CN103207242B - Method for rapidly identifying monoacetylmorphine and morphine in hair - Google Patents
Method for rapidly identifying monoacetylmorphine and morphine in hair Download PDFInfo
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Abstract
The invention provides a method for rapidly identifying monoacetylmorphine and morphine in hair. The method sequentially comprises the following steps: 1, placing hair to be detected, an extract liquid, internal standard morphine-d3 and a billiard ball in a crusher, and carrying out micro-crushing treatment; 2, centrifuging a mixture obtained after the micro-crushing treatment; and 3, taking the supernatant of the centrifuged mixture, and carrying out liquid chromatography-tandem mass spectrometry analysis of the supernatant. The method for rapidly identifying monoacetylmorphine and morphine in hair can realize the simple and rapid separation and purification of monoacetylmorphine and morphine molecules in a complex biological matrix, has the advantages of strong specificity, strong selectivity and high sensitivity, can be used for detecting a practical drug addict hair sample, and can also be used for identifying and detecting heroin addict related cases in the forensic toxicological analysis field.
Description
Technical field
The present invention relates to a kind of rapid identification method, particularly relate to and a kind ofly Crushing of Ultrafine extractive technique and Liquid Chromatography-Tandem Mass Spectrometry technology are applied in the method analyzed in hair in monoacetylmorphine and morphine.
Background technology
According to " 2010 world's drug Use Report ", it is the first that the total number of persons that poison taken the photograph by China's heroin occupies the whole world, is one of serious at present social concern.Heroin is sucked and is injected and absorbs well, can penetrate blood-brain barrier in a large number, rapid generation effect.After heroin enters human body, under the effect of hemolipase, rapid metabolization becomes 6-monoacetylmorphine, then becomes morphine at liver metabolism further and is combined with Artogicurol.The metabolic product of heroin in urine has 6-monoacetylmorphine, the normorphine (free or combination) of free morphine, morphine-3-glucuronidation, morphine-6-glucuronidation and trace, codeine, Dilauid etc.
Chinese patent CN101813675A discloses a kind of LC-MS/MS analytical approach detecting opiates in whole blood, urine, wherein liquid chromatography and mass spectrographic condition are as follows respectively: 1) chromatographic condition: mobile phase by A, B two component form, wherein component A is the water containing 2mmol/L ammonium formate and 0.05% (v/v) formic acid, B component for containing the acetonitrile of 2mmol/L ammonium formate and 0.05% (v/v) formic acid, A, B two the volume ratio of component be 90: 10; Column temperature is 45 DEG C; Flow velocity is 0.2mL/min; Sample size is 10 μ L.2) Mass Spectrometry Conditions: detection mode is multiple-reaction monitoring MRM; Scan mode is positive ion scanning; Electron spray voltage is 3200V; Atomization gas flow velocity is N
2600 L/hr; Taper hole blowback air flow velocity is N
250 L/hr; Ion source temperature is 105 DEG C; Collision gas is argon gas; Inside be designated as morphine-d3.
Chinese patent CN101493415A discloses a kind of morphine quantitative and Sparklet testing method, utilizes Surface enhanced raman spectroscopy (being called for short SERS) quantitatively to detect the method for morphine concentration.Preparation SERS active-substrate, gets AgNO
3soluble in water, be mixed with AgNO
3aqueous solution, heat, to after 78 DEG C ~ 92 DEG C, adds trisodium citrate, stirs 60 minutes simultaneously, obtains the elargol of green-yellow; High concentration silver colloid is obtained by after elargol high speed centrifugation; Aqueous morphine solution is mixed with part high concentration silver colloid and carries out Raman spectrum test, obtain morphine-elargol SERS spectrogram; Get rest high concentration elargol background and carry out Raman spectrum test, obtain elargol background SERS spectrogram.Two spectrogram computing machines are carried out the baseline correction of spectrum peak, obtain high-quality morphine SERS spectrogram; Contrast with the morphine raman spectrum strength-concentration curve of standard, draw the concentration of morphine.
When relating to the identification of heroin abuse, often because of heroin characteristic metabolic thing monoacetylmorphine, metabolism is fast in vivo, takes drugs and can not to detect monoacetylmorphine and morphine after 12 hours in urine simultaneously and cannot provide valuable information.The morphine positive of urine can come from the metabolism of heroin, also can come from and use containing the alkaloidal medicine of opiates or food.Therefore, the unique channel solving this difficult problem is by hair analysis, detects the monoacetylmorphine in hair and morphine, provides the evidence that heroin is abused.
Hair analysis easily obtains with it, easily preserve, object is stable, limit for length when detecting, can reflect the long period (some months even several years) the unique advantage such as drug use situation and be with a wide range of applications in forensic toxicology, clinical toxicology and drug-testing field.
Monoacetylmorphine, morphine are solidificated in the denatured keratin of hair, must first make it be that free state extracts again.At present the extracting method of monoacetylmorphine in hair and morphine is mainly contained to acid hydrolysis is spent the night, solvent extraction method, ultrasonic extraction, freeze grinding method etc.In recent years, owing to must not detain more than 24 hours to suspect, it is quick, accurate thus to require the qualification of drug addict.
Adopt acid hydrolysis and solvent extraction method all to need to spend the night, length consuming time, the needs detected fast can not be met.And heroin and metabolin monoacetylmorphine instability thereof, heat or long-time placement etc. are easily decomposed, thus the methyl alcohol of existing employing is ultrasonic waits hair pre-treating method, part monoacetylmorphine may be caused and be decomposed into morphine, thus have impact on the reliability of target compound qualitative results and the accuracy of quantitative result in hair.Freeze grinding technology is hair pretreatment technology newly developed in recent years, and at hair can be made in processing procedure to be in-196 DEG C all the time, the pulverization process of hair adds the contact area with solvent simultaneously, effectively improves hair Chinese traditional medicine release efficiency.But freeze grinding technology is consuming time also long, usually need 3 hours, and need time freezing to use a large amount of liquid nitrogen, cost is high.
Summary of the invention
The present invention in order to solve Problems existing in existing qualification monoacetylmorphine and morphine method, provide a kind of extract based on Crushing of Ultrafine and Liquid Chromatography-Tandem Mass Spectrometry technology express-analysis hair in the method for monoacetylmorphine and morphine.The method can easy, separation and purification monoacetylmorphine and morphine molecule from complex biological matrix rapidly, meets the qualification of forensic toxicological analysis field heroin druggers Related Cases and the needs of detection.
A kind of method of monoacetylmorphine and morphine in Rapid identification hair is provided to achieve these goals, comprises following sequential steps: step 1: by hair to be detected and extract, interior mark morphine-d3, hit pearl and be together placed in pulverize in instrument and carry out Crushing of Ultrafine process.Step 2: the potpourri obtained after Crushing of Ultrafine process is carried out centrifuging.Step 3: the supernatant liquor getting potpourri after centrifuging, carries out liquid chromatography-tandem mass spectrometry analysis to supernatant liquor.
In the above-mentioned method provided, wherein said method also comprises the de-pollution plot before to hair identification, and the process of described decontamination dye comprises embathes with methylene chloride, water and methylene chloride successively to hair.Hair is respectively generally 1 ~ 5min respectively embathing in liquid the time of embathing.
In the above-mentioned method provided, wherein said method also comprises the de-pollution plot before to hair identification, and the process of described decontamination dye comprises hair successively with the washing of sodium dodecylsulphonate, liquid detergent, water and acetone.The wash time of hair is 1 ~ 5 min.
In the above-mentioned method provided, wherein said method also comprises the de-pollution plot before to hair identification, and the process of described decontamination dye is included in hair and adds normal hexane and acetone carries out ultrasound wave process.Hair ultrasonic treatment time is 15 ~ 60s.
In the above-mentioned method provided, the time controling of wherein said Crushing of Ultrafine process is between 2 ~ 5min, and jolting frequency is 3000 ~ 8000 turns/min.
In the above-mentioned method provided, the potpourri that wherein said extract is made up of with the volume ratio of 70:30 acetonitrile and ammonium acetate/aqueous formic acid, described ammonium acetate/aqueous formic acid is made up of 20mmol/L ammonium acetate and 0.1% formic acid.
In the above-mentioned method provided, the condition that wherein said liquid chromatography-tandem mass spectrometry is analyzed is as follows:
1) liquid phase chromatogram condition: mobile phase is made up of A, B, wherein A is the buffer solution containing 20mmol/L ammonium acetate and 0.1% (v/v) formic acid, the acetonitrile that B is, the volume ratio of described A, B is 20:80 between 0 ~ 2min, be 85:15 between 2 ~ 2.5min, be 20:80 between 2.5 ~ 10min; Flow velocity: 250 μ L/min; Sample size: 5 μ L.
2) Mass Spectrometry Conditions:
Detection mode: multiple-reaction monitoring pattern/MRM; Scan mode: positive ion scan pattern/ESI+; Ion spray voltage: 5.5 kV; Collision gas nitrogen: 7 psi; Gas curtain gas: 10 psi; Atomization gas: 20 psi; Assisted gas: 40 psi; Ion source temperature: 450 DEG C; Interior mark: morphine-d3.
The method that the invention provides monoacetylmorphine and morphine in qualification hair can realize easy, separation and purification monoacetylmorphine and morphine molecule from complex biological matrix rapidly, its specificity, selectivity are strong, highly sensitive, can be applicable to the detection of actual drug addict's hair sample, be applied to qualification and the detection of forensic toxicological analysis field heroin druggers Related Cases.
Accompanying drawing explanation
Fig. 1 is the scanning electron microscope diagram of hair before Crushing of Ultrafine process.
Fig. 2 is the scanning electron microscope diagram of single hair before Crushing of Ultrafine process.
Fig. 3 is the scanning electron microscope diagram of hair after Crushing of Ultrafine process.
Fig. 4 is the scanning electron microscope diagram of single hair after Crushing of Ultrafine process.
Fig. 5 is the scanning electron microscope diagram of hair structure after Crushing of Ultrafine process.
Embodiment
The invention provides a kind of method of monoacetylmorphine and morphine in Rapid identification hair, first by hair to be detected and extract, interior mark morphine-d3, hit pearl and be together placed in pulverize in instrument and carry out Crushing of Ultrafine process; The potpourri obtained after Crushing of Ultrafine process is carried out centrifuging; Get the supernatant liquor of potpourri after centrifuging, liquid chromatography-tandem mass spectrometry analysis is carried out to supernatant liquor.
Be described further the method for monoacetylmorphine and morphine in Rapid identification hair provided by the invention by the following examples, better to understand the content of the invention, but the content of embodiment does not limit the claimed scope of the invention.
sample pretreatment
Must contaminate through washing agent and organic solvent decontamination for before Heroin Abusers hair treatment, organic solvent generally includes acetone, methyl alcohol, methylene chloride, normal hexane etc.Only use water and methyl alcohol effectively can not remove external contamination.One or more methods provided can be selected below: hair sample is respectively embathed 1 ~ 5min with 5mL methylene chloride, 5mL water, 5mL methylene chloride by (1) successively to the pre-service of hair.(2) hair sample will be got and use 10mL 0.1% sodium dodecylsulphonate (SDS), 10mL 0.1% liquid detergent, 10mL water, 10mL acetone vibration washing 1 ~ 5min successively.(3) hair sample is used respectively 1mL normal hexane, acetone ultrasound wave process 15 ~ 60s.
Pretreated hair, is cut into the segment that about 1 ~ 2mm is long, use to be identified after naturally drying.After the hair sample metal spraying before pulverizing, carry out scanning electron microscope, and record scanning electron microscope diagram.
the extraction of monoacetylmorphine and morphine
Monoacetylmorphine and morphine are solidificated in the denatured keratin of hair, must first make it be that free state extracts again.The present invention takes Crushing of Ultrafine extraction method to extract measurement monoacetylmorphine in hair and morphine.
Get the hair sample shredded, accurately take 50mg, be placed in polyacrylamide plastic tube, add the extract (potpourri that extract is made up of with the volume ratio of 70:30 acetonitrile and ammonium acetate/aqueous formic acid, wherein ammonium acetate/aqueous formic acid is made up of 20mmol/L ammonium acetate and 0.1% formic acid) 0.6mL, interior mark morphine-d3 50ng, then the glass adding 0.5 ~ 1g hits pearl, by plastic tube good seal, be placed in full-automatic cell crusher Crushing of Ultrafine.The jolting time of crusher setting, jolting frequency was 3000 ~ 8000 turns/min at 2 ~ 5min.After Crushing of Ultrafine terminates, cooling, centrifugal, get supernatant 200 μ L direct injected.After Crushing of Ultrafine, hair structure is destroyed, and the monoacetylmorphine in hair and morphine discharge.After the hair sample metal spraying after pulverizing, carry out scanning electron microscope, and record scanning electron microscope diagram.
liquid chromatography-tandem mass spectrometry is analyzed
Liquid phase chromatogram condition
Chromatographic column: Resteck Allure PFP propyl group post (100mm × 2.1mm, 5 μm), frontly connects Phenomenex guard column (4mm × 2mm).Mobile phase is made up of with acetonitrile (B) 20 mmol/L ammonium acetates and 0.1% formic acid buffer solution (A), and the volume ratio of mobile phase A and B component is 20:80 between 0 ~ 2min, is 85:15 between 2 ~ 2.5min, is 20:80 between 2.5 ~ 10min.Flow velocity is 250 μ L/min, and sample size is 5 μ L.
Tandem mass spectrum condition
Electric spray ion source (ESI), positive ion scan pattern/ESI+, adopts multiple-reaction monitoring pattern/MRM to detect.Ion spray voltage (IS): 5.5 kV; Collision gas nitrogen (CAD): 7 psi (1 psi ≈ 6.9 kPa), gas curtain gas (CUR): 10 psi; Atomization gas (GS1): 20 psi, assisted gas (GS2): 40 psi; Ion source temperature (TEM): 450 DEG C.
The mass spectrometry parameters of each compound, in table 1, selects two pairs of parent ion/daughter ions to carrying out qualitative analysis, and wherein first pair of ion pair is used for quantitative test.
Table 1 liquid chromatography-tandem mass spectrometry parameter
According to the suggestion of international hair analysis association (SOHT), monoacetylmorphine and morphine composition to be detected in Heroin Abusers hair simultaneously, and the concentration threshold of monoacetylmorphine and morphine all reaches the judge index of 0.2 ng/mg, by the result of hair analysis and These parameters being compared, judge whether suspect is Heroin Abusers thus.
embodiment 1
Paste about 100, root clip suspect hair, measure overall length 15cm, record and be placed in paper bag, preserve under room temperature.Cut root of hair portion 3 cm hair, successively with 0.1% sodium dodecylsulphonate, 0.1% liquid detergent of 10mL, the water of 10mL, acetone vibration washing 2 min of 10mL of 10 milliliters.Dry under room temperature.Hair section after cleaning is cut into the long segment of about 1 mm.Get the hair sample shredded, accurately take 50 mg, be placed in polyacrylamide plastic tube, add extract 0.6mL, interior mark morphine-d3 50ng, then the glass adding 0.5g hits pearl, by plastic tube good seal, is placed in full-automatic cell crusher Crushing of Ultrafine.Full-automatic cell crusher setup parameter is: jolting time 3min, jolting frequency 5000 turns/min.After Crushing of Ultrafine terminates, cooling, centrifugal, get supernatant 200 μ L direct injected.Sample is carried out above-mentioned liquid chromatography-tandem mass spectrometry analysis, obtains experimental data as follows: in 0 ~ 3cm hair section, detect the monoacetylmorphine of 1.23ng/mg concentration and the morphine of 0.59ng/mg concentration.
Detect monoacetylmorphine and morphine composition in suspect's hair swatch simultaneously, the mass concentration of monoacetylmorphine and morphine is 1.23ng/mg and 0.59ng/mg, and the concentration threshold meeting monoacetylmorphine and morphine in the Heroin Abusers hair of international hair analysis association suggestion is the judge index of 0.2 ng/mg.And the confirmation index that SOHT once recommended heroin to abuse is monoacetylmorphine/morphine concentration ratio is greater than 1.3.In this example, the ratio of hair monoacetylmorphine/morphine is 2.1, is greater than and confirms index 1.3.Therefore, the artificial Heroin Abusers of this suspicion can be thought.
embodiment 2
Paste about 100, root clip suspect hair, measure overall length 4.5cm, record and be placed in paper bag, preserve under room temperature.Cut root of hair portion 3cm hair, successively with 10mL 0.1% sodium dodecylsulphonate, 10mL 0.1% liquid detergent, 10mL water, 10mL acetone vibration washing 2 min.Dry under room temperature.Hair section after cleaning is cut into the long segment of about 1mm.Get the hair sample shredded, accurately take 50mg, be placed in polyacrylamide plastic tube, add extract 0.6mL, interior mark morphine-d3 50ng, then the glass adding 0.5g hits pearl, by plastic tube good seal, is placed in full-automatic cell crusher Crushing of Ultrafine.Full-automatic cell crusher setup parameter is: jolting time 3min, jolting frequency 5000 turns/min.After Crushing of Ultrafine terminates, cooling, centrifugal, get supernatant 200 μ L direct injected.Sample is carried out above-mentioned liquid chromatography-tandem mass spectrometry analysis, and obtaining experimental data is: 0 ~ 3cm hair Duan Zhongwei detects monoacetylmorphine, but checks out concentration to be the morphine of 0.17ng/mg.
In suspect's hair swatch, concentrations is the morphine composition of 0.17ng/mg, but do not detect monoacetylmorphine composition, do not meet in the Heroin Abusers hair that international hair analysis association (SOHT) advises and will detect monoacetylmorphine and morphine composition simultaneously, and the concentration threshold of monoacetylmorphine and morphine (cut-off) is the judge index of 0.2 ng/mg.Therefore judge that this suspect is not Heroin Abusers, the morphine in its hair may derive from certain and take the drug-induced containing morphine composition (as contained morphine composition in some cough mixture).
control experiment
Gather the hair of some, adopt 0.1mol/L HCl acid-hydrolysis method, methanol purification supercritical ultrasonics technology, freeze grinding method and the process of Crushing of Ultrafine extraction method respectively, and calculate the extraction ratio adopting each method to obtain, compare accordingly.
In table 2 control test, various extracting method and extracting method of the present invention compares
| Acid hydrolysis | Methyl alcohol is ultrasonic | Freeze grinding | Crushing of Ultrafine of the present invention extracts | |
| Extraction step | Loaded down with trivial details | Generally | Loaded down with trivial details | Easy |
| Extract consuming time | >16h | >16h | 2~3h | 5min |
| Monoacetylmorphine is hydrolyzed | Generally | Many | Less | Less |
| Extraction efficiency | 49~56% | 52~61% | 73~85% | 64~75% |
The rear discoveries such as 0.1mol/L HCl hydrolyse over night, methyl alcohol are ultrasonic, freeze grinding, Crushing of Ultrafine method extract monoacetylmorphine and morphine in hair extraction step, ease, consuming time, extraction efficiency are compared by above table, the extraction efficiency that Crushing of Ultrafine extracts is higher, monoacetylmorphine hydrolysis is less, extraction and analysis is the fastest, be suitable for the Rapid identification judging in real case that heroin is abused, and easy and simple to handle, cost is low.
Be described in detail specific embodiments of the invention above, but it is just as example, the present invention is not restricted to specific embodiment described above.To those skilled in the art, any equivalent modifications that the present invention is carried out and substituting also all among category of the present invention.Therefore, equalization conversion done without departing from the spirit and scope of the invention and amendment, all should contain within the scope of the invention.
Claims (9)
1. the method for monoacetylmorphine and morphine in Rapid identification hair, is characterized in that, comprise following sequential steps:
Step 1: by hair to be detected and extract, interior mark morphine-d3, hit pearl and be together placed in pulverize in instrument and carry out Crushing of Ultrafine process; The potpourri that described extract forms with the volume ratio of 70:30 for acetonitrile and ammonium acetate/aqueous formic acid, described ammonium acetate/aqueous formic acid is made up of 20mmol/L ammonium acetate and 0.1% formic acid;
Step 2: the potpourri obtained after Crushing of Ultrafine process is carried out centrifuging;
Step 3: the supernatant liquor getting potpourri after centrifuging, carries out liquid chromatography-tandem mass spectrometry analysis to supernatant liquor;
1) liquid phase chromatogram condition: mobile phase is made up of A, B, wherein A is the buffer solution containing 20mmol/L ammonium acetate and 0.1% formic acid, and B is acetonitrile, and the volume ratio of described A, B is 20:80 between 0 ~ 2min, be 85:15 between 2 ~ 2.5min, be 20:80 between 2.5 ~ 10min;
Flow velocity: 250 μ L/min;
Sample size: 5 μ L;
2) Mass Spectrometry Conditions:
Detection mode: multiple-reaction monitoring pattern/MRM;
Scan mode: positive ion scan pattern/ESI+;
Ion spray voltage: 5.5kV;
Collision gas nitrogen: 7psi;
Gas curtain gas: 10psi; Atomization gas: 20psi;
Assisted gas: 40psi;
Ion source temperature: 450 DEG C;
Interior mark: morphine-d3.
2. method according to claim 1, is characterized in that, described method also comprises the de-pollution plot before to hair identification, and the process of described decontamination dye comprises embathes with methylene chloride, water and methylene chloride successively to hair.
3. method according to claim 2, is characterized in that, described hair is respectively 1 ~ 5min respectively embathing in liquid the time of embathing.
4. method according to claim 1, is characterized in that, described method also comprises the de-pollution plot before to hair identification, and the process of described decontamination dye comprises hair successively with the washing of sodium dodecylsulphonate, liquid detergent, water and acetone.
5. method according to claim 4, is characterized in that, the wash time of described hair is 1 ~ 5min.
6. method according to claim 1, is characterized in that, described method also comprises the de-pollution plot before to hair identification, and the process of described decontamination dye is included in hair and adds normal hexane and acetone carries out ultrasound wave process.
7. method according to claim 6, is characterized in that, described hair ultrasonic treatment time is 15 ~ 60s.
8. method according to claim 1, is characterized in that, the time controling of described Crushing of Ultrafine process is between 2 ~ 5min.
9. method according to claim 1, is characterized in that, the jolting frequency of described Crushing of Ultrafine process is 3000 ~ 8000 turns/min.
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| CN104422762A (en) * | 2013-09-11 | 2015-03-18 | 杭州优玛达生物科技有限公司 | Drug testing enzyme linked immunosorbent assay kit and detection method thereof |
| CN103592400B (en) * | 2013-09-24 | 2015-07-29 | 广州正孚检测技术有限公司 | The extraction of opioid and detection method in hair |
| CN108802205A (en) * | 2017-05-02 | 2018-11-13 | 广州正孚检测技术有限公司 | The extraction of cocaines substance and detection method in hair |
| CN107449644A (en) * | 2017-07-10 | 2017-12-08 | 张红丽 | A kind of method of amphetamine and drugs such as morphine in rapid field examination hair |
| CN108287206B (en) * | 2018-03-29 | 2020-11-06 | 河北医科大学 | Method for quantitatively detecting barbiturates in hair and application |
| CN108627595B (en) * | 2018-04-24 | 2021-04-09 | 司法鉴定科学研究院 | Method for simultaneously detecting 12 alkaline drugs in hair |
| CN111562323A (en) * | 2020-05-09 | 2020-08-21 | 北京神州永安科技有限公司 | Kit for detecting drugs in hair and detection method thereof |
| CN111751537A (en) * | 2020-05-21 | 2020-10-09 | 佛山市顺德区公安局 | Test strip, device and method for detecting trace drugs |
| CN112229918A (en) * | 2020-07-09 | 2021-01-15 | 中山大学 | UPLC-MS/MS method for determining distribution of metabolites in heroin addicted rats and mice and application thereof |
| CN112903852A (en) * | 2021-01-22 | 2021-06-04 | 广州金域司法鉴定技术有限公司 | Method for detecting 10 drugs in hair |
| CN115452995B (en) * | 2022-09-23 | 2024-01-19 | 司法鉴定科学研究院 | Method for inspecting medicine in single sub-millimeter length hair |
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