Lysergic acid 3-pentyl amide

{{Short description|Chemical compound}}

{{Drugbox

| verifiedrevid = 452017671

| drug_name = LSP

| image = LS3P_structure.png

| width = 165px

| tradename =

| legal_AU =

| legal_CA =

| legal_DE = NpSG

| legal_UK = PSA

| legal_US =

| legal_status =

| routes_of_administration =

| metabolism =

| excretion =

| CAS_number_Ref = {{cascite|correct|CAS}}

| CAS_number = 162105-96-6

| ChEMBL = 424777

| PubChem = 10019984

| ChemSpiderID = 8195557

| synonyms = LSP; Lysergic acid 3-pentyl amide; N-(3-Pentyl)lysergamide

| IUPAC_name = (8β)-6-methyl-N-(3-pentyl)-9,10-didehydroergoline-8-carboxamide

| C=21 | H=27 | N=3 | O=1

| SMILES = [H][C@@]12C(C3=C4C(NC=C4C2)=CC=C3)=C[C@@H](C(NC(CC)CC)=O)CN1C

| StdInChI = 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

| StdInChIKey = ZQONRMXCBQXYCK-AUUYWEPGSA-N

}}

Lysergic acid 3-pentyl amide (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,{{cite journal | first = David E. | last = Nichols | name-list-style = vanc | title = LSD and Its Lysergamide Cousins. | journal = The Heffter Review of Psychedelic Research | date = 2001 | volume = 2 | pages = 80–87 }} 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.{{cite journal | vauthors = Monte AP, Marona-Lewicka D, Kanthasamy A, Sanders-Bush E, Nichols DE | title = Stereoselective LSD-like activity in a series of d-lysergic acid amides of (R)- and (S)-2-aminoalkanes | journal = Journal of Medicinal Chemistry | volume = 38 | issue = 6 | pages = 958–66 | date = March 1995 | pmid = 7699712 | doi = 10.1021/jm00006a015 }}