Studies on the Metabolism of 3-O-tert.-Butylmorphine, a New Morphine Derivative, by the Rat
1. The O-dealkylation of 3-O-tert.-butylmorphine, a new derivative of morphine, has been compared to the O-dealkylation of codeine by the rat. Rats were given either 3-O-tert.-butylmorphine or codeine intraperitoneally and 24 h urine samples were collected and analysed for morphine by a quantitative...
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| Veröffentlicht in: | Xenobiotica 1971, Vol.1 (3), p.273-285 |
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| creator | Kamm, Jerome J. Bastone, Vivian B. Mohacsi, Erno Vane, Floie M. |
| description | 1. The O-dealkylation of 3-O-tert.-butylmorphine, a new derivative of morphine, has been compared to the O-dealkylation of codeine by the rat. Rats were given either 3-O-tert.-butylmorphine or codeine intraperitoneally and 24 h urine samples were collected and analysed for morphine by a quantitative gas chromatographic procedure. With codeine, about 7% of the dose was excreted as morphine. In contrast, about 0.3% of a dose of 3-O-tert.-butylmorphine was recovered from urine as morphine. These results indicate that, unlike codeine, 3-O-tert.-butylmorphine is not O-dealkylated to any appreciable extent by the rat.
2. Three metabolites of 3-O-tert.-butylmorphine have been recovered from rat urine, resolved by gas chromatography and identified by mass spectroscopy as 3-O-tert.-butylnormorphine, 3-O-(2-hydroxymethyl-2-propyl)morphine and 3-O-(2-hydroxymethyl-2-propyl)normorphine. The identities of the last two metabolites were confirmed by comparison of their mass spectra with the mass spectra of synthetic reference compounds.
3. Compared with codeine and morphine, 3-O-tert.-butylmorphine was virtually devoid of analgesic or antitussive properties, and was inactive as a morphine antagonist. |
| doi_str_mv | 10.3109/00498257109033176 |
| format | Article |
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2. Three metabolites of 3-O-tert.-butylmorphine have been recovered from rat urine, resolved by gas chromatography and identified by mass spectroscopy as 3-O-tert.-butylnormorphine, 3-O-(2-hydroxymethyl-2-propyl)morphine and 3-O-(2-hydroxymethyl-2-propyl)normorphine. The identities of the last two metabolites were confirmed by comparison of their mass spectra with the mass spectra of synthetic reference compounds.
3. Compared with codeine and morphine, 3-O-tert.-butylmorphine was virtually devoid of analgesic or antitussive properties, and was inactive as a morphine antagonist.</description><identifier>ISSN: 0049-8254</identifier><identifier>EISSN: 1366-5928</identifier><identifier>DOI: 10.3109/00498257109033176</identifier><identifier>PMID: 5153714</identifier><language>eng</language><publisher>England: Informa UK Ltd</publisher><subject>Animals ; Chromatography, Gas ; Codeine - isolation & purification ; Codeine - metabolism ; Codeine - urine ; Dealkylation ; Drug Stability ; Glucuronidase ; Hydrolysis ; Male ; Mass Spectrometry ; Mathematics ; Models, Structural ; Morphinans - isolation & purification ; Morphinans - metabolism ; Morphinans - urine ; Morphine - urine ; Oxidation-Reduction ; Rats ; Sulfatases</subject><ispartof>Xenobiotica, 1971, Vol.1 (3), p.273-285</ispartof><rights>1971 Informa UK Ltd All rights reserved: reproduction in whole or part not permitted 1971</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c316t-b7eb27f626a41d2aca146102789f1664ba0757a01301a75bdfa009b3234e31ed3</citedby><cites>FETCH-LOGICAL-c316t-b7eb27f626a41d2aca146102789f1664ba0757a01301a75bdfa009b3234e31ed3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.tandfonline.com/doi/pdf/10.3109/00498257109033176$$EPDF$$P50$$Ginformaworld$$H</linktopdf><linktohtml>$$Uhttps://www.tandfonline.com/doi/full/10.3109/00498257109033176$$EHTML$$P50$$Ginformaworld$$H</linktohtml><link.rule.ids>315,781,785,4025,27925,27926,27927,59649,59755,60438,60544,61223,61258,61404,61439</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/5153714$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Kamm, Jerome J.</creatorcontrib><creatorcontrib>Bastone, Vivian B.</creatorcontrib><creatorcontrib>Mohacsi, Erno</creatorcontrib><creatorcontrib>Vane, Floie M.</creatorcontrib><title>Studies on the Metabolism of 3-O-tert.-Butylmorphine, a New Morphine Derivative, by the Rat</title><title>Xenobiotica</title><addtitle>Xenobiotica</addtitle><description>1. The O-dealkylation of 3-O-tert.-butylmorphine, a new derivative of morphine, has been compared to the O-dealkylation of codeine by the rat. Rats were given either 3-O-tert.-butylmorphine or codeine intraperitoneally and 24 h urine samples were collected and analysed for morphine by a quantitative gas chromatographic procedure. With codeine, about 7% of the dose was excreted as morphine. In contrast, about 0.3% of a dose of 3-O-tert.-butylmorphine was recovered from urine as morphine. These results indicate that, unlike codeine, 3-O-tert.-butylmorphine is not O-dealkylated to any appreciable extent by the rat.
2. Three metabolites of 3-O-tert.-butylmorphine have been recovered from rat urine, resolved by gas chromatography and identified by mass spectroscopy as 3-O-tert.-butylnormorphine, 3-O-(2-hydroxymethyl-2-propyl)morphine and 3-O-(2-hydroxymethyl-2-propyl)normorphine. The identities of the last two metabolites were confirmed by comparison of their mass spectra with the mass spectra of synthetic reference compounds.
3. Compared with codeine and morphine, 3-O-tert.-butylmorphine was virtually devoid of analgesic or antitussive properties, and was inactive as a morphine antagonist.</description><subject>Animals</subject><subject>Chromatography, Gas</subject><subject>Codeine - isolation & purification</subject><subject>Codeine - metabolism</subject><subject>Codeine - urine</subject><subject>Dealkylation</subject><subject>Drug Stability</subject><subject>Glucuronidase</subject><subject>Hydrolysis</subject><subject>Male</subject><subject>Mass Spectrometry</subject><subject>Mathematics</subject><subject>Models, Structural</subject><subject>Morphinans - isolation & purification</subject><subject>Morphinans - metabolism</subject><subject>Morphinans - urine</subject><subject>Morphine - urine</subject><subject>Oxidation-Reduction</subject><subject>Rats</subject><subject>Sulfatases</subject><issn>0049-8254</issn><issn>1366-5928</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1971</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kE9P3DAQxS0Egi3tB-CA5BOnBjx2Ym8EF0pbQOKPVMqJQzRJJlqjJF5sB7Tfvll2hYRQOc2M3ns_jR5jeyAOFYj8SIg0n8rMjLtQCozeYBNQWidZLqebbLLUk9GQ7rAvITwKITRIuc22M8iUgXTCHu7iUFsK3PU8zohfU8TStTZ03DVcJbdJJB8Pkx9DXLSd8_OZ7ek7R35DL_x6ffOf5O0zRvs8SuXiFfQH41e21WAb6Nt67rL737_-nl0kV7fnl2enV0mlQMekNFRK02ipMYVaYoWQahDSTPMGtE5LFCYzKEAJQJOVdYNC5KWSKiUFVKtddrDizr17GijEorOhorbFntwQiikomecyHY2wMlbeheCpKebedugXBYhiWWjxodAxs7-GD2VH9Vti3eCon6x02zfOd_jifFsXERet843HvrJhif4__vhdfEbYxlmFnopHN_h-7O2T5_4BRHyT1w</recordid><startdate>1971</startdate><enddate>1971</enddate><creator>Kamm, Jerome J.</creator><creator>Bastone, Vivian B.</creator><creator>Mohacsi, Erno</creator><creator>Vane, Floie M.</creator><general>Informa UK Ltd</general><general>Taylor & Francis</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>1971</creationdate><title>Studies on the Metabolism of 3-O-tert.-Butylmorphine, a New Morphine Derivative, by the Rat</title><author>Kamm, Jerome J. ; Bastone, Vivian B. ; Mohacsi, Erno ; Vane, Floie M.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c316t-b7eb27f626a41d2aca146102789f1664ba0757a01301a75bdfa009b3234e31ed3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1971</creationdate><topic>Animals</topic><topic>Chromatography, Gas</topic><topic>Codeine - isolation & purification</topic><topic>Codeine - metabolism</topic><topic>Codeine - urine</topic><topic>Dealkylation</topic><topic>Drug Stability</topic><topic>Glucuronidase</topic><topic>Hydrolysis</topic><topic>Male</topic><topic>Mass Spectrometry</topic><topic>Mathematics</topic><topic>Models, Structural</topic><topic>Morphinans - isolation & purification</topic><topic>Morphinans - metabolism</topic><topic>Morphinans - urine</topic><topic>Morphine - urine</topic><topic>Oxidation-Reduction</topic><topic>Rats</topic><topic>Sulfatases</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Kamm, Jerome J.</creatorcontrib><creatorcontrib>Bastone, Vivian B.</creatorcontrib><creatorcontrib>Mohacsi, Erno</creatorcontrib><creatorcontrib>Vane, Floie M.</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Xenobiotica</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Kamm, Jerome J.</au><au>Bastone, Vivian B.</au><au>Mohacsi, Erno</au><au>Vane, Floie M.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Studies on the Metabolism of 3-O-tert.-Butylmorphine, a New Morphine Derivative, by the Rat</atitle><jtitle>Xenobiotica</jtitle><addtitle>Xenobiotica</addtitle><date>1971</date><risdate>1971</risdate><volume>1</volume><issue>3</issue><spage>273</spage><epage>285</epage><pages>273-285</pages><issn>0049-8254</issn><eissn>1366-5928</eissn><abstract>1. The O-dealkylation of 3-O-tert.-butylmorphine, a new derivative of morphine, has been compared to the O-dealkylation of codeine by the rat. Rats were given either 3-O-tert.-butylmorphine or codeine intraperitoneally and 24 h urine samples were collected and analysed for morphine by a quantitative gas chromatographic procedure. With codeine, about 7% of the dose was excreted as morphine. In contrast, about 0.3% of a dose of 3-O-tert.-butylmorphine was recovered from urine as morphine. These results indicate that, unlike codeine, 3-O-tert.-butylmorphine is not O-dealkylated to any appreciable extent by the rat.
2. Three metabolites of 3-O-tert.-butylmorphine have been recovered from rat urine, resolved by gas chromatography and identified by mass spectroscopy as 3-O-tert.-butylnormorphine, 3-O-(2-hydroxymethyl-2-propyl)morphine and 3-O-(2-hydroxymethyl-2-propyl)normorphine. The identities of the last two metabolites were confirmed by comparison of their mass spectra with the mass spectra of synthetic reference compounds.
3. Compared with codeine and morphine, 3-O-tert.-butylmorphine was virtually devoid of analgesic or antitussive properties, and was inactive as a morphine antagonist.</abstract><cop>England</cop><pub>Informa UK Ltd</pub><pmid>5153714</pmid><doi>10.3109/00498257109033176</doi><tpages>13</tpages></addata></record> |
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| ispartof | Xenobiotica, 1971, Vol.1 (3), p.273-285 |
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| language | eng |
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| source | MEDLINE; Taylor & Francis Medical Library - CRKN; Taylor & Francis Journals Complete |
| subjects | Animals Chromatography, Gas Codeine - isolation & purification Codeine - metabolism Codeine - urine Dealkylation Drug Stability Glucuronidase Hydrolysis Male Mass Spectrometry Mathematics Models, Structural Morphinans - isolation & purification Morphinans - metabolism Morphinans - urine Morphine - urine Oxidation-Reduction Rats Sulfatases |
| title | Studies on the Metabolism of 3-O-tert.-Butylmorphine, a New Morphine Derivative, by the Rat |
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