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Legality of THC-Analogues

vecktor said:
you would be suprised to learn that it isn't. acylation of the 3 position is un-natural in indole, along with the friedel crafts catalyst co-orinating with the nitrogen..
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While I would agree Freidel Crafts is probably not a very attractive method, I see no problems with going the other way.

Indoles are smoothly acylated under mild conditions at the 3 position. The oxalyl chloride acylation of indoles is the basis for the classical Speeter-Anthony tryptamine synthesis.

I don't see why naphthoyl chloride would not work as well?
 
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retired_chemist said:
While I would agree Freidel Crafts is probably not a very attractive method, I see no problems with going the other way.

Indoles are smoothly acylated under mild conditions at the 3 position. The oxalyl chloride acylation of indoles is the basis for the classical Speeter-Anthony tryptamine synthesis.

I don't see why naphthoyl chloride would not work as well?
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oxalyl chloride is the highly reactive exception, try acylating indole with acetic anhydride or acetyl chloride.
the huffman group succeeded in fair to poor yields using naphthoylchloride and an alkylaluminium chloride catalyst.
a similar problem was encountered in the synthesis of pravindoline the parent of all these compounds.

it is certainly worth reading huffmans papers on the subject
 
Yes, oxalyl chloride is an exception, but alkylation of indoles in the 3 position is not very hard at all, there are many examples, like Heterocycles, 2001, 55(4), 653-660. Also many possibilities for the oxidation of benzylic carbon atoms.

Another odd brave one who is all for reduction of structures, like your naphtoyl indole very much, fastandbulbous.
 
Ah i didn't think of the extra reactivity of oxalyl chloride. Naphthoyl chloride should be more reactive than acetyl chloride though, reactive enough i've no idea. Does it have to be naphthoyl, anyone any idea if the benzoyl derivative would be active?

While I would agree Freidel Crafts is probably not a very attractive method, I see no problems with going the other way.
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What do you mean the other way?
 
we're really not supposed to talk too much about synth of course as much as we may like to , but more importantly since i am pretty confident the synth can be done rather easily i would still like confirmation by FnB and gabbachris of effect profiles and clarification of what exactly they tasted, dose, route....=D
 
Yeah i know, i do like it tho! Still curious weather it needs to be naphthoyl or if benzoyl would do.
 
Look into Bergman? acylation using Ethylmagnesium bromide, but I guess look at Huffman's papers first, presumably they would have tried that.
 
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Ah ok, thats sort of what i was thinking, didn't realise you could just use a ton of grignard on the acid tho!
 
The paper I have uses methyl magnesium bromide followed by 2-naphthoyl chlorideto do the indole-3 substitution, a mechanism that i'm not sure I understand.
Alternatively I thought you could start from indole-3-carboxaldehyde, react that with napthen-2-yl magnesium bromide, do the indolic N substitution, then finally oxidize that alcohol produced in the first reaction to an ketone.

There are plenty of ways one can get to product here.
 
could start from indole-3-carboxaldehyde, react that with napthen-2-yl magnesium bromide,
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would take 2 equivalents of grignard though. also an extra step.

methyl magnesium bromide followed by 2-naphthoyl chlorideto do the indole-3 substitution,
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i guess it deprotonates the indole and the amide anion makes the ring more nucleophilic. nice idea. 2-naphthoyl chloride? what are they making?
 
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The one I mentioned. The aminoalkylindole cannabinoid, the one with the ethylmorpholinyl ring off the indole N .
And why two equivalents of Grignard? R-MgBr reaction with R'-CHO (aldehyde) should form R-CHOH-R' cleanly with no further reaction occuring.
 
fastandbulbous said:
^ Sounds a lot like the cannabinoid I've tried. Very clean & clear headed, like a very non-sedating sativa type of intoxication. Also cave the same sort of brightness and very noticably, munchies from hell (how to empty a 'fridge in an hour!) =D

Best of all, no fuzzy headedness the day after, that would be quite pronounced for the same level of intoxication with THC & co.
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oh also as well as clarifying if what you tested was indeed the structure above, dose and route can you comment on if there was a ceiling as is seen with WIN55212-2 as I have heard (at ~3mg I believe for that as commonly reported)
 
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And why two equivalents of Grignard? R-MgBr reaction with R'-CHO (aldehyde) should form R-CHOH-R' cleanly with no further reaction occuring.
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Because the NH of the indole will get (at least partially) deprotonated before addition to the aldehyde. The deprotonated indole could then add to the aldehyde. Would probably work ok though if it was added to a large excess of the grignard.
 
fastandbulbous said:
^ Sounds a lot like the cannabinoid I've tried. Very clean & clear headed, like a very non-sedating sativa type of intoxication. Also cave the same sort of brightness and very noticably, munchies from hell (how to empty a 'fridge in an hour!) =D

Best of all, no fuzzy headedness the day after, that would be quite pronounced for the same level of intoxication with THC & co.
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just wanted to 'bump' again to inquire for dose and route of administration

TIA
 
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by chance i have aquired some of the nahphtanoyl compound also ,

active

orally round 5-10 mg : no psychedelic buzz , just nice and stoney feeling with waves of warmth going through the body.

smoking 3-14 mg : the low doses give a short serotonic release and a nice high feeling after , the high doses are psychedelic for about 15 minutes and heavenly stoned for another 1,5 hours.

and yes , the chemistry is "very" simple albeit a little hazardous.
 
^ thanks...

hmm a bit odd that the reports seem somewhat markedly disparate

did you find it overall cleaner and less sedating as remarked on by FnB?
 
most definetly more clean and less "hangover" than THC.

but me not sure if F&B and me have taken the same compound

btw , thc is only fat-solutable within the body , seems this compound desolves easier.
(even orally it hits within 20 minutes)
 
i have seen an 'ad' for the compound you took ( i think)...how did you arrive in that being a naphthoylindole...where was this made known?

and i hope FnB can enlighten if this was the same "synthetic cannabinoid" and the one that is his Huffman alternative
 
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