LSD Analogs II. N-[2-(3-Pyridyl)ethyl]-β-alanine Derivatives

Liska, Kenneth J.; Tadepalli, Anjaneyulu S.

doi:10.1002/jps.2600571228

Cited by 3 publications

(1 citation statement)

References 7 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Compounds of general structure XXIV, which can be viewed as lysergic acid analogs, in which the indole system has been replaced by pyridine and where rings C and D are open, were found to have no anti-5hydroxytryptamine activity (35). Two of these did, however, show a slight but significant 5-hydroxytryptamine potentiating action (XXIV, RI = H, Rz = OEt, NEtz).…”

Section: Xi1 Xi11mentioning

confidence: 99%

Structural Analogs of Lysergic Acid

Campaigne¹,

Knapp²

1971

Journal of Pharmaceutical Sciences

View full text Add to dashboard Cite

Section: Xi1 Xi11mentioning

confidence: 99%

Structural Analogs of Lysergic Acid

Campaigne¹,

Knapp²

1971

Journal of Pharmaceutical Sciences

View full text Add to dashboard Cite

Nucleophilic addition of 2‐, 3‐, or 4‐[2‐(methylamino)ethyl]pyridine to the aziridine, 7‐methyl‐7‐azabicyclo[4.1.0]heptane

Rees

1990

Journal of Heterocyclic Chem

View full text Add to dashboard Cite

The synthesis of trans‐(±)‐N‐methyl‐N‐[2‐[methyl[2‐(3‐pyridyl)ethyl]amino]cyclohexyl]‐4‐benzofuranacetamide dihydrochloride, 1 which is a 3‐[2‐(methylamino)ethyl]pyridyl derivative of the kappa opioid analgesic trans‐(±)‐N‐methyl‐N‐[2‐(1‐pyrrolidinyl)cyclohexyl]benzofuran‐4‐acetamide monohydrochloride, 2 is described. The key intermediate is trans‐(±)‐N,N'‐dimethyl‐N‐[2‐(3‐pyridyl)ethyl]‐1,2‐cyclohexanediamine, 9 which is formed by nucleophilic addition of 3‐[2‐(methylamino)ethyl]pyridine 6 to the aziridine, 7‐methyl‐7‐azabicyclo[4.1.0]heptane, 4. During attempts to prepare the 2‐ or 4‐isomeric pyridyl derivatives of 1 it was discovered that both 2‐ or 4‐[2‐(methylamino)ethyl]pyridine, 5 or 7 are converted to N‐methyl‐N,N‐di‐[2‐(2‐pyridyl)ethylamine] 11 and N‐methyl‐N,N‐di[2‐(4‐pyridyl)ethylamine] 13 respectively by refluxing in toluene in the presence of ammonium chloride. The 3‐isomer, 6 is unchanged after treatment under identical conditions. Careful control of the reaction conditions enabled the aziridine 4 to be ring opened with the pyridyl amines 5 or 7 to give the 1,2‐diamines trans‐(±)‐N,N′‐dimethyl‐N‐[2‐(2‐pyridyl)ethyl]‐1,2‐cyclohexanediamine, 8 or trans‐(±)‐N,N′‐dimethyl‐N‐[2‐(4‐pyridyl)ethyl]‐1,2‐cyclohexane diamine 10 respectively.

show abstract

Effects of morpholino-, pyrrolidino-, piperizino-, and cyclo-derivatives of beta-alanine on brain amines and amino acids

Leonard

Liska

1971

Life Sciences

View full text Add to dashboard Cite

LSD Analogs II. N-[2-(3-Pyridyl)ethyl]-β-alanine Derivatives

Cited by 3 publications

References 7 publications

Structural Analogs of Lysergic Acid

Structural Analogs of Lysergic Acid

Nucleophilic addition of 2‐, 3‐, or 4‐[2‐(methylamino)ethyl]pyridine to the aziridine, 7‐methyl‐7‐azabicyclo[4.1.0]heptane

Effects of morpholino-, pyrrolidino-, piperizino-, and cyclo-derivatives of beta-alanine on brain amines and amino acids

Contact Info

Product

Resources

About