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Synthesis and identification of pilocarpic acid diesters, prodrugs of pilocarpine.
J Pharm Biomed Anal 1991; 9(6):457-64JP

Abstract

A series of new pilocarpic acid diesters were synthesized to obtain prodrugs for pilocarpine with varying physico-chemical properties. Thermospray liquid chromatography-mass spectrometry (TSP-LC-MS), liquid chromatography with UV-detection (LC-UV) and NMR-spectroscopy were used for the identification of the synthetic products and for evaluation of their purity including typical impurities (pilocarpic acid monoester, pilocarpine). TSP-LC-MS-analysis was performed in the reversed-phase mode using acetonitrile (60%)-0.2 M ammonium acetate (40%) as mobile phase. In LC-UV-analysis chromatographic separation was carried out on a reversed-phase column and the mobile phase consisted of methanol (71%) and 0.02 M potassium dihydrogen phosphate, pH 4.5 (29%). Electron ionization-mass spectrometry (EI-MS) was used for elucidation of structures. Elemental compositions of the substances were verified with high resolution-mass spectrometry (HR-MS). The complete establishment of structures presented was based on 1H-, and COSY-NMR-spectroscopy joined to TSP-LC-MS-analysis.

Authors+Show Affiliations

Department of Pharmaceutical Chemistry, University of Kuopio, Finland.No affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

1747398

Citation

Järvinen, T, et al. "Synthesis and Identification of Pilocarpic Acid Diesters, Prodrugs of Pilocarpine." Journal of Pharmaceutical and Biomedical Analysis, vol. 9, no. 6, 1991, pp. 457-64.
Järvinen T, Auriola S, Peura P, et al. Synthesis and identification of pilocarpic acid diesters, prodrugs of pilocarpine. J Pharm Biomed Anal. 1991;9(6):457-64.
Järvinen, T., Auriola, S., Peura, P., Suhonen, P., Urtti, A., & Vepsäläinen, J. (1991). Synthesis and identification of pilocarpic acid diesters, prodrugs of pilocarpine. Journal of Pharmaceutical and Biomedical Analysis, 9(6), pp. 457-64.
Järvinen T, et al. Synthesis and Identification of Pilocarpic Acid Diesters, Prodrugs of Pilocarpine. J Pharm Biomed Anal. 1991;9(6):457-64. PubMed PMID: 1747398.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Synthesis and identification of pilocarpic acid diesters, prodrugs of pilocarpine. AU - Järvinen,T, AU - Auriola,S, AU - Peura,P, AU - Suhonen,P, AU - Urtti,A, AU - Vepsäläinen,J, PY - 1991/1/1/pubmed PY - 1991/1/1/medline PY - 1991/1/1/entrez SP - 457 EP - 64 JF - Journal of pharmaceutical and biomedical analysis JO - J Pharm Biomed Anal VL - 9 IS - 6 N2 - A series of new pilocarpic acid diesters were synthesized to obtain prodrugs for pilocarpine with varying physico-chemical properties. Thermospray liquid chromatography-mass spectrometry (TSP-LC-MS), liquid chromatography with UV-detection (LC-UV) and NMR-spectroscopy were used for the identification of the synthetic products and for evaluation of their purity including typical impurities (pilocarpic acid monoester, pilocarpine). TSP-LC-MS-analysis was performed in the reversed-phase mode using acetonitrile (60%)-0.2 M ammonium acetate (40%) as mobile phase. In LC-UV-analysis chromatographic separation was carried out on a reversed-phase column and the mobile phase consisted of methanol (71%) and 0.02 M potassium dihydrogen phosphate, pH 4.5 (29%). Electron ionization-mass spectrometry (EI-MS) was used for elucidation of structures. Elemental compositions of the substances were verified with high resolution-mass spectrometry (HR-MS). The complete establishment of structures presented was based on 1H-, and COSY-NMR-spectroscopy joined to TSP-LC-MS-analysis. SN - 0731-7085 UR - https://www.unboundmedicine.com/medline/citation/1747398/Synthesis_and_identification_of_pilocarpic_acid_diesters_prodrugs_of_pilocarpine_ L2 - https://linkinghub.elsevier.com/retrieve/pii/0731-7085(91)80247-7 DB - PRIME DP - Unbound Medicine ER -