Lysergic acid 3-pentyl amide

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]

Lysergic acid 3-pentyl amide
Clinical data
Other namesLysergic acid 3-pentyl amide
Legal status
Legal status
Identifiers
IUPAC name
  • (8β)- 6-methyl- N- (3-pentyl)- 9,10- didehydroergoline- 8-carboxamide
PubChem CID
ChemSpider
ChEMBL
Chemical and physical data
FormulaC21H27N3O
Molar mass337.467 g·mol−1
3D model (JSmol)
SMILES
  • [H][C@@]12C(C3=C4C(NC=C4C2)=CC=C3)=C[C@@H](C(NC(CC)CC)=O)CN1C
InChI
  • InChI=1S/C21H27N3O/c1-4-15(5-2)23-21(25)14-9-17-16-7-6-8-18-20(16)13(11-22-18)10-19(17)24(3)12-14/h6-9,11,14-15,19,22H,4-5,10,12H2,1-3H3,(H,23,25)/t14-,19-/m1/s1
  • Key:ZQONRMXCBQXYCK-AUUYWEPGSA-N
  (verify)

See also

References
  1. Nichols DE (2001). "LSD and Its Lysergamide Cousins". The Heffter Review of Psychedelic Research. 2: 80–87.
  2. Monte AP, Marona-Lewicka D, Kanthasamy A, Sanders-Bush E, Nichols DE (March 1995). "Stereoselective LSD-like activity in a series of d-lysergic acid amides of (R)- and (S)-2-aminoalkanes". Journal of Medicinal Chemistry. 38 (6): 958–66. doi:10.1021/jm00006a015. PMID 7699712.
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