Chemistry:Lysergic acid 2-butyl amide

Short description: Chemical compound

Lysergic acid 2-butyl amide

Clinical data
Other names	(6aR,9R)- N- (R)- 2-butyl- 7-methyl- 4,6,6a,7,8,9- hexahydroindolo- [4,3-fg] quinoline- 9-carboxamide
Legal status
Legal status	DE: NpSG (Industrial and scientific use only) UK: Under Psychoactive Substances Act Illegal in France
Identifiers
IUPAC name (8β)-6-Methyl-N-[(1R)-1-methylpropyl]-9,10-didehydroergoline-8-carboxamide
CAS Number	137765-82-3 Y (R,R) isomer, freebase 137765-83-4 (R,R) isomer, maleate salt
PubChem CID	15119692
ChemSpider	23157987 N
UNII	RK6W726WK8
Chemical and physical data
Formula	C20H25N3O
Molar mass	323.440 g·mol−1
3D model (JSmol)	Interactive image
SMILES CN1C[C@@H](C(N[C@H](C)CC)=O)C=C2C1CC3=CNC4=C3C2=CC=C4
InChI InChI=1S/C20H25N3O/c1-4-12(2)22-20(24)14-8-16-15-6-5-7-17-19(15)13(10-21-17)9-18(16)23(3)11-14/h5-8,10,12,14,18,21H,4,9,11H2,1-3H3,(H,22,24)/t12-,14-,18-/m1/s1 N Key:NYFSQPDQLFFBRA-RVZJWNSFSA-N N
NY (what is this?)  (verify)

Lysergic acid 2-butyl amide (2-Butyllysergamide, LSB) is an analogue of LSD originally developed by Richard Pioch at Eli Lilly in the 1950s, but mostly publicised through research conducted by the team led by David E. Nichols at Purdue University. It is a structural isomer of LSD, with the two ethyl groups on the amide nitrogen having been replaced by a single sec-butyl group, joined at the 2-position. It is one of the few lysergamide derivatives to exceed the potency of LSD in animal drug discrimination assays, with the (R) isomer having an ED₅₀ of 33nmol/kg for producing drug-appropriate responding, vs 48nmol/kg for LSD itself. The corresponding (R)-2-pentyl analogue has higher binding affinity for the 5-HT_1A and 5-HT_2A receptors, but is less potent in producing drug-appropriate responding, suggesting that the butyl compound has a higher efficacy at the receptor target. The drug discrimination assay for LSD in rats involves both 5-HT_1A and 5-HT_2A mediated components, and while lysergic acid 2-butyl amide is more potent than LSD as a 5-HT_1A agonist, it is slightly less potent as a 5-HT_2A agonist, and so would probably be slightly less potent than LSD as a hallucinogen in humans. The main use for this drug has been in studies of the binding site at the 5-HT_2A receptor through which LSD exerts most of its pharmacological effects, with the stereoselective activity of these unsymmetric monoalkyl lysergamides foreshadowing the subsequent development of compounds such as lysergic acid 2,4-dimethylazetidide (LSZ).

See also

• Lysergic acid 3-pentyl amide
• Methylisopropyllysergamide