LPD-824

LPD-824
Clinical data
Other names	LPD-824; LPD824; N-Pyrrolidyllysergamide; Lysergic acid pyrrolidide; LA-Pyr; LSD-Pyr
Drug class	Serotonin receptor modulator; Serotonin 5-HT2A receptor agonist; Serotonergic psychedelic; Hallucinogen
Identifiers
	IUPAC name (8β)-6-Methyl-8-(pyrrolidin-1-ylcarbonyl)-9,10-didehydroergoline;
CAS Number	2385-87-7 ;
PubChem CID	200628;
ChemSpider	173678 ;
ChEMBL	ChEMBL302524 ;
CompTox Dashboard (EPA)	DTXSID20946653 ;
Chemical and physical data
Formula	C20H23N3O
Molar mass	321.424 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C(N1CCCC1)[C@@H]4C=C3c5cccc2c5c(c[nH]2)C[C@H]3N(C4)C;
	InChI InChI=1S/C20H23N3O/c1-22-12-14(20(24)23-7-2-3-8-23)9-16-15-5-4-6-17-19(15)13(11-21-17)10-18(16)22/h4-6,9,11,14,18,21H,2-3,7-8,10,12H2,1H3/t14-,18-/m1/s1 ; Key:SETDYMMXQQXCRP-RDTXWAMCSA-N ;
	(verify)

N-Pyrrolidyllysergamide (LPD-824), also known as lysergic acid pyrrolidide (LA-Pyr), is a psychedelic drug 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-diethylamide moiety has been cyclized into an N,N-pyrrolidide ring.^[1]^[2]

^ ^a ^b "Erowid Online Books : "TIHKAL" - #26 LSD-25".
^ ^a ^b Parrish JC (30 October 2007). "Toward a molecular understanding of hallucinogen action". Purdue e-Pubs. Figure A.1 The series of amide substituted LSD derivatives used in this study. [...] LA-Pyr [...] Table A.1 Results of competition binding experiments and IP accumulation assays for the series of ergolines illustrated in Figure A.1. [...] LA-Pyr [...]
^ Nichols DE (2012). "Structure–activity relationships of serotonin 5-HT2A agonists". Wiley Interdisciplinary Reviews: Membrane Transport and Signaling. 1 (5): 559–579. doi:10.1002/wmts.42. ISSN 2190-460X. TABLE 1 5-HT2A Receptor Affinity and Functional Effects of Selected Lysergamides1 [...] 1 Data from Parrish.42. [...] 42. Parrish JC. Toward a molecular understanding of hallucinogen action. 2006. Purdue University.
^ Dunn WJ, Bederka JP (February 1974). "The role of hydrophobicity in the antiserotonin activity of LSD analogs". Research Communications in Chemical Pathology and Pharmacology. 7 (2): 275–285. PMID 4818374.