CN110455849A - The quick Testing and appraisal method of ephedrine and pseudoephedrine based on NMR - Google Patents
The quick Testing and appraisal method of ephedrine and pseudoephedrine based on NMR Download PDFInfo
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- CN110455849A CN110455849A CN201910726828.8A CN201910726828A CN110455849A CN 110455849 A CN110455849 A CN 110455849A CN 201910726828 A CN201910726828 A CN 201910726828A CN 110455849 A CN110455849 A CN 110455849A
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- ephedrine
- pseudoephedrine
- nmr
- chemical shift
- deuterated methanol
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N24/00—Investigating or analyzing materials by the use of nuclear magnetic resonance, electron paramagnetic resonance or other spin effects
- G01N24/08—Investigating or analyzing materials by the use of nuclear magnetic resonance, electron paramagnetic resonance or other spin effects by using nuclear magnetic resonance
- G01N24/087—Structure determination of a chemical compound, e.g. of a biomolecule such as a protein
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Abstract
A kind of quick Testing and appraisal method of ephedrine and pseudoephedrine based on NMR selects deuterated methanol to make solvent through NMR testing standard ephedrine and pseudoephedrine and obtain1H NMR figure, the chemical shift of figure Ephedrine 1-H and pseudoephedrine 1-H are identified respectively in the two sides of deuterated methanol chemical shift to be realized by notable difference.The present invention is on the experiment basis of optimization solvent selection, and using optimal deuterated methanol as solvent, the chemical shift using 1 trumpeter's property central atom of ephedrine and pseudoephedrine has apparent difference, measures to realize to the fast qualitative identification of the two and relative amount.
Description
Technical field
It is specifically a kind of total based on nuclear-magnetism the present invention relates to a kind of illicit drugs inspection technology of chemical industry measurement field branch
The ephedrine of vibration (NMR) and the quick Testing and appraisal method of pseudoephedrine.
Background technique
Ephedrine and pseudoephedrine are a pair of of optical isomers, and structure is as follows:
The two is made in drugs processing
Manufacture ice the direct material of malicious crystal methamphetamine (Metamfetamine).In order to cooperate increasingly complicated the international and domestic of sternness of strike to be involved in drug traffic
The test sensitivity work of the precursor chemicals such as crime, ephedrine and pseudoephedrine should quickly be kept up with, in favor of full chain
Accurate beat drugs crime, the supervision toxogen material of total factor.
Early there is research for the analysis of ephedrine and pseudoephedrine both at home and abroad, but is mostly using infra-red sepectrometry (FT-
IR), gas chromatography-mass spectrography method (GC-MS), liquid phase chromatogram-mass spectrometry combination method (LC-MS), and use special color
Column or specifically configured mobile phase eluent are composed, or GC- is carried out to object again after using special derivatization reagent derivatization
MS, LC-MS analysis, since the two has similar physicochemical property, these methods or requirement are high, cumbersome, or
Effect is not too much ideal.
Summary of the invention
The present invention In view of the above shortcomings of the prior art, proposes a kind of ephedrine based on NMR and pseudoephedrine
Quick Testing and appraisal method, using optimal deuterated methanol as solvent, utilizes Chinese ephedra on the experiment basis of optimization solvent selection
The chemical shift of 1 trumpeter's property central atom of alkali and pseudoephedrine has apparent difference, reflects to realize to the fast qualitative of the two
The measurement of fixed and relative amount.
The present invention is achieved by the following technical solutions:
The present invention selects deuterated methanol (chemical shift δ=3.30,4.87 of solvent peak) to make solvent through NMR testing standard fiber crops
Yellow alkali and pseudoephedrine simultaneously obtain1H NMR figure, the chemical shift of figure Ephedrine 1-H and pseudoephedrine 1-H are respectively in deuterated first
The two sides of alcohol chemical shift, to realize the Rapid identification of the two by this notable difference.
The chemical shift δ of the ephedrine 1-HH1=5.10-5.13ppm, on the left side of deuterated methanol chemical shift；It is pseudo-
The chemical shift δ of ephedrine 1-HH1=4.51-4.53ppm, on the right side of deuterated methanol chemical shift.
The relative amount measurement refers to: according to No. 1 chiral centre of mixing sample Ephedrine to be measured and pseudoephedrine
The integrated value of upper H spectral peak area on NMR spectra realizes the quick relative amount measurement of object.
The ephedrine1H NMR data are as follows: 7.28~7.43ppm (m, 5H, ArH), 5.10~5.13ppm (d,
1H, CH), 3.39~3.45ppm (m, 1H, CH), 2.76ppm (s, 3H, CH3), 1.04~1.06ppm (d, 3H, CH3)；Described
Pseudoephedrine1H NMR data are as follows: 7.31~7.44ppm (m, 5H, ArH), 4.51~4.53ppm (d, 1H, CH), 3.31~
3.38ppm (m, 1H, CH), 2.71 (s, 3H, CH3), 1.07~1.09ppm (d, 3H, CH3)。
The ephedrine and pseudoephedrine13C NMR spectra essential difference is also that the chemical shift of C1 is different: ephedrine
The chemical shift δ of C1C1The chemical shift δ of=71.75ppm, pseudoephedrine C1C1=75.56ppm.
The ephedrine13C NMR data are as follows: 141.40ppm (Ar-C), 129.56ppm (Ar-C), 128.97ppm
(Ar-C), 126.98ppm (Ar-C), 71.75ppm (C1), 61.41ppm (C2), 31.47ppm (C4), 9.99ppm (C3)
The pseudoephedrine13C NMR data are as follows: 141.91ppm (Ar-C), 129.84ppm (Ar-C),
129.78ppm (Ar-C), 128.19ppm (Ar-C), 75.56ppm (C1), 61.73ppm (C2), 30.43ppm (C4), 12.59
(C3)ppm.Technical effect
Compared with prior art, the present invention leads to C and H in molecule using the difference of ephedrine and pseudoephedrine space structure
Locating chemical environment is different, therefore uses nuclear magnetic resonance apparatus, and make solvent using deuterated methanol, shows different nuclear-magnetisms
Resonate wave spectrogram1H NMR and13C NMR signal, and then realize that the inspection to the two is reflected by the holographic information of both wave spectrums
It is fixed, the difference of C and H atom chemical shift on especially No. 1 chiral centre.The method can a very convenient, succinct, intuitive, mesh
That is clear distinguishes the two.It is easy to operate, judge that conveniently method is reliable, in being involved in drug traffic for related ephedrine and pseudoephedrine
It is effective, practical, reliable in case inspection.In the relative amount detection for controlling ephedrine and pseudoephedrine in drug quality control
Also easily and fast, can be widely applied.
Detailed description of the invention
Fig. 1 is ephedrine (a) and pseudoephedrine (b)1H NMR spectra；
Fig. 2 is ephedrine (a) and pseudoephedrine (b)13C NMR spectra；
Fig. 3 is that ephedrine is based on pseudoephedrine1The relative amount of H NMR measures；
In figure: a 2:3, b 2:1；
Fig. 4 is embodiment NMR spectra
In figure: a is1H NMR, b are13C NMR。
Specific embodiment
The present embodiment, which is verified in the following manner using nuclear magnetic resonance technique method, measures sample Ephedrine and puppet fiber crops
The relative amount of yellow alkali realizes the determination of its relative amount using the size of the integral area of No. 1 chiral centre H in NMR spectra,
By two groups of contrived experiments, integral calculation is carried out to No. 1 H being connected on carbon with hydroxyl on map, it can be to the opposite of the two
Content is measured.
First group of experiment: dissolving ephedrine and pseudoephedrine with deuterated methanol according to the ratio of 2:3, measures 1H NMR,
According to the integral ratio of map, the integrated value at No. 1 peak H of ephedrine and pseudoephedrine is 2:3, consistent with the mixed proportion of beginning
(Fig. 3 a)；
Second group of experiment: dissolving ephedrine and pseudoephedrine with deuterated methanol according to the ratio of 2:1, measures 1H NMR,
According to the integral ratio of map, the integrated value at ephedrine and the peak pseudoephedrine a-H is 2:1, (figure consistent with the mixed proportion of beginning
3b)。
By the experiment of specific solvent optimization, the experiment of practical qualitative detection and relative amount measurement experiment, under conventional environment
(ambient air atmosphere is not necessarily to special experiment environment) runs the above method with the parameter of actual sample optimization, can obtain
Experimental data be: the NMR spectra of the specific sample of peak position chemical shift, and according to the specific value of peak position chemical shift determine
The ownership of target to be measured, while can realize that the opposite of target to be measured contains according to the integral area of peak position if it is mixture
Amount detection.
Compared with prior art, this method is easy to operate, and experiment condition is ambient air atmosphere, is not necessarily to special reality
Test environment；The analysis detection speed of sample is fast, easy to operate；Characteristic signal for distinguishing ephedrine and pseudoephedrine is clear；
Relative amount measures accuracy in detection height, and step is succinct.No matter from it is qualitative or from relative amount measure angle, the technology is significantly
Optimize conventional case checking procedure, is conducive to quick Testing and appraisal.
Above-mentioned specific implementation can by those skilled in the art under the premise of without departing substantially from the principle of the invention and objective with difference
Mode carry out local directed complete set to it, protection scope of the present invention is subject to claims and not by above-mentioned specific implementation institute
Limit, each implementation within its scope is by the constraint of the present invention.
Claims (6)
1. a kind of quick Testing and appraisal method of ephedrine and pseudoephedrine based on NMR, it is characterised in that, select deuterated methanol
Make solvent through NMR testing standard ephedrine and pseudoephedrine and obtains1H NMR figure, figure Ephedrine 1-H and pseudoephedrine 1-H
Chemical shift respectively in the two sides of deuterated methanol chemical shift, thus pass through notable difference realize identification.
2. the quick Testing and appraisal method of the ephedrine and pseudoephedrine according to claim 1 based on NMR, feature
It is chemical shift δ=3.30,4.87 of the solvent peak of the deuterated methanol.
3. the quick Testing and appraisal method of the ephedrine and pseudoephedrine according to claim 1 based on NMR, feature
It is the chemical shift δ of the ephedrine 1-HH1=5.10-5.13ppm, on the left side of deuterated methanol chemical shift；False path
The chemical shift δ of alkali 1-HH1=4.51-4.53ppm, on the right side of deuterated methanol chemical shift.
4. the quick Testing and appraisal method of the ephedrine and pseudoephedrine according to claim 1 based on NMR, feature
It is, the ephedrine1H NMR data are as follows: 7.28~7.43ppm (m, 5H, ArH), 5.10~5.13ppm (d, 1H, CH),
3.39~3.45ppm (m, 1H, CH), 2.76ppm (s, 3H, CH3), 1.04~1.06ppm (d, 3H, CH3)；The False path
Alkali1H NMR data are as follows: 7.31~7.44ppm (m, 5H, ArH), 4.51~4.53ppm (d, 1H, CH), 3.31~3.38ppm
(m,1H,CH),2.71(s,3H,CH3), 1.07~1.09ppm (d, 3H, CH3)。
5. the quick Testing and appraisal method of the ephedrine and pseudoephedrine according to claim 1 based on NMR, feature
It is the chemical shift δ of the ephedrine C1C1The chemical shift δ of=71.75ppm, pseudoephedrine C1C1=75.56ppm.
6. the quick Testing and appraisal method of the ephedrine and pseudoephedrine according to claim 1 based on NMR, feature
It is, the ephedrine13C NMR data are as follows: 141.40ppm (Ar-C), 129.56ppm (Ar-C), 128.97ppm (Ar-
C),126.98ppm(Ar-C),71.75ppm(C1),61.41ppm(C2),31.47ppm(C4),9.99ppm(C3)；The puppet
Ephedrine13C NMR data are as follows: 141.91ppm (Ar-C), 129.84ppm (Ar-C), 129.78ppm (Ar-C),
128.19ppm(Ar-C),75.56ppm(C1),61.73ppm(C2),30.43ppm(C4),12.59(C3)ppm。
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5135863A (en) * | 1988-12-23 | 1992-08-04 | Syntex (U.S.A.) Inc. | Compositions and methods for determining the presence of amphetamines in a sample suspected of containing amphetamine and/or methamphetamine |
| WO2006056098A1 (en) * | 2004-11-23 | 2006-06-01 | Institute Of Pharmacology And Toxicology Academy Of Military Medical Sciences P.L.A. China | The process for resolving dl-epherine, pseudoephedrine or the derivatives thereof and the resolving agents |
| CN106543013A (en) * | 2016-11-01 | 2017-03-29 | 中国药科大学 | Method for preparing cathine and cathine |
-
2019
- 2019-08-07 CN CN201910726828.8A patent/CN110455849A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5135863A (en) * | 1988-12-23 | 1992-08-04 | Syntex (U.S.A.) Inc. | Compositions and methods for determining the presence of amphetamines in a sample suspected of containing amphetamine and/or methamphetamine |
| WO2006056098A1 (en) * | 2004-11-23 | 2006-06-01 | Institute Of Pharmacology And Toxicology Academy Of Military Medical Sciences P.L.A. China | The process for resolving dl-epherine, pseudoephedrine or the derivatives thereof and the resolving agents |
| CN106543013A (en) * | 2016-11-01 | 2017-03-29 | 中国药科大学 | Method for preparing cathine and cathine |
Non-Patent Citations (1)
| Title |
|---|
| 石鸿昌等: "麻黄碱和伪麻黄碱及其对映体的核磁共振分析", 《中国医药工业杂志》 * |
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Application publication date: 20191115 |