Lysergic acid 2-butyl amide (LSB), also known as 2-butyllysergamide, is an analogue of

LSD Lysergic acid diethylamide, commonly known as LSD (from German ; often referred to as acid or lucy), is a semisynthetic, hallucinogenic compound derived from ergot, known for its powerful psychological effects and serotonergic activity. I ...

originally developed by Richard Pioch at

Eli Lilly Eli Lilly (July 8, 1838 – June 6, 1898) was a Union Army officer, pharmacist, chemist, and businessman who founded Eli Lilly and Company. Lilly enlisted in the Union Army during the American Civil War and recruited a company of men to ...

in the 1950s, but mostly publicised through research conducted by the team led by David E. Nichols at

Purdue University Purdue University is a Public university#United States, public Land-grant university, land-grant research university in West Lafayette, Indiana, United States, and the flagship campus of the Purdue University system. The university was founded ...

. It is a

structural isomer In chemistry, a structural isomer (or constitutional isomer in the IUPAC nomenclature) of a compound is a compound that contains the same number and type of atoms, but with a different connectivity (i.e. arrangement of bonds) between them. The ...

of LSD, with the two ethyl groups on the amide nitrogen having been replaced by a single sec-butyl group, joined at the 2-position.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 In biochemistry and pharmacology, a ligand is a substance that forms a complex with a biomolecule to serve a biological purpose. The etymology stems from Latin ''ligare'', which means 'to bind'. In protein-ligand binding, the ligand is usuall ...

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 Efficacy is the ability to perform a task to a satisfactory or expected degree. The word comes from the same roots as '' effectiveness'', and it has often been used synonymously, although in pharmacology a distinction is now often made betwee ...

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 Receptor may refer to: * Sensory receptor, in physiology, any neurite structure that, on receiving environmental stimuli, produces an informative nerve impulse *Receptor (biochemistry), in biochemistry, a protein molecule that receives and respond ...

through which LSD exerts most of its pharmacological effects,David E. Nichols. LSD and Its Lysergamide Cousins. ''The Heffter Review of Psychedelic Research''. 2001;2:80-87. with the stereoselective activity of these unsymmetric monoalkyl lysergamides foreshadowing the subsequent development of compounds such as

lysergic acid 2,4-dimethylazetidide Lysergic acid 2,4-dimethylazetidide, also known as LSZ, LA-SS-Az, or LA-Azetidide, is an analog of LSD developed by the team led by David E. Nichols at Purdue University. It was developed as a rigid analog of LSD with the diethylamide group co ...

(LSZ).

References

{{Ergolines Designer drugs Drugs developed by Eli Lilly and Company Psychedelic lysergamides

See also

References