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Chlornaltrexamine 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 67025-94-9 PubChem 5486190 SMILES 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 Molecular formula C24H32Cl2N2O3 Molar mass 467.43 g/mol  Y(what is this?)  (verify) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox references 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 Chloroxymorphamine, an irreversible full agonist Naloxazone, an irreversible μ-opioid antagonist Oxymorphazone, an irreversible full agonist References ^ 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.  ^ 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.  ^ 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. doi:10.1126/science.86208. PMID 86208. http://www.sciencemag.org/cgi/pmidlookup?view=long&pmid=86208.  ^ 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. http://jpet.aspetjournals.org/cgi/pmidlookup?view=long&pmid=6162947.  ^ 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.  ^ 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.  This analgesic-related article is a stub. You can help Wikipedia by expanding it.v · d · e