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 (1S,5R,13R,14S,17R)-10-(2,4-dinitrophenoxy)-4-methyl-12-oxa-4-azapentacyclo [9.6.1.0^1,13.0^5,17.0^7,18]octadeca-7(18),8,10,15-tetraen-14-ol
Other names 7,8-Didehydro-3-α-(2',4'- dinitro)phenoxy-4,5-α-epoxy-17-methylmorphinan-6-α-ol
Identifiers
CAS Number	58534-70-6^N 63732-56-9 (HCl)^N
3D model (JSmol)	Interactive image
ChemSpider	4676589^Y
PubChem CID	5745390
CompTox Dashboard (EPA)	DTXSID90974089
InChI 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^Y Key: LRGWIFMZKBJNGI-KARMISDFSA-N^Y 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
SMILES [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
Chemical formula	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 ^YN ?)
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.