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Cannabis Testing R E S E a R C H P R O D U C T S & T E S T I N G S E R V I C E S

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Cannabis Testing R E S E A R C H P R O D U C T S & T E S T I N G S E R V I C E S PESTICIDES CANNABINOIDS TERPENES CANADA PESTICIDE MIX 1 MYCOTOXINS CANADA PESTICIDE MIX 2 HEAVY METALS CANADA PESTICIDE MIX 3 RESIDUAL SOLVENTS PESTICIDE MIX (95 PESTICIDE) C O N T E N T S S Y N F I N E - S T A N D A R D S . C O M the contents CANNABINOIDS STANDARD MIXTURES Standards, Metabolites & Stable Mixed standard solution of pesticides 03 Labeled Isotopes 15 as per Health Canada mandate TERPENES CANNABIS TESTING Standards and labeled isotopes of 16 SERVICES 06 over 35 commonly found terpenes ISO certified & Health Canada approved; ensuring your compliance PESTICIDES As of May 15, 2018, there are only 20 10 Offering a comprehensive portfolio of pesticides standards registered pesticides approved by PMRA for use on cannabis (marijuana) that is MYCOTOXINS produced commercially indoors. ISO certified mycotoxin solutions for 12 accurate validation and detection QUALITY YOU CAN RELY ON *APPLIED FOR P A G E 0 3 S Y N F I N E - S T A N D A R D S . C O M Cannabinoids STANDARDS, METABOLITES, INTERMEDIATES AND STABLE-LABELED INTERNAL STANDARDS A cannabinoid is one of a class of diverse chemical compounds that acts on cannabinoid receptors in cells that alter neurotransmitter release in the brain. Cannabis sativa L. has been used therapeutically for thousands of years. TETRAHYDROCANNABINOL It was well known that the plant had psychotropic effects, inducing a “high.” However, the cause of those effects was not understood until recently. Research into the effects of the plant led to the discovery of cannabinoids, which can now be separated into 3 classes: phytocannabinoids, endocannabinoids, and synthetic cannabinoids. Besides THC, the strongest psychotropically active component, cannabis contains numerous other cannabinoids and phytochemicals. Some effects of cannabis preparations are caused by the actions of cannabinoids other than THC. For THC is one of at least 113 cannabinoids instance, cannabidiol (CBD)—after THC, the identified in cannabis. It is the principal cannabinoid that occurs in the highest concentration psychoactive constituent of cannabis. in many strains of cannabis—possesses antiemetic, neuroprotective, and anti-inflammatory properties. P A G E 0 4 S Y N F I N E - S T A N D A R D S . C O M Here are some of our products relevant to cannabinoids testing & research Product Cat No. Abnormal Cannabidiol A108910 Δ9-Tetrahydro Cannabinol D296955 Cannabidiol Diacetate C175308 Cannabinoids STANDARDS, O-1821 A100803 METABOLITES, INTERMEDIATES AND (-)-Cannabidiol C175300 STABLE-LABELED (+)-Cannabidiol C175305 INTERNAL STANDARDS (-)-Desoxycannabidiol D296945 (-)-Didesoxycannabidiol D296950 6α-Hydroxycannabidiol H824805 6β-Hydroxycannabidiol H824810 1’’-Hydroxycannabidiol H824815 2’’-Hydroxycannabidiol H824820 3’’-Hydroxycannabidiol H824825 4’’-Hydroxycannabidiol H824830 5’’-Hydroxycannabidiol H824835 7-Hydroxycannabidiol H877000 Cannabidivarin C175290 Cannabielsoin C175335 6-Oxocannabidiol Diacetate O848485 STABLE LABELED Product Cat No. Desoxy THC-d9 D296957 THE CHEMISTRY OF CBD Δ9-THC-d3 T295025 Δ9-THC-d3 (100μg/ml in Methanol) KIT2040 Δ9-THC-d3 (1mg/ml in Methanol) KIT2045 (-)-Cannabidiol-d9 C175302 Cannabidiolic Acid-d9 C175332 (-)-Desoxycannabidiol-d9 D296947 7-Hydroxycannabidiol-d9 H877002 (-)-Cannabidiol-d9 KIT1442 Abnormal Cannabidiol-d9 A108912 Cannabidivarin-D5 C175292 Despite minor stylistic differences, the only true chemical Cannabigerolic Acid-d9 C175322 differences are in the highlighted regions. This break in the Cannabidiol-7-oic Acid-d11 C175375 ring structure from THC to CBD allows CBD more Cannabigerolic Acid-d9 C175377 flexibility, and the additional hydrogen (H) on the oxygen Cannabidivarin-D5 C175292 (O) allows for an additional type of bond (hydrogen bond). * Cannabigerolic Acid-d9 C175322 6α-Hydroxycannabidiol-d11 H824807 *SOURCE: HTTPS://HIGHTIMES.COM/HEALTH/CBD/THE-CHEMISTRY-OF-CBD/ FOR MORE INFORMATION, VISIT: WWW.SYNFINE-STANDARDS.COM UNIQUE AND QUALITY PRODUCTS RESEARCH SCIENTIST, MIT P A G E 0 6 S Y N F I N E - S T A N D A R D S . C O M Terpenes METABOLITES, INTERMEDIATES AND STABLE-LABELED INTERNAL STANDARDS Over 100 different terpenes have been identified in the cannabis plant, and every strain tends toward a unique terpene type and composition. Terpenes play a key role in differentiating the effects MYRCENE of various cannabis strains. Some terpenes promote relaxation and stress-relief, while others promote focus and acuity. Terpenoids, not cannabinoids, are responsible for the aroma of cannabis. Terpenoids are pharmacologically versatile: they are lipophilic, interact with cell membranes, neuronal and muscle ion channels, neurotransmitter receptors, G-protein coupled (odorant) receptors, second messenger systems and enzymes. As the most prominent cannabis terpene, scientists have figured out the myrcene makes around 65% of all terpenes in numerous cannabis strains. FOR MORE INFORMATION, VISIT: WWW.SYNFINE-STANDARDS.COM P A G E 0 7 S Y N F I N E - S T A N D A R D S . C O M CANNABIS TERPENOID BIOSYNTHESIS Geranyl pyrophosphate is formed as a precursor via the deoxyxylulose pathway in cannabis and is a parent compound to both phytocannabinoids and Terpenes terpenoids. STANDARDS, METABOLITES, d-limonene is the second most widely distributed INTERMEDIATES AND terpenoid in nature and is the precursor to other STABLE-LABELED INTERNAL STANDARDS monoterpenoids through species-specific synthetic schemes. Phytocannabinoid and cannabis terpenoid biosynthesis SOURCE: BR J PHARMACOL. 2011 AUG; 163(7): 1344–1364. FOR MORE INFORMATION, VISIT: WWW.SYNFINE-STANDARDS.COM P A G E 0 8 S Y N F I N E - S T A N D A R D S . C O M Here are some of our products relevant to terpenes testing & research Product Cat No. (−)-α-Bisabolol L375800 (±)-α-Bisabolol D480775 TeCrapnneanbeinsoids (-)-Epi-α-bisabolol A697860 STANDARDS, STANDARDS, Borneol B675420 METABMOELTIATBEOSL,ITES, INTERMIENTDEIRAMTEDSIA ATNESD AND (−)-Borneol B675545 STABLES-TLAABBLEE-LAEBDELED Camphene C165050 INTERNIANLTE SRTNALN DSTAARNDASRDS Delta 3-Carene C183450 Beta-Caryophyllene C184725 Alpha-cedrene C364863 (+)-β-Cedrene C364868 (+) Fenchol F247453 Geraniol G367000 α -Humulene H674570 Isoborneol I780070 Limonene L461753 Linalool L465950 Myrcene M875300 Nerol N390095 Terpinolene T116630 STABLE LABELED Product Cat No. Borneol-2,3.3-d3 B675422 THE CHEMISTRY OF TERPENES Geraniol-D6 G367002 (+)-Limonene-d5 L461742 (-)-Limonene-d5 L461747 β-Myrcene-d6 M875302 α-Farnesene-d6 F102427 Isopentenyl pyrophosphate (IPP) and dimethylallyl pyrophosphate (DMAPP) condense to produce geranyl pyrophosphate, precursor to all terpenes and terpenoids. *SOURCE: HTTPS://EN.WIKIPEDIA.ORG/WIKI/TERPENE FOR MORE INFORMATION, VISIT: WWW.SYNFINE-STANDARDS.COM SYNFINE-STANDARDS.COM CANNABIS USERS 70% OF CANNABIS USERS ARE AGE 25 OR OLDER 50% OF CANADIANS HAVE USED CANNABIS PESTICIDE DETECTION HEALTH CANADA MANDATE: TESTING OF CANNABIS FOR MEDICAL PURPOSES FOR UNAUTHORIZED PEST CONTROL PRODUCTS LICENCED PRODUCERS MUST ALSO ADHERE TO SECTION 66 OF THE ACMPR WHICH STATES THAT “FRESH OR DRIED MARIHUANA OR MARIHUANA PLANTS OR SEEDS MUST NOT BE TREATED WITH A PEST CONTROL PRODUCT UNLESS THE PRODUCT IS REGISTERED FOR USE ON MARIHUANA UNDER THE PEST CONTROL PRODUCTS ACT OR IS OTHERWISE AUTHORIZED FOR USE UNDER THAT ACT” HEALTH CANADA P A G E 1 0 S Y N F I N E - S T A N D A R D S . C O M Pesticides METABOLITES, INTERMEDIATES AND STABLE-LABELED INTERNAL STANDARDS According to government sources, there has been at least ten product recalls from a wide range of licensed producers over the past year. Recently, the MYCLOBUTANIL: FUNGICIDE Candian regulator has announced that it will now require all licensed producers to conduct mandatory testing of all cannabis products destined for sale for the presence of unauthorized pesticides. The Access to Cannabis for Medical Purposes Regulations makes it clear that only the 20 pesticides listed under the Pesticides Act for use on cannabis crops may be used at any point in cannabis production. Most widely used banned pesticide. Considered “slightly hazardous” by the World Health Organization, a “Bad Actor” by the Pesticide Action Network and its own label warns of nervous system problems and toxic fumes. FOR MORE INFORMATION, VISIT: WWW.SYNFINE-STANDARDS.COM P A G E 1 1 S Y N F I N E - S T A N D A R D S . C O M Here are some of our products relevant to pesticide testing & research Product Cat No. Abamectin A107000 Aldicarb A514650 PCeasntincaidbeinsoids Bifenazate B383020 STANDARDS, STANDARDS, Carbofuran C176590 METABMOELTIATBEOSL,ITES, INTERMIENTDEIRAMTEDSIA ATNESD AND Chlorpyrifos C425300 STABLES-TLAABBLEE-LAEBDELED Cyfluthrin C989510 INTERNIANLTE SRTNALN DSTAARNDASRDS Cypermethrin C183450 Daminozide D134700 Diazinon D416880 Ethoprophos E890530 Etoxazole E936600 Fenoxycarb F248870 Flonicamid F405710 Hexythiazox H298500 Malathion M111000 Metalaxyl M258740 Methiocarb M225240 STABLE LABELED Nerol N390095 Naled N245300 Product Cat No. Aldicarb-d3 A514652 For the complete list of 95 pesticides to be tested in Azoxystrobin-d4 A965152 cannabis products (as per Health Canada Mandate); please visit www.synfine-standards.com Boscalid-d4 B675852 Carbofuran-d3 C176592 Carbofuran-13C6 C176593 Cyfluthrin Phenoxy-d5 C989512 WORLD'S PESTICIDE USAGE, Daminozide-d4 D416717 BY CLASS Dichlorvos-d6 D435952 Diazinon-d10 D416882 Dimethoate-d6 D460507 Fipronil- 13C2 15N2 F342202 Fludioxonil-13C3 F427002 Imidacloprid-d4 I274992 Kresoxim-methyl-d7 K659002 Malathion-d6 M111002 Insecticides acting on target sites such as acetylcholinesterase (organophosphates and methyl carbamates), voltage-gated sodium channels (pyrethroids), nicotinic acetylcholine receptors (neonicotinoids) and ligand-gated chloride channels (macrocyclic lactones and phenylpyrazoles) account for more than 75% of total insecticides sales *SOURCE: HTTP://WWW.ESSENTIALCHEMICALINDUSTRY.ORG/MATERIALS- AND-APPLICATIONS/CROP-PROTECTION-CHEMICALS.HTML FOR MORE INFORMATION, VISIT: WWW.SYNFINE-STANDARDS.COM Mycotoxins Cannabis cultivators and processors must be aware of these potentially life- threatening chemicals 1 2 S Y N F I N E - S T A N D A R D S . C O M P A G E 1 3 S Y N F I N E - S T A N D A R D S .
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  • Table of Natural Cannabinoids

    Table of Natural Cannabinoids

    Table of Natural Cannabinoids Scientific research continues to develop and further identify individual cannabinoids in cannabis strains and how they affect symptoms of illnesses suffered by patients. The table below identifies the chemical properties of the natural cannabinoids found in the average strains of cannabis. Levels of each of these chemicals will vary with varietal strain, growing method, and plant age. Individual cannabinoids can be enhanced or eliminated depending on need. Cannabigerol- type (CBG) Cannabigerol Cannabigerol Cannabigerovarin (E)-CBG-C monomethyl (E)-CBGV-C 5 Cannabinerolic 3 ether acid A (E)-CBGM-C 5 (Z)-CBGA-C A A 5 Cannabigerolic Cannabigerolic Cannabigerovarinic acid acid A acid A A (E)-CBGA-C5 A monomethyl (E)-CBGVA-C3 A ether (E)-CBGAM- C5 A Cannabichrom ene-type (CBC) (±)- (±)- Cannabichromen (±)- Cannabivarichromene, (±)- e Cannabichrome (±)- Cannabichrome CBC-C5 nic acid A Cannabichromevarin varinic CBCA-C5 A CBCV-C3 acid A CBCVA-C3 A Cannabidiol- type (CBD) 1 | Page (−)-Cannabidiol Cannabidiol Cannabidiol-C4 (−)- Cannabidiorc CBD-C5 momomethyl CBD-C4 Cannabidivarin ol ether CBDV-C3 CBD-C1 CBDM-C5 Cannabidiolic Cannabidivarini acid c acid CBDA-C5 CBDVA-C3 Cannabinodiol- type (CBND) Cannabinodiol Cannabinodivar CBND-C5 in CBND-C3 Tetrahydrocan nabinol-type (THC) 9 9 9 Δ - Δ - Δ - Δ9- Tetrahydrocanna Tetrahydrocan Tetrahydrocannabivarin 9 Tetrahydrocan binol nabinol-C4 Δ -THCV-C3 9 9 nabiorcol Δ -THC-C5 Δ -THC-C4 9 Δ -THCO-C1 9 9 Δ -Tetrahydro- Δ9-Tetrahydro- Δ -Tetrahydro- Δ9-Tetrahydro- cannabinolic
  • Cannabinoids and Zebrafish Issue Date: 2013-05-22

    Cannabinoids and Zebrafish Issue Date: 2013-05-22

    Cover Page The handle http://hdl.handle.net/1887/20899 holds various files of this Leiden University dissertation. Author: Akhtar, Muhammad Tayyab Title: Cannabinoids and zebrafish Issue Date: 2013-05-22 Cannabinoids and zebrafish Muhammad Tayyab Akhtar Muhammad Tayyab Akhtar Cannabinoids and zebrafish ISBN: 978-94-6203-345-0 Printed by: Wöhrmann Print Service Cover art and designed by M khurshid and MT Akhtar Cannabinoids and zebrafish PROEFSCHRIFT ter verkrijging van de graad van Doctor aan de Universiteit Leiden, op gezag van Rector Magnificus prof.mr. C.J.J.M. Stolker, volgens besluit van het College voor Promoties te verdedigen op woensdag 22 mei 2013 klokke 10:00 uur door Muhammad Tayyab Akhtar geboren te Rahim Yar Khan (Pakistan) in 1984 Promotiecommissie Promotor: Prof. Dr. R. Verpoorte Co-promotores: Dr. F. van der Kooy Dr. Y.H. Choi Overige leden: Prof. Dr. S. Gibbons (The School of Pharmacy, London) Dr. F. Hollmann (TU Delft) Prof. Dr. M.K. Richardson Prof. Dr. P.G.L. Klinkhamer Prof. Dr. C.J. ten Cate To My Father and Family! CONTENTS Chapter 1 General introduction 9 Chapter 2 Biotransformation of cannabinoids 21 Chapter 3 Hydroxylation and further oxidation of Δ9-tetrahydrocannabinol by alkane-degrading bacteria. 53 Chapter 4 Hydroxylation and glycosylation of Δ9-THC by Catharanthus roseus cell suspension culture analyzed by HPLC-PDA and mass spectrometry 73 Chapter 5 Developmental effects of cannabinoids on zebrafish larvae 89 Chapter 6 Metabolic effects of cannabinoids in zebrafish (Danio rerio) embryo determined by 1H NMR metabolomics. 117 Chapter 7 Metabolic effects of carrier solvents and culture buffers in zebrafish embryos determined by 1H NMR metabolomics.