6-Methylenedihydrodesoxymorphine

6-Methylenedihydrodesoxymorphine (6-MDDM) is an analgesic effects.

6-Methylenedihydrodesoxymorphine is a potent morphine.[1] Compared to morphine it has a faster onset of action and similar duration of effects.^[1] It produces around the same degree of respiratory depression as morphine, but less inhibition of gastrointestinal motility. Animal studies show it to be a potent analgesic which produces significant analgesic effects even at low doses which produce comparatively few side effects,^[2] however it has never been developed for medical use in humans.

6-Methylenedihydrodesoxymorphine is synthesised in two steps; first a pyridine. The second step tends to be incomplete and often gives fairly low yields, but these can be improved by changing the reaction conditions.^[3][4]

References

1. ^ Abdel-Rahman MA, Elliott HW, Binks R, Küng W, Rapoport H. Synthesis and Pharmacology of 6-Methylenedihydrodesoxymorphine. Journal of Medicinal Chemistry. 1966; 9(1):1-6.
2. ^ Okun R, Elliott HW. Acute Pharmacological Studies of Some New Morphine Derivatives. Journal of Pharmacology And Experimental Therapeutics. 1958; 124(3): 255-259.
3. ^ Chadha MS, Rapoport H. The Preparation of Some 6-Methylated Dihydrodesoxymorphines. Journal of the American Chemical Society. 1957; 79(21):5730-5734.
4. ^ Wiegert PE, De La Mater G, McElheny GC, Patterson LA. Physical Constants of 6-Methylenedihydrodesoxymorphine. Journal of Organic Chemistry. 1961; 26(12):5249-5250.