Chemistry:MLA-74

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MLA-74, also known as 1-methyllysergic acid ethylamide (1-methyl-LAE) or as 1-methyl-N-ethyllysergamide, is a psychedelic drug of the lysergamide family related to lysergic acid diethylamide (LSD).[1][2][3] It is the 1-methyl derivative of lysergic acid ethylamide (LAE-32).[1][4][2][3] Extensive metabolism of other 1-methylated lysergamides to their secondary amine derivatives, for instance methysergide (1-methylmethylergometrine) conversion into methylergometrine, has been observed.[5][6]

Use and effects

An active dose of MLA-74 in humans is described as being approximately 2 mg orally and the drug is said to have about 4 to 5% of the potency of LSD.[1][2][7][8][9][10][11][12] It is also said to have a faster onset and shorter duration than LSD.[10][12] For comparison, LAE-32 has a listed dose range of 0.5 to 1.6 mg orally, approximately 5 to 10% of the potency of LSD, and is likewise described as faster onset and shorter duration.[1][2][7][8][9][10] MLA-74 is about 8-fold less potent than its analogue MLD-41 (1-methyl-LSD).[1] Both MLA-74 and LAE-32 are described as producing LSD-like psychic effects in humans.[10][12] However, they are both described as producing only slight or weak hallucinogenic effects.[13]

Interactions

Pharmacology

Pharamcodynamics

MLA-74 shows about 8.35 times the antiserotonergic activity of LSD in the isolated rat uterus in vitro and about 70-fold the activity of LAE-32 in this assay.[1][14][15][12] Unlike LAE-32, MLA-74 is practically devoid of pyretogenic effects in rabbits and is listed as having 0% of the activity of LSD in this regard.[1][14]

History

MLA-74 was first described in the scientific literature by the late 1950s.[15][16][11][12]

See also

  • Substituted lysergamide
  • MLD-41 (1-methyl-LSD)
  • MPD-75 (1-methyl-LPD)
  • ALA-10 (1-acetyl-LAE; 1A-LAE)

References

  1. ↑ 1.0 1.1 1.2 1.3 1.4 1.5 1.6 "Some Compounds With Hallucinogenic Activity". Ergot Alkaloids and Related Compounds. Handbook of Experimental Pharmacology (HEP). 49. Berlin, Heidelberg: Springer Berlin Heidelberg. 1978. pp. 567–614. doi:10.1007/978-3-642-66775-6_8. ISBN 978-3-642-66777-0. https://bibliography.maps.org/resources/download/8769#page=30. "Table 2. Psychotomimetic activity and some pharmacodynamic effects of structural analogues of LSD [...]" 
  2. ↑ 2.0 2.1 2.2 2.3 "Basic Pharmacology and Effects". Hallucinogens: A Forensic Drug Handbook. Forensic Drug Handbook Series. Elsevier Science. 2003. pp. 67–137. ISBN 978-0-12-433951-4. https://web.archive.org/web/20250223164514/https://citeseerx.ist.psu.edu/document?repid=rep1&type=pdf&doi=6bb3a7499da8e9852b39cd4db16891147c83f5c6. 
  3. ↑ 3.0 3.1 Shulgin, Alexander; Shulgin, Ann (September 1997). TiHKAL: The Continuation. Berkeley, California: Transform Press. ISBN 0-9630096-9-9. OCLC 38503252. http://www.erowid.org/library/books_online/tihkal/tihkal.shtml.  https://erowid.org/library/books_online/tihkal/tihkal26.shtml
  4. ↑ "Chemical Background". Ergot Alkaloids and Related Compounds. Handbook of Experimental Pharmacology (HEP). 49. Berlin, Heidelberg: Springer Berlin Heidelberg. 1978. pp. 29–85. doi:10.1007/978-3-642-66775-6_2. ISBN 978-3-642-66777-0. 
  5. ↑ "Multipotent and Poly-therapeutic Fungal Alkaloids of Claviceps purpurea". Medicinal Plants and Fungi: Recent Advances in Research and Development. Medicinal and Aromatic Plants of the World. 4. 2017. pp. 229–252. doi:10.1007/978-981-10-5978-0_8. ISBN 978-981-10-5977-3. "Metabolites of methysergide also exhibit pharmacological activity. Methylergometrine (one of methysergide’s metabolites) is responsible for methysergide’s therapeutic effects regarding migraine treatment (Müller-Schweinitzer and Tapparelli 1986). [...] The systemic availability of methysergide after oral administration is only 13%, due to a high degree of first-pass metabolism by N-1 demethylation to methylergometrine. After oral administration, the plasma concentrations of the metabolite are considerably higher than those of the parent drug, and the area under the plasma concentration curve (AUC) for methylergometrine is more than ten times greater than for methysergide." 
  6. ↑ "Methylergometrine, an active metabolite of methysergide". Cephalalgia 6 (1): 35–41. March 1986. doi:10.1046/j.1468-2982.1986.0601035.x. PMID 3698092. 
  7. ↑ 7.0 7.1 "Structure-activity relationships of the classic hallucinogens and their analogs". NIDA Research Monograph 146: 74–91. 1994. PMID 8742795. 
  8. ↑ 8.0 8.1 "Chemistry of Psychotomimetics". Psychotropic Agents, Part III: Alcohol and Psychotomimetics, Psychotropic Effects of Central Acting Drugs. Handbook of Experimental Pharmacology. 55 / 3. Berlin: Springer Berlin Heidelberg. 1982. pp. 3–29. doi:10.1007/978-3-642-67770-0_1. ISBN 978-3-642-67772-4. OCLC 8130916. https://bitnest.netfirms.com/external/10.1007/978-3-642-67770-0_1. 
  9. ↑ 9.0 9.1 "Hallucinogens". Burger's Medicinal Chemistry. 3 (4 ed.). New York: Wiley. 1980. pp. 1109–1137. ISBN 978-0-471-01572-7. OCLC 219960627. https://citeseerx.ist.psu.edu/document?repid=rep1&type=pdf&doi=6ac0c892ee380436f614d3aae0686ef617b2e0c5. 
  10. ↑ 10.0 10.1 10.2 10.3 "Indolealkylamines and Related Compounds". Hallucinogenic Agents. Bristol: Wright-Scientechnica. 1975. pp. 98–144. ISBN 978-0-85608-011-1. OCLC 2176880. https://bitnest.netfirms.com/external/Books/978-0-85608-011-1#page=55. "Table 4.3.—Comparative Hallucinogenic Potencies in Man of Derivatives of D-Lysergic Acid. [...]" 
  11. ↑ 11.0 11.1 "Comparison of Abnormal Behavioral States Induced by Psychotropic Drugs in Animals and Man". Proceedings of the 1st International Congress of Neuro-Psychopharmacology, Rome, September 1958. Amsterdam: Elsevier. 1959. pp. 117–123. https://bibliography.maps.org/resources/download/19108. 
  12. ↑ 12.0 12.1 12.2 12.3 12.4 "Relationships of psychotomimetic to anti-serotonin potencies of congeners of lysergic acid diethylamide (LSD-25)". Psychopharmacologia 1: 20–28. 1959. doi:10.1007/BF00408108. PMID 14405872. https://bibliography.maps.org/resources/download/13773#page=4. 
  13. ↑ "Structure-Activity Relationship among Hallucinogenic Agents". Origin and Mechanisms of Hallucinations. Boston, MA: Springer US. 1970. pp. 345–376. doi:10.1007/978-1-4615-8645-6_29. ISBN 978-1-4615-8647-0. http://link.springer.com/10.1007/978-1-4615-8645-6_29. Retrieved 12 October 2025. "A relation in the same direction might exist between the two N-monoethyl analogues ALA-10 and MLA-74, if judged by their LD50; both are only slightly psychotomimetic. The unsubstituted N-monoethyl analogue of LSD itself is a weak hallucinogen only [122]." 
  14. ↑ 14.0 14.1 "D-Lysergic acid diethylamide (LSD): A review of its present status". Clinical Pharmacology and Therapeutics 6 (2): 183–255. 1965. doi:10.1002/cpt196562183. PMID 14288188. https://bibliography.maps.org/resources/download/2117. 
  15. ↑ 15.0 15.1 "Comparative study on the serotonin antagonism of amide derivatives of lysergic acid and of ergot alkaloids". The Journal of Pharmacology and Experimental Therapeutics 122 (1): 124–136. January 1958. doi:10.1016/S0022-3565(25)11933-2. PMID 13502837. https://bibliography.maps.org/resources/download/19096. 
  16. ↑ "Comparison of lysergic acid derivatives and antihistamines as inhibitors of the edema provoked in the rat's paw by serotonin". International Archives of Allergy and Applied Immunology 12 (1–2): 89–97. 1958. doi:10.1159/000228445. PMID 13549054. 



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