{{cs1 config|name-list-style=vanc|display-authors=6}} {{Infobox drug | drug_name = | image = LME-54.svg | image_class = skin-invert-image | width = 175px | image2 = LME-54 3D.png | image_class2 = bg-transparent | width2 = 225px
<!-- Clinical data --> | pronounce = | tradename = | Drugs.com = | MedlinePlus = | licence_CA = | licence_EU = | DailyMedID = | licence_US = | pregnancy_AU = | pregnancy_category = | dependency_liability = | addiction_liability = | routes_of_administration = Oral<ref name="Abramson_1965" /> | class = Serotonergic psychedelic; Hallucinogen | ATC_prefix = None | ATC_suffix =
<!-- Legal status --> | legal_status =
<!-- Pharmacokinetic data --> | bioavailability = | protein_bound = | metabolism = | metabolites = | onset = | elimination_half-life = | duration_of_action = | excretion =
<!-- Identifiers --> | CAS_number = | CAS_supplemental = | PubChem = 164763851 | PubChemSubstance = | IUPHAR_ligand = | DrugBank = | ChemSpiderID = | UNII = | KEGG = | ChEBI = | ChEMBL = | NIAID_ChemDB = | PDB_ligand = | synonyms = LME54; LME; Lysergic acid methylethylamide; LA-methylethylamide; ''N''-Ethyl-''N''-methyllysergamide; ''N''-Ethyl-''N'',6-dimethyl-9,10-didehydroergoline-8β-carboxamide
<!-- Chemical data --> | IUPAC_name = (6''aR'',9''R'')-''N''-ethyl-''N'',7-dimethyl-6,6''a'',8,9-tetrahydro-4''H''-indolo[4,3-fg]quinoline-9-carboxamide | C=19 | H=23 | N=3 | O=1 | SMILES = CCN(C)C(=O)[C@H]1CN([C@@H]2CC3=CNC4=CC=CC(=C34)C2=C1)C | StdInChI = 1S/C19H23N3O/c1-4-21(2)19(23)13-8-15-14-6-5-7-16-18(14)12(10-20-16)9-17(15)22(3)11-13/h5-8,10,13,17,20H,4,9,11H2,1-3H3/t13-,17-/m1/s1 | StdInChIKey = BROWGWCWLHAXPI-CXAGYDPISA-N }}
'''LME-54''', or simply '''LME''', also known as '''lysergic acid methylethylamide''' or as '''''N''-methyl-''N''-ethyllysergamide''', is a serotonergic psychedelic of the lysergamide family related to lysergic acid diethylamide (LSD; LSD-25).<ref name="Shulgin_1976">{{cite book | vauthors = Shulgin AT | veditors = Gordon M | chapter = Psychotomimetic Agents | title = Psychopharmacological Agents: Use, Misuse and Abuse | volume = 4 | pages = 59–146 | date = 1976 | doi = 10.1016/b978-0-12-290559-9.50011-9 | series = Medicinal Chemistry: A Series of Monographs | isbn = 978-0-12-290559-9 | publisher = Academic Press | chapter-url = https://bitnest.netfirms.com/external/10.1016/B978-0-12-290559-9.50011-9 }}</ref><ref name="Shulgin_1980">{{cite book | vauthors = Shulgin AT | veditors = Burger A, Wolf ME | chapter = Hallucinogens | title = Burger's Medicinal Chemistry | location = New York | volume = 3 | pages = 1109–1137 | date = 1980 | chapter-url = https://citeseerx.ist.psu.edu/document?repid=rep1&type=pdf&doi=6ac0c892ee380436f614d3aae0686ef617b2e0c5 | edition = 4 | publisher = Wiley | isbn = 978-0-471-01572-7 | oclc = 219960627 | url = https://books.google.com/books?id=2b3wAAAAMAAJ }}</ref><ref name="Shulgin_1982">{{cite book | vauthors = Shulgin AT | veditors = Hoffmeister F, Stille G | chapter = Chemistry of Psychotomimetics | title = Psychotropic Agents, Part III: Alcohol and Psychotomimetics, Psychotropic Effects of Central Acting Drugs | location = Berlin | volume = 55 | issue = Part 3 | pages = 3–29 | date = 1982 | doi = 10.1007/978-3-642-67770-0_1 | series = Handbook of Experimental Pharmacology | publisher = Springer Berlin Heidelberg | isbn = 978-3-642-67772-4 | oclc = 8130916 | url = https://books.google.com/books?id=mrT8CAAAQBAJ | chapter-url = https://bitnest.netfirms.com/external/10.1007/978-3-642-67770-0_1 }}</ref><ref name="Shulgin_2003">{{cite book | vauthors = Shulgin AT | veditors = Laing RR | chapter = Basic Pharmacology and Effects | title = Hallucinogens: A Forensic Drug Handbook | pages = 67–137 | year = 2003 | publisher = Elsevier Science | series = Forensic Drug Handbook Series | isbn = 978-0-12-433951-4 | url = https://books.google.com/books?id=l1DrqgobbcwC | chapter-url = https://citeseerx.ist.psu.edu/document?repid=rep1&type=pdf&doi=6bb3a7499da8e9852b39cd4db16891147c83f5c6 | access-date = 1 February 2025 }}</ref><ref name="Abramson_1965" /> It is the analogue of LSD in which one of the ''N''-ethyl groups has been replaced with an ''N''-methyl group.<ref name="Shulgin_1976" /><ref name="Shulgin_1980" /><ref name="Shulgin_1982" />
The drug was tested in humans at a dose of 25{{nbsp}}μg and was found to produce no effects at this dose in several subjects and to produce weaker effects than a 25{{nbsp}}μg dose of LSD in one subject.<ref name="Abramson_1965" /> Higher doses do not appear to have been assessed.<ref name="Abramson_1965" /> Based on these findings, LME-54 has been described as weakly active or active but less so than LSD with no specific numbers available.<ref name="Shulgin_1976" /><ref name="Shulgin_1980" /><ref name="Shulgin_1982" /><ref name="Shulgin_2003" /><ref name="Oberlender_1989" /><ref name="Pfaff_1994">{{cite journal | vauthors = Pfaff RC, Huang X, Marona-Lewicka D, Oberlender R, Nichols DE | title = Lysergamides revisited | journal = NIDA Research Monograph | volume = 146 | pages = 52–73 | date = 1994 | pmid = 8742794 | url = https://archives.nida.nih.gov/sites/default/files/monograph146.pdf#page=57 | quote = TABLE 2. Relative human potency of lysergic acid amides [...] }}</ref> Its antiserotonergic activity ''in vitro'' does not appear to have been reported.<ref name="Oberlender_1989">{{cite web | vauthors = Oberlender RA | title = Stereoselective aspects of hallucinogenic drug action and drug discrimination studies of entactogens | date = May 1989 | publisher = Purdue University | website = Purdue e-Pubs | url = https://bitnest.netfirms.com/external/Theses/Oberlender1989 | quote = Table 2. Relative potency values for lysergic acid amides. [...] }}</ref>
LME-54 was first described in the scientific literature by Harold Alexander Abramson and Andre Rolo by 1965.<ref name="Abramson_1965">{{cite journal | vauthors = Abramson HA, Rolo A | title = Lysergic acid diethylamide (LSD-25). 38. Comparison with action of methysergide and psilocybin on test subjects | journal = The Journal of Asthma Research | volume = 3 | issue = 1 | pages = 81–96 | date = September 1965 | pmid = 5318626 | doi = 10.3109/02770906509106904 }}</ref><ref name="Abramson_1967">{{cite book | vauthors = Abramson HA, Rolo A | veditors = Abramson HA | chapter = Comparison of LSD with Methysergide and Psilocybin on Test Subjects | title = The Use of LSD in Psychotherapy and Alcoholism: The Second International Conference on the Use of LSD in Psychotherapy and Alcoholism, May 8th–May 10th, 1965 | location = Indianapolis | pages = 53–73 | date = 1967 | publisher = The Bobbs-Merill Company | oclc = 302168 | url = https://books.google.com/books?id=KiRsAAAAMAAJ | chapter-url = https://www.samorini.it/doc1/alt_aut/ad/abramson-the-use-of-lsd-in-psychotherapy-and-alcoholism.pdf#page=70 }}</ref> It is not a controlled substance in Canada as of 2025.<ref name="CDSA">{{cite web | title=Controlled Drugs and Substances Act | website=Department of Justice Canada | url=https://laws-lois.justice.gc.ca/eng/acts/c-38.8/FullText.html | access-date=19 January 2026}}</ref>
==See also== * Substituted lysergamide * Lysergic acid methylpropylamide (LMP-55) * lysergic acid ethylpropylamide (LEP-57) * Lysergic acid ethylamide (LAE-32)
==References== {{Reflist}}
==External links== * [https://isomerdesign.com/pihkal/explore/5325 LME-54 - Isomer Design]
{{Psychedelics}} {{Ergolines}}
Category:Carboxamides Category:Ethyl compounds Category:Methyl compounds Category:Psychedelic lysergamides