LME-54

Last updated

LME-54
LA-methylethylamide structure.png
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 [1]
Drug class Serotonergic 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
Formula C19H23N3O
Molar mass 309.413 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). [2] [3] [4] [5] [1] It is the analogue of LSD in which one of the N-ethyl groups has been replaced with an N-methyl group. [2] [3] [4]

Contents

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. [1] Higher doses do not appear to have been assessed. [1] Based on these findings, LME-54 has been described as weakly active or active but less so than LSD with no specific numbers available. [2] [3] [4] [5] [6] [7] Its antiserotonergic activity in vitro does not appear to have been reported. [6]

LME-54 was first described in the scientific literature by Harold Alexander Abramson and Andre Rolo by 1965. [1] [8]

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.



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