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- Q6710119 subject Q7930599.
- Q6710119 subject Q8375173.
- Q6710119 subject Q9010304.
- Q6710119 abstract "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 It is a structural isomer of LSD, with the two ethyl groups on the amide nitrogen having been replaced by a single butyl group, joined at the 2-position.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-HT1A and 5-HT2A 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-HT1A and 5-HT2A mediated components, and while lysergic acid 2-butyl amide is more potent than LSD as a 5-HT1A agonist, it is slightly less potent as a 5-HT2A 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-HT2A 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).".
- Q6710119 casNumber "137765-82-3".
- Q6710119 casSupplemental "(R,R) isomer, freebase".
- Q6710119 casSupplemental "137765-83-4 (R,R) isomer, maleate salt".
- Q6710119 iupacName "(8β)-6-Methyl-N-[(1R)-1-methylpropyl]-9,10-didehydroergoline-8-carboxamide".
- Q6710119 pubchem "15119692".
- Q6710119 thumbnail SBULSD.svg?width=300.
- Q6710119 wikiPageWikiLink Q14891424.
- Q6710119 wikiPageWikiLink Q15409386.
- Q6710119 wikiPageWikiLink Q17145461.
- Q6710119 wikiPageWikiLink Q208467.
- Q6710119 wikiPageWikiLink Q217741.
- Q6710119 wikiPageWikiLink Q23118.
- Q6710119 wikiPageWikiLink Q238509.
- Q6710119 wikiPageWikiLink Q3017818.
- Q6710119 wikiPageWikiLink Q632240.
- Q6710119 wikiPageWikiLink Q6710118.
- Q6710119 wikiPageWikiLink Q6710121.
- Q6710119 wikiPageWikiLink Q7361732.
- Q6710119 wikiPageWikiLink Q7930599.
- Q6710119 wikiPageWikiLink Q8375173.
- Q6710119 wikiPageWikiLink Q898254.
- Q6710119 wikiPageWikiLink Q9010304.
- Q6710119 casNumber "137765".
- Q6710119 casSupplemental "137765".
- Q6710119 casSupplemental "isomer, freebase".
- Q6710119 iupacName "-6".
- Q6710119 pubchem "15119692".
- Q6710119 type ChemicalSubstance.
- Q6710119 type Drug.
- Q6710119 type ChemicalObject.
- Q6710119 type Thing.
- Q6710119 type Q8386.
- Q6710119 comment "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 butyl group, joined at the 2-position.".
- Q6710119 label "Lysergic acid 2-butyl amide".
- Q6710119 depiction SBULSD.svg.