Lysergic acid cyclobutylamide

Lysergic acid cyclobutylamide
Clinical data
Other names	LAcB; C4AL; N-Cyclobutyllysergamide; N-Cyclobutyl-lysergamide; NCB-LA
Identifiers
	IUPAC name (6aR,9R)-N-cyclobutyl-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide;
PubChem CID	129844515;
Chemical and physical data
Formula	C20H23N3O
Molar mass	321.424 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CN1C[C@@H](C=C2[C@H]1CC3=CNC4=CC=CC2=C34)C(=O)NC5CCC5;
	InChI InChI=1S/C20H23N3O/c1-23-11-13(20(24)22-14-4-2-5-14)8-16-15-6-3-7-17-19(15)12(10-21-17)9-18(16)23/h3,6-8,10,13-14,18,21H,2,4-5,9,11H2,1H3,(H,22,24)/t13-,18-/m1/s1; Key:FFKNJJLUPIWGFL-FZKQIMNGSA-N;

Lysergic acid cyclobutylamide (LAcB or C₄AL), also known as N-cyclobutyllysergamide (NCB-LA), is a semisynthetic lysergamide that is synthesized from naturally occurring ergot alkaloids found in Claviceps purpurea.^[1]^[2] It has oxytocic effects on the isolated rat uterus similarly to other lysergamides, shows antiserotonergic effects in the isolated rat intestine similarly to lysergic acid diethylamide (LSD), has mydriatic effects similarly to LSD when administered to mice, and produces other biological effects.^[1]^[3] Despite being more effective than LSD in various bioassays however, LAcB did not have psychedelic effects in humans.^[1] The drug was first described in the scientific literature by 1958.^[3]

Other namesLAcB; C₄AL; N-Cyclobutyllysergamide; N-Cyclobutyl-lysergamide; NCB-LA

FormulaC₂₀H₂₃N₃O

Molar mass321.424 g·mol⁻¹

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Clinical data


Other names	LAcB; C₄AL; N-Cyclobutyllysergamide; N-Cyclobutyl-lysergamide; NCB-LA
Identifiers
IUPAC name (6aR,9R)-N-cyclobutyl-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide
PubChem CID	129844515
Chemical and physical data
Formula	C₂₀H₂₃N₃O
Molar mass	321.424 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CN1C[C@@H](C=C2[C@H]1CC3=CNC4=CC=CC2=C34)C(=O)NC5CCC5
InChI InChI=1S/C20H23N3O/c1-23-11-13(20(24)22-14-4-2-5-14)8-16-15-6-3-7-17-19(15)12(10-21-17)9-18(16)23/h3,6-8,10,13-14,18,21H,2,4-5,9,11H2,1H3,(H,22,24)/t13-,18-/m1/s1 Key:FFKNJJLUPIWGFL-FZKQIMNGSA-N