MLA-74

Last updated

MLA-74
MLA-74.svg
Clinical data
Other namesMLA74; 1-Methyllysergic acid ethylamide; 1-Methyl-LAE; 1-Methyl-N-ethyllysergamide
Routes of
administration 		Oral
Drug class Serotonin receptor modulator; Serotonergic psychedelic; Hallucinogen
ATC code
  • None
Identifiers
  • (6aR,9R)-N-ethyl-4,7-dimethyl-6,6a,8,9-tetrahydroindolo[4,3-fg]quinoline-9-carboxamide
CAS Number
PubChem CID
ChemSpider
Chemical and physical data
Formula C19H23N3O
Molar mass 309.413 g·mol−1
3D model (JSmol)
  • CCNC(=O)[C@H]1CN([C@@H]2CC3=CN(C4=CC=CC(=C34)C2=C1)C)C
  • InChI=1S/C19H23N3O/c1-4-20-19(23)13-8-15-14-6-5-7-16-18(14)12(10-21(16)2)9-17(15)22(3)11-13/h5-8,10,13,17H,4,9,11H2,1-3H3,(H,20,23)/t13-,17-/m1/s1
  • Key:OLUVTYNEBIODME-CXAGYDPISA-N

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]

Contents

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

References

  1. 1 2 3 4 5 6 7 Fanchamps A (1978). "Some Compounds With Hallucinogenic Activity". In Berde B, Schild HO (eds.). Ergot Alkaloids and Related Compounds. Handbook of Experimental Pharmacology (HEP). Vol. 49. Berlin, Heidelberg: Springer Berlin Heidelberg. pp. 567–614. doi:10.1007/978-3-642-66775-6_8. ISBN   978-3-642-66777-0. Archived from the original on 30 March 2025. Table 2. Psychotomimetic activity and some pharmacodynamic effects of structural analogues of LSD [...]
  2. 1 2 3 4 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.
  3. 1 2 Shulgin A, Shulgin A (September 1997). TiHKAL: The Continuation. Berkeley, California: Transform Press. ISBN   0-9630096-9-9. OCLC   38503252. https://erowid.org/library/books_online/tihkal/tihkal26.shtml
  4. ↑ Rutschmann J, Stadler PA (1978). "Chemical Background". In Berde B, Schild HO (eds.). Ergot Alkaloids and Related Compounds. Handbook of Experimental Pharmacology (HEP). Vol. 49. Berlin, Heidelberg: Springer Berlin Heidelberg. pp. 29–85. doi:10.1007/978-3-642-66775-6_2. ISBN   978-3-642-66777-0.
  5. ↑ Majrashi M, Ramesh S, Deruiter J, Mulabagal V, Pondugula S, Clark R, et al. (2017). "Multipotent and Poly-therapeutic Fungal Alkaloids of Claviceps purpurea". In Agrawal DC, Tsay HS, Shyur LF, Wu YC, Wang SY (eds.). Medicinal Plants and Fungi: Recent Advances in Research and Development. Medicinal and Aromatic Plants of the World. Vol. 4. pp. 229–252. doi:10.1007/978-981-10-5978-0_8. ISBN   978-981-10-5977-3. ISSN   2352-6831. 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. ↑ Müller-Schweinitzer E, Tapparelli C (March 1986). "Methylergometrine, an active metabolite of methysergide". Cephalalgia. 6 (1): 35–41. doi:10.1046/j.1468-2982.1986.0601035.x. PMID   3698092. S2CID   5778173.
  7. 1 2 Jacob P, Shulgin AT (1994). "Structure-activity relationships of the classic hallucinogens and their analogs". NIDA Research Monograph. 146: 74–91. PMID   8742795.
  8. 1 2 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 / 3. Berlin: Springer Berlin Heidelberg. pp. 3–29. doi:10.1007/978-3-642-67770-0_1. ISBN   978-3-642-67772-4. OCLC   8130916.
  9. 1 2 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.
  10. 1 2 3 4 Brimblecombe RW, Pinder RM (1975). "Indolealkylamines and Related Compounds". Hallucinogenic Agents. Bristol: Wright-Scientechnica. pp. 98–144. ISBN   978-0-85608-011-1. OCLC   2176880. OL   4850660M. Table 4.3.—Comparative Hallucinogenic Potencies in Man of Derivatives of D-Lysergic Acid. [...]
  11. 1 2 Cerletti A (1959). "Comparison of Abnormal Behavioral States Induced by Psychotropic Drugs in Animals and Man". In Bradley PB, Deniker P, Radouco-Thomas C (eds.). Proceedings of the 1st International Congress of Neuro-Psychopharmacology, Rome, September 1958. Amsterdam: Elsevier. pp. 117–123. Archived from the original on 30 March 2025.
  12. 1 2 3 4 5 Isbell H, Miner EJ, Logan CR (1959). "Relationships of psychotomimetic to anti-serotonin potencies of congeners of lysergic acid diethylamide (LSD-25)". Psychopharmacologia. 1: 20–28. doi:10.1007/BF00408108. PMID   14405872. Archived from the original on 7 April 2022.
  13. ↑ Keup W (1970). "Structure-Activity Relationship among Hallucinogenic Agents". Origin and Mechanisms of Hallucinations. Boston, MA: Springer US. pp. 345–376. doi:10.1007/978-1-4615-8645-6_29. ISBN   978-1-4615-8647-0 . 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. 1 2 Hoffer A (1965). "D-Lysergic acid diethylamide (LSD): A review of its present status". Clinical Pharmacology and Therapeutics. 6 (2): 183–255. doi:10.1002/cpt196562183. PMID   14288188. Archived from the original on 30 March 2025.
  15. 1 2 Cerletti A, Doepfner W (January 1958). "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. doi:10.1016/S0022-3565(25)11933-2. PMID   13502837. Archived from the original on 30 June 2025.
  16. ↑ Doepfner W, Cerletti A (1958). "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. doi:10.1159/000228445. PMID   13549054.
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