Lysergic acid 3-pentylamide

LSP

Clinical data
Other names	LSP; Lysergic acid 3-pentylamide; N-(3-Pentyl)lysergamide; (8β)-6-Methyl-N-(3-pentyl)-9,10-didehydroergoline-8-carboxamide
Drug class	Serotonin receptor modulator; 5-HT2A receptor agonist
Legal status
Legal status	DE: NpSG (Industrial and scientific use only) UK: Under Psychoactive Substances Act
Identifiers
IUPAC name (6aR,9R)-7-methyl-N-pentan-3-yl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide
CAS Number	162105-96-6^Y
PubChem CID	10019984
ChemSpider	8195557
ChEMBL	ChEMBL424777
CompTox Dashboard (EPA)	DTXSID001029687
Chemical and physical data
Formula	C21H27N3O
Molar mass	337.467 g·mol^−1
3D model (JSmol)	Interactive image
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
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Lysergic acid 3-pentylamide (LSP), also known as N-(3-pentyl)lysergamide, 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-HT_1A and 5-HT_2A 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-HT_2A 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

• Substituted lysergamide
• Cepentil
• Lysergic acid 2-butylamide (LSB)
• MiPLA

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.

External links

• LSP - Isomer Design