Chemistry:IPLA

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iPLA, also known as N-isopropyllysergamide, as well as lysergic acid isopropylamide (LAiP), is a serotonin receptor modulator and possible serotonergic psychedelic of the lysergamide family related to lysergic acid diethylamide (LSD).[1][2][3][4] It is the analogue of LSD in which the N,N-diethyl groups have been replaced with an N-isopropyl group.[1][2][3][4]

In an early study, iPLA showed about 22.2% of the antiserotonergic activity of LSD in the isolated rat uterus.[5][6][7] The drug is known to bind with high affinity (Ki) to the serotonin 5-HT2A, 5-HT2C, and 5-HT1A receptors.[1][2][3][4] It is a potent agonist of the serotonin 5-HT2A receptor.[1] iPLA fully substituted for LSD in rodent drug discrimination tests with a potency of about half that of LSD itself, findings which suggest that iPLA may have psychedelic effects in humans.[2][3][4]

iPLA was first described in the scientific literature by Albert Hofmann and colleagues by 1955.[8][9] Subsequently, it was studied in more detail by David E. Nichols and colleagues in the 1990s.[3][4]

See also

References

  1. ↑ 1.0 1.1 1.2 1.3 "Chemistry and Structure–Activity Relationships of Psychedelics". Behavioral Neurobiology of Psychedelic Drugs. Current Topics in Behavioral Neurosciences. 36. Berlin, Heidelberg: Springer Berlin Heidelberg. 2017. pp. 1–43. doi:10.1007/7854_2017_475. ISBN 978-3-662-55878-2. 
  2. ↑ 2.0 2.1 2.2 2.3 "LSD and Its Lysergamide Cousins". The Heffter Review of Psychedelic Research (Heffter Research Institute) 2: 80–87. 2001. ISSN 1534-9640. https://www.heffter.org/wp-content/uploads/2020/04/chap6.pdf. "Table 3. Affinity for 5-HT2A and 5-HT1A receptors and potency in the rat two-lever drug discrimination assay for selected lysergic acid amides. [...]". 
  3. ↑ 3.0 3.1 3.2 3.3 3.4 "Lysergamides revisited". NIDA Research Monograph 146: 52–73. 1994. PMID 8742794. https://archives.nida.nih.gov/sites/default/files/monograph146.pdf#page=57. "The series of isopropyl amides has recently been completed with the synthesis of the N-isopropyl, in addition to the N-methyl-N-isopropyl, N-ethyl-N-isopropyl, and the N,N-diisopropyl, as shown in figure 12. With the exception of the N,N-diisopropylamide, all compounds completely substitute in the DD paradigm in rats trained to discriminate LSD from saline. In table 6, the receptor-binding data for displacement of [3H]-ketanserin from rat cortical homogenate are shown. [...] TABLE 6. Radioligand binding data for N-methyl-N-isopropyl lysergamides: [3H]-ketanserin displacement (unpublished results) [...]". 
  4. ↑ 4.0 4.1 4.2 4.3 4.4 "Drug discrimination and receptor binding studies of N-isopropyl lysergamide derivatives". Pharmacology Biochemistry and Behavior 47 (3): 667–673. 1994. doi:10.1016/0091-3057(94)90172-4. PMID 8208787. https://linkinghub.elsevier.com/retrieve/pii/0091305794901724. Retrieved 27 July 2025. 
  5. ↑ "Stereoselective aspects of hallucinogenic drug action and drug discrimination studies of entactogens". Purdue University. May 1989. https://bitnest.netfirms.com/external/Theses/Oberlender1989#page=49. "Table 2. Relative potency values for lysergic acid amides. [...]" 
  6. ↑ "Comparative study on the serotonin antagonism of amide derivatives of lysergic acid and of ergot alkaloids". The Journal of Pharmacology and Experimental Therapeutics 122 (1): 124–136. January 1958. doi:10.1016/S0022-3565(25)11933-2. PMID 13502837. https://bibliography.maps.org/resources/download/19096. 
  7. ↑ "Lysergic acid diethylamide and related substances". Annals of the New York Academy of Sciences 66 (3): 668–676. March 1957. doi:10.1111/j.1749-6632.1957.tb40756.x. PMID 13425249. Bibcode: 1957NYASA..66..668R. https://bibliography.maps.org/resources/download/17981. "Finally, we have the disubstituted amides of d-lysergic acid: the dimethyl, diethyl. di-isopropyl, and dibutyl amides. They are 3 to 5 times weaker than LSD in their antagonism toward serotonin.". 
  8. ↑ "Amide der stereoisomeren Lysergsäuren und Dihydro-lysergsäuren. 38. Mitteilung über Mutterkornalkaloide". Helvetica Chimica Acta 38 (2): 421–433. 1955. doi:10.1002/hlca.19550380207. ISSN 0018-019X. Bibcode: 1955HChAc..38..421S. 
  9. ↑ "Psychotomimetic Drugs: Chemical and Pharmacological Aspects". Acta Physiologica et Pharmacologica Neerlandica 8: 240–258. June 1959. PMID 13852489. https://www.samorini.it/doc1/alt_aut/ek/hofmann-psychotomimetic-drugs.pdf. 

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