Chlornaltrexamine

Source: Wikipedia, the free encyclopedia.
Chlornaltrexamine
Names
IUPAC name
6β-[Bis(2-chloroethyl)amino]-17-(cyclopropylmethyl)-4,5α-epoxymorphinan-3,14-diol
Systematic IUPAC name
(4R,4aS,7R,7aR,12bS)-7-[Bis(2-chloroethyl)amino]-3-(cyclopropylmethyl)-2,3,4,4a,5,6,7,7a-octahydro-1H-4,12-methano[1]benzofuro[3,2-e]isoquinoline-4a,9-diol
Other names
α-Chlornaltrexamine
Identifiers
3D model (
JSmol
)
ChemSpider
  • InChI=1S/C24H32Cl2N2O3/c25-8-11-27(12-9-26)17-5-6-24(30)19-13-16-3-4-18(29)21-20(16)23(24,22(17)31-21)7-10-28(19)14-15-1-2-15/h3-4,15,17,19,22,29-30H,1-2,5-14H2/t17-,19-,22+,23+,24-/m1/s1 ☒N
    Key: OSLQQDMGHVQLCH-HRMPSQMFSA-N ☒N
  • InChI=1/C24H32Cl2N2O3/c25-8-11-27(12-9-26)17-5-6-24(30)19-13-16-3-4-18(29)21-20(16)23(24,22(17)31-21)7-10-28(19)14-15-1-2-15/h3-4,15,17,19,22,29-30H,1-2,5-14H2/t17-,19-,22+,23+,24-/m1/s1
    Key: OSLQQDMGHVQLCH-HRMPSQMFBW
  • O[C@@]13[C@]2([C@@H]5[C@H](N(CCCl)CCCl)CC3)C4=C(C=CC(O)=C4O5)C[C@H]1N(CC6CC6)CC2
Properties
C24H32Cl2N2O3
Molar mass 467.43 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Chlornaltrexamine is an irreversible mixed

μ-opioid receptors, which forms a covalent bond to the binding site. It is 22 times more potent than morphine. Its alkylating group is a bis(chloroalkyl)amino-residue similar to that of the nitrogen mustards.[1][2][3][4][5][6]

See also

References