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Mushrooms, Mycology and Psychedelics > The Psychedelic Experience
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Comparison of the molecular structures of the three types of psychedelics * 1
    #28958136 -


Credit: Designer Drug Exposé: Lysergamides. Tripsitter. Tripsitter and Justin Cooke, Dec 16, 2023


An interesting difference is seen when comparing the 3D structures of ergoamides with tryptamines. Despite the fact that the two share positions, the upper part of the tryptamine component of ergoamides is flat, while that part juts out in the tryptamines (the top part of the ergoamides juts out in a similar way). It's as if you took a tryptamine, ironed it out, and then stuck something fancy on to it. David Nichols refers to ergoamides as “rigidified tryptamines”.


LSD / DMT

There are three main chemical types that are agonists at this receptor: the tryptamines, ergolines related to LSD, which can be considered to be rigidified tryptamines, and the phenethylamines.

Structure–activity relationships of serotonin 5-HT2A agonists. David Nichols, 2012, WIREs Membr Transp Signal, 1: 559-579. DOI: 10.1002/wmts.42 (Introduction)


Nichols also says that ergoamides are complex, which is apparent from the first image.

Because of its complex structure, only a few modifications of LSD have been carried out, and those involved alterations of the amide function, reduction of the 2,3- or 9,10-double bonds, substitutions on the indole nitrogen or at the 2-position, and changes in the alkyl group on the basic nitrogen atom. Unfortunately, very few of these changes have been studied using modern molecular pharmacology methods, and only some of them have been assessed in human psychopharmacology. (From the 'Ergolines' section of the above article)

Edited by s240779 (09/23/24 02:58 PM)

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Re: Comparison of the molecular structures of the three types of psychedelics [Re: s240779]
    #28959433 -

Lysergamides get trapped in the receptor due to some part of their structure, which is suspected as the reason for their potency and duration.

Personally I would be very curious about how they're interacting with dopamine receptors. I don't think anyone has looked closely at LSD's interaction with dopamine receptors especially with regard to functional selectivity.

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Re: Comparison of the molecular structures of the three types of psychedelics [Re: nooneman]
    #29059379 -

nooneman said:
Lysergamides get trapped in the receptor due to some part of their structure, which is suspected as the reason for their potency and duration.


Same reason some ergolines cause gangrene.

“The low molecular ergolines are lacking the complex peptide moiety, which is apparently responsible for the persistence of the ergopeptines at the receptor molecules.”

Eich E. 2008. Solanaceae and convolvulaceae - secondary metabolites: biosynthesis, chemotaxonomy, biological and economic significance: a handbook. Berlin, Heidelberg: Springer-Verlag. doi:10.1007/978-3-540-74541-9. 4.2.5.1 Mechanisms of Action and Therapeutic Relevance, p. 249


--------------------
AI Thread

Northerner said:
I agree psilocybin is smokable though.

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