Opinions - Do you consider LSD a tryptamine?

[nibble]

I was recently having this argument elsewhere and had always been of the opinion that LSD-25 is absolutely not a substituted tryptamine or tryptamine derivative, simply an ergoline. It carries the skeleton of course but it is embedded in a complex structure that would go beyond strictly substitution. I was provided with quotes from Shulgin about ibogaine, he refers to it as "a complexly substituted tryptamine" he goes on to state in the ibogaine TiHKAL entry "As to indolic alkaloids in general, there are well over two thousand of them, with a few dozen being added every year. And most of these are kosher tryptamines in that they carry the tryptamine structural skeleton". Those comments would suggest Shulgin considers ibogaine a tryptamine, despite not being strictly substituted with functional groups on the skeleton.

What is everyones opinion on this? Can it be considered a tryptamine or is it just an ergoline?

Reputation Comments on this post:

Interesting question. You could have also posted a contrary opinion to Shulgin and his argumentation.

[The Rad Mad Hatter]

SWIMs no chemist nor does he claim to know much about chemistry, but he was always under the impression that it was a tryptamine along with DMT and psylocybin. It would seem that it would be an ergoline since it derived from ergot, but I 90% sure its also a tryptamine. I was under the impression that there were only 2 main classes of psychedelics, tryptamines and phenethelamines(sp).

Again i could be totally wrong, chemistry isnt my strong point when it comes to psychedelics.

[doubledama]

As far as the "skeleton" you speak of, lucy more closely resembles a substituted tryptamine than the other class of halucinogens, phenethylamines (refer to Indole ring for more info). The structure of a tryptamine is there, however as you suspected I would most likely classify this as a ergoline compound unlike psilocybin or seratonin.

[Greenport]

Saying LSD isn't a tryptamine is like saying tyrosine isn't a phenol. Well, tyrosine is a phenol - it's a phenol subsitituted at the para-position. Likewise LSD and all ergolines contain a tryptamine structure, except that hydrogens are likewise replaced with carbons and other molecules.

As a matter of fact if swiY looks closely she will see a molecule of DMT in LSD, not just a tryptamine.

Why should LSD, being a 4- and alpha-substituted tryptamine, be not considered a tryptamine, when psilocin - a 4-substituted tryptamine and AMT, an alpha-substituted tryptamine be considered tryptamines?

Not only that, but LSD attaches itself to the same receptors that most other tryptamines do, which states that the tryptamine pattern obviously has something to do with the inner workings of the body and that at least the human body still sees LSD as a tryptamine.

Now granted we have a more specific word for such compounds, ergolines. That is generally the best way to refer to them but ergolines are (at least the way swiM sees it) tryptamines.

Reputation Comments on this post:

very good and detailed answer