LME-54

LME-54
Clinical data
Other namesLME54; LME; Lysergic acid methylethylamide; LA-methylethylamide; N-Ethyl-N-methyllysergamide; N-Ethyl-N,6-dimethyl-9,10-didehydroergoline-8β-carboxamide
Routes of
administration		Oral
Drug classSerotonergic psychedelic; Hallucinogen
ATC code
  • None
Identifiers
  • (6aR,9R)-N-ethyl-N,7-dimethyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide
PubChem CID
Chemical and physical data
FormulaC19H23N3O
Molar mass309.413 g·mol−1
3D model (JSmol)
  • CCN(C)C(=O)[C@H]1CN([C@@H]2CC3=CNC4=CC=CC(=C34)C2=C1)C
  • InChI=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
  • Key: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). It is the analogue of LSD in which one of the N-ethyl groups has been replaced with an N-methyl group.

The drug was tested in humans at a dose of 25 μg and was found to produce no effects at this dose in several subjects and to produce weaker effects than a 25 μg dose of LSD in one subject. Higher doses do not appear to have been assessed. Based on these findings, LME-54 has been described as weakly active or active but less so than LSD with no specific numbers available. Its antiserotonergic activity in vitro does not appear to have been reported.

LME-54 was first described in the scientific literature by Harold Alexander Abramson and Andre Rolo by 1965. It is not a controlled substance in Canada as of 2025.

See also

References

  1. 1 2 3 4 5 Abramson HA, Rolo A (September 1965). "Lysergic acid diethylamide (LSD-25). 38. Comparison with action of methysergide and psilocybin on test subjects". The Journal of Asthma Research. 3 (1): 81–96. doi:10.3109/02770906509106904. PMID 5318626.
  2. 1 2 3 Shulgin AT (1976). "Psychotomimetic Agents". In Gordon M (ed.). Psychopharmacological Agents: Use, Misuse and Abuse. Medicinal Chemistry: A Series of Monographs. Vol. 4. Academic Press. pp. 59–146. doi:10.1016/b978-0-12-290559-9.50011-9. ISBN 978-0-12-290559-9.
  3. 1 2 3 Shulgin AT (1980). "Hallucinogens". In Burger A, Wolf ME (eds.). Burger's Medicinal Chemistry. Vol. 3 (4 ed.). New York: Wiley. pp. 1109–1137. ISBN 978-0-471-01572-7. OCLC 219960627.
  4. 1 2 3 Shulgin AT (1982). "Chemistry of Psychotomimetics". In Hoffmeister F, Stille G (eds.). Psychotropic Agents, Part III: Alcohol and Psychotomimetics, Psychotropic Effects of Central Acting Drugs. Handbook of Experimental Pharmacology. Vol. 55. Berlin: Springer Berlin Heidelberg. pp. 3–29. doi:10.1007/978-3-642-67770-0_1. ISBN 978-3-642-67772-4. OCLC 8130916.
  5. 1 2 Shulgin AT (2003). "Basic Pharmacology and Effects". In Laing RR (ed.). Hallucinogens: A Forensic Drug Handbook. Forensic Drug Handbook Series. Elsevier Science. pp. 67–137. ISBN 978-0-12-433951-4. Retrieved 1 February 2025.
  6. 1 2 Oberlender RA (May 1989). "Stereoselective aspects of hallucinogenic drug action and drug discrimination studies of entactogens". Purdue e-Pubs. Purdue University. Table 2. Relative potency values for lysergic acid amides. [...]
  7. ↑ Pfaff RC, Huang X, Marona-Lewicka D, Oberlender R, Nichols DE (1994). "Lysergamides revisited" (PDF). NIDA Research Monograph. 146: 52–73. PMID 8742794. TABLE 2. Relative human potency of lysergic acid amides [...]
  8. ↑ Abramson HA, Rolo A (1967). "Comparison of LSD with Methysergide and Psilocybin on Test Subjects" (PDF). In Abramson HA (ed.). 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. Indianapolis: The Bobbs-Merill Company. pp. 53–73. OCLC 302168.
  9. ↑ "Controlled Drugs and Substances Act". Department of Justice Canada. Retrieved 19 January 2026.