beta-Funaltrexamine
Names | |
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IUPAC name Methyl (2E)-4-{[17-(cyclopropylmethyl)-3,14-dihydroxy-4,5α-epoxymorphinan-6β-yl]amino}-4-oxobut-2-enoate | |
Systematic 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 | |
3D model (JSmol) | |
Abbreviations | β-FNA |
ChEBI | |
ChEMBL | |
ChemSpider | |
KEGG | |
PubChem CID | |
CompTox Dashboard (EPA) | |
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Properties | |
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). |
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. In addition to its μ-opioid receptor irreversible antagonism, β-FNA is an agonist of the κ-opioid receptor and produces κ-opioid-receptor-mediated analgesic effects in animals.[2][3] This has limited its usefulness and contributed to the development of methocinnamox as a functionally irreversible antagonist of the μ-opioid receptor with no agonistic actions.[2]
See also
[edit]References
[edit]- ^ 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. Bibcode:2012Natur.485..321M. doi:10.1038/nature10954. PMC 3523197. PMID 22437502.
- ^ a b Broadbear JH, Sumpter TL, Burke TF, Husbands SM, Lewis JW, Woods JH, Traynor JR (September 2000). "Methocinnamox is a potent, long-lasting, and selective antagonist of morphine-mediated antinociception in the mouse: comparison with clocinnamox, beta-funaltrexamine, and beta-chlornaltrexamine". J Pharmacol Exp Ther. 294 (3): 933–940. PMID 10945843.
- ^ Qi JA, Heyman JS, Sheldon RJ, Koslo RJ, Porreca F (March 1990). "Mu antagonist and kappa agonist properties of beta-funaltrexamine (beta-FNA) in vivo: long-lasting spinal analgesia in mice". J Pharmacol Exp Ther. 252 (3): 1006–1011. PMID 2156986.