?

 

[Ham-milton]

by AA-DA do you mean NADA?

I can't imagine it'd be very stable, though.

 

[LuxEtVeritas]

yes since the paper refers to NADAs in general i used the AA-DA abbreviation

 

[Ham-milton]

Okay, is it the one in the structure you're talking about, specifically, though?

It looks awfully difficult to synthesize, though.

 

[MattPsy]

Howso? Isn't that long alkyl chain just arachidionic (spelling?) acid? In which case you could form the acid chloride (via SOCl2, or PCl5 etc) and react that with dopamine...

 

[Ham-milton]

yeah, it is. That's starting with the arachidoic acid, though. I was thinking from further back. I dunno how available the aa is, though.

 

[wungchow]

looks like it would only affect the PNS (like acetaminophen's active metabolite)

 

[5-HT2]

I wonder whether there's an endogenous fatty acid amide synthase that can make that molecule. Might have some interesting neurobiological implications…

 

[LuxEtVeritas]

it occurs naturally if that is what you were wondering

 

[5-HT2]

^^^yeah, I just did a search on n-arachidonyl dopamine and indeed some researchers have found it endogenously. Because of this, I'm going to hazard a speculation that, like other endocannabinoids, it probably isn't recreational in any practical sense.

 

[Riemann Zeta]

Amandamide is enjoyable (doubtless less enjoyable than weed or pure (-)-THC), at least if you can get it into the brain without it being destroyed by FAAH. Stable amandamide derivatives are self-administered in rats, so I assume they are worth something. I bet dopa-AA is destroyed by the gut, though.