IPLA

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]

Other namesIPLA; N-Isopropyllysergamide; Lysergic acid isopropylamide; LAiP

Drug classSerotonin receptor modulator; Possible serotonergic psychedelic or hallucinogen

ATC code

• None

PubChem CID

• 5282400

Quick facts Clinical data, Other names ...

iPLA

Clinical data
Other names	IPLA; N-Isopropyllysergamide; Lysergic acid isopropylamide; LAiP
Drug class	Serotonin receptor modulator; Possible serotonergic psychedelic or hallucinogen
ATC code	None
Identifiers
IUPAC name (6aR,9R)-7-methyl-N-propan-2-yl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide
PubChem CID	5282400
ChemSpider	4445555
Chemical and physical data
Formula	C19H23N3O
Molar mass	309.413 g·mol−1
3D model (JSmol)	Interactive image
SMILES CC(C)NC(=O)[C@H]1CN([C@@H]2CC3=CNC4=CC=CC(=C34)C2=C1)C
InChI 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

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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 (K_i) to the serotonin 5-HT_2A, 5-HT_2C, and 5-HT_1A receptors.^[1][2][3][4] It is a potent agonist of the serotonin 5-HT_2A 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] It is not a controlled substance in Canada as of 2025.^[10]