{{cs1 config|name-list-style=vanc|display-authors=6}} {{Lowercase title}} {{Infobox drug | drug_name = iPLA | image = IPLA structure.svg | image_class = skin-invert-image | width = 175px | image2 = iPLA 3D.png | image_class2 = bg-transparent | width2 = 225px
<!-- Clinical data --> | pronounce = | tradename = | Drugs.com = | MedlinePlus = | licence_CA = | licence_EU = | DailyMedID = | licence_US = | pregnancy_AU = | pregnancy_category = | dependency_liability = | addiction_liability = | routes_of_administration = | class = Serotonin receptor modulator; Possible serotonergic psychedelic or hallucinogen | ATC_prefix = None | ATC_suffix =
<!-- Legal status --> | legal_status =
<!-- Pharmacokinetic data --> | bioavailability = | protein_bound = | metabolism = | metabolites = | onset = | elimination_half-life = | duration_of_action = | excretion =
<!-- Identifiers --> | CAS_number = | CAS_supplemental = | PubChem = 5282400 | PubChemSubstance = | IUPHAR_ligand = | DrugBank = | ChemSpiderID = 4445555 | UNII = | KEGG = | ChEBI = | ChEMBL = | NIAID_ChemDB = | PDB_ligand = | synonyms = IPLA; ''N''-Isopropyllysergamide; Lysergic acid isopropylamide; LAiP
<!-- Chemical data --> | IUPAC_name = (6a''R'',9''R'')-7-methyl-''N''-propan-2-yl-6,6a,8,9-tetrahydro-4''H''-indolo[4,3-fg]quinoline-9-carboxamide | C=19 | H=23 | N=3 | O=1 | SMILES = CC(C)NC(=O)[C@H]1CN([C@@H]2CC3=CNC4=CC=CC(=C34)C2=C1)C | StdInChI = 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 | StdInChIKey = 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).<ref name="Nichols_2017">{{cite book | vauthors = Nichols DE | chapter = Chemistry and Structure–Activity Relationships of Psychedelics | title = Behavioral Neurobiology of Psychedelic Drugs | series = Current Topics in Behavioral Neurosciences | volume = 36 | pages = 1–43 | date = 2017 | pmid = 28401524 | doi = 10.1007/7854_2017_475 | publisher = Springer Berlin Heidelberg | publication-place = Berlin, Heidelberg | isbn = 978-3-662-55878-2 }}</ref><ref name="Nichols_2001">{{cite journal | vauthors = Nichols DE | title = LSD and Its Lysergamide Cousins | journal = The Heffter Review of Psychedelic Research | volume = 2 | pages = 80–87 | date = 2001 | publisher = Heffter Research Institute | issn = 1534-9640 | url = https://www.heffter.org/wp-content/uploads/2020/04/chap6.pdf | quote = 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. [...] }}</ref><ref name="Pfaff_1994">{{cite journal | vauthors = Pfaff RC, Huang X, Marona-Lewicka D, Oberlender R, Nichols DE | title = Lysergamides revisited | journal = NIDA Research Monograph | volume = 146 | pages = 52–73 | date = 1994 | pmid = 8742794 | url = https://archives.nida.nih.gov/sites/default/files/monograph146.pdf#page=57 | quote = 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) [...] | archive-date = 2023-08-05 | access-date = 2025-07-27 | archive-url = https://web.archive.org/web/20230805004551/https://archives.nida.nih.gov/sites/default/files/monograph146.pdf#page=57 | url-status = dead }}</ref><ref name="Huang_1994">{{cite journal | vauthors = Huang X, Marona-Lewicka D, Pfaff RC, Nichols DE | title = Drug discrimination and receptor binding studies of N-isopropyl lysergamide derivatives | journal = Pharmacology Biochemistry and Behavior | volume = 47 | issue = 3 | pages = 667–673 | date = 1994 | pmid = 8208787 | doi = 10.1016/0091-3057(94)90172-4 | url = https://linkinghub.elsevier.com/retrieve/pii/0091305794901724 | access-date = 27 July 2025 | url-access = subscription }}</ref> It is the analogue of LSD in which the ''N'',''N''-diethyl groups have been replaced with an ''N''-isopropyl group.<ref name="Nichols_2017" /><ref name="Nichols_2001" /><ref name="Pfaff_1994" /><ref name="Huang_1994" />
In an early study, iPLA showed about 22.2% of the antiserotonergic activity of LSD in the isolated rat uterus.<ref name="Oberlender_1989">{{cite web | vauthors = Oberlender RA | title = Stereoselective aspects of hallucinogenic drug action and drug discrimination studies of entactogens | date = May 1989 | publisher = Purdue University | website = Purdue e-Pubs | url = https://bitnest.netfirms.com/external/Theses/Oberlender1989#page=49 | quote = Table 2. Relative potency values for lysergic acid amides. [...] }}</ref><ref name="Cerletti_1958">{{cite journal | vauthors = Cerletti A, Doepfner W | title = Comparative study on the serotonin antagonism of amide derivatives of lysergic acid and of ergot alkaloids | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 122 | issue = 1 | pages = 124–136 | date = January 1958 | pmid = 13502837 | doi = 10.1016/S0022-3565(25)11933-2 | url = https://bibliography.maps.org/resources/download/19096 | archive-url = https://web.archive.org/web/20250630233202/https://bibliography.maps.org/resources/download/19096 | archive-date = 2025-06-30 }}</ref><ref name="Rothlin_1957">{{cite journal | vauthors = Rothlin E | title = Lysergic acid diethylamide and related substances | journal = Annals of the New York Academy of Sciences | volume = 66 | issue = 3 | pages = 668–676 | date = March 1957 | pmid = 13425249 | doi = 10.1111/j.1749-6632.1957.tb40756.x | bibcode = 1957NYASA..66..668R | url = https://bibliography.maps.org/resources/download/17981 | archive-url = https://web.archive.org/web/20250712025029/https://bibliography.maps.org/resources/download/17981 | archive-date = 12 July 2025 | quote = 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. }}</ref> The drug is known to bind with high affinity (K<sub>i</sub>) to the serotonin 5-HT<sub>2A</sub>, 5-HT<sub>2C</sub>, and 5-HT<sub>1A</sub> receptors.<ref name="Nichols_2017" /><ref name="Nichols_2001" /><ref name="Pfaff_1994" /><ref name="Huang_1994" /> It is a potent agonist of the serotonin 5-HT<sub>2A</sub> receptor.<ref name="Nichols_2017" /> 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.<ref name="Nichols_2001" /><ref name="Pfaff_1994" /><ref name="Huang_1994" />
iPLA was first described in the scientific literature by Albert Hofmann and colleagues by 1955.<ref name="Stoll_1955">{{cite journal | vauthors = Stoll A, Hofmann A | title = Amide der stereoisomeren Lysergsäuren und Dihydro-lysergsäuren. 38. Mitteilung über Mutterkornalkaloide | journal = Helvetica Chimica Acta | volume = 38 | issue = 2 | pages = 421–433 | date = 1955 | doi = 10.1002/hlca.19550380207 | bibcode = 1955HChAc..38..421S | trans-title = Amides of stereoisomeric lysergic and dihydrolysergic acids. 38. Ergot alkaloids | issn = 0018-019X }}</ref><ref name="Hofmann_1959">{{cite journal | vauthors = Hofmann A | title = Psychotomimetic Drugs: Chemical and Pharmacological Aspects | journal = Acta Physiologica et Pharmacologica Neerlandica | volume = 8 | pages = 240–258 | date = June 1959 | pmid = 13852489 | url = https://www.samorini.it/doc1/alt_aut/ek/hofmann-psychotomimetic-drugs.pdf }}</ref> Subsequently, it was studied in more detail by David E. Nichols and colleagues in the 1990s.<ref name="Pfaff_1994" /><ref name="Huang_1994" /> It is not a controlled substance in Canada as of 2025.<ref name="CDSA">{{cite web | title=Controlled Drugs and Substances Act | website=Department of Justice Canada | url=https://laws-lois.justice.gc.ca/eng/acts/c-38.8/FullText.html | access-date=19 January 2026}}</ref>
==See also== * Substituted lysergamide * Lysergic acid propylamide * MiPLA (lysergic acid methylisopropylamide) * EiPLA (lysergic acid ethylisopropylamide) * DiPLA (lysergic acid diisopropylamide) * Lysergic acid ''tert''-butylamide (LAtB)
==References== {{Reflist}}
==External links== * [https://isomerdesign.com/pihkal/explore/5567 iPLA - Isomer Design]
{{Psychedelics}} {{Serotonin receptor modulators}} {{Ergolines}}
Category:5-HT2A agonists Category:Carboxamides Category:David E. Nichols Category:Diethylamino compounds Category:Isopropyl compounds Category:Psychedelic lysergamides Category:Serotonin receptor modulators