2,4-Dinitrophenylmorphine

2,4-Dinitrophenylmorphine is an analog of morphine in which a hydroxyl group is substituted with a dinitro phenoxy group.[1][2]

2,4-Dinitrophenylmorphine
Names
IUPAC name
3-(2,4-Dinitrophenoxy)-17-methyl-7,8-didehydro-4,5α-epoxymorphinan-6α-ol
Systematic IUPAC name
(4R,4aR,7S,7aR,12bS)-9-(2,4-Dinitrophenoxy)-3-methyl-2,3,4,4a,7,7a-hexahydro-1H-4,12-methano[1]benzofuro[3,2-e]isoquinolin-7-ol
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • InChI=1S/C23H21N3O7/c1-24-9-8-23-14-4-5-17(27)22(23)33-21-19(6-2-12(20(21)23)10-15(14)24)32-18-7-3-13(25(28)29)11-16(18)26(30)31/h2-7,11,14-15,17,22,27H,8-10H2,1H3/t14-,15+,17-,22-,23-/m0/s1 checkY
    Key: LRGWIFMZKBJNGI-KARMISDFSA-N checkY
  • InChI=1/C23H21N3O7/c1-24-9-8-23-14-4-5-17(27)22(23)33-21-19(6-2-12(20(21)23)10-15(14)24)32-18-7-3-13(25(28)29)11-16(18)26(30)31/h2-7,11,14-15,17,22,27H,8-10H2,1H3/t14-,15+,17-,22-,23-/m0/s1
    Key: LRGWIFMZKBJNGI-KARMISDFBG
  • [O-][N+](=O)c6ccc(Oc2c1O[C@@H]4[C@@]35c1c(cc2)C[C@@H](N(CC3)C)[C@@H]5/C=C\[C@@H]4O)c([N+]([O-])=O)c6
Properties
C23H21N3O7
Molar mass 451.43 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Infobox references

Properties

Being an analog of morphine, it would be expected to have the same effects on the body as a typical opioid. Also, as dinitrophenol is a metabolic and respiratory stimulant, this morphine derivative was invented in Austria in 1931 as a narcotic analgesic with less potential to depress respiration.[3]

References
  1. Eddy, N. B.; Sumwalt, M. (1939). "Studies of Morphine, Codeine, and Their Derivatives. XV. 2,4-Dinitrophenylmorphine" (PDF). Journal of Pharmacology and Experimental Therapeutics. 67 (2): 127–141.
  2. Huggins, R. A.; Bryan, A. R. (1951). "Some cardiovascular actions of dinitrophenylmorphine hydrochloride". Texas Reports on Biology and Medicine. 9 (2): 314–318. PMID 14835466.
  3. Reynolds and Randall, "Morphine and Allied Drugs", U of Toronto, 1957 pp 203 et al.



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