This rapid method correlated well (R2=0.9944) with the commonly used Fast Blue B method and absorbance measurement of colored azo complex at 520nm. A more specific reagent is, Cannabinoids: Extraction Methods, Analysis, and Physicochemical Characterization, Korte et al. Peterson et al. external Several reasons have been presented on the need for efficient, fast, and sensitive methods to analyze total content of ARs in cereal grains, including the use of ARs as biomarkers of whole grain or measure of ARs in breeding programs of cereal crops. Marquis, Meyer's, Mecke, Ehrlich's, FORENSIC SCIENCES | Thin-Layer Chromatography, Encyclopedia of Analytical Science (Second Edition), ml)), which, after overspraying with hydrochloric acid, gives blue to violet colors with cannabinoids. Text 1984-06-26 DocumentStructure De Faubert Maunder used diethylamine as a mordant bleach reagent since its low boiling point allows it to be sprayed as a liquid and diffuse as a vapor through the thin-layer chromatographic support. (=A. gillilandii Reynolds) (Dring et al., 1984). Many eluent mixtures have been tested according to the reports in the literature, for example, isooctaneethyl acetateacetic acid (30:10:1, v/v/v) [70]; petroleum etherdiethyl ether (90:10) [71]; acetonemethylene chloridediisopropyl etherhexane (1:1:3:20,v/v/v/v) [72]; toluenechloroformmethanol (100:10:1,v/v/v) [73]; hexanedioxane (90:10, v/v) with double migration [74]; and hexanediethyl ether (80:20, v/v) [75]. Text 195 0 obj 2010-10-20T03:38:05+01:00 Possible values are: bibliography, abstract, description, claims, drawings, search-report, amendment ScienceDirect is a registered trademark of Elsevier B.V. ScienceDirect is a registered trademark of Elsevier B.V. Gas Chromatography Mass Spectrometry (GCMS), Analysis of other phenolics (capsaicin, gingerol, and alkylresorcinols), Recent Advances in Natural Products Analysis, ). Samples in the range of 78750nmol were successfully analyzed. external Cristina Lujan Ramirez, Maria Sandra Churio, in Studies in Natural Products Chemistry, 2019. 37165) (Aspland, 1997; http://ns.ist.cmu.ac.th/riseat/documents/a_dyes.pdf). endstream DocId Ractifs, trousses de ractifs et mthodes pour la dtection des cannabinoides With a portable reader a colorimetric quantitation may be performed. Lang Alt HyTSwoc [5laQIBHADED2mtFOE.c}088GNg9w '0 Jb Alkyl-saturated AR homologs also can be separated on Silica Gel Si60 RP-18 plates developed with methanol: water (95:5, v/v) (Rejman and Kozubek, 2004). Although not generally known as poisonous plants, some obscure references point towards the toxic properties of a few species and there is a tale of their use in meat as a hyaena bait (R.G. luggage, passports, currency, and also on the skin or the tongue. 2-Naphthylamine is known to be a human carcinogen based on sufficient proof of carcinogenicity in humans. 5-nitro-o-anisidine is widely used to produce an azo scarlet pigment. - B190 for a publication or B871/ctry for an international publication Real - B330/ctry for a priority external 37085), Fast Scarlet G Base (Azoic Diazo Component 12, C.I. http://ns.adobe.com/xap/1.0/mm/ external Fischedick et al. external 0132313 From: Handbook of Analytical Separations, 2008, Ismail Shah, Kamal Niaz, in Recent Advances in Natural Products Analysis, 2020. Total number of pages The reductive enzymes present in the body such as NaDPH-cytochrome reductase and cytochrome-450 can reduce the azo and amino groups. Correction Code - XML ST36 element: B151+B132EP - See WIPO ST50 for correction code definition V)gB0iW8#8w8_QQj@&A)/g>'K t;\ $FZUn(4T%)0C&Zi8bxEB;PAom?W= These plants from Africa and Arabia do not generally contain poisons, although a rat-like odour was recorded for Aloe ballyi Reynolds (Reynolds, 1966). Contains number and filing date of the international patent document Seq Text OPLC offered a higher efficiency, reproducibility, smaller consumption of developing eluent, and shorter analysis delay as well as the possibility of working in a semipreparative way [76]. Initially the modification was due to the unavailability of the Fast Blue BF4 reagent that was replaced by Fast Blue B ZnCl2 salt that was commercially available. The colorimetric method of detection and quantification is simple, reliable, and inexpensive. <>stream Contains an ordered list of bookmark-related data (name, number of the first page, number of 3). [<>] "F$H:R!zFQd?r9\A&GrQhE]a4zBgE#H *B=0HIpp0MxJ$D1D, VKYdE"EI2EBGt4MzNr!YK ?%_&#(0J:EAiQ(()WT6U@P+!~mDe!hh/']B/?a0nhF!X8kc&5S6lIa2cKMA!E#dV(kel }}Cq9 http://www.epo.org/patent-bibliographic-data/1.0/ IL external The colorimetric method based on diazonium salt Fast Blue B BF4 developed by Tluscik, Kozubek, and Mejbaum-Katzenellenbogen (1981) has been modified several times. G01N 33/94 - B220/date for an application or B861/date for an international application Bag Text Reagents, test kits and methods for the detection of cannabinoids - European Patent Office - EP 0132313 B1 The detection limit for opiates is 25ng of morphine equivalent. application/pdf Wieland, private communication). Later chemical modifications were driven by optimization of sample throughput and stability of the colored complex. classification-ipcr/text, or B511, B512 - See WIPO ST8 for content structure description Number of the first page of a given DocumentSection Besides these fast bases there are other bases or their salts which are also harmful and should not be used; these include Fast Yellow GC Base (http://actrav.itcilo.org/actrav-english/telearn/osh/ic/95512.htm [accessed 16 February 2010]), Fast Red A1 salt (http://msds.chem.ox.ac.uk/FA/fast_red_A1_salt.html [accessed 16 February 2010]), Black K salt (http://msds.chem.ox.ac.uk/FA/fast_black_k_salt.html [accessed 16 February 2010]) and Fast Red violet diazonium salt (Woods and Ellis, 1994). Korte et al. Contains number and filing date of the patent document InternationalPublication The separation of cannabinoids 9-THC, CBN, and CBD is far from an easy task due to their structural similarities. B1 The sample may consist of a powder and/or tablets found in the possession of an individual, it may originate from a much larger seizure of material, for example, a consignment being smuggled across international borders, or may be from a number of samples taken from the site of manufacture of the drug, i.e., an illicit laboratory. The most remarkable discovery of coniine alkaloids was made in aloes (Fig. Contains list of priorities (country code, publication number and date) of the patent <> Thin layer chromatography (TLC) is a suitable method for screening different kinds of samples. The Herosol (Mistral Detection Ltd., Jerusalem, Israel) field kit consists of a spray reagent and special test paper. uuid:99b8c185-1dd1-11b2-0a00-884f8c093600 external The first consists of a silica gel plate sprayed with diethylamine immediately before use and a mobile phase of xylenehexanediethylamine (25:10:1 by vol). The powders deposit on the body and also enter the body through inhalation. 194 0 obj patent C07C245/00 Reagents, test kits and methods for the detection of cannabinoids This technique works by using Oasis MAX solid phase extraction cartridges for the cleanup of sample. A longer color permanence was observed when the chromogenic reactive was sprayed after the evaporation of surplus solvent, but before total volatilization. In these cases harmful effects were due to misidentification of the plants, so that an uncommon poisonous species was mistaken for a more usual one, used previously with beneficial results. Sample preparation with Hybrid SPE-supported extraction was found to be most effective for alkyl resorcinol extraction, with recoveries of 77%82% from 100L of plasma. The within- and between-day precision values of total alkyl resorcinol content in a quality control sample, determined as the coefficients of variation, were on average 7% and 10%, respectively. Publication or Application or Priority Number - XML ST36 element: While investigating the aloe exudate compounds by TLC, a zone staining yellow with, Parry and Matambo, 1992; Parry and Wenyika, 1994, 3,3-dimethyl-4,4-diaminodiphenylmethane. Contains list of proprietors of the patent document According to EU Directive 2002/61/EC twenty-two amines are banned (Table 19.3). Since the number of individual drugs encountered in these types of investigation is relatively small, a better indication of the drug involved may be obtained by use of a more specific location reagent, such as Marquis reagent (a mixture of formaldehyde solution (1ml) with sulfuric acid (9ml)) for alkaloids related to morphine, and/or running control substances on the same plate as the unknown sample. Text Following the German ban in 1994, several other European community countries (EU member states) introduced similar regulations. In the second set of circumstances the toxicological investigation drugs are encountered after ingestion by an individual. A suspected surface (e.g. Contains title or an alternative list of titles of the patent document - XML ST36 element: B541 Where analysis of huge number of valuable samples is required, the analytical methods must be rapid, sensitive, and repeatable. Priority 1 196 0 obj Gas chromatography with MS and flame ionization detections (FID) has been used for the analysis of alkylresorcinols. The average total alkylresorcinol recovery was 9212% and it was within the reported range. Galand et al. While investigating the aloe exudate compounds by TLC, a zone staining yellow with Fast Blue B (0.5% aqueous solution) was noted in a few species. A more specific reagent is Fast blue B solution (a freshly prepared 1% solution of Fast blue B salt (diazotized o-dianisidine)), with which cannabidiol gives an orange color, cannabinol a violet color, and 9-tetrahydrocannabinol a red color. Spiro, Baruch NumberOfPages Bookmark Coniine alkaloids present in Aloe species revealed by TLC and levels of -coniceine, when present, determined by reaction with sodium nitroprusside. Thus, they may serve as a complement/alternative to commonly used methods of dietary assessment in epidemiological studies. <> A plasma sample (0.2mL) can be used without preincubation with water. 37105), Fast Red GTR Base (Azoic Diazo Component 29, C.I. Many of these chemicals are under eco-pressure (Chattopadhyay and Kumar, 2001). 199 0 obj However, GC methods provide comparatively better resolution and are commonly used for the analysis of alkylresorcinols. Various diazo components which are known to be carcinogenic and prohibited are Fast Red TR Base (Azoic Diazo Component 11, C.I. ACC 7 is also forbidden. This type of investigation is usually characterized by a large amount, in analytical terms, of material that is available for analysis; this is usually in the milligram range, but often kilograms of sample are accessible. A violet color indicates the presence of heroin. This new method had a limit of detection (1.11.8nmol/L) and limit of quantification (3.56.1nmol/L) in plasma for the different alkyl resorcinol homologues. Contains country code, publication number/date, correction code, and kind of the published Patent Bibliographic Data Schema V. 1.0 15 These may include drugs of abuse, as well as those prescribed for medicinal use and a number of other miscellaneous poisons. Date (title language) and B542 - default value depends on the value of the attribute @lang in the element ep-patentdocument endobj DocId Various diazo components which are known to be carcinogenic and prohibited are Fast Red TR Base (Azoic Diazo Component 11, C.I. Seq Bookmark 1 claims No analytical procedure is currently available for 4-aminoazobenzene. Number of pages of a given DocumentSection AMD showed higher resolution exhibiting neither diffusion nor spot stretching. Some HPLC methods have longer run times due to poor resolution between the unsaturated homologs and saturated side chains. 219 0 obj %PDF-1.4 % external uuid:ec1a2cf6-1dd1-11b2-0a00-841e42080100 They were able to separate the compounds by using silica gel TLC plates, dimethylformamide/cyclohexane as an eluent, and, Handbook of Textile and Industrial Dyeing. Therefore, these tests may be used for the detection of drugs in sweat or saliva. These alkaloids have been found in a surprising range of plants. European Patent Office - B210 for an application or B861/dnum/anum for an international application Workers engaged in diazotisation of these amines are exposed to the flying dust of these carcinogenic chemicals. During selection of an ACC and azoic diazo component care should be taken and it is advisable to consult Safety Data Sheets for the materials. 191 0 obj 1 1983-07-25 Kulawinek and Kozubek (2008) reported that the most general methods used for the determination of total AR content are based on spectrophotometry. 37270), Fast Blue BB Base (Azoic Diazo Component 20, C.I. 37255), Fast Blue B Base (Azoic Diazo Component 48, C.I. Bag Text By continuing you agree to the use of cookies. 1991-09-18 Senior, Janet et al The whole procedure is performed in a plastic pouch by visual inspection. Table 1. Contains abstract or an ordered list of abstracts of the patent document - XML ST36 element: The micro-colorimetric method has been reported for quantitative determination of ARs in plant material (Tucik et al., 1981). Advances in HPLC that allow higher back pressure (>1000bar) and smaller particle size columns (<3m) provide better resolution of ARs. Abstract Narcopouch (ODV Inc., Paris, ME, USA) is a battery of color tests for the detection of opiates, amphetamines, cocaine, barbiturates, cannabinoids, and lysergic acid diethylamide (LSD) in street samples. <>stream applied TLC to verify the hashish constituents CBDA, CBD, CBN, and several isomers of THC. Plant of Aloe ruspoliana Baker, growing in Illaut, N. Kenya (photo: P. Brandham). A number of the tablets that are encountered during the examination of illicit drugs contain the same active ingredients as the drug powders described above. http://www.epo.org/patent-bibliographic-data/1.0/ <> N')].uJr Later a hospital survey of poisoning by herbal remedies added another species, A. christianii Reynolds to the hazardous list (Nyazema, 1984). This was followed by more observations on the toxic nature of these species (Parry and Matambo, 1992; Parry and Wenyika, 1994). Inventor In toxicological cases the compounds of interest are invariably part of a complex biological matrix, such as urine, blood, or tissue, and often bound to proteins from which they must be released before analysis. external The amount of active material in a toxicology case, in contrast to the milligrams or kilograms available when illicit drugs are involved, is invariably at the nanogram per milliliter level or below. patent - B320/date for a priority TLC may be used for samples, such as stomach contents and urine, that contain the greatest amount of drugs and their metabolites, but the levels found in blood are usually low and preclude the use of TLC. 1983-06-27 Infusions of three Aloe species, A. chabaudii Schnl., A. globuligemma Pole Evans and A. ortholopha Christian & Milne-Redh., which had been drunk as a herbal medicine caused deaths in rural Africa (Drummond et al., 1975). Applicant This test uses color reactions with several reagents, e.g. Developing agents are all diazotisable amines or diamines or substituted anilines, toluidines, anisidines, azobenzenes or diphenylamines. The rapid and sensitive gas chromatography mass spectrometry (GC-MS) technique can be used for quantification of alkyl resorcinol homologues C17:0, C19:0, C21:0, C23:0, and C25:0 in the human plasma. However, the pigment on reduction will produce 2,4-diaminoanisole (4-methoxy-m-phenylene diamine), since both the azo and nitro groups of the pigment are reduced to amino groups. Provides a structure for describing bookmarks of a patent document external This last reagent is the most preferred and was shown to be the most sensitive for the visualization of ARs (Iliev et al., 2009). ARs are commonly analyzed by three different techniques, colorimetric, GCMS, and HPLC-MS. List of banned aromatic amines according to the EU Directive 2002/61/EC. used high-performance TLC (HPTLC) after a simple decarboxylation procedure to convert THCA into 9-THC by means of normal-phase HPTLC plates with an automated spotter and a densitometric and UV scanner. In drugs cases the compounds of interest may be separated relatively easily from the few other materials present, such as excipients. DocumentSection They are being suggested to be used as selective biomarkers of wheat, rye, and whole-grain intake. Many Aloe species are intensely bitter due to the presence of anthrone-C-glycosides, notably barbaloin, which give them their purgative properties and many other phenolic compounds have been noted throughout the genus (Reynolds, 1985, 2004) but none of these substances are toxic. The results obtained from these methods are usually calculated from appropriate calibration curves prepared on the basis of weight concentrations of a standard AR analog and are expressed in mg/g dry matter (DM) (Tucik et al., 1981). Contains list of representatives of the patent document (2012) developed a HPLC method for the separation of alkylresorcinols from 15 cereal grains and 90 cereal products and compared the performance of three different detectors (UV, FD, and CAED). CorrectionCode G01N 33/94 description patent document 2 Ardrey, in Encyclopedia of Analytical Science (Second Edition), 2005. EP Approximately 3050 samples can be analyzed in 1 day with this method. 1.4 In this method, preferential coupling of diazo dye Fast Blue B BF4 to alkylresorcinol particles having both free hydroxyl groups attached to the aromatic ring in the meta-position yields reddish-violet products with a maximum absorption at 520nm. 200 0 obj DocId In our lab, they turn a red color with vanillin-HCl reagent, bright-red color with p-anisaldehyde-sulfuric acid reagent, and pink to deep crimson with Fast Blue B ZnCl2 salt. The majority of the active ingredients of drug powders that are encountered in forensic examinations are basic in nature and may therefore be examined using one of the general systems described in the article on Toxicological Analysis. Landberg, Aman, and Kamal Eldin (2009) used an OasisMax solid phase extraction cartridge for sample cleanup to develop a rapid GCMS method for the quantification of alkyl resorcinols in human plasma. R.E. When analyzing the chromogenic reagent, Fast Blue BB was found to be superior to Fast Blue B [69]. Fast Blue B and RR dissolved more slowly in water and imparted a yellow background to the plate. In drugs cases the compound(s) of interest may usually be defined readily; toxicology cases may be complicated by the presence of the many naturally occurring compounds in the body and the presence of drug metabolites, which in some cases are found to the total exclusion of the parent drug. pages) - B110 for a publication or B871/dnum/pnum for an international publication Reagents, test kits and methods for the detection of cannabinoids 2010-12-06T04:11:23+01:00 Contains list of inventors of the patent document URI Reagents, test kits and methods for the detection of cannabinoids They were able to separate the compounds by using silica gel TLC plates, dimethylformamide/cyclohexane as an eluent, and Fast Blue B salt as a revealing reagent [68]. Number The improved GC-MS technique presented could be used for rapid analysis of alkylresorcinols in relatively small sample volumes (Landberg et al., 2009). The colors obtained with the Fast blue B reagent may be intensified by overspraying with sodium hydroxide or by exposing the plate to ammonia fumes. skin) is wiped with the paper, which is then sprayed with Herosol. http://www.epo.org/patent-bibliographic-data/1.0/ x- [ 0}y)7ta>jT7@t`q2&6ZL?_yxg)zLU*uSkSeO4?c. R -25 S>Vd`rn~Y&+`;A4 A9 =-tl`;~p Gp| [`L` "AYA+Cb(R, *T2B- The testing devices are simple and robust, and usually based on well-known color reactions. Provides a structure for document identification related data en Bag Text <>/PageMode/UseOutlines/Outlines 219 0 R/Metadata 194 0 R/Pages 191 0 R/OpenAction 200 0 R/StructTreeRoot 43 0 R/Type/Catalog/OutputIntents 195 0 R>> xapMM Schema Recently, Sampietro, Jimenez, Belizn, Vattuone, and Cataln (2013) developed a micro method for the quantification of 5-n-alkylresorcinols in grain and grain products. abstract/@lang and abstract/p - first abstract in the ordered list depends on the value of the attribute @lang in the element ep-patent-document internal Amines 5 and 6 are analysed indirectly via reduction to the amines 18 and 19, respectively. Present methods require larger volumes of solvent like >10mL/sample and have relatively less daily sample throughput. Coniine, conhydrinone and conhydrin were also found in some of the species (Dring et al., 1984; Nash et al., 1992) (Table 1). Real 3. Text (summarized from Dring et al., 1984; Nash et al., 1992). Maciej J. Bogusz, in Handbook of Analytical Separations, 2008. Although only a small number of species out of the c 400 known from Africa and Arabia are poisonous, this emphasizes the need for accurate taxonomy when using wild-derived plants medicinally. Use of 96 well plates made possible the extraction of 160 samples each day. The colorimetric method of detection and quantification is simple, reliable, and inexpensive. Adobe PDF Library 8.0 EP-0132313-B1-19910918 Devanand L. Luthria, K.M. used automated multiple development (AMD) and optimum performance laminar chromatography (OPLC) techniques in order to improve the results from traditional TLC for the identification and quantitation of Indian hemp components. endobj 37175), Fast Blue RR (Azoic Diazo Component 24, C.I. external The content of alkylresorcinols was estimated using calibration curve (110mg) prepared for pure rye 5-n-pentadecylresorcinol as the reference compound (Zarnowski and Suzuki, 2004). DocId Bag DocId B The colorimetric method based on diazonium salt, Tluscik, Kozubek, and Mejbaum-Katzenellenbogen (1981), Sampietro, Jimenez, Belizn, Vattuone, and Cataln (2013), Hemlock alkaloids from Socrates to poison aloes, ) but none of these substances are toxic. endobj Narcopouch (ODV Inc., Paris, ME, USA) is a battery of color tests for the detection of opiates, amphetamines, cocaine, barbiturates, cannabinoids, and lysergic acid diethylamide (LSD) in street samples. 2y.-;!KZ ^i"L0- @8(r;q7Ly&Qq4j|9 The limit of quantification and detection for the three methods were significantly different. EP0132313 In this method 5-N alkylresorcinols are detected from ground and intact whole grains using Fast Blue RR ZnCl2 to yield colored azo derivatives that were measured at 490nm with a shorter incubation time (15min). endobj Jouve S.A., EPO - Publication - KB, TaggedPDF v1.27 7 wG xR^[ochg`>b$*~ :Eb~,m,-,Y*6X[F=3Y~d tizf6~`{v.Ng#{}}jc1X6fm;'_9 r:8q:O:8uJqnv=MmR 4 Ross et al. Chromatographic separation using HPLC and GC with UV, fluorescence (FD), Coulombic array electrochemical detection (CAED), and MS detection methods has been used for the analysis of alkylresorcinols. They carried out method validation by determining the limits of quantification and detection (LOQ and LOD), the linear dynamic range, and the repeatability. CountryCode The first, the drugs investigation, is that in which the possession, illicit manufacture, and/or distribution of drugs of abuse, such as cannabis, heroin, amphetamine, and LSD, are involved. This reagent reacts with both phenols and amines, so eventually the latter was pursued leading to the isolation of -coniceine as its hydrochloride from A. sabaea Schweinf.

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