• N&PD Moderators: Skorpio | thegreenhand

  • Neuroscience & Pharmacology Discussion Welcome Guest
    Posting Rules Bluelight Rules
    Recent Journal Articles Chemistry Mega-Thread
    FREE Chemistry Databases! Self-Education Guide

Lucigenol

AuraithX

AuraithX

Bluelighter
Joined
May 22, 2006
Messages
4,504
Does anyone have any information on this chemical? A link to the papers Nichols wrote on it would be handy.

Stability/Dosage would be useful also if anyone knows.


Cheers,
 
Last edited:
(R)-3-((1-methylpyrrolidin-2-yl)methyl)-1H-indol-4-ol. An absolutely horrible name choice- that's the name of a chemical in glow sticks.

Doesn't look like it's very stable, and according to Vector the 5-MeO analogue was tested in humans and wasn't great.
 
Aaaaah.... thanks.

Googled it but came up with zilch- info please.
 
dbailey11 said:
What's it supposed to be, a stimulant or a psych?
Click to expand...

It's a psychedelic with a lot of sedative-like properties (not much cop IMO). Active at 1-1.5mg in humans


It's an analog of LSD.
Click to expand...

It's not as it doesn't have any C or D ring like LSD. If it has to be an analogue of anything, I'd vote for AMT/5-methoxyAMT by it's structure (alpha methyl extended and attached to amine,with additional methyl group added to give a 5 membered heterocyclic structure)
 
Is it already proven active?, because I heard that it was inactive in a human trail, but that might also because the wrong isomer was used????
 
I only know about in vitro trials and in vivo, using rats; binding studies (...conformational energies) suggest a different binding mode than LSD at the 5HT2A-receptor. It's said to have around a 10th of the potency of LSD...
 
It's weird in that the stereochemistry around C5 of the most active isomer is the opposite of the conformation of all the other optically active compounds that are psychedelic 5HT2as agonists.

As regards activity, I'm quoting directly from some communication from a synthetic organic chemist (with a liking for psychedelics!) I know. Personally, the methoxy group in the indolic 5 position is a good enough reason for me to avoid it...
 
funny FB
because this one has a hydroxy on the 4 position ,
therefor i would also call it an analog of psylocin if anything.

and still as far as i know it's not active in humans.

(still waiting on the right isomer)
 
I have heard small whispers of a psychedelic with the name "lucigenol." No one seems to know what the exact structure that corresponds with this name is? For some reason, the claim has been made that it is analogue of LSD, which it is clearly not. Also, some think that it is a 5-MeO compound, others a psilocin-like 4-OH tryptamine (with maybe 10x the potency of psilocin). Can anyone confirm that this compound (first synthesized by Nichols) has actually been officially named "lucigenol" and has actually been tested by humans as a psychedelic? If so, why would it be predicted to have a strong sedative effect?

Note: the (R)-enantiomer is the more active isomer from the paper.
 

Attachments

  • untitled.png
    untitled.png
    4 KB · Views: 321
I thought it was sedating since it was an analogue of LSA or some such? I could be totally off base though.

*ss wants a sedating psych*
 
Are you a member of Blacklight.in samadhi? I've posted a lot of (what I hope is) really good information about the structural activity relationships of depressants.

Most relevant to your particular desires has to be the GABA-A a1-selective ligands. These seem to require a pentagonal ring w/ one or more nitrogens (three seems to be the max, but I'm not sure) and usually one or more double bonds, but thalidomide has none, but I can't find data on it's selectivity. Off of that a chain that looks like this: C-C(=O)-N, with the N usually being disubstituted (except of course, again in thalidomide and CL-218-872).

This basic structure should make the potential psychedelic-sedatives obvious: it's obviously something that the basic tryptamine structure can be modified to accomodate, simply changing the amine to an amide (ie: a ketone on the alpha carbon).

I can't find anything on the 5HT2a selectivity or the sort of potency we could expect from these.

Obviously the hope would be for much stronger preference for 5HT2a over GABA-A a1-subunit containing receptors since a1 agonists are so well known as strong hypnotics and amnesics.

I think that these might make great potential psychedelics for the anxiety-impaired. I'm certainly one of these, so I've been quite restricted from using psychedelics except when I've had a long period of preperation before partaking in any of the sacraments.

With PTSD and potentially unsettling, upsetting and unwanted flashbacks so common after a particularly bad trip (they are of course extremely uncommon on the whole with psychedelic users, but the risk goes greatly up among those unfortunate enough to have had a really bad trip), these offer two advantages: they'd be less prone to inducing bad trips, and if one were to develop, as they certainly can (look at the bad 'trips' resulting from Zolpidem), taking a higher dose could be used to produce complete amnesia of the experience.

A lot of the more new-agish psychedelic users will be quick to say "that won't solve anything, that'll simply push it into the back of the mind and repress the experience." However, when considering the horrible things that have happened to and done by people under the influence of GABAergic drugs that produced complete amnesia, and don't seem to harm or even affect the experiencee unless discovered through some other route, I think it's safe to say that it's simply hippy hogwash to borrow a phrase I once heard at a George Bush 2004 rally.

(to think, as I originally wrote all that, it was only one sentence, and now it's only two! I could never parody Kurt Vonnegut, that's for sure)
 
Look to the nichols paper, plenty of good info to be had...

Active dose appears to be between .5mg to1mg, though higher for one isomer, I cant think which is which offhand though.
 
(R) isomer is a lot more potent, I forget how much. Look at the paper if u want to know.

Binding affinity for 5-HT2A receptor is 13 +/- 2 nM (Ki [125I]DOI).
 
I personally like a nice stimulating psychedelic (the more amphetaminergic the better, as long the PNS side effects aren't too annoying), so I guess this one is not for me. Then again, I guess I've been lucky in the fact that I've never had a bad trip.
 
MattPsy said:
(R) isomer is a lot more potent, I forget how much. Look at the paper if u want to know.

Binding affinity for 5-HT2A receptor is 13 +/- 2 nM (Ki [125I]DOI).
Click to expand...

Is that the 4-hydroxy compound? I was talking about the 5-methoxy one.

Crossed wires...
 
Oh. I thought it best to post the data for the title compound.

The 5-MeO one is 9.5 +/- 1.6 nM (Ki [125I]DOI). Even higher affinity than the 4-OH one, as y'all can see.
 
You must log in or register to reply here.
Top