Chlornaltrexamine
 | |
| Names | |
|---|---|
| IUPAC name
6-(Bis(2-chloroethyl)amino)-17-(cyclopropylmethyl)-4,5-epoxy-(5α,6β)-morphinan-3,14-diol | |
| Other names
α-Chlornaltrexamine | |
| Identifiers | |
67025-94-9  | |
| 3D model (Jmol) | Interactive image |
| ChemSpider | 4588895  |
| PubChem | 5486190 |
| |
| |
| Properties | |
| C24H32Cl2N2O3 | |
| Molar mass | 467.43 g/mol |
| Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| verify (what is ?) | |
| Infobox references | |
Chlornaltrexamine is an irreversible mixed agonist–antagonist for μ-opioid receptors, which forms a covalent bond to the active site. It is twenty-two 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.
- ↑ 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.
- ↑ 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): 503–6. doi:10.1021/jm00358a009. PMID 6300401.
This article is issued from Wikipedia - version of the 5/25/2016. The text is available under the Creative Commons Attribution/Share Alike but additional terms may apply for the media files.