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Ringed Mescaline Analogue/Chemical Masturbation Thread

fastandbulbous, I know I've already harrased you via PM, but any chance you would look over my structures and tell me what I have left out?

I know I don't have the Ganesha/2C-G family, nor many of the MDA analogues...but as far as the rest, am I leaving anything out?

In that case, cyclicization results in a very unpleasant intoxication and I suspect that it would hold true for tryptamines using any cyclicized/heterocyclic amine group such as morpholine & azetidine
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Even with (3-[2-(1-methylazetidin-2-yl)ethyl]-1H-indole? That's a different beast than a tryptamine with cyclicization on the end.
 
With regard to low potency of mescaline derivatives, 3C-AL is pretty damn potent, at least 10 times mescaline and about 2.5 times 3C-E. And feels just like mesc (as does 3C-E), i dunno whats up with the reports in pihkal! :\
 
What about the 5 ring incorporated in to the ethylamine part of the tryptamine not stuck on the end.

These results also suggest that both 1 and 3 would possess LSD-like psychopharmacology in humans.
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Taken from Nichols: Further Studies on oxygenated Tryptamines with LSD-like Activity Incorporating a Chiral Pyrrolidine Moiety into the Side Chain
 

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saw an old (70's) Nichols paper where he made 5,8-dimethoxy-1,2,3,4-tetrahydronaphthalen-2-amine. It was reported to be pretty much inactive, not suprisingly! Would be really interested to see the brominated version though, i wonder if he still has some he could whack a bromine on! I would guess this would be more potent than his other benzocyclobutane / pentane analogs and would prove (i think!) a link between lsd and phens.
 
What about substitution of phenmetrazine not just on the phenyl ring (I remember F&B already naming and discussing dragonfly-phenmetrazines) but all the way with the diethylamide part of LSD.
 

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Interesting, that ether should be an ok replacement for the double bond, though it introduces another stereocenter. Someone needs to systematically add each of the elements of lsd to 2cb or 2cb-fly. I'd start with the six membered ring to hold the amine in the same position as in lsd, then the double bond then the other six membered ring with the amide. Then N-methylate each of them. Should be relatively easy to do the first ring and the double bond.
 
What about substitution of phenmetrazine not just on the phenyl ring (I remember F&B already naming and discussing dragonfly-phenmetrazines) but all the way with the diethylamide part of LSD.
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The compound you're talking is probably inactive, re totally devoid of any LSD-like activity. Like FnB said : The structure of lyserig acid is rigid and flat. If you look the LSD molecule from the edge, Only the amide is rotating out of this lysergic acid plane. It isn't the case for your phenmethrazine analogue, sorry !


MGS, you're talking about new cyclised-tryptamine analogues. Shulgin made the pyrrolidine version of DET. It result a total frightening effect psychoactive...

Perhaps more or less carbons in the cycle get a better psychedelic activity ?? The 5-meO-DET is frightening, DPT is a really worthwile psychoactive --> but what about the azacycloheptane analogue ???

The possible interesting other N-alkyls are probably the fluorinated-ones (trifluoroethyls, ... ).

Note : Dr Nichols has synthethised a cross between LSD and DOX !!!

Substituted naphthofurans as hallucinogenic phenethylamine-ergoline hybrid molecules with unexpected muscarinic antagonist activity
Monte AP, Marona-Lewicka D, Lewis MM, Mailman RB, Wainscott DB, Nelson DL, Nichols DE

http://www.erowid.org/references/refs_view.php?A=ShowDoc1&ID=6532
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Thanks for the link vanadium, cant believe i didnt see that, i searched pretty specifically, goddamn scifinder.

Thats pretty suprising it was no good, to me anyway. LuxEtVeritas, why do u say u dont think they have much potential (i know they dont, now, but before seeing that paper i'd have thought there was a good chance something like that would work well)
 
This isn't a ringed mescaline analogue, but on the subject of theoretical chemical masturbation... I've been dreaming about halogenated tryptamines. Particularly 4-substituted variants.

4-Bromo-n,n-Dimethyltryptamine
4-Chloro-n,n-Dimethyltryptamine
4-Fluoro-n,n-Dimethyltryptamine
4-Iodo-n,n-Dimethyltryptamine

Somebody will have to synth and test these, as well as however many nitrogen variants you care to think up.... halo-DETs, halo-DPTs, halo-DiPTs, halo-MiPTs, etc.

I wonder what would happen if somebody made an n,n-Dibromotryptamine? 8o
 
IndoleDreamStudies said:
I wonder what would happen if somebody made an n,n-Dibromotryptamine? 8o
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He would be brominated/oxidized quite fast...well if you wanna get brown!
 
Hey !!!

Halotryptamines are probably less potent : excepting fluor,halogens are heavy atom and worse h-bond donnor than Oxygen or nitrogen. halogenated tryptamines bind less the 5-HT2A receptor.

Dr Nichols have reported some fluorinated-tryptamines, he put a fluor atom in the position 4 of the well-known 5-MeO-DMT !

For the next experience,I should try to brominate the DMT or DPT, it isnt difficult ...
 

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Reminisant B said:
What about substitution of phenmetrazine not just on the phenyl ring (I remember F&B already naming and discussing dragonfly-phenmetrazines) but all the way with the diethylamide part of LSD.
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You mean the duck/duckling series? thread here

If you notice the date (April 1st) it was done half tongue in cheek with only a trace of seriousness about it. They may have some activity, but that would only be a fraction of their comic activity (DOM-duck - Donald's long lost cousin - is shown below! =D)
 

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What about making a (safe) N-substituted dihaloalkyltryptamine? Say N,N-ditrifluoromethyltryptamine. Or even 1-trifluoromethyl-N,N-DMT. 1-Methylation still gives an active compound.

Vanadium said:
Hey !!!

Halotryptamines are probably less potent : excepting fluor,halogens are heavy atom and worse h-bond donnor than Oxygen or nitrogen. halogenated tryptamines bind less the 5-HT2A receptor.

Dr Nichols have reported some fluorinated-tryptamines, he put a fluor atom in the position 4 of the well-known 5-MeO-DMT !

For the next experience,I should try to brominate the DMT or DPT, it isnt difficult ...
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^ Yeah they could be quite interesting. F in many ways acts just like a H atom, similar size and such. Well, I see CF3I is a commercial chemical (but it is somewhat expensive compared to plain MeI) sooo, if anyone feels like cooking some up...
Can't see a easy way of making the fluoromethyl one, neither CHFI or fluoromethanal are easily available (can fluoromethanal even exist =/ ?).
 
Fluorometh anal,yeah,why not :)

This whole fluorostuff smells a lot like high-pressure chemistry,but rightfully done,it will give you cleverass compounds.
 
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