6,14-Endoethenotetrahydrooripavine

6,14-Endoethenotetrahydrooripavine is the central nucleus, or backbone, of a class of morphinan opioids known as the Bentley compounds and may be considered their "privileged scaffold".^[1][2] These include but are not limited to etorphine and buprenorphine. They usually have thebaine or oripavine as their precursor in their syntheses (and are thus termed "thevinols" and "orvinols", respectively).

6,14-Endoethenotetrahydrooripavine

Names
IUPAC name (4R,7S,7aR,12bR)-7-Methoxy-3-methyl-2,3,4,4a,7,7a-hexahydro-1H-4al5-4a,7-ethano-4,12-methanobenzofuro[3,2-e]isoquinolin-9-ol
Identifiers
3D model (JSmol)	Interactive image
PubChem CID	59866315
InChI InChI=1S/C20H23NO3/c1-21-10-9-20-15-12-3-4-13(22)16(15)24-17(20)19(23-2)7-5-18(20,6-8-19)14(21)11-12/h3-5,7,14,17,22H,6,8-11H2,1-2H3/t14-,17+,18?,19-,20+/m1/s1
SMILES [H][C@]12OC3=C4C(C[C@H]5N(C)CC[C@@]14[C@@]51CC[C@]2(OC)C=C1)=CC=C3O
Properties
Chemical formula	C20H23NO3
Molar mass	325.408 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

See also

• Bridged oripavine derivatives
• Acetorphine
• Thienorphine

References

1. Bentley, Kenneth W.; Hardy, Denis G. (June 1967). "Novel analgesics and molecular rearrangements in the morphine-thebaine group. III. Alcohols of the 6,14-endo-ethenotetrahydrooripavine series and derived analogs of N-allylnormorphine and -norcodeine". Journal of the American Chemical Society. 89 (13): 3281–3292. doi:10.1021/ja00989a032. ISSN 0002-7863. PMID 6042764.
2. PubChem. "6,14-Endoethenotetrahydrooripavine". pubchem.ncbi.nlm.nih.gov. Retrieved 2022-11-21.