Allylbenzene
Bluelighter
- Joined
- Jul 25, 2025
- Messages
- 1,137
Let's not forget the very real possibility of in-vivo rxn/adduct formation; after all, excluding a possible scenario before it's been (dis)proven isn't reasonable.
I think downwardsfromzero (dmt-nexus) outlined it quite well:
And besides even if you were able to form these N-acyl hemiaminals (like LSH is one), I'd be surprised of them being pharmacologically relevant as anything but a prodrug as they'd very rapidly degrade in the aqueous soup that is your body.
I think downwardsfromzero (dmt-nexus) outlined it quite well:
This was one of the more visual attempts with natural lysergamide-containing seeds. The experience followed a night involving the consumption of a significant amount of brandy, thus there was an incontestable residue of acetaldehyde in my body.
The seeds themselves, being HBWR, were much more likely to have contained LSA as the principal alkaloid; they will not have been particularly fresh. Although the inference counts as purely anecdotal, I feel it supports at least one of these ideas:
While I consider the last option the least likely, and in the past I have argued against the possibility of it happening, it's still not something I would discount entirely. Still, I wouldn't bank on it and would advise all readers that acetaldehyde conversion of seed extracts containing lysergamide are best carried out in vitro as ethanol and acetaldehyde present health hazards when ingested!
- ...that the 1-acetaldehyde adduct of LSA (or, possibly from what we've learned so far, iso-LSA) is likely to be more of a visionary entheogen than plain LSA itself.
- ...that post-alcoholic acidity in the body promotes the formation of the more visionary iso-LSA from the LSA equilibrium mixture in vivo.
- ...that under physiological conditions, acetaldehyde inhibits the breakdown of LSH such that - in the aforementioned instance - sufficient LSH reached the appropriate receptor sites to produce a mild but significant entheogenic experience.
- ...and/or...:
- ...that, under physiological conditions, acetaldehyde reacts with LSA at the amide nitrogen to (re-)form LSH.
The acetaldehyde adduct would be C2H5O, as CH3COH attached at the indolic nitrogen - another 1-hydroxyethyl group, just like in LSH. From what you describe, this seems like an argument for soaking one's N¹-unsubstituted lysergamides in cold peppermint sherry for a while before consumption. Would this also include tryptamines such as DMT-containing potions for oral consumption, one might wonder? And what about psiloc(yb)in?
As I've mentioned, my most successful plant-derived lysergamide experience - in dreams, of course - albeit with HBWR, coincided with intake of a fairly large quantity of brandy which, in all likelihood, produced a significant level of acetaldehyde within my body, exposing the plant lysergamides to the correct conditions (as reported in the Austin & Fraenkel-Conrat PNAS paper) within my stomach for the putative 1-(1-hydroxyethyl) or, rather, it seems, the 1-(1-ethoxyethyl) derivative to be formed. In this case, the effects were clearly stimulating, unlike the sedative effects usually reported for HBWR. I see that brandy weighs in fairly well on the acetaldehyde content scale as well, btw (post #17)
Looking at the PNAS paper, and the molecular structure "indole after p8441", what we appear to get is a 1-(1-ethoxyethyl)indole, with an ethyl group on the oxygen atom. This would be more lipophilic than the 1-(1-hydroxyethyl) derivative, as would, incidentally, the cinnamaldehyde adduct proposed by 69ron. It is only with the combination of both ethanol and acetaldehyde (EDIT: rather. an alcohol and an aldehyde; see below) that we get a stable product. It would seem likely that under mildly acidic conditions ethanol and cinnamaldehyde (or, we might also surmise, any other sufficiently stable, sterically unhindered aldehyde) would also form a stable adduct.
...
And isovaleraldehyde would lead to the production of a 1-(1-ethoxy-3-methyl-1-butyl)indole derivative under this scheme. That'll have to do for now as I need to sleep. [EDIT: also of interest, we see the following: "Reaction mixtures were also prepared using 1-, 3-, and 4-carbon-chain aldehydes and alcohols. After 24 hr of reaction ... these alternative mixtures were analyzed on the same HPLC system. Reaction products (data not shown) were detected in all cases, except when the aldehyde was formaldehyde, and product retention time increased along with the length of the reagents' carbon chains. The yields decreased with increasing alcohol and aldehyde chain length (methanol/acetaldehyde - butanol/butyraldehyde)."]
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