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Lysergic acid methylamide

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Lysergic acid methylamide
Clinical data
Other namesLysergic acid methylamide; LAM; Lysergic acid monomethylamide; LA-methylamide; LA-monomethylamide; N-Methyllysergamide; NM-LA; N-Methyl-LSA; N-Methylergine; N,6-Dimethyl-9,10-didehydroergoline-8β-carboxamide
Routes of
administration		Oral[1][2][3]
Drug classSerotonin receptor modulator
ATC code
  • None
Identifiers
  • (6aR,9R)-N,7-dimethyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide
CAS Number
PubChem CID
ChemSpider
Chemical and physical data
FormulaC17H19N3O
Molar mass281.359 g·mol−1
3D model (JSmol)
  • CNC(=O)[C@H]1CN([C@@H]2CC3=CNC4=CC=CC(=C34)C2=C1)C
  • InChI=1S/C17H19N3O/c1-18-17(21)11-6-13-12-4-3-5-14-16(12)10(8-19-14)7-15(13)20(2)9-11/h3-6,8,11,15,19H,7,9H2,1-2H3,(H,18,21)/t11-,15-/m1/s1
  • Key:NINBUXQQTOVMAB-IAQYHMDHSA-N

Lysergic acid methylamide (LAM), also known as N-methyllysergamide (NM-LA), is a serotonin receptor modulator of the lysergamide family.[1][2][4] It is the N-methyl derivative of ergine (lysergic acid amide; LSA) and the analogue of lysergic acid diethylamide (LSD) in which the N,N-diethyl groups have been replaced with one N-methyl group.[1][2][4]

It is active in humans at a dose of approximately 500 μg and has roughly 20% of the potency of LSD as a drug.[1][2][3] However, it has been said to produce autonomic effects but to produce no psychoactive or hallucinogenic effects at this dose.[3][2][5] The drug has about 6.3% of the antiserotonergic potency of LSD in the isolated rat uterus in vitro.[4][3][6][7]

LAM was first described in the scientific literature by Albert Hofmann and colleagues by 1955.[8][9][10][11]

See also

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References

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  1. ^ a b c d Jacob P, Shulgin AT (1994). "Structure-activity relationships of the classic hallucinogens and their analogs" (PDF). NIDA Research Monograph. 146: 74–91. PMID 8742795.
  2. ^ a b c d e 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. ^ a b c d Rothlin E (March 1957). "Lysergic acid diethylamide and related substances". Annals of the New York Academy of Sciences. 66 (3): 668–676. doi:10.1111/j.1749-6632.1957.tb40756.x. PMID 13425249. TABLE 1 INHIBITION OF SEROTONIN BY VARIOUS AMIDES OF LYSERGIC ACID [...] It is noteworthy, from the chemical point of view, that only the monoethylamide and the diethylamide, whether of lysergic acid or of acetyl-lysergic acid, are able to produce significant psychic changes. Thus there can be no doubt that the ethyl group is particularly important in this respect. In this connection, it may be mentioned that the monomethylamide and dimethylamide and the monopropylamide and dipropylamide do not possess any psychic action. On the other hand, both in animals and in man the 4 latter compounds are capable of eliciting autonomic actions in doses in which the monoethylamide, for example, is completely inactive. Thus, a dose of 50 μg. of the dimethylamide of d-lysergic acid is sufficient to elicit marked autonomic responses, whereas as much as 500 μg. of the monoethylamide of d-lysergic acid are necessary to produce similar effects. With the latter compound, however, simultaneous psychic changes occur, whereas the monomethylamide and dimethylamide in doses sufficient to elicit autonomic responses cause no changes in the psyche.
  4. ^ a b c 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. [...]
  5. ^ Mangner TJ (1978). Potential Psychotomimetic Antagonists. N,N-Diethyl-1-methyl-3-aryl-1,2,5,6-tetrahydropyridine-5-carboxamides (Ph.D. thesis). University of Michigan. doi:10.7302/11268. Archived from the original on 30 March 2025. Table 1. Human psychotomimetic potencies of LSD analogs. [...]
  6. ^ Gupta SP, Singh P, Bindal MC (1 December 1983). "QSAR studies on hallucinogens". Chemical Reviews. 83 (6): 633–649. doi:10.1021/cr00058a003. ISSN 0009-2665. Retrieved 29 June 2025.
  7. ^ 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.
  8. ^ Hofmann A, Stoll A (1955). "Amide der stereoisomeren Lysergsäuren und Dihydro‐lysergsäuren. 38. Mitteilung über Mutterkornalkaloide" [Amides of stereoisomeric lysergic and dihydrolysergic acids. 38. Ergot alkaloids]. Helvetica Chimica Acta. 38 (2): 421–433. doi:10.1002/hlca.19550380207. ISSN 0018-019X. Retrieved 5 June 2025.
  9. ^ Cerletti A (1956). "Lysergic Acid Diethylamide (LSD) and Related Compounds". In Abramson HA (ed.). Neuropharmacology: Transactions of the 2nd Conference, May 25-27, 1955, Princeton, N.J. New York: Josiah Macy. pp. 9–84. Cerletti: I have forgotten to tell you that a whole series of compounds homologous to LSD, such as the diethyl-, the dipropyl-, the di-isopropyland the di-butylamide of lysergic acid, has been prepared by Stoll and Hofmann (6). Besides these, the corresponding monosubstituted amides, for example, lysergic acid methylamide or lysergic acid ethylamide have been studied. The last named substance, known as LAE-32, is of special interest. It is the monothylamide of lysergic acid and is a compound which, when administered in doses about ten times higher than LSD, like LSD, produces very remarkable psychic changes but, in contrast to LSD, seems to be less stimulating and more depressing.
  10. ^ Hofmann A (1958). "The LSD-Psychosis: III. Lysergic Acid Diethylamide and Related Compounds. Relationship Between Spatial Arrangement and Mental Effects". In Rinkel M (ed.). Chemical Concepts of Psychosis: Proceedings of the Symposium on Chemical Concepts of Psychosis held at the Second International Congress of Psychiatry in Zurich, Switzerland, September 1 to 7, 1957. New York: McDowell, Obolensky. pp. 85–90. doi:10.1037/11190-006. Archived from the original on 4 June 2025. TABLE I Variations in the acid amide group of the LSD molecule. Amides of d-lysergic acid (C15H15N2.COR) prepared for pharmacological investigation. [...]
  11. ^ Hofmann A (June 1959). "Psychotomimetic drugs; chemical and pharmacological aspects" (PDF). Acta Physiologica et Pharmacologica Neerlandica. 8: 240–258. PMID 13852489. Systematic variations of the substituents in the amide grouping has resulted in the synthesis of a great number of substances (STOLL and HOFMANN, 1955) which are listed in table 1. [...] TABLE 1 Variations in the acid amide group of the LSD molecule Amides of d-lysergic acid (C12H15N2–COR) prepared for pharmacological investigation [...] R: [...] d-lysergic acid pyrrolinide
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