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    Benzoylecgonine
    Benzoylecgonine
    Information
    CAS No. 519-09-5 Price
    Catalog No.CFN00191Purity>=98%
    Molecular Weight289.33Type of CompoundAlkaloids
    FormulaC16H19NO4Physical DescriptionPowder
    Download     COA    MSDSSimilar structuralComparison (Web)
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    Biological Activity
    Description: Benzoylecgonine, validated methodologies from matrices other than blood that can be obtained in the autopsy room would be useful to the forensic toxicologist in the evaluation of a specific forensic case. Benzoylecgonine causes oxidative stress, it and oxytocin increase myometrial contractility, while atosiban and ritodrine induce myometrial relaxation.
    In vitro:
    Drug Test Anal. 2013 Aug;5(8):646-56.
    A redox proteomic investigation of oxidative stress caused by benzoylecgonine in the freshwater bivalve Dreissena polymorpha.[Pubmed: 22991338]
    Drugs of abuse and their human metabolites have been recently recognized as emerging environmental contaminants. Notwithstanding the fact that these kinds of compounds share some features with pharmaceuticals, their ecotoxicology has not yet been extensively investigated, although some of their characteristics may potentially threaten aquatic ecosystems. One of the most abundant drugs found in rivers and wastewaters is Benzoylecgonine (BE), the main metabolite of cocaine.
    METHODS AND RESULTS:
    We applied a redox proteomics approach to evaluate changes in the proteome of Dreissena polymorpha exposed to two different concentrations of BE (0.5 and 1 µg/l). Exposures were performed in vivo for a period of 14 days and the effect of oxidative stress on protein thiol and carbonyl groups in mussel gills were evaluated. One-dimensional electrophoresis did not reveal a reduction in protein thiol content but showed a significant increase of protein carbonylation at both doses tested. Then, protein profiling using two-dimensional gel electrophoresis was performed with subsequent matrix assisted laser desorption/ionization time-of-flight (MALDI-TOF) and TOF/TOF with LIFT technique and linear ion trap combined with orbitrap mass spectrometer (LTQ-Orbitrap).
    CONCLUSIONS:
    This yielded de novo protein sequences suitable for database searching. These preliminary results and protein identifications obtained suggest that BE causes oxidative stress. Oxidative modifications were detected in differing classes of proteins such as those of the cytoskeleton, energetic metabolism and stress response.
    In vivo:
    J Forensic Leg Med. 2014 Mar;23:37-43.
    Determination of cocaine and its major metabolite benzoylecgonine in several matrices obtained from deceased individuals with presumed drug consumption prior to death.[Pubmed: 24661704]
    In particular, when femoral blood is unavailable for analysis for the presence of systemic exposure to cocaine and its principal metabolite, Benzoylecgonine, validated methodologies from matrices other than blood that can be obtained in the autopsy room would be useful to the forensic toxicologist in the evaluation of a specific forensic case.
    METHODS AND RESULTS:
    To address this issue, we implemented and compared in our study the systematic evaluation of extraction, chromatographic separation, and quantification of cocaine and Benzoylecgonine in different biological matrices (right and left cardiac blood, femoral arterial and venous blood, urine, vitreous humor, cerebrospinal fluid, brain accumbens nucleus, brain ventral tegmental area, and liver).
    CONCLUSIONS:
    The methods were applied to evaluate a thanatological case using all the study matrices, showing unequal postmortem distribution of cocaine and Benzoylecgonine throughout the different matrices tested.
    Am J Forensic Med Pathol. 2015 Jun;36(2):84-7.
    The effect of chronic renal failure on the benzoylecgonine blood level: a case report.[Pubmed: 25881815]
    Chronic renal failure results in reduced elimination of a variety of substances within the blood, including numerous drugs and their metabolites.
    METHODS AND RESULTS:
    This report describes a case of a man who died in jail, after less than 48 hours of being incarcerated, wherein postmortem toxicology testing revealed a blood Benzoylecgonine level of 0.25 mg/L with no cocaine detected, suggesting possible recent cocaine use in jail.
    CONCLUSIONS:
    Autopsy and investigation revealed severe underlying cardiovascular disease and dialysis-dependent CRF, thus accounting for the elevated Benzoylecgonine levels and allaying concerns that the man obtained and used cocaine in jail.
    Analyst. 2015 Sep 21;140(18):6254-9.
    Rapid detection of cocaine, benzoylecgonine and methylecgonine in fingerprints using surface mass spectrometry.[Pubmed: 25977942]
    Latent fingerprints provide a potential route to the secure, high throughput and non-invasive detection of drugs of abuse.
    METHODS AND RESULTS:
    In this study we show for the first time that the excreted metabolites of drugs of abuse can be detected in fingerprints using ambient mass spectrometry. Fingerprints and oral fluid were taken from patients attending a drug and alcohol treatment service. Gas chromatography mass spectrometry (GC-MS) was used to test the oral fluid of patients for the presence of cocaine and Benzoylecgonine. The corresponding fingerprints were analysed using Desorption Electrospray Ionization (DESI) which operates under ambient conditions and Ion Mobility Tandem Mass Spectrometry Matrix Assisted Laser Desorption Ionization (MALDI-IMS-MS/MS) and Secondary Ion Mass Spectrometry (SIMS). The detection of cocaine, Benzoylecgonine (BZE) and methylecgonine (EME) in latent fingerprints using both DESI and MALDI showed good correlation with oral fluid testing. The sensitivity of SIMS was found to be insufficient for this application.
    CONCLUSIONS:
    These results provide exciting opportunities for the use of fingerprints as a new sampling medium for secure, non-invasive drug detection. The mass spectrometry techniques used here offer a high level of selectivity and consume only a small area of a single fingerprint, allowing repeat and high throughput analyses of a single sample.
    Benzoylecgonine Description
    Source: The herbs of Erythroxylum coca
    Solvent: Chloroform, Dichloromethane, Ethyl Acetate, DMSO, Acetone, etc.
    Storage: Providing storage is as stated on the product vial and the vial is kept tightly sealed, the product can be stored for up to 24 months(2-8C).

    Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20C. Generally, these will be useable for up to two weeks. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour.

    Need more advice on solubility, usage and handling? Please email to: service@chemfaces.com

    After receiving: The packaging of the product may have turned upside down during transportation, resulting in the natural compounds adhering to the neck or cap of the vial. take the vial out of its packaging and gently shake to let the compounds fall to the bottom of the vial. for liquid products, centrifuge at 200-500 RPM to gather the liquid at the bottom of the vial. try to avoid loss or contamination during handling.
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    Calculate Dilution Ratios(Only for Reference)
    1 mg 5 mg 10 mg 20 mg 25 mg
    1 mM 3.4563 mL 17.2813 mL 34.5626 mL 69.1252 mL 86.4065 mL
    5 mM 0.6913 mL 3.4563 mL 6.9125 mL 13.825 mL 17.2813 mL
    10 mM 0.3456 mL 1.7281 mL 3.4563 mL 6.9125 mL 8.6407 mL
    50 mM 0.0691 mL 0.3456 mL 0.6913 mL 1.3825 mL 1.7281 mL
    100 mM 0.0346 mL 0.1728 mL 0.3456 mL 0.6913 mL 0.8641 mL
    * Note: If you are in the process of experiment, it's need to make the dilution ratios of the samples. The dilution data of the sheet for your reference. Normally, it's can get a better solubility within lower of Concentrations.
    Protocol
    Animal Research:
    Clin Exp Obstet Gynecol. 2012;39(1):36-42.
    The effects of benzoylecgonine, oxytocin, ritodrine and atosiban on the contractility of myometrium. An experimental study.[Pubmed: 22675953]
    To investigate the response of pregnant and non pregnant rat myometrium to Benzoylecgonine, a cocaine metabolite, and oxytocin and to investigate the efficiency of ritodrine and atosiban to overcome the effects of Benzoylecgonine and oxytocin.
    METHODS AND RESULTS:
    Isolation of rat myometrial tissue and recording of contractile activity with isotonic muscle transducer. Benzoylecgonine and oxytocin increase myometrial contractility, while atosiban and ritodrine induce myometrial relaxation. Atosiban was able to revoke the action of oxytocin but not the action of Benzoylecgonine. Ritodrine was able to induce muscle relaxation in both oxytocin and Benzoylecgonine administration.
    CONCLUSIONS:
    Cocaine metabolites seem to act on the myometrium through different pathways compared with oxytocin. After comparing two widely used tocolytic agents: atosiban and ritodrine, it is indicated that only ritodrine, a beta2 adrenergic receptor agonist, can inhibit the action of cocaine metabolites. This finding indicates that the actions of cocaine on adrenergic mechanisms are responsible to a large part for its effects on myometrium contractility. The use of beta2 adrenergic receptor agonists seems to be preferable for the treatment of myometrial contractions induced by cocaine consumption.