[machinelf]

Hi...

I have NO background in chemistry and that's why I came here to ask you folks a question. Terence Mckenna (also not a chemist) used to say something provocative about the chemical makeup of psilocybin (the active chemical in some psychedelic mushrooms) --

“I’ve mentioned that psilocin, which is what psilocybin quickly becomes as it enters your metabolism, is 4 hydroxy dimethyltryptamine. It is the only 4-substituted indole in all of organic nature. Let this rattle around in your mind for a moment. It is the only 4-substituted indole known to exist on earth. It happens to be this psychedelic substance that occurs in about eighty species of fungi, most of which are native to the New World. Psilocybin has a unique chemical signature that says, “I am artificial; I come from outside.”

Now, whether magic mushrooms came from outer space is an interesting hypothesis. And I'm not really looking to figure that out here.

What I am interested in is this idea that --

"It is the only 4-substituted indole in all of organic nature."

Is there truth to this statement?

If so, do chemists find this of interest?

Does this chemical makeup truly stand out as something unique in our terrestrial chemistry?

I appreciate your thoughts and I appreciate any efforts to make them understandable in layman terms. :-)

Thanks very much!

[Fluorine]

In short, no this is not true. T. McKenna has a lot of bold claims for a well studied field, I'd recommend Richard E. Schultes and Jonathan Ott for starters instead.

In length; indole is a naturally occurring molecule which is also quite commonly the parent structure of many other compounds, both natural and synthetic. One of the more notable derivatives is tryptamine which includes things like serotonin, melatonin, psilocin, psilocybin, and by a stretch harmala alkaloids, ibogaine, ergolines, many others.

Is psilocin the only naturally 4-substituted indole? No, psilocybin, aeruginascin, baeocystin, and norbaeocystin are naturally occurring and 4-substituted indoles. They are all from fungi but this doesn't mean they are necessarily anymore diverse than other sources. Certain sea creatures contain 6-halogenated tryptamines which are, to my knowledge, have never been found in plants or fungi. There are many examples of exclusive substitutions it comes down to which enzymes the are available and involved. It's not a surprise fungi create unique pattern that is limited to a handful of genera.

Indole                                Tryptamine

do chemists find this of interest?

It depends on the chemist but in general not likely. Jochen Gartz for example showed addition unsubstituted synthetic substrates could be enzymatically converted into their 4-hydroxy and 4-phosphoryloxy counter parts respectively. There are many other scientists, including chemists, researching in this field ("psychedelics") but not because the 4-substitution is so unique or bizarre, which it's not compared to the diversity of nature.

[g-bones]

completely false, many natural products contain substitution at the 4-position.  Here is a paper that describes a small few from the Garg group at UCLA:

http://pubs.acs.org/doi/pdf/10.1021/ja200437g

[machinelf]

Thanks very much for the helpful and informative responses!

I'm a fan of McKenna's riffings on culture. I think he's pretty sharp, provocative and entertaining in that realm.

Thanks again!