IPLA

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;

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]

Quick facts Clinical data, Other names ...

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]

See also