Lysergic acid propylamide

Lysergic acid propylamide
Clinical data
Other names	LAP; Lysergic acid monopropylamide; NP-LA; N-Propyllysergamide; N-Propylergine; N-Propyl-LSA; 6-Methyl-N-propyl-9,10-didehydroergoline-8β-carboxamide
Drug class	Serotonin receptor modulator
ATC code	None;
Identifiers
	IUPAC name (6aR,9R)-7-methyl-N-propyl-4,6,6a,7,8,9-hexahydroindolo[4,3-fg]quinoline-9-carboxamide;
PubChem CID	86217901;
Chemical and physical data
Formula	C19H23N3O
Molar mass	309.413 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCCNC(=O)[C@H]1CN(C)[C@H]2C(=C1)c1cccc3c1c(C2)c[nH]3;
	InChI InChI=1S/C19H23N3O/c1-3-7-20-19(23)13-8-15-14-5-4-6-16-18(14)12(10-21-16)9-17(15)22(2)11-13/h4-6,8,10,13,17,21H,3,7,9,11H2,1-2H3,(H,20,23)/t13-,17-/m1/s1; Key:VHECNRXVHIGFCO-CXAGYDPISA-N;

Lysergic acid propylamide (LAP), also known as N-propyllysergamide (NP-LA), is a serotonin receptor modulator of the lysergamide family related to lysergic acid diethylamide (LSD). It is the analogue of LSD in which the N,N-diethyl groups have been replaced with an N-propyl group and is also the N-propyl derivative of ergine (lysergic acid amide; LSA).