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Β-Chlornaltrexamine

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Β-Chlornaltrexamine
Names
IUPAC name 6-(Bis(2-chloroethyl)amino)- 17-(cyclopropylmethyl)- 4,5-epoxy- (5-α,6-β)- morphinan- 3,14-diol
Other names α-chlornaltrexamine
Identifiers
CAS Number
3D model (JSmol)
PubChem CID
CompTox Dashboard (EPA)
SMILES
  • O132(5(N(CCCl)CCCl)CC3)C4=C(C=CC(O)=C4O5)C1N(CC6CC6)CC2
Properties
Chemical formula C24H32Cl2N2O3
Molar mass 467.43 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

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.

See also

References

  1. Portoghese PS, Larson DL, Jiang JB, Takemori AE, Caruso TP (1978). "6β--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. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)
  2. Portoghese PS, Larson DL, Jiang JB, Caruso TP, Takemori AE (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. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)
  3. Caruso TP, Takemori AE, Larson DL, Portoghese PS (1979). "Chloroxymorphamine, and opioid receptor site-directed alkylating agent having narcotic agonist activity". Science. 204 (4390): 316–8. doi:10.1126/science.86208. PMID 86208. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)
  4. Caruso TP, Larson DL, Portoghese PS, Takemori AE (1980). "Pharmacological studies with an alkylating narcotic agonist, chloroxymorphamine, and antagonist, chlornaltrexamine". J. Pharmacol. Exp. Ther. 213 (3): 539–44. PMID 6162947. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)
  5. Caruso TP, Larson DL, Portoghese PS, Takemori AE (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. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)
  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. doi:10.1021/jm00358a009. PMID 6300401.{{cite journal}}: CS1 maint: multiple names: authors list (link)


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