LAMPA

{{short description|Chemical compound}}

{{cs1 config|name-list-style=vanc|display-authors=6}}

{{Drugbox

| IUPAC_name = N,7-dimethyl-N-propyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide

| image = LAMPA.svg

| width = 180

| tradename =

| legal_AU =

| legal_CA =

| legal_UK =

| legal_US = Schedule I (isomer of LSD)

| legal_US_comment =

| routes_of_administration =

| CAS_number = 40158-98-3

| PubChem = 613620

| ChemSpiderID = 533384

| synonyms = LMP; LAMP; N-Methyl-N-propyllysergamide;

| C = 20

| H = 25

| N = 3

| O = 1

| smiles = CCCN(C)C(=O)C1CN(C2CC3=CNC4=CC=CC(=C34)C2=C1)C

| StdInChI = InChI=1S/C20H25N3O/c1-4-8-22(2)20(24)14-9-16-15-6-5-7-17-19(15)13(11-21-17)10-18(16)23(3)12-14/h5-7,9,11,14,18,21H,4,8,10,12H2,1-3H3

| StdInChIKey = CZRJGQXHVRNZRZ-UHFFFAOYSA-N

}}

Lysergic acid methylpropylamide (LAMPA, LAMP, or LMP), also known as N-methyl-N-propyllysergamide, is a structural analogue of lysergic acid diethylamide (LSD) that has been studied as a potential treatment for alcoholism.{{cite book | vauthors = Abramson HA, Rolo A | chapter = Comparison of LSD with methysergide and psilocybin on test subjects. | veditors = Abramson HA | title = The use of LSD in psychotherapy and alcoholism. |date=1967 |pages=53–57 |chapter-url=https://www.samorini.it/doc1/alt_aut/ad/abramson-the-use-of-lsd-in-psychotherapy-and-alcoholism.pdf |access-date=15 May 2022 |publisher=Bobbs-Merrill Company Inc.}} In animal studies, LAMPA was found to be nearly equipotent to ECPLA and MIPLA for inducing a head-twitch response. LAMPA appears to be significantly less potent than LSD in humans, producing little to no noticeable effects at doses of 100 μg.{{cite journal | vauthors = Halberstadt AL, Klein LM, Chatha M, Valenzuela LB, Stratford A, Wallach J, Nichols DE, Brandt SD | title = Pharmacological characterization of the LSD analog N-ethyl-N-cyclopropyl lysergamide (ECPLA) | journal = Psychopharmacology | volume = 236 | issue = 2 | pages = 799–808 | date = February 2019 | pmid = 30298278 | doi = 10.1007/s00213-018-5055-9 | pmc = 6848745 }} It shows reduced-efficacy partial agonism of the serotonin 5-HT_2A receptor relative to LSD, which may be responsible for its equivocal hallucinogenic effects.{{cite journal | vauthors = Pottie E, Glatfelter GC, Baumann MH, Stove CP | title=Differential in Vitro Activation Profiles for Psychedelic versus Non-psychedelic Ergolines at the 5-HT2A Receptor | journal=Emerging Trends in Drugs, Addictions, and Health | volume=4 | date=2024 | doi=10.1016/j.etdah.2023.100109 | doi-access=free | page=100109}}