beta-Funaltrexamine

β-Funaltrexamine (β-FNA) is an irreversible (covalently bonding) opioid antagonist that was used to create the first crystal structure of the μ-opioid receptor.[1] Chemically, it is a naltrexone derivative with a methyl-fumaramide group in the 6-position.

β-Funaltrexamine
Names
IUPAC name
Methyl (2E)-4-{[17-(cyclopropylmethyl)-3,14-dihydroxy-4,5α-epoxymorphinan-6β-yl]amino}-4-oxobut-2-enoate
Preferred IUPAC name
Methyl (2E)-4-{[(4R,4aS,7R,7aR,12bS)-3-(cyclopropylmethyl)-4a,9-dihydroxy-2,3,4,4a,5,6,7,7a-octahydro-1H-4,12-methano[1]benzofuro[3,2-e]isoquinolin-7-yl]amino}-4-oxobut-2-enoate
Identifiers
CAS Number
3D model (JSmol)
Abbreviations β-FNA
ChEBI
ChEMBL
ChemSpider
KEGG
PubChem CID
InChI
  • InChI=1S/C25H30N2O6/c1-32-20(30)7-6-19(29)26-16-8-9-25(31)18-12-15-4-5-17(28)22-21(15)24(25,23(16)33-22)10-11-27(18)13-14-2-3-14/h4-7,14,16,18,23,28,31H,2-3,8-13H2,1H3,(H,26,29)/b7-6+/t16-,18-,23+,24+,25-/m1/s1
    Key: PQKHESYTSKMWFP-WZJCLRDWSA-N
SMILES
  • COC(=O)/C=C/C(=O)N[C@@H]1CC[C@]2([C@H]3Cc4ccc(c5c4[C@]2([C@H]1O5)CCN3CC6CC6)O)O
Properties
Chemical formula
 C25H30N2O6
Molar mass 454.523 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

References
  1. Manglik A, Kruse AC, Kobilka TS, Thian FS, Mathiesen JM, Sunahara RK, et al. (March 2012). "Crystal structure of the µ-opioid receptor bound to a morphinan antagonist". Nature. 485 (7398): 321–6. doi:10.1038/nature10954. PMC 3523197. PMID 22437502.
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