Lysergic acid 3-pentyl amide

Lysergic acid 3-pentyl amide
Clinical data
Other names	Lysergic acid 3-pentyl amide
Legal status
Legal status	DE: NpSG (Industrial and scientific use only); UK: Under Psychoactive Substances Act;
Identifiers
	IUPAC name (8β)- 6-methyl- N- (3-pentyl)- 9,10- didehydroergoline- 8-carboxamide;
CAS Number	162105-96-6 ;
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;
	(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-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]

References

^ 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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[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.

[1]

[2]

Lysergic acid 3-pentyl amide

See also

References