LSA adducts

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It has been documented that Lysergic Acid Amide (LSA) is capable of forming adducts with various aldehydes. Such adducts can form spontaneously during extraction of LSA if aldehydes are introduced to the solution, and can alter the subjective and physiological effects of LSA.

Lysergic Acid Hydroxyethylamide

Lysergic Acid Hydroxyethylamide (LSH) is one example of such adducts, produced from LSA and acetaldehyde.

Due to the low boiling point of acetaldehyde (20.2 °C), LSH is very unstable and readily decomposes back into LSA and acetaldehyde. LSH and possibly other adducts are formed naturally in LSA containing plants, possibly explaining the differences in reported effects, as fresh seeds may contain higher levels of LSH.

LSA is possibly not the main active principal of Ipomea seeds as commonly thought, and appears instead to be a decomposition product of lysergic acid hydroxyethylamide (LSH). LSH is reported to have psychedelic properties similar to that of Lysergic Acid Diethylamide (LSD). Animal tests have shown that LSH produces stimulant effects similar to LSD, while LSA produces sedation. LSH is said to produce less vasoconstriction than LSA.

Lysergic Acid Amide	Acetaldehyde	Lysergic Acid Hydroxyethylamide

Production

Anecdotal reports indicate that LSH can be produced by mixing LSA and acetaldehyde in an acidic solution. It is also thought that LSA can form adducts with other aldehydes, some of which have been reported to be active, although scientific evidence is lacking.

Peppermint essential oil or fresh peppermint leaves have been used during extraction to produce LSH and other adducts, however the acetaldehyde content of most peppermint oil is very low. There are other aldehydes present in higher quantities however, so it is likely that other adducts will be formed. Due to the low boiling point of acetaldehyde, extraction must be carried out at a low temperature and the product is not easily stored. The process is notoriously difficult to achieve leading to many people refuting the adduct theory.

Cinnamylidene-bislysergamide

Cinnamylidene-bislysergamide, a theoretical adduct of two molecules of LSA and one of cinnamaldehyde, may be produced by introducing cinnamon bark essential oil to LSA. It appears to produce radically different subjective experiences to LSA, with a rapid onset, rapid peak, and far shorter duration.

The 2:1 ratio is theorised based on similar cinnamaldehyde adducts such as cinnamylidene-bisacetamide and cinnamylidene-bisphenylacetamide, which are proven to form without the need for a catalyst.

Lysergic Acid Amide	Cinnamaldehyde	Cinnamylidene-bislysergamide