N1-Methyl-lysergic acid diethylamide

N1-Methyl-lysergic acid diethylamide (MLD-41) is a derivative of LSD that has about one-third the psychoactive effects. It has been studied in cross-tolerance of LSD.[1]

N1-Methyl-lysergic acid diethylamide
Clinical data
Other namesMLD-41; N1-Methyl-Lysergic Acid Diethylamide
Routes of
administration		Oral
Pharmacokinetic data
MetabolismHepatic
ExcretionRenal
Identifiers
IUPAC name
  • (8β)-N,N-Diethyl-1,6-dimethyl-9,10-didehydroergoline-8-carboxamide
CAS Number
PubChem CID
ChemSpider
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC21H27N3O
Molar mass337.467 g·mol−1
3D model (JSmol)
SMILES
  • O=C(N(CC)CC)[C@@H]3/C=C2/c4cccc1c4c(cn1C)C[C@H]2N(C3)C
InChI
  • InChI=1S/C21H27N3O/c1-5-24(6-2)21(25)15-10-17-16-8-7-9-18-20(16)14(12-22(18)3)11-19(17)23(4)13-15/h7-10,12,15,19H,5-6,11,13H2,1-4H3/t15-,19-/m1/s1 Y
  • Key:VQZYKSWQIQANKB-DNVCBOLYSA-N Y
  (verify)

Metabolism of other 1-methylated-ergoloids to their secondary amine derivatives has been frequently noted in mammals.[2]

References
  1. Abramson HA, Rolo A, Sklarofsky B, Stache J (January 1960). "Production of cross-tolerance to psychosis-producing doses of lysergic acid diethylamide and psilocybin". The Journal of Psychology. 49 (1): 151–4. doi:10.1080/00223980.1960.9916396.
  2. Müller-Schweinitzer E, Tapparelli C (March 1986). "Methylergometrine, an active metabolite of methysergide". Cephalalgia: An International Journal of Headache. 6 (1): 35–41. doi:10.1046/j.1468-2982.1986.0601035.x. PMID 3698092. S2CID 5778173.


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