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Lysergic acid 3-pentyl amide





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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
  • DE: NpSG (Industrial and scientific use only)
  • UK: Under Psychoactive Substances Act
  • Identifiers
    • (8β)- 6-methyl- N- (3-pentyl)- 9,10- didehydroergoline- 8-carboxamide

    PubChem CID
    ChemSpider
    ChEMBL
    CompTox Dashboard (EPA)
    Chemical and physical data
    FormulaC21H27N3O
    Molar mass337.467 g·mol−1
    3D model (JSmol)
    • [H][C@@]12C(C3=C4C(NC=C4C2)=CC=C3)=C[C@@H](C(NC(CC)CC)=O)CN1C

    • 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

    edit

    References

    edit
    1. ^ Nichols DE (2001). "LSD and Its Lysergamide Cousins". The Heffter Review of Psychedelic Research. 2: 80–87.
  • ^ 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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  • Retrieved from "https://en.wikipedia.org/w/index.php?title=Lysergic_acid_3-pentyl_amide&oldid=1203745862"
     



    Last edited on 5 February 2024, at 14:06  





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    This page was last edited on 5 February 2024, at 14:06 (UTC).

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