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The Difference Between Tryptamines and Ergolines

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love_sex_desire

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Oct 7, 2004
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What are the differences between tryptamines and ergolines? Are ergolines a sub-category of tryptamines, and therefore tryptamines themselves? I have heard that LSD is a tryptamine and an ergoline from different sources, and some of these sources seem to suggest there is a difference. I understand that LSD is an ergoline, considering it is related to ergot, but since LSD is in TiHKAL, I was wondering, is it truly a tryptamine? If so, is LSA and other ergoline alkaloids also tryptamines?
 
All ergolines are tryptamines, but not all tryptamines are ergolines

I loved the SATs
 
Does the progression end at lysergamides or is there a heavier class of alkaloids that includes the lysergamide skeleton?
 
Lysergamides are just substituted ergolines. They're not sufficiently different to be considered a seperate class. From tryptamine to ergoline you've got a big change.
 
this ergoline tryptamine phenethylamine obsession is a totally pointless classification.

ergolines also contain the phenethylamine structure and the phenyl piperidine structure but they are not phenethylamines nor are they phenyl piperidines.

they also contain the tetralin structure and numerous other structures.

ergolines are ergolines period.
 
vecktor said:
this ergoline tryptamine phenethylamine obsession is a totally pointless classification.

ergolines also contain the phenethylamine structure and the phenyl piperidine structure but they are not phenethylamines nor are they phenyl piperidines.

they also contain the tetralin structure and numerous other structures.

ergolines are ergolines period.
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If ergolines are distinct, yet contain both the tryptamine and phenethylamine structure within their structure, is there any reason or speculation as to why Shulgin put the lysergamides such as LSD and ALD-52 in TiHKAL instead of PiHKAL? Are lysergamindes more related to tryptamines than phenethylamines, even though lysergamides contain both with their structure? Or was it merely a choice because the lysergamindes could have been put into either?
 
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I suspect it had more to do with chronology of events in his life.
 
tryptamine is a more complex structure than phenethylamine, so the tryptamine skeleton within the lysergic acid structure probably has more meaning. also, LSD feels more than tryptamines than phenethylamines subjectively.
 
I can't comment on Shulgin's reasons to sort LSD into TIHKAL instead of PIHKAL, but at least from the biochemical point of view it makes some sense. The ergolines are synthesized in nature from tryptophane, and therefore, can be classified together with the tryptamines.

From a pharmacological perspective, I can only agree with Vecktor in this case: The binding modes within the 5HT-receptors (the main targets of named compound) differ and it makes no sense to group them all together.

- Murphy
 
Additionally, in academic literature, you'll see LSD classified with tryptamines frequently, while I've never seen it put in with phenethylamines.
 
Ergolines also tend to be pervasively promiscuous ligands, binding at serotonergic receptors, dopaminergic receptors and adrenergic receptors.
 
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