Product Information

TocrisetTM: Endocannabinoid Tocriset Cat.No. 2180 Batch No.03

Description:

A TocrisetTM consists of 3-5 key compounds that are active within a defined pharmacological area or a particular signalling pathway. Freeze dried compounds are supplied in a quantity such that the addition of 0.5 or 1 ml of solvent produces a stock concentration of 10 or 5 mM respectively. Compounds unsuitable for lyophilisation are provided pre-dissolved in DMSO.

Product Specifications:

Tocriset products are of the same purity as normal catalogue items, typically >98%. Please consult the individual certificate of analysis (CoA) for specific information relating to the purity of a particular compound. The CoA’s can be found www.tocris.com under the catalogue and batch numbers listed below:

Product Cat.No. Batch No. 1339 12 NADA 1568 4 Noladin ether 1411 5 Virodhamine 1569 1

Solubility and Storage Information:

Recommended solvents to use to dissolve the products are listed below. After addition of solvent, the solution should be vortexed. Solubility can often be encouraged by sonication or gentle warming (60°C maximum). Any compounds which may have solubility issues have been indicated in the solubility table below. The solubility data provided is accurate to the best of Tocris’ knowledge.

Information concerning product stability, particularly in solution, has rarely been reported and in most cases we can only offer a general guide. Our standard recommendations are;

SOLIDS: Provided storage is as stated on the product label and the vial is kept tightly sealed, the product can be stored for up to 6 months from date of receipt.

SOLUTIONS: We recommend that stock solutions, once prepared, are stored aliquoted in tightly sealed vials at -20° C or below and used within 1 month. Wherever possible solutions should be made up and stored on the same day. Please note that the prepared stock solutions are light sensitive and should be protected from light.

Water Ethanol DMSO Anandamide : ; ; NADA : ; ; Noladin ether : ; ; Virodhamine : ; ;

2 2

et al 3 NO

O 1 37 40 = 21.2 i H

H

22 23 C C 347.54 903 . Hanus 364.57 48

(2002) Further (2000) Synthesis and (K 1 et al et al

and full at CB

1

M). Causes sedation, μ 1569 LIGHT SENSITIVE 1411 LIGHT SENSITIVE Suhara et al (2004) Noladin ether, a putative > 3 i

tagonist activity at the CB1 -20°C -20°C 1020. Sauer 274 2794.

. )

301 ,

M μ 3662. Duncan 3662. Tocris Cat. No: Structural Molecular Weight: Structural Molecular Formula: Registry No: [287937-12-6] Storage: Tocris Cat. No: No: Cat. Tocris Structural Molecular Weight: Structural Molecular Formula: Registry No: [222723-55-9] Storage : linked receptor. Br.J.Pharmacol. 142 509.

receptors (K 2 i/o (2002) Characterization of a novel G

2 /CB et al 1 neurotransmission in rat mesenteric arteries via a Endogenous receptor mixed Endogenousthe agonist CB for y -

Sugiura et al (1999) Evidence that the cannabinoid CB1 receptor is a 2-

values are 1.9 and 1.4 0 5 C E agonist/antagonist found in higher concentrations peripherally than anandamide. Partial agonist/antagonist at CB Virodamine - ( References: Porter endocannabinoid, virodhamine, with an receptor. J.Pharmacol.Exp.Ther. characterization of the novel endocannabinoid virodhamine. 2002 Symposium on the , International Cannabinoid Research Society. biological activities of 2-arachidonoylglycerol, an endogenous , its metabolicallyand ether-linked stable analogues.Chem.Pharm.Bull. (2001) 2-Arachidonyl glyceryl ether, an endogenous agonist of the cannabinoid CB arachidonoylglycerol receptor.J.Biol.Chem. receptor. Proc.Natl.Acad.Sci.USA 98 endocannabinoid, attenuates sensory neurotransmission in the rat isolated mesenteric arterial bed via a non-CB References: import permit) a CDSA require customers (Canadian nM). Has low affinity for CB hypothermia, intestinal immobility and mild antinociception in vivo. Attenuates sensor Noladin Ether

50 2

3 et al

Sancho NO NO 37

41 1

H H

631. 22 28 C 132 C 347.54 439.64 (2002) An An (2002) De Petrocellis De (2001) Structure-activity et al

values: 0.25 and 12 817. 817. i

et al et 351 receptors respectively; (1999) Pharmacology of 2 1339 Huang LIGHT SENSITIVE 1568 Ross 8400. LIGHT SENSITIVE 9 9 -induced NF-kB activation via 429. α 52. B activation through a cannabinoid 635. 63 Pertwee κ 6 -20°C 483 -20°C and CB receptors (K 1 . Biochem.J. 2 1946. -acyl-dopamines: novel synthetic CB synthetic novel -acyl-dopamines: N 258 in vivo Tocris Cat. No: No: Cat. Tocris Structural Molecular Weight: Structural Molecular Formula: Registry No: [94421-68-8] Storage: Tocris Cat. No: No: Cat. Tocris Structural Molecular Weight: Structural Molecular Formula: Registry No: [199875-69-9] Storage : over CB and and

1 (2000) (2000)

et al et al

- Endogenous cannabinoid and vanilloid receptor

tors. Proc.Natl.Acad.Sci.USA p on of IKK. IKK. on of i Devane et al(1992) Isolation and structure of a brain constituent that binds : Bisogno = 89 and 371 nM at CB i : Potent endogenous cannabinoid and vanilloid receptor -

= 5.68 for rVR1). Also blocks TNF- i M respectively), and potent agonist at TRPV1 (VR1) receptors (EC cannabinoid receptor ligands. Curr.Med.Chem.

Anandamide import permit) a CDSA require customers (Canadian References direct inhibit relationship for the endogenous cannabinoid, anandamide, and certain of its analogues at vanilloid receptors in transfected cells and vas deferens. Br.J.Pharmacol. to the cannabinoid receptor. Science agonist (K pK receptor-independent pathway. Mol.Pharmacol. et al (2003) Anandamide inhibits nuclear factor- cannabinoid-receptor ligands and inhibitors of anandamide inactivation with with inactivation anandamide of inhibitors and ligands cannabinoid-receptor in vitro activity cannabimimetic ~ 50 nM). Metabolically stable and competitively inhibits FAAH and anandamide transport. NADA References agonist, Selective for CB (2000) Overlap between the ligand recognition properties of the anandamide anandamide the of properties recognition ligand the between Overlap (2000) with uptake of anandamide inhibitors receptor: vanilloid VR1 the and transporter Lett. FEBS activity. capsaicin-like negligible μ native and recombinant at potency with high substance capsaicin-like endogenous rece VR1 vanilloid

Material Safety Data Sheet

TocrisetTM: Endocannabinoid Tocriset Cat.No.2180 Batch No.03

1. COMPOSITION/INFORMATION ON INGREDIENTS 9. FIRST-AID MEASURES For batch specific information, please see Product Information sheet. In cases of SKIN CONTACT: Wash with copious amounts of water for at least 15 minutes. Remove contaminated clothing and shoes and wash 2. PHYSICAL AND CHEMICAL PROPERTIES before wearing. In case of eye contact, flush with copious amounts of For batch specific information, please see Product Information sheet. water for at least 15 minutes

3. HANDLING AND STORAGE In cases of INHALATION: remove to fresh air and monitor breathing. If Use in a chemical fume hood, with air supplied by an independent breathing becomes difficult, give oxygen. If breathing stops, give artificial system. Avoid inhalation, contact with eyes, skin and clothing. Avoid respiration. prolonged or repeated exposure. In cases of INGESTION: if swallowed, rinse mouth out with water, contact Material should be stored in a tightly sealed container under the storage local poison centre and call a physician. condition stated on the Product Information sheet and on the vial label. 10. FIREFIGHTING MEASURES 4. STABILITY AND REACTIVITY Extinguishing Media: Material is non-combustible. Use extinguishing Stability: Stable under normal handling conditions media appropriate to surrounding fire conditions

Conditions to avoid: Not applicable for this product Unusual Fire and Explosive Hazards: May emit toxic gases upon thermal decomposition Hazardous Combustion/Decomposition of Product: May emit toxic gasses such as carbon dioxide, and nitrogen oxide on thermal Special Fire-Fighting Procedures: Wear protective clothing to prevent decomposition. contact with skin and eyes.

5. HAZARDS IDENTIFICATION 11. ACCIDENTAL RELEASE MEASURES Exposure may cause irritation to eyes, mucous membranes, upper Wear appropriate protective clothing. Cover spillage with suitable respiratory tract and skin. absorbent material. Using non-spark tools, sweep up material and place in an appropriate container. Decontaminate spill site with 10% caustic 6. TOXICOLOGICAL IDENTIFICATION solution and ventilate area until after disposal is complete. Hold all To the best of our knowledge, the chemical, physical and toxicological material for appropriate disposal as described under DISPOSAL properties have not been fully investigated. CONDITIONS.

RTECS No: Not assigned 12. ECOLOGICAL INFORMATION Target Organs: Eyes, Respiratory system, Skin Data not yet available – treat as potentially toxic if released into the Toxicity Data: No data available environment

7. REGULATORY INFORMATION 13. DISPOSAL CONDITIONS Classification: Caution: Substance not fully tested yet. As specific country, federal, state and local environmental regulations are varied and change frequently, we recommend that you contact your local Safety Phrases: S22 – Do not breathe dust department for Health Services for information on the correct disposal of S24/25 – Avoid contact with skin and eyes this product. S36/37/39 – Wear suitable protective clothing, gloves and eye/face protection 14. TRANSPORT INFORMATION U.N. Number: Not assigned Risk Phrases: Proper Shipping Name: Not assigned IATA Class: Not assigned IATA Packing group: Not assigned 8. EXPOSURE CONTROL/PERSONAL PROTECTION Wear appropriate chemical resistant gloves, safety goggles and other 15. OTHER INFORMATION protective clothing to prevent contact with eyes and skin. Laboratory Due to the nature of this material, it must only be handled by suitably should be equipped with a safety shower and eye wash station. Avoid qualified experienced scientists in appropriately equipped and authorised prolonged or repeated exposure. Do not breathe dust. Do not get in eyes, facilities. The above information is believed to be correct but does not on skin or on clothing. Wash thoroughly after handling. purport to be all inclusive and should be used as a guide only for experienced personnel. Always consult your safety advisor and follow appropriate local and national safety legislature. The absence of warning must not, under any circumstance, be taken to mean that no hazard exists.