Analytical chemistry of pentazocine metabolites produced by the greyhound Public Deposited

http://ir.library.oregonstate.edu/concern/graduate_thesis_or_dissertations/mp48sh74c

Descriptions

Attribute NameValues
Creator
Abstract or Summary
  • This thesis concerns itself mainly with analytical methods development and analytical applications in the field of drug metabolism studies. The determination of the analgesic pentazocine and its metabolites in the greyhound are studied. Pentazocine and all of its possible metabolites are isolated from the greyhound urine by a the multi-solvent extraction and XAD-2 column after enzymatic hydrolysis. The optimization of subsequently applied chromatographic separation techniques are studied, and a useful strategy for the separation of analgesics like pentazocine and its metabolites is devised. As a result, nine pentazocine metabolites were recovered from the greyhound urine and metabolic isomers were successfully separated by the HPLC assay developed. Mass spectroscopic fragmentations of trimethylsilylated pentazocine upon electron impact (EI) are described. The identification of positional isomers due to different functional group attachment to the end of the side chain is achieved by the fragmentations proposed. The EI mass spectra of nine pentazocine metabolites including three pairs of new metabolic isomers are interpreted based on the fact that the biotransformation of a drug results in structurally similar metabolites. A complete NMR assignment of pentazocine is conducted emphasizing the choice and utilization of selected 1D and 2D NMR methods to determine the molecular structure and conformation of a complex organic molecule. An NMR analysis protocol is proposed whereby a pentazocine metabolite can be characterized without a synthetic reference. A newly discovered pentazocine metabolite is identified as 8-methoxyl pentazocine by using the NMR analysis strategies devised. These results show three pairs of new metabolic isomers of pentazocine in greyhound urine. Three of the new isomers have a methoxyl group attached to the aromatic ring at the 8-position and a hydroxyl group at the 9-position. Their isomers are formed by interchanging these two groups between these two sites. It is concluded that, in addition to oxidative metabolism on the side chain observed in most other species, pentazocine has also undergone the hydroxylation and methylation of the aromatic ring in the greyhound metabolism.
Resource Type
Date Available
Date Copyright
Date Issued
Degree Level
Degree Name
Degree Field
Degree Grantor
Commencement Year
Advisor
Academic Affiliation
Non-Academic Affiliation
Subject
Rights Statement
Peer Reviewed
Language
Digitization Specifications
  • File scanned at 300 ppi (Monochrome) using Capture Perfect 3.0.82 on a Canon DR-9080C in PDF format. CVista PdfCompressor 4.0 was used for pdf compression and textual OCR.
Replaces
Additional Information
  • description.provenance : Approved for entry into archive by Patricia Black(patricia.black@oregonstate.edu) on 2013-05-08T16:05:17Z (GMT) No. of bitstreams: 1 XiaoGuang1990.pdf: 1853882 bytes, checksum: a4aa11ee724509a2a97cd682c9052034 (MD5)
  • description.provenance : Approved for entry into archive by Patricia Black(patricia.black@oregonstate.edu) on 2013-07-16T18:05:02Z (GMT) No. of bitstreams: 1 XiaoGuang1990.pdf: 1853882 bytes, checksum: a4aa11ee724509a2a97cd682c9052034 (MD5)
  • description.provenance : Submitted by Kim Stowell (ksscannerosu@gmail.com) on 2013-05-03T21:34:12Z No. of bitstreams: 1 XiaoGuang1990.pdf: 1853882 bytes, checksum: a4aa11ee724509a2a97cd682c9052034 (MD5)
  • description.provenance : Made available in DSpace on 2013-07-16T18:05:02Z (GMT). No. of bitstreams: 1 XiaoGuang1990.pdf: 1853882 bytes, checksum: a4aa11ee724509a2a97cd682c9052034 (MD5) Previous issue date: 1989-12-13

Relationships

In Administrative Set:
Last modified: 08/23/2017

Downloadable Content

Download PDF
Citations:

EndNote | Zotero | Mendeley

Items