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Lysergic acid 2-butyl amide
Systematic (IUPAC) name
(8β)- 6-methyl- N- [(1R)- 1-methylpropyl]- 9,10- didehydroergoline- 8-carboxamide
Identifiers
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PubChem  ?
Chemical data
Formula C 20H25N3O 
Mol. mass 323.431 g/mol
SMILES eMolecules & PubChem
Synonyms (6aR,9R)- N- (R)- 2-butyl- 7-methyl- 4,6,6a,7,8,9- hexahydroindolo- [4,3-fg] quinoline- 9-carboxamide

Lysergic acid 2-butyl amide

Pharmacokinetic data
Bioavailability  ?
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Lysergic acid 2-butyl amide is an analogue of LSD developed 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 It is a structural isomer of LSD, with the two ethyl groups on the amide nitrogen having been replaced by a single butyl group, joined at the 2-position.[1] It is one of the few lysergamide derivatives to exceed the potency of LSD in animal drug discrimination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.[2] 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,[3] with the stereoselective activity of these unsymmetric monoalkyl lysergamides foreshadowing the subsequent development of compounds such as Lysergic acid 2,4-dimethylazetidide.

References

  1. ^ Oberlender R, Pfaff RC, Johnson MP, Huang XM, Nichols DE. Stereoselective LSD-like activity in d-lysergic acid amides of (R)- and (S)-2-aminobutane. Journal of Medicinal Chemistry. 1992 Jan 24;35(2):203-11. PMID 1732537
  2. ^ Monte AP, Marona-Lewicka D, Kanthasamy A, Sanders-Bush E, Nichols DE. Stereoselective LSD-like activity in a series of d-lysergic acid amides of (R)- and (S)-2-aminoalkanes. Journal of Medicinal Chemistry. 1995 Mar 17;38(6):958-66. PMID 7699712
  3. ^ David E. Nichols. LSD and Its Lysergamide Cousins. The Heffter Review of Psychedelic Research. 2001;2:80-87.
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