Dihydroisocodeine

Dihydroisocodeine
Names
	IUPAC name 3-Methoxy-17-methyl-4,5α-epoxymorphinan-6β-ol
	Systematic IUPAC name (4R,4aR,7R,7aR,12bS)-9-Methoxy-3-methyl-2,3,4,4a,5,6,7,7a-octahydro-1H-4,12-methano[1]benzofuro[3,2-e]isoquinolin-7-ol
	Other names DHIC
Identifiers
CAS Number	795-38-0 ;
3D model (JSmol)	Interactive image;
ChemSpider	4591214;
PubChem CID	5492898;
UNII	9H2016E13H ;
CompTox Dashboard (EPA)	DTXSID2048907 ;
	InChI InChI=1S/C18H23NO3/c1-19-8-7-18-11-4-5-13(20)17(18)22-16-14(21-2)6-3-10(15(16)18)9-12(11)19/h3,6,11-13,17,20H,4-5,7-9H2,1-2H3/t11-,12+,13+,17-,18-/m0/s1 Key: RBOXVHNMENFORY-KEMUOJQUSA-N;
	SMILES CN1CC[C@]23[C@@H]4[C@H]1CC5=C2C(=C(C=C5)OC)O[C@H]3[C@@H](CC4)O;
Properties
Chemical formula	C18H23NO3
Molar mass	301.386 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Dihydroisocodeine is an opioid.^[1] The National Research Council of the United States reported in 1941 that isocodeine is one of four isomers of codeine known at the time (heterocodeine can be considered a fifth) and DHIC, then in use in Europe as a pharmaceutical, was four times stronger than dihydrocodeine as isocodeine is four times stronger than codeine. The other isomers of codeine are allocodeine and pseudocodeine and they are active drugs as is heterocodeine, which is estimated to be up to 108 times as potent as codeine. ^[2]

References

^ Parker, KA; Fokas, D (2006). "Enantioselective synthesis of (−)-dihydrocodeinone: A short formal synthesis of (−)-morphine". The Journal of Organic Chemistry. 71 (2): 449–55. doi:10.1021/jo0513008. PMID 16408951.
^ Report of the Committee On Drug Addiction 1929-1941 With Monographs; National Research Council (US) New York, Washington, Philadelphia 1941, 1116 pages

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[1] Parker, KA; Fokas, D (2006). "Enantioselective synthesis of (−)-dihydrocodeinone: A short formal synthesis of (−)-morphine". The Journal of Organic Chemistry. 71 (2): 449–55. doi:10.1021/jo0513008. PMID 16408951.

[2] Report of the Committee On Drug Addiction 1929-1941 With Monographs; National Research Council (US) New York, Washington, Philadelphia 1941, 1116 pages

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