Isocodeine

Isocodeine is an opioid research chemical related to codeine. It is an epimer of codeine that can be prepared from codeine via a Mitsunobu reaction.[1]

Isocodeine
Names
IUPAC name
(5α,6β)-3-Methoxy-17-methyl-7,8-didehydro-4,5-epoxymorphinan-6-ol
Preferred IUPAC name
(4R,4aR,7R,7aR,12bS)-9-Methoxy-3-methyl-2,3,4,4a,7,7a-hexahydro-1H-4,12-methano[1]benzofuro[3,2-e]isoquinolin-7-ol
Other names
6-Isocodeine; α-Isocodeine
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.007.366
EC Number
  • 208-101-3
PubChem CID
UNII
InChI
  • InChI=1S/C18H21NO3/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,7-9H2,1-2H3/t11-,12+,13+,17-,18-/m0/s1
    Key: OROGSEYTTFOCAN-KEMUOJQUSA-N
SMILES
  • O[C@@H]2\C=C/[C@H]5[C@@H]4N(CC[C@@]51c3c(O[C@H]12)c(OC)ccc3C4)C
Properties
Chemical formula
 C18H21NO3
Molar mass 299.370 g·mol−1
Melting point 173 to 174 °C (343 to 345 °F; 446 to 447 K)[1]
Hazards
GHS labelling:
Pictograms
Signal word
 Danger
Hazard statements
 H301, H302, H331
Precautionary statements
 P261, P264, P270, P271, P301+P310, P301+P312, P304+P340, P311, P321, P330, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Dozens of derivatives and analogs of isocodeine and the related compound isomorphine have been produced.[2] One of these, dihydroisocodeine is a pharmaceutical four times stronger than dihydrocodeine and thus six times stronger than codeine which was used more extensively in the past in Continental Europe and other locales. Other isomers of codeine include allocodeine, pseudocodeine, heterocodeine and substances with intermediate qualities such as pseudoallocodeine and formylallocodeine can be prepared in the laboratory.[3]

References
  1. Simon, Csaba; Hosztafi, Sándor; Makleit, Sándor (1991). "Application of the Mitsunobu Reaction for the Preparation of Isomorphine and Isocodeine Derivatives". Synthetic Communications. 21 (3): 407–412. doi:10.1080/00397919108016763.
  2. Report of Committee on drug addiction, 1929-1941 (Report). National Research Council (US).
  3. Report of the Committee On Drug Addiction 1929-1941 with Monographs, 1941, National Research Council (US) Washington DC, 1116 pages (Chapter 7)



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