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(Redirected from Isopropyllysergamide)
IPLA
Clinical data
Other namesIPLA; N-Isopropyllysergamide; Lysergic acid isopropylamide; LAiP
Drug classSerotonin receptor modulator; Possible serotonergic psychedelic or hallucinogen
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
PubChem CID
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 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

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References

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  1. ^ a b c d Nichols, David E. (2017). "Chemistry and Structure–Activity Relationships of Psychedelics". Behavioral Neurobiology of Psychedelic Drugs. Vol. 36. Berlin, Heidelberg: Springer Berlin Heidelberg. pp. 1–43. doi:10.1007/7854_2017_475. ISBN 978-3-662-55878-2.
  2. ^ a b c d Nichols 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. ^ a b c d e Pfaff 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. ^ a b c d e Huang, Xuemei; Marona-Lewicka, Danuta; Pfaff, Robert C.; Nichols, David E. (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. Retrieved 27 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 from the original on 2025-06-30.
  7. ^ Rothlin E (March 1957). "Lysergic acid diethylamide and related substances". Ann N Y Acad Sci. 66 (3): 668–676. doi:10.1111/j.1749-6632.1957.tb40756.x. PMID 13425249. Archived from the 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. doi:10.1002/hlca.19550380207. ISSN 0018-019X.
  9. ^ Hofmann A (June 1959). "Psychotomimetic Drugs: Chemical and Pharmacological Aspects" (PDF). Acta Physiol Pharmacol Neerl. 8: 240–258. PMID 13852489.
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