3,5-dimethoxy-4-allyloxyphenethylamine

[Incunabula]

.....also known as Allylescaline or AL, I was just wondering what could be surmised from it's structure in regards to pharmacology?

Allylescaline in pihkal

Allylescaline in wikipedia

 

[cannibalsnail]

http://letmegooglethat.com/?q=allylescaline

 

[sekio]

FROM a SAR point of view, this would probably have good affinity for the alpha-adrenergic, 5-ht2-a/b/c, and 5-ht1a like mescaline.

 

[endotropic]

Now I'm no chemist, but wouldn't the terminal alkene at the 4 position be likely to form covalent bonds?

 

[sekio]

No, not really. Allyl groups are reasonably stable. (see 5-MeO-DALT, AL-LAD, etc.).

I rememeber the amphetamine version of this (or was it 4-propoxy)going around before, don't know too much on the acute effects though.

 

[doppelgänger1]

If AL-LAD is stable, why isn't it sold by rc-vendors then? I always thought the problem with LSD analogues was their stability?

 

[sekio]

The simple fact is that no vendors want to risk their asses selling obvious analogs of the most potent classical psychedelic. And all known syntheses for AL-LAD etc proceed from lysergic acid/LSD as precursors, and those are controlled almost worldwide.

 

[NeuroPsyence]

FROM a SAR point of view, this would probably have good affinity for the alpha-adrenergic, 5-ht2-a/b/c, and 5-ht1a like mescaline.

Does Mescaline actually have a high affinity at 5-HT2a and 5-HT2c? This study¹ suggests that its affinity is negligable for both, with Ki values greater than 10,000 at both receptors. But Nichols' study² from a few years earlier put their Ki values at 550 and 300 for 2a and 2c, respectively. Can anyone shed some light on this?

1) Ray TS (2010) Psychedelics and the Human Receptorome. PLoS ONE 5(2): e9019. doi:10.1371/journal.pone.0009019

2) Nichols DE. Hallucinogens. Pharmacology & Therapeutics 101 (2004) 131Ð 181, 2004; 101:131-181.

-NeuroPsyence

 

[sekio]

Mescaline has poor affinity, but good efficacy at 5-HT2a.

Some of the 2c- compounds definitely have higher affinities for 5-ht2a. I have seen very little on the SAR of 4-sub mescaline derivatives, though, so I can't be more helpful.