6-Methylenedihydrodesoxymorphine

6-Methylenedihydrodesoxymorphine
	File:6-methylenehydromorphone.svg
Clinical data
Synonyms	6-MDDM, 6-Methylenedihydrodesoxymorphine
Identifiers
	IUPAC name 4,5-α-epoxy-17-methyl-6-methylenemorphinan-3-ol;
CAS Number	3414-84-4;
PubChem CID	5492874;
E number	{{#property:P628}}
ECHA InfoCard	{{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value).
Chemical and physical data
Formula	C18H21NO2
Molar mass	283.36 g/mol

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6-Methylenedihydrodesoxymorphine (6-MDDM) is an opiate analogue that is a derivative of hydromorphone, where the 6-ketone group has been replaced by methylene. It has sedative and analgesic effects.

6-Methylenedihydrodesoxymorphine is a potent μ-opioid agonist, reportedly up to 80x stronger than morphine.[2] 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 Wittig reaction is used, reacting hydrocodone with methylenetriphenylphosphorane and an alkyl lithium reagent in diethyl ether to form 6-Methylenedihydrodesoxycodeine. The 3-methoxy group is then cleaved to hydroxy, by reaction with 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

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

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[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.

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6-Methylenedihydrodesoxymorphine

References

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