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iPLA

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(Redirected fromIsopropyllysergamide)

Pharmaceutical compound
iPLA
Clinical data
Other namesIPLA;N-Isopropyllysergamide; Lysergic acid isopropylamide; LAiP
Drug classSerotonin receptor modulator; Possibleserotonergic psychedelic orhallucinogen
ATC code
  • None
Identifiers
  • (6aR,9R)-7-methyl-N-propan-2-yl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide
PubChemCID
ChemSpider
Chemical and physical data
FormulaC19H23N3O
Molar mass309.413 g·mol−1
3D model (JSmol)
  • CC(C)NC(=O)[C@H]1CN([C@@H]2CC3=CNC4=CC=CC(=C34)C2=C1)C
  • InChI=1S/C19H23N3O/c1-11(2)21-19(23)13-7-15-14-5-4-6-16-18(14)12(9-20-16)8-17(15)22(3)10-13/h4-7,9,11,13,17,20H,8,10H2,1-3H3,(H,21,23)/t13-,17-/m1/s1
  • Key:XSQDFRPRMRYUHM-CXAGYDPISA-N

iPLA, also known asN-isopropyllysergamide, as well aslysergic acid isopropylamide (LAiP), is aserotonin receptor modulator and possibleserotonergic psychedelic of thelysergamide family related tolysergic acid diethylamide (LSD).[1][2][3][4] It is theanalogue of LSD in which theN,N-diethyl groups have been replaced with anN-isopropyl group.[1][2][3][4]

In an early study, iPLA showed about 22.2% of theantiserotonergic activity of LSD in the isolated ratuterus.[5][6][7] The drug is known to bind with highaffinity (Ki) to theserotonin5-HT2A,5-HT2C, and5-HT1A receptors.[1][2][3][4] It is apotentagonist of the serotonin 5-HT2A receptor.[1] iPLA fully substituted for LSD in rodentdrug discrimination tests with a potency of about half that of LSD itself, findings which suggest that iPLA may havepsychedelic effects in humans.[2][3][4]

iPLA was first described in thescientific literature byAlbert Hofmann and colleagues by 1955.[8][9] Subsequently, it was studied in more detail byDavid E. Nichols and colleagues in the 1990s.[3][4] It is not acontrolled substance inCanada as of 2025.[10]

See also

[edit]

References

[edit]
  1. ^abcdNichols DE (2017). "Chemistry and Structure–Activity Relationships of Psychedelics".Behavioral Neurobiology of Psychedelic Drugs. Current Topics in Behavioral Neurosciences. Vol. 36. Berlin, Heidelberg: Springer Berlin Heidelberg. pp. 1–43.doi:10.1007/7854_2017_475.ISBN 978-3-662-55878-2.PMID 28401524.
  2. ^abcdNichols DE (2001)."LSD and Its Lysergamide Cousins"(PDF).The Heffter Review of Psychedelic Research.2.Heffter Research Institute:80–87.ISSN 1534-9640.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. ^abcdePfaff RC, Huang X, Marona-Lewicka D, Oberlender R, Nichols DE (1994)."Lysergamides revisited"(PDF).NIDA Research Monograph.146:52–73.PMID 8742794.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. ^abcdeHuang X, Marona-Lewicka D, Pfaff RC, Nichols DE (1994)."Drug discrimination and receptor binding studies of N-isopropyl lysergamide derivatives".Pharmacology Biochemistry and Behavior.47 (3):667–673.doi:10.1016/0091-3057(94)90172-4.PMID 8208787. Retrieved27 July 2025.
  5. ^Oberlender RA (May 1989)."Stereoselective aspects of hallucinogenic drug action and drug discrimination studies of entactogens".Purdue e-Pubs. Purdue University.Table 2. Relative potency values for lysergic acid amides. [...]
  6. ^Cerletti A, Doepfner W (January 1958)."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.doi:10.1016/S0022-3565(25)11933-2.PMID 13502837. Archived fromthe original on 2025-06-30.
  7. ^Rothlin E (March 1957)."Lysergic acid diethylamide and related substances".Annals of the New York Academy of Sciences.66 (3):668–676.Bibcode:1957NYASA..66..668R.doi:10.1111/j.1749-6632.1957.tb40756.x.PMID 13425249. Archived fromthe original on 12 July 2025.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. ^Stoll A, Hofmann A (1955). "Amide der stereoisomeren Lysergsäuren und Dihydro-lysergsäuren. 38. Mitteilung über Mutterkornalkaloide" [Amides of stereoisomeric lysergic and dihydrolysergic acids. 38. Ergot alkaloids].Helvetica Chimica Acta.38 (2):421–433.Bibcode:1955HChAc..38..421S.doi:10.1002/hlca.19550380207.ISSN 0018-019X.
  9. ^Hofmann A (June 1959)."Psychotomimetic Drugs: Chemical and Pharmacological Aspects"(PDF).Acta Physiologica et Pharmacologica Neerlandica.8:240–258.PMID 13852489.
  10. ^"Controlled Drugs and Substances Act".Department of Justice Canada. Retrieved19 January 2026.

External links

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