Lysergic acid 3-pentyl amide

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Lysergic acid 3-pentyl amide
LS3P structure.png
Systematic (IUPAC) name
(8β)- 6-methyl- N- (3-pentyl)- 9,10- didehydroergoline- 8-carboxamide
Clinical data
Legal status
?
Identifiers
CAS number  YesY
ATC code ?
PubChem CID 10019984
Synonyms Lysergic acid 3-pentyl amide
Chemical data
Formula C21H27N3O 
Mol. mass 337.459 g/mol
 YesY (what is this?)  (verify)

Lysergic acid 3-pentyl amide (3-Pentyllysergamide, LSP) is an analogue of LSD originally researched by David E. Nichols and colleagues at Purdue University. It has similar binding affinity to LSD itself as both a 5-HT1A and 5-HT2A agonist, and produces similar behavioral and physiological responses in animals with only slightly lower potency than LSD. Other isomers of this compound have also been explored, with the 1-pentylamide being around 75% the potency of LSD,[1] while the (R)-2-pentylamide shows similar 5-HT2A binding affinity to LSD in vitro but has only around half the potency of LSD in producing drug-appropriate responding in mice, and the (S)-2-pentylamide is inactive.[2]

See also[edit]

References[edit]

  1. ^ David E. Nichols. LSD and Its Lysergamide Cousins. The Heffter Review of Psychedelic Research. 2001;2:80-87.
  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. doi:10.1021/jm00006a015 PMID 7699712