LSA adducts: Difference between revisions

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It has been documented that '''~~Lysergic Acid Amide~~''' ~~(LSA~~) is capable of forming adducts with various aldehydes. <ref>~~http~~://www.nature.com/~~nature~~/~~journal/v192/n4802/abs~~/192552a0~~.html~~</ref> ~~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. <ref>http://herbpedia~~.~~wikidot.com/</ref>~~

It has been documented that [[lysergic acid amide]] ('''LSA''') is capable of forming adducts with various aldehydes.<ref>{{cite journal | vauthors=((Arcamone, F.)), ((Chain, E. B.)), ((Ferretti, A.)), ((Pennella, P.)) | journal=Nature | title=Formation of 2,3-Dihydroxybenzoic Acid in Fermentation Liquors during the Submerged Culture Production of Lysergic Acid α-Hydroxyethylamide by Claviceps paspali Stevens and Hall | volume=192 | issue=4802 | pages=552–553 | date= November 1961 | url=https://www.nature.com/articles/192552a0 | issn=1476-4687 | doi=10.1038/192552a0}}</ref>

==Lysergic acid hydroxyethylamide (LSH)==

Lysergic acid hydroxyethylamide (LSH) is one example of such adducts, which is produced from LSA and acetaldehyde.

~~==Lysergic Acid Hydroxyethylamide==~~

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.

~~'''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 vaguely similar to that of lysergic acid diethylamide (LSD). Animal tests have shown that LSH produces [[stimulation|stimulant]] effects similar to LSD while LSA produces [[sedation|sedative]] effects. LSH is also said to produce less vasoconstriction than LSA, though this has yet to be scientifically confirmed.

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.

{| class="wikitable"

|-

! Lysergic Acid Amide !! Acetaldehyde !! Lysergic Acid Hydroxyethylamide

|- align="center"

| [[File:~~LSA2~~.~~png~~]] || [[File:Acetaldehyde.~~png~~]]|| [[File:~~LSH2~~.~~png~~]]

| [[File:LSA.svg|150px]] || [[File:Acetaldehyde.svg]]|| [[File:LSH.svg|150px]]

|}

{{#set:Featured=true

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}}

===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.

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 and nobody has ever been able to show any formation of LSH with an lab method. This is consistent with the very very low reactivity of amides like LSA.

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.

Peppermint essential oil or fresh peppermint leaves have been used during extraction attempt 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, so if any adducts formed, they would not be LSH. Due to the low boiling point of acetaldehyde, an 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 significantly shorter duration.

'''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.{{citation needed}}

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.

{| class="wikitable"

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! Lysergic Acid Amide !! Cinnamaldehyde !! Cinnamylidene-bislysergamide

|- align="center"

| [[File:~~Lsa~~.~~png~~]] || [[File:Cinnamaldehyde.~~gif~~]]|| [[File:Cinnamylidene-~~Bislysergamide~~.~~png~~]]

| [[File:LSA.svg]] || [[File:Cinnamaldehyde.svg]]|| [[File:Cinnamylidene-bislysergamide.svg]]

|}

==External links==

*[https://en.wikipedia.org/wiki/Lysergic_acid_hydroxyethylamide Lysergic acid hydroxyethylamide (Wikipedia)]

*[https://isomerdesign.com/PiHKAL/explore.php?id=5364 LSH (Isomer Design)]

=References=

@@ Line 1: / Line 1: @@
-It has been documented that '''Lysergic Acid Amide''' (LSA) is capable of forming adducts with various aldehydes. <ref>http://www.nature.com/nature/journal/v192/n4802/abs/192552a0.html</ref> 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. <ref>http://herbpedia.wikidot.com/</ref>
+{{SubstanceBox/LSA}}
+It has been documented that [[lysergic acid amide]] ('''LSA''') is capable of forming adducts with various aldehydes.<ref>{{cite journal | vauthors=((Arcamone, F.)), ((Chain, E. B.)), ((Ferretti, A.)), ((Pennella, P.)) | journal=Nature | title=Formation of 2,3-Dihydroxybenzoic Acid in Fermentation Liquors during the Submerged Culture Production of Lysergic Acid α-Hydroxyethylamide by Claviceps paspali Stevens and Hall | volume=192 | issue=4802 | pages=552–553 | date= November 1961 | url=https://www.nature.com/articles/192552a0 | issn=1476-4687 | doi=10.1038/192552a0}}</ref>
+==Lysergic acid hydroxyethylamide (LSH)==
+Lysergic acid hydroxyethylamide (LSH) is one example of such adducts, which is produced from LSA and acetaldehyde.
-==Lysergic Acid Hydroxyethylamide==
+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.
-'''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 vaguely similar to that of lysergic acid diethylamide (LSD). Animal tests have shown that LSH produces [[stimulation|stimulant]] effects similar to LSD while LSA produces [[sedation|sedative]] effects. LSH is also said to produce less vasoconstriction than LSA, though this has yet to be scientifically confirmed.
-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.
 {| class="wikitable"
 |-
 ! Lysergic Acid Amide !! Acetaldehyde !! Lysergic Acid Hydroxyethylamide
 |- align="center"
-| [[File:LSA2.png]] || [[File:Acetaldehyde.png]]|| [[File:LSH2.png]]
+| [[File:LSA.svg|150px]] || [[File:Acetaldehyde.svg]]|| [[File:LSH.svg|150px]]
 |}
 {{#set:Featured=true
@@ Line 21: / Line 21: @@
 }}
 ===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.
+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 and nobody has ever been able to show any formation of LSH with an lab method. This is consistent with the very very low reactivity of amides like LSA.
-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.
+Peppermint essential oil or fresh peppermint leaves have been used during extraction attempt 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, so if any adducts formed, they would not be LSH. Due to the low boiling point of acetaldehyde, an 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 significantly shorter duration.
-'''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.{{citation needed}}
-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.
 {| class="wikitable"
@@ Line 35: / Line 34: @@
 ! Lysergic Acid Amide !! Cinnamaldehyde !! Cinnamylidene-bislysergamide
 |- align="center"
-| [[File:Lsa.png]] || [[File:Cinnamaldehyde.gif]]|| [[File:Cinnamylidene-Bislysergamide.png]]
+| [[File:LSA.svg]] || [[File:Cinnamaldehyde.svg]]|| [[File:Cinnamylidene-bislysergamide.svg]]
 |}
+==External links==
+*[https://en.wikipedia.org/wiki/Lysergic_acid_hydroxyethylamide Lysergic acid hydroxyethylamide (Wikipedia)]
+*[https://isomerdesign.com/PiHKAL/explore.php?id=5364 LSH (Isomer Design)]
 =References=
 <references />