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alpha-keto-tryptamines/3-acetamideindoles

nuke

nuke

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alpha-carbonyl-tryptamines/3-acetamideindoles

They should be UK legal, no? Any ideas on the activity? Do phenacetamides have any activity? I know they're sigma-1 agonists and dopamine beta-hydroxylase inhibitors, but I haven't seen anything in the literature about stimulant activity.

The very hydrophobic region of AMT is replaced with the fairly hydrophobic region of a double bonded oxygen, but will that effectively inhibit metabolism and allow for a reasonably favourable geometric orientation? What if it's subsituted, eg 3-n,n-dimethylacetamideindole?
 
Last edited:
The very hydrophobic region of AMT is replaced with the fairly hydrophobic region of a double bonded oxygen, but will that effectively inhibit metabolism and allow for a reasonably favourable geometric orientation? What if it's subsituted, eg 3-n,n-dimethylacetamideindole?
Click to expand...

When you mention the "hydrophobic" region of AMT i dont think you're referring to the indole ring... are you talking about the amine? the amine group isnt hydrophobic at all its hydrophillic and the carbonyl group you wish to substitute in at the alpha position will make it even more hydrophillic....

I dont really understand your question but in amides the orientation of the orbitals of the nitrogen and carbonyl carbon are favoured when they are allowed to overlap, this may hinder its ability to rotate around the C-N bond...
 
I'm refering to the alpha-methyl position. Ketones are hydrophillic but not to a huge extent like alcohols. I just wonder how easily the ketone can be hydrolysized off, the body usually doesn't have much trouble with them, so in and of itself it might not be active, but the substitutions might be.

the amide also has a different geometry of the hydrophobic alpha-position than amt (flat as opposed to pyrimidal), and i'm not sure the carbon being oriented in that position specifically contributes to the potency of amt, something that might affect potency if the un-nitrogen substituted compound itself can escape metabolism long enough to be active
 
The alpha position is where the methyl substituent is located, i think thats what you mean though, anyway..

Where do you get alcohols being hugely hydrophillic compared to ketones? Ketones have a much larger dipole moment than alcohols and are very much able to participate in hydrogen bonding.

As for replacing the methyl substituent with a carbonyl group thus making it an amide, i have no idea how it would affect reactivity.. Cathinone and amphetamine can be compared in reactivity but the keto group in cathinone is at the beta position.. it would be much different in the alpha position.

Sorry i couldnt be much help.
 
Acyl said:
Where do you get alcohols being hugely hydrophillic compared to ketones? Ketones have a much larger dipole moment than alcohols and are very much able to participate in hydrogen bonding.
Click to expand...

Okay, so maybe it's not. I fixed the title, too.
 
3-acetamideindoles are probalby inactive. I think this compound can be easily destroyed by MAOs without his methyl "protector" group.

Perhaps N-acetyl-AMT or b-oxo-AMT (beta keto form of AMT ) would be a better choice of "carbonyl" AMT-analogues :\
 
N-acetyl-AMT seems like it would be much easier to explore anyway, someone should buy some acetic anhydride and test it out for science.
 
hiyall,

i think the beta ketone alpha methyl/ethyl tryptamines are an intersting idea.
another possible lead in similar direction comes from way back many moons
ago and was posted on the board of bees.

*****
Legendary Assholium (known in Russian circles by some different nickname)
once mentioned having synthesized indanyl analogue of methcatinone
(1-indanyl-2-aminopropanone).

He went like this:
Indene -->Pd/Cindane ---> (C2H5COOH, H3PO4*P2O5) 1-indanyl-propanone
---> CuBr2 1-indanyl-2-bromo-propanone --->NH3
1-indanyl-2-amino-propanone.

The only thing he said was "...was it long since you experienced something so
amazing it made you catch your breath? Then try this!"

Unfortunately, our contact w/him is nearly lost.

Antoncho

*****

based on his numbering and synth route it looks to me more like a indanyl
version of beta-ketone-AMT than a methcathinone version of IAP. could be
some interesting new territory here. anyone else have thoughts or further refs
on this?

el_mago
 
I suppose it depends which way round the indanyl moety is,
if the side chain is attached to the benzene part than it is IAP like, if its attached to the 5 carbon ring it is sort of AMT like in a round about way.
1-indanyl doesn't help in clarifying because it could be 1-indan-5-yl or whatever.

However there are a few clues here as to which it is and I will lay money on it being the IAP analogue,with the side chain coming out of the benzene part of the indanyl group.
 
hiya,

ya the guys not exactly clear/correct with his naming... your estimates probably better than mine. and since he himself was comparing it to methcathinone perhaps another reason to lean towards the 1(5-indanyl) interpretation.

could it be that the methcathinone analogue of IAP is a winner and was overlooked due to IAP being not so hot with the monkeys? perhaps worth a
shot...

el_mago
 
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