CN113075343A - 一种羟胺及其盐的检测方法 - Google Patents
一种羟胺及其盐的检测方法 Download PDFInfo
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- CN113075343A CN113075343A CN202010007597.8A CN202010007597A CN113075343A CN 113075343 A CN113075343 A CN 113075343A CN 202010007597 A CN202010007597 A CN 202010007597A CN 113075343 A CN113075343 A CN 113075343A
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- hydroxylamine
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- piperidone
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- 238000001514 detection method Methods 0.000 title claims abstract description 39
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 title claims abstract description 34
- 150000003839 salts Chemical class 0.000 title claims abstract description 18
- 150000001875 compounds Chemical class 0.000 claims abstract description 17
- 239000007810 chemical reaction solvent Substances 0.000 claims abstract description 5
- 239000007788 liquid Substances 0.000 claims abstract description 5
- 239000003513 alkali Substances 0.000 claims abstract description 3
- 239000000243 solution Substances 0.000 claims description 84
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 72
- 238000000034 method Methods 0.000 claims description 46
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 30
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 22
- 238000010828 elution Methods 0.000 claims description 12
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 11
- 235000019253 formic acid Nutrition 0.000 claims description 11
- SJZKULRDWHPHGG-UHFFFAOYSA-N 1-benzylpiperidin-4-one Chemical compound C1CC(=O)CCN1CC1=CC=CC=C1 SJZKULRDWHPHGG-UHFFFAOYSA-N 0.000 claims description 10
- 238000001035 drying Methods 0.000 claims description 10
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 9
- 235000011114 ammonium hydroxide Nutrition 0.000 claims description 9
- 150000002500 ions Chemical class 0.000 claims description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 6
- 238000001819 mass spectrum Methods 0.000 claims description 5
- 239000003643 water by type Substances 0.000 claims description 5
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 4
- 238000004587 chromatography analysis Methods 0.000 claims description 4
- 238000001360 collision-induced dissociation Methods 0.000 claims description 3
- 238000004949 mass spectrometry Methods 0.000 claims description 3
- OCNWYKFGWLGNHZ-UHFFFAOYSA-N 1-butylpiperidin-4-one Chemical compound CCCCN1CCC(=O)CC1 OCNWYKFGWLGNHZ-UHFFFAOYSA-N 0.000 claims description 2
- BDVKAMAALQXGLM-UHFFFAOYSA-N 1-ethylpiperidin-4-one Chemical compound CCN1CCC(=O)CC1 BDVKAMAALQXGLM-UHFFFAOYSA-N 0.000 claims description 2
- VPGLFNOKHAIGEC-UHFFFAOYSA-N 1-phenylpiperidin-4-one Chemical compound C1CC(=O)CCN1C1=CC=CC=C1 VPGLFNOKHAIGEC-UHFFFAOYSA-N 0.000 claims description 2
- YGDZKYYCJUNORF-UHFFFAOYSA-N 1-propylpiperidin-4-one Chemical compound CCCN1CCC(=O)CC1 YGDZKYYCJUNORF-UHFFFAOYSA-N 0.000 claims description 2
- 230000005526 G1 to G0 transition Effects 0.000 claims description 2
- 239000007864 aqueous solution Substances 0.000 claims description 2
- 239000002585 base Substances 0.000 claims description 2
- 125000001072 heteroaryl group Chemical group 0.000 claims description 2
- YTJSFYQNRXLOIC-UHFFFAOYSA-N octadecylsilane Chemical compound CCCCCCCCCCCCCCCCCC[SiH3] YTJSFYQNRXLOIC-UHFFFAOYSA-N 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
- 230000035945 sensitivity Effects 0.000 abstract description 13
- 238000006243 chemical reaction Methods 0.000 abstract description 3
- 238000001212 derivatisation Methods 0.000 abstract description 3
- 239000000523 sample Substances 0.000 description 50
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 40
- 238000002360 preparation method Methods 0.000 description 40
- 238000012360 testing method Methods 0.000 description 30
- 239000012490 blank solution Substances 0.000 description 25
- 239000000047 product Substances 0.000 description 23
- 239000003153 chemical reaction reagent Substances 0.000 description 20
- 239000012071 phase Substances 0.000 description 19
- 239000012086 standard solution Substances 0.000 description 17
- 239000011550 stock solution Substances 0.000 description 16
- 238000005303 weighing Methods 0.000 description 16
- 238000004128 high performance liquid chromatography Methods 0.000 description 15
- 238000007865 diluting Methods 0.000 description 11
- 239000012088 reference solution Substances 0.000 description 10
- 239000013558 reference substance Substances 0.000 description 9
- 239000012085 test solution Substances 0.000 description 9
- 239000003814 drug Substances 0.000 description 7
- 239000012488 sample solution Substances 0.000 description 7
- 238000011084 recovery Methods 0.000 description 6
- 229910021642 ultra pure water Inorganic materials 0.000 description 6
- 239000012498 ultrapure water Substances 0.000 description 6
- BXUJVINGXQGNFD-UHFFFAOYSA-N 1-(3-ethoxy-4-methoxyphenyl)-2-methylsulfonylethanamine Chemical compound CCOC1=CC(C(N)CS(C)(=O)=O)=CC=C1OC BXUJVINGXQGNFD-UHFFFAOYSA-N 0.000 description 5
- 150000002443 hydroxylamines Chemical class 0.000 description 5
- 229940079593 drug Drugs 0.000 description 4
- 238000004255 ion exchange chromatography Methods 0.000 description 4
- 238000001209 resonance light scattering Methods 0.000 description 4
- 229960004099 azithromycin Drugs 0.000 description 3
- MQTOSJVFKKJCRP-BICOPXKESA-N azithromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)N(C)C[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 MQTOSJVFKKJCRP-BICOPXKESA-N 0.000 description 3
- 238000010790 dilution Methods 0.000 description 3
- 239000012895 dilution Substances 0.000 description 3
- 238000000589 high-performance liquid chromatography-mass spectrometry Methods 0.000 description 3
- 238000000889 atomisation Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- BQSJTQLCZDPROO-UHFFFAOYSA-N febuxostat Chemical compound C1=C(C#N)C(OCC(C)C)=CC=C1C1=NC(C)=C(C(O)=O)S1 BQSJTQLCZDPROO-UHFFFAOYSA-N 0.000 description 2
- 229960005101 febuxostat Drugs 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 230000001738 genotoxic effect Effects 0.000 description 2
- NILJXUMQIIUAFY-UHFFFAOYSA-N hydroxylamine;nitric acid Chemical compound ON.O[N+]([O-])=O NILJXUMQIIUAFY-UHFFFAOYSA-N 0.000 description 2
- 238000004811 liquid chromatography Methods 0.000 description 2
- 230000014759 maintenance of location Effects 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000011002 quantification Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 238000009210 therapy by ultrasound Methods 0.000 description 2
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 description 1
- RXZBMPWDPOLZGW-XMRMVWPWSA-N (E)-roxithromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=N/OCOCCOC)/[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 RXZBMPWDPOLZGW-XMRMVWPWSA-N 0.000 description 1
- 125000005915 C6-C14 aryl group Chemical group 0.000 description 1
- 206010064571 Gene mutation Diseases 0.000 description 1
- VSNHCAURESNICA-UHFFFAOYSA-N Hydroxyurea Chemical compound NC(=O)NO VSNHCAURESNICA-UHFFFAOYSA-N 0.000 description 1
- 239000005916 Methomyl Substances 0.000 description 1
- 108010021062 Micafungin Proteins 0.000 description 1
- 206010028400 Mutagenic effect Diseases 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000008186 active pharmaceutical agent Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 229940041181 antineoplastic drug Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 229960002626 clarithromycin Drugs 0.000 description 1
- AGOYDEPGAOXOCK-KCBOHYOISA-N clarithromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@](C)([C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)OC)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 AGOYDEPGAOXOCK-KCBOHYOISA-N 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 238000007872 degassing Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- HQVFCQRVQFYGRJ-UHFFFAOYSA-N formic acid;hydrate Chemical compound O.OC=O HQVFCQRVQFYGRJ-UHFFFAOYSA-N 0.000 description 1
- 231100000025 genetic toxicology Toxicity 0.000 description 1
- 231100000024 genotoxic Toxicity 0.000 description 1
- 229960001330 hydroxycarbamide Drugs 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- UHXUZOCRWCRNSJ-QPJJXVBHSA-N methomyl Chemical compound CNC(=O)O\N=C(/C)SC UHXUZOCRWCRNSJ-QPJJXVBHSA-N 0.000 description 1
- 229960004806 micafungin sodium Drugs 0.000 description 1
- KOOAFHGJVIVFMZ-WZPXRXMFSA-M micafungin sodium Chemical compound [Na+].C1=CC(OCCCCC)=CC=C1C1=CC(C=2C=CC(=CC=2)C(=O)N[C@@H]2C(N[C@H](C(=O)N3C[C@H](O)C[C@H]3C(=O)N[C@H](C(=O)N[C@H](C(=O)N3C[C@H](C)[C@H](O)[C@H]3C(=O)N[C@H](O)[C@H](O)C2)[C@H](O)CC(N)=O)[C@H](O)[C@@H](O)C=2C=C(OS([O-])(=O)=O)C(O)=CC=2)[C@@H](C)O)=O)=NO1 KOOAFHGJVIVFMZ-WZPXRXMFSA-M 0.000 description 1
- 230000003505 mutagenic effect Effects 0.000 description 1
- 231100000243 mutagenic effect Toxicity 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 125000005429 oxyalkyl group Chemical group 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- RAPZEAPATHNIPO-UHFFFAOYSA-N risperidone Chemical compound FC1=CC=C2C(C3CCN(CC3)CCC=3C(=O)N4CCCCC4=NC=3C)=NOC2=C1 RAPZEAPATHNIPO-UHFFFAOYSA-N 0.000 description 1
- 229960001534 risperidone Drugs 0.000 description 1
- 229960005224 roxithromycin Drugs 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 238000010183 spectrum analysis Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229960005404 sulfamethoxazole Drugs 0.000 description 1
- JLKIGFTWXXRPMT-UHFFFAOYSA-N sulphamethoxazole Chemical compound O1C(C)=CC(NS(=O)(=O)C=2C=CC(N)=CC=2)=N1 JLKIGFTWXXRPMT-UHFFFAOYSA-N 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000002604 ultrasonography Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
- G01N30/02—Column chromatography
- G01N30/88—Integrated analysis systems specially adapted therefor, not covered by a single one of the groups G01N30/04 - G01N30/86
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
- G01N30/02—Column chromatography
- G01N30/88—Integrated analysis systems specially adapted therefor, not covered by a single one of the groups G01N30/04 - G01N30/86
- G01N2030/8809—Integrated analysis systems specially adapted therefor, not covered by a single one of the groups G01N30/04 - G01N30/86 analysis specially adapted for the sample
- G01N2030/884—Integrated analysis systems specially adapted therefor, not covered by a single one of the groups G01N30/04 - G01N30/86 analysis specially adapted for the sample organic compounds
Landscapes
- Physics & Mathematics (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Analytical Chemistry (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- General Physics & Mathematics (AREA)
- Immunology (AREA)
- Pathology (AREA)
- Investigating Or Analysing Biological Materials (AREA)
- Other Investigation Or Analysis Of Materials By Electrical Means (AREA)
Abstract
Description
Claims (10)
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CN202010007597.8A CN113075343B (zh) | 2020-01-04 | 2020-01-04 | 一种羟胺及其盐的检测方法 |
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CN202010007597.8A CN113075343B (zh) | 2020-01-04 | 2020-01-04 | 一种羟胺及其盐的检测方法 |
Publications (2)
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CN113075343A true CN113075343A (zh) | 2021-07-06 |
CN113075343B CN113075343B (zh) | 2024-02-23 |
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Citations (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1993014077A1 (en) * | 1992-01-21 | 1993-07-22 | Glaxo Group Limited | Piperidineacetic acid derivatives as inhibitors of fibrinogen-dependent blood platelet aggregation |
US5334614A (en) * | 1992-05-12 | 1994-08-02 | Zeneca Ltd. | Hydroxylamine derivatives |
CN1112104A (zh) * | 1993-12-03 | 1995-11-22 | 弗·哈夫曼-拉罗切有限公司 | 乙酸衍生物 |
WO2000024740A1 (fr) * | 1998-10-22 | 2000-05-04 | Sanofi-Synthelabo | Procede de preparation de derives de 4-(2-amino-1,3-thiazol-4-yl)benzenecarboximidamide |
US20060094758A1 (en) * | 2002-06-24 | 2006-05-04 | Carl-Magnus Andersson | N-substituted piperidine derivatives as serotonin receptor agents |
US20120126107A1 (en) * | 2010-05-27 | 2012-05-24 | Bingfang Yue | Enhanced Sensitivity for Analysis of Carbonyl Containing Compounds Using Mass Spectrometry |
CN107121516A (zh) * | 2017-06-23 | 2017-09-01 | 浙江中烟工业有限责任公司 | 一种衍生‑顶空气相色谱法测定烟用水基胶中的甲醛、乙醛和丙酮的方法 |
CN107632076A (zh) * | 2017-08-10 | 2018-01-26 | 合肥利夫生物科技有限公司 | 一种反应液中羟胺残留量快速仪器分析方法 |
CN109425666A (zh) * | 2017-08-28 | 2019-03-05 | 广东东阳光药业有限公司 | 一种酰氯衍生物的lc-ms分析方法 |
CN109632979A (zh) * | 2018-11-12 | 2019-04-16 | 上海大学 | 氨基羟基脲共存时的羟胺分析方法 |
-
2020
- 2020-01-04 CN CN202010007597.8A patent/CN113075343B/zh active Active
Patent Citations (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1993014077A1 (en) * | 1992-01-21 | 1993-07-22 | Glaxo Group Limited | Piperidineacetic acid derivatives as inhibitors of fibrinogen-dependent blood platelet aggregation |
US5334614A (en) * | 1992-05-12 | 1994-08-02 | Zeneca Ltd. | Hydroxylamine derivatives |
CN1112104A (zh) * | 1993-12-03 | 1995-11-22 | 弗·哈夫曼-拉罗切有限公司 | 乙酸衍生物 |
WO2000024740A1 (fr) * | 1998-10-22 | 2000-05-04 | Sanofi-Synthelabo | Procede de preparation de derives de 4-(2-amino-1,3-thiazol-4-yl)benzenecarboximidamide |
US20060094758A1 (en) * | 2002-06-24 | 2006-05-04 | Carl-Magnus Andersson | N-substituted piperidine derivatives as serotonin receptor agents |
US20120126107A1 (en) * | 2010-05-27 | 2012-05-24 | Bingfang Yue | Enhanced Sensitivity for Analysis of Carbonyl Containing Compounds Using Mass Spectrometry |
CN107121516A (zh) * | 2017-06-23 | 2017-09-01 | 浙江中烟工业有限责任公司 | 一种衍生‑顶空气相色谱法测定烟用水基胶中的甲醛、乙醛和丙酮的方法 |
CN107632076A (zh) * | 2017-08-10 | 2018-01-26 | 合肥利夫生物科技有限公司 | 一种反应液中羟胺残留量快速仪器分析方法 |
CN109425666A (zh) * | 2017-08-28 | 2019-03-05 | 广东东阳光药业有限公司 | 一种酰氯衍生物的lc-ms分析方法 |
CN109632979A (zh) * | 2018-11-12 | 2019-04-16 | 上海大学 | 氨基羟基脲共存时的羟胺分析方法 |
Non-Patent Citations (2)
Title |
---|
YUTA MATSUOKA 等: "Rapid andconvenientdetectionofascorbicacidusingafluorescent nitroxide switch", FREE RADICALBIOLOGYANDMEDICINE, vol. 53, pages 2112 - 2118 * |
丁宏伟 等: "利培酮中盐酸羟胺的柱前衍生化-GC法测定", 中国医药工业杂志, vol. 47, no. 04, pages 454 - 456 * |
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CN113075343B (zh) | 2024-02-23 |
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