Nor-LSD

Nor-LSD
Clinical data
Other names	norLSD; N,N-Diethyl-6-norlysergamide; N-Desmethyllysergic acid diethylamide; N-Desmethyl-LSD; Norlysergic acid diethylamide; N-Demethyl-LSD; 9,10-Didehydro-N,N-diethylergoline-8β-carboxamide; H-LAD; NORLAD; NOR-LAD; 6-Nor-LSD
Drug class	Serotonin receptor modulator; Serotonergic psychedelic; Hallucinogen
ATC code	None;
Identifiers
	IUPAC name (6aR,9R)-N,N-diethyl-4,6,6a,7,8,9-hexahydroindolo[4,3-fg]quinoline-9-carboxamide;
CAS Number	35779-43-2;
PubChem CID	169713;
ChemSpider	148419;
ChEMBL	ChEMBL21343;
CompTox Dashboard (EPA)	DTXSID80189307 ;
ECHA InfoCard	100.164.623
Chemical and physical data
Formula	C19H23N3O
Molar mass	309.413 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCN(CC)C(=O)[C@H]1CN[C@@H]2CC3=CNC4=CC=CC(=C34)C2=C1;
	InChI InChI=1S/C19H23N3O/c1-3-22(4-2)19(23)13-8-15-14-6-5-7-16-18(14)12(10-20-16)9-17(15)21-11-13/h5-8,10,13,17,20-21H,3-4,9,11H2,1-2H3/t13-,17-/m1/s1; Key:SUXLVXOMPKZBOV-CXAGYDPISA-N;

Nor-LSD, or norLSD, also known as N,N-diethyl-6-norlysergamide or as N-desmethyllysergic acid diethylamide (N-desmethyl-LSD), is a serotonin receptor modulator and putative psychedelic of the lysergamide family related to lysergic acid diethylamide (LSD).^[1]^[2]^[3]^[4] It is the analogue of LSD in which the methyl group at the 6 position of the ergoline ring system has been removed.^[2]^[3]

^ Nichols DE, Oberlender R, McKenna DJ (1991). "Stereochemical Aspects of Hallucinogenesis". In Watson RR (ed.). Biochemistry and Physiology of Substance Abuse. Vol. 3. Boca Raton, Fla.: CRC Press. pp. 1–39. ISBN 978-0-8493-4463-3. OCLC 26748320. TABLE 1 Effects of N-(6)-Alkyl Subtituents on LSD-Like Behavior and Serotonin Receptor Affinity in Rats [...]
^ ^a ^b Cite error: The named reference Hoffman_1987 was invoked but never defined (see the help page).
^ ^a ^b Hoffman AJ, Nichols DE (September 1985). "Synthesis and LSD-like discriminative stimulus properties in a series of N(6)-alkyl norlysergic acid N,N-diethylamide derivatives". Journal of Medicinal Chemistry. 28 (9): 1252–1255. doi:10.1021/jm00147a022. PMID 4032428.
^ Pfaff RC, Huang X, Marona-Lewicka D, Oberlender R, Nichols DE (1994). "Lysergamides revisited". NIDA Research Monograph. 146: 52–73. PMID 8742794. TABLE 1. Drug discrimination ED50 values and receptor affinities of N(6)-alkyl-nor-LSD derivatives [...]

[NicholsOberlenderMcKenna1991-1] Nichols DE, Oberlender R, McKenna DJ (1991). "Stereochemical Aspects of Hallucinogenesis". In Watson RR (ed.). Biochemistry and Physiology of Substance Abuse. Vol. 3. Boca Raton, Fla.: CRC Press. pp. 1–39. ISBN 978-0-8493-4463-3. OCLC 26748320. TABLE 1 Effects of N-(6)-Alkyl Subtituents on LSD-Like Behavior and Serotonin Receptor Affinity in Rats [...]

[Hoffman_1987-2] Cite error: The named reference Hoffman_1987 was invoked but never defined (see the help page).

[Hoffman_1985-3] Hoffman AJ, Nichols DE (September 1985). "Synthesis and LSD-like discriminative stimulus properties in a series of N(6)-alkyl norlysergic acid N,N-diethylamide derivatives". Journal of Medicinal Chemistry. 28 (9): 1252–1255. doi:10.1021/jm00147a022. PMID 4032428.

[Pfaff_1994-4] Pfaff RC, Huang X, Marona-Lewicka D, Oberlender R, Nichols DE (1994). "Lysergamides revisited". NIDA Research Monograph. 146: 52–73. PMID 8742794. TABLE 1. Drug discrimination ED50 values and receptor affinities of N(6)-alkyl-nor-LSD derivatives [...]

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