102129-05-5

Upstream product

• 109-04-6 2-bromo-pyridine 
• 6105-74-4 2-methyl-1-(piperidin-1-yl)propan-2-amine 
• 17697-46-0 1,1-Dimethyl-1-nitro-2-piperidinoethan 
• 79-03-8 propionyl chloride 
• 54151-65-4 2--pyridin 

Relevant academic research and scientific papers

Stereochemical researches about drugs. Part 11. Conformation of aminoalkyl acylamino-pyridines and their relation with morphine structure

The conformation of (R,S)-propiram and 8 analogues are investigated spectroscopically. Active analgesics are only found among the E-forms of the amides, in which the CH2 group of the propionyl substituent hangs over the pyridine ring - which itself stands vertical with respect to the planar amide group. The R-enantiomer of propiram is morphine-agonistic and corresponds to N-methylmorphinan in its spatial arrangement.

2 Acylaminopyridine derivatives having agonistic and antagonistic activity to morphine

A search for potent analgesic substances with low abuse potentials yielded N (1 methyl 2 piperidinoethyl) N (2 pyridyl)propionamide fumarate (propiram fumarate). This compound has no chemical relationship to morphine and has morphine antagonistic as well as morphine agonistic properties. Of the derivatives of propiram tested for their analgesic efficacy, the compounds having a high analgesic potency, with a favorable therapeutic index were those in which the piperidine ring had been replaced by an azabicyclic group, the larger ring of which was a 6 or 7 membered ring. Regarding activity and toxicity, the morphine antagonistic and morphine agonistic effects of particularly interesting substances were investigated. Slight to moderate morphine antagonism was established in a number of propiram derivatives. Like propiram, these substances also have morphine agonistic properties and thus are considered partial agonists. Compounds of nalorphine type, i.e. mainly potent morphine antagonists, have not been found. A few moderately to highly effective propiram derivatives, e.g. phenyl substituted derivatives or derivatives containing an azabicyclic group, showed distinct morphine agonistic properties. These properties were in some cases very pronounced with weak or no morphine antagonism.