Chlornaltrexamine
Chlornaltrexamine.svg
Names
IUPAC name
6-(Bis(2-chloroethyl)amino)-17-(cyclopropylmethyl)-4,5-epoxy-(5α,6β)-morphinan-3,14-diol
Preferred 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 agonist–antagonist for μ-opioid receptors, which forms a covalent bond to the active 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

  1. ^ Portoghese PS, Larson DL, Jiang JB, Takemori AE, Caruso TP (July 1978). "6β-[N,N-Bis(2-chloroethyl)amino]-17-(cyclopropylmethyl)-4,5α-epoxy-3,14-dihydroxymorphinan(chlornaltrexamine) a potent opioid receptor alkylating agent with ultralong narcotic antagonist actitivty". J. Med. Chem. 21 (7): 598–9. doi:10.1021/jm00205a002. PMID 209185.
  2. ^ Portoghese PS, Larson DL, Jiang JB, Caruso TP, Takemori AE (February 1979). "Synthesis and pharmacologic characterization of an alkylating analogue (chlornaltrexamine) of naltrexone with ultralong-lasting narcotic antagonist properties". J. Med. Chem. 22 (2): 168–73. doi:10.1021/jm00188a008. PMID 218009.
  3. ^ Caruso TP, Takemori AE, Larson DL, Portoghese PS (April 1979). "Chloroxymorphamine, and opioid receptor site-directed alkylating agent having narcotic agonist activity". Science. 204 (4390): 316–8. Bibcode:1979Sci...204..316C. doi:10.1126/science.86208. PMID 86208.
  4. ^ Caruso TP, Larson DL, Portoghese PS, Takemori AE (June 1980). "Pharmacological studies with an alkylating narcotic agonist, chloroxymorphamine, and antagonist, chlornaltrexamine". J. Pharmacol. Exp. Ther. 213 (3): 539–44. PMID 6162947.
  5. ^ Caruso TP, Larson DL, Portoghese PS, Takemori AE (December 1980). "Isolation of selective 3H-chlornaltrexamine-bound complexes, possible opioid receptor components in brains of mice". Life Sci. 27 (22): 2063–9. doi:10.1016/0024-3205(80)90485-3. PMID 6259471.
  6. ^ Sayre LM, Takemori AE, Portoghese PS (1983). "Alkylation of opioid receptor subtypes by α-chlornaltrexamine produces concurrent irreversible agonistic and irreversible antagonistic activities". J. Med. Chem. 26 (4): 503–6. doi:10.1021/jm00358a009. PMID 6300401.