Chlornaltrexamine
From Self-sufficiency
| Chlornaltrexamine | |
|---|---|
| File:Chlornaltrexamine.png | |
| 6-(Bis(2-chloroethyl)amino)- 17-(cyclopropylmethyl)- 4,5-epoxy- (5-alpha,6-beta)- morphinan- 3,14-diol | |
| Other names alpha-chlornaltrexamine | |
| style="background: #F8EABA; text-align: center;" colspan="2" | Identifiers | |
| CAS number | 67025-94-9 |
| PubChem | 5486190 |
| SMILES | Script error: No such module "collapsible list". |
| style="background: #F8EABA; text-align: center;" colspan="2" | Properties | |
| Molecular formula | C24H32Cl2N2O3 |
| Molar mass | 467.43 g/mol |
| 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
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- ↑ Portoghese PS, DL Larson, JB Jiang, AE Takemori, TP Caruso. 6beta-[N,N-Bis(2-chloroethyl)amino]-17-(cyclopropylmethyl)-4,5alpha-epoxy-3,14-dihydroxymorphinan(chlornaltrexamine) a potent opioid receptor alkylating agent with ultralong narcotic antagonist actitivty. Journal of Medicinal Chemistry. 21(7): 598-9, Jul 1978. http://medline.cos.com/cgi-bin/getRec?209185
- ↑ Portoghese PS, DL Larson, JB Jiang, TP Caruso, AE Takemori. Synthesis and pharmacologic characterization of an alkylating analogue (chlornaltrexamine) of naltrexone with ultralong-lasting narcotic antagonist properties. Journal of Medicinal Chemistry. 22(2): 168-73, Feb 1979. http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=Retrieve&db=pubmed&dopt=Abstract&list_uids=218009&query_hl=1
- ↑ Caruso TP, AE Takemori, DL Larson, PS Portoghese. Chloroxymorphamine, an opioid receptor site-directed alkylating agent having narcotic agonist activity. Science. 204(4390): 316-8, Apr 1979. http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=Retrieve&db=pubmed&dopt=Abstract&list_uids=86208&query_hl=1
- ↑ Caruso TP, DL Larson, PS Portoghese, AE Takemori. Pharmacological studies with an alkylating narcotic agonist, chloroxymorphamine, and antagonist, chlornaltrexamine. Journal of Pharmacology and Experimental Therapeutics. 213(3): 539-44, Jun 1980. http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=Retrieve&db=pubmed&dopt=Abstract&list_uids=6162947&query_hl=1
- ↑ Caruso TP, DL Larson, PS Portoghese, AE Takemori. Isolation of selective 3H-chlornaltrexamine-bound complexes, possible opioid receptor components in brains of mice. Life Sciences. 27(22): 2063-9, Dec 1980. http://medline.cos.com/cgi-bin/getRec?6259471
- ↑ L. M. Sayre; A. E. Takemori; P. S. Portoghese (1983). Journal of Medicinal Chemistry. 26 (4): 503. doi:10.1021/jm00358a009. Missing or empty
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