THC-O-Acetate...?

[Acyl]

I ran into the wikipedia article for this compound

http://upload.wikimedia.org/wikipedia/en/7/7d/THCacetate.png

Contains an acetyl group at the phenolic oxygen. I cant seem to find any information on the compound outside the wikipedia article though, has anyone got any info on effects? This molecule seems like a fairly interesting target, would be pretty easily accessible to the home chemist if I may add.

My guess is that the acetyl group will increase the potency, especially if you're trying to bake it with food.


Also what do you all think about making a methyl ether out of plain ol THC? Do you think it would have the same sort of activity relationship as methylated phenethylamines vs hydroxyphenethylamines?

Hydroxyphenethylamines are not able to cross the blood brain barrier at all (or as well), whereas methyl ester phenethylamines are....

 

[MattPsy]

The effects should be the similar to plain ol' THC as the acetyl group will be hydrolysed off, like diacetylmorphine (heroin) is. It may be different, like heroin is to morphine (I guess because it has better CNS effects due to passing the BBB better, so less peripheral effects are produced) though.
I know the phosphate ester of THC is water soluble, so it can be injected if desired, or snorted, or any of the other methods THC normally doesn't work through because it's insoluble in water... so I would expect the THC acetyl ester will be too, and similar.

Hydroxyphenethylamines? I assume you mean phenylethyl-NH-OH ?
Thy may not pass the BBB but MDA-OH works just fine, all evidence points toward the OH being stripped off. I'd be intersted to know what happens if that can be converted to an ester ( so, phenylethyl-NH-O-C(=0)-Alkyl ), if indeed this is possible, I haven't ever seen a structure like that.

 

[Acyl]

No I meant with Ar-OH vs Ar-O-R.. the hydroxy group bonded to the aromatic ring.

The hydroxyl amines are a different story...

 

[Morninggloryseed]

Hydroxyphenethylamines? I assume you mean phenylethyl-NH-OH ?
Thy may not pass the BBB but MDA-OH works just fine, all evidence points toward the OH being stripped off. I'd be intersted to know what happens if that can be converted to an ester ( so, phenylethyl-NH-O-C(=0)-Alkyl ), if indeed this is possible, I haven't ever seen a structure like that.

Actually Shulgin speculates that once in the body, it is just as likely that MDA is turned into MDA-OH...and that is the active drug.

 

[Acyl]

What is his argument for this? just curious

 

[enoughorangejuice?]

Anyone ever heard of THC-O-Phosphate, seems very interesting. It is a water soluble derivative of THC. They created it a couple decades ago so they could IV THC for research purposes.

http://en.wikipedia.org/wiki/THC-O-phosphate

 

[MattPsy]

I know the phosphate ester of THC is water soluble, so it can be injected if desired, or snorted, or any of the other methods THC normally doesn't work through because it's insoluble in water... so I would expect the THC acetyl ester will be too, and similar.

enoughorangejuice - I've already mentioned this above !

Very interesting MGS... *ponders*

Acyl - i'm not familliar enough with the SAR's of cannabinoids to make any sort of prediction. If a hydrophillic region is required for binding, methylation of the aryl hydroxy might prove to be disadvantegous.

 

[fastandbulbous]

so I would expect the THC acetyl ester will be too, and similar.

If you mean water soluble, I wouldn't think so. The phosphate ester is capable of forming salts via the other two free H+ ions, but the acetyl ester doesn't have any free hydrogen ions so will not be polar (so insoluble)