Tryptophol

[nAON]

Apologies for vague thread, but does anyone know anything about this chemical? I got curious after I read that it can induce sleep. Have done some searching about but most of the research I found was fairly random or on it as a chemical precursor to stuff like DMT.

 

[sekio]

As far as I know this would be no more active than phenethyl alcohol.

It probably smells really funny too.

 

[Hammilton]

It could be a roundabout way to get to DMT I suppose. Other than that, I don't see any reason for it. I doubt it'd be active. Benzyl alcohol isn't much of a depressant, so this is definitely not gonna be.

Tryptopol? is this your name? Since it's not a tryptamine the name makes little sense. Indolethylol or something based on indole makes sense.

 

[tryp2fun]

It could be a roundabout way to get to DMT I suppose. Other than that, I don't see any reason for it. I doubt it'd be active. Benzyl alcohol isn't much of a depressant, so this is definitely not gonna be.

Tryptopol? is this your name? Since it's not a tryptamine the name makes little sense. Indolethylol or something based on indole makes sense.

Tryptophol is the common name for indole-3-ethanol, or more precisely, 3-(2-hydroxyethyl)indole.

 

[gladiolus]

actually, tryptophol is on my list of things to try. I'm surprised actually that there's not more mention of it online. I guess the basic thing is to substitute the NH2 with an OH group. That took us from GABA to GHB,
OOP refers to phenethyl alcohol, which according to memory has a smell and taste of roses. I would imagine this to be quite a blissful intoxicant.
Applying the same logic, to the indole completes the hallucinogenic package. Therefore I predict that Tryptophol (which I liken to a slumberous shroom sopophoria) would probably be a very blissful compound. I have a feeling it may be incredibly soporiphic.

 

[sekio]

Given the inactivity of plain tryptamine, and the facr that closely related indole-alkyl-carboxylic acids are plant growth regulation chemicals, I doubt very much tryptophol or PEA-alcohol will be intoxicants at all.

 

[gladiolus]

plain tryptamine IS active if administered IV. If administered with an MAOI it should provide the same deal. It is LSD-like, according to shulgin. Also of interest would be the -OH derivatives of glycine, acetylcholine and NMDA.

 

[Black]

It is LSD-like, according to shulgin.

read further

Most instructive was the statement that the tryptamine syndrome was similar to the LSD syndrome. This equation has been broadly quoted, but it is valuable to read, first hand, the explicit observations of central activity that supported this conclusion. These are quoted here:

"Shortly after the onset of the infusions, three of the patients became aware of the experimental setting and complained of a heaviness, tiredness or numbness of the limbs which subsequently became generalized to other parts of the body. With continued infusion, a variety of other visceral symptoms and signs emerged which have been previously described following administration of LSD and mescaline, including nausea, vomiting, dizziness, sweating, acute or dulled hearing, metallic taste, and a heaviness of body. Further, in 2 of the 4 subjects, there were visual changes (subsequently described as a heaviness behind the eyes, a clouding of vision, and lines or cobwebs)."

The tryptamine experience sounds pretty heavy, and it is almost as if every negative LSD or mescaline property was exhumed and displayed, to justify tryptamine as being similar to this widely accepted psychedelic drug.

 

[nAON]

Fair enough. Through what mechanism would it induce sleep then - perhaps degraded to melatonin?

 

[King Kong]

I would imagine this to be quite a blissful intoxicant.
Applying the same logic, to the indole completes the hallucinogenic package. Therefore I predict that Tryptophol (which I liken to a slumberous shroom sopophoria) would probably be a very blissful compound. I have a feeling it may be incredibly soporiphic.

It's pure speculation based on almost nothing!
Tryptophol is apparently the compound inducing sleep in sleeping sickness: http://www.ncbi.nlm.nih.gov/pubmed/7241135?dopt=AbstractPlus

It doesn't really look like it mimics hallucinogens... and it doesn't seem to be interesting .
But if you try it, don't forget to write a report!

Fair enough. Through what mechanism would it induce sleep then

I can't really find anything in the scientific literature. It's strange that people aren't more interested to elucidate this mechanism.

 

[gladiolus]

I have for many years been exploring the human pharmacology of these types of alcohols (eg. 1-ethynylcyclohexanol etc) and I have also for years been exploring the tryptamine molecule, including the beta-acetoxy indole variant of phenibut, as well as ingesting orally available tryptamine derivatives like 4-Aco Trytpamine, which is orally active and hallucinogenic in both rats and man.
So, yeah, I'm pretty sure what the effect of tryptophol will be like.

 

[King Kong]

Maybe I misunderstood you (sorry, my English is quite poor), but you were saying that tryptophol should maintain a similar hallucinogen activity compared to related tryptamines?! Or in other words, that tryptophol should have a similar binding for the 5-HT2A receptor.
This means that the neutral (at physiological conditions) hydroxyl function could substitute the cationic amine* function. It’s possible, but very unlikely! The alcohol shouldn’t be able to maintain the important and strong binding with the aspartate residue. And I see no evidences which could approve your theory. I also don’t see how understanding the pharmacology of compounds you listed would help you address this issue?

Maybe I am totally wrong, but claiming that tryptophol have a similar pharmacological profile than tryptamines appears to me very hypothetical.
Sorry again for my shaggy English. Good night!

* http://www.jbc.org/content/271/25/14672.long

 

[Hammilton]

I have for many years been exploring the human pharmacology of these types of alcohols (eg. 1-ethynylcyclohexanol etc) and I have also for years been exploring the tryptamine molecule, including the beta-acetoxy indole variant of phenibut, as well as ingesting orally available tryptamine derivatives like 4-Aco Trytpamine, which is orally active and hallucinogenic in both rats and man.
So, yeah, I'm pretty sure what the effect of tryptophol will be like.

Actually, as I re-read everything you've written, I kept being reminded that I HAD thought that you one of the more intelligent members here and asking myself why the hell you're now spewing this retardery? Do you have a business selling tryptophol or something because the absolute lack of reason to think that this would be active- even at multi-gram doses- and moronic, baseless claims to the contrary lead me to only one conclusion- you've got a kilo of the stuff (because the chinese don't want to make less), realized it was inactive and now want to hype it a bit so you can try to move it and recoup your money.

These types of alcohols? 1-ethynylcyclohexanol has NOTHING in common with this compound. It's a non-aromatic tertiary alcohol with a highly reactive ethynyl group.
Nor does this compound have ANYTHING in common with tryptamines. It is extremely well established that the amine is required for activity at 5HT2a.
Additionally, the SAR of alcohol depressants is extremely well established and aromatic heterocycles are effectively a death blow, especially for ones as large as indole.