Cannabinoïdes

CB2R/FAAH modulator-3 (compound 27) is a modulator targeting at CB2R and FAAH.

Stability Air Sensitive, Light Sensitive, Moisture Sensitive, Temperature Sensitive Applications N-Acetyl-4-benzoquinone Imine (NAPQI) is a toxic metabolite of Acetaminophen (A161220), an analgesic and antipyretic agent used as a pain reliever to treat headache, muscle aches, and arthritis (1,2,3). N-Acetyl-4-benzoquinone Imine can react with cysteine residues of hepatic proteins to yield Acetaminophen-cysteine (A161255) (4). References (1) Jaeschke, H., et al.: Toxicol. Sci., 89, 31 (2006) (2) O’Malley G. F., et al.: J Med Toxicol. 11, 317 (2015)(3) McGill, M. R. and Jaeschke, H. Pharm Res. 30, 2174 (2013)(4) Frey, S. M., et al.: J Med Toxicol. 11, 218 (2015)

Pregnenolone (Arthenolone) is an endogenous steroid hormone synthesized from cholesterol, used in the treatment of Alzheimer's disease.

Stability Hygroscopic Applications 3-Cysteinylacetaminophen Trifluoroacetic Acid Salt is a metabolite of Acetaminophen (A161220), an analgesic and antipyretic agent used as a pain reliever to treat headache, muscle aches, and arthritis (1,2,3). References (1) McGill, M. R. and Jaeschke, H. Pharm Res. 30, 2174 (2013)(2) Fairbrother, J.E., et al.: Anal. Profiles Drug Subs., 3, 1 (1974) (3) Hinson, J.A., et al.: Rev. Biochem. Toxicol., 2, 103 (1980)

Applications 2-(2,4-Dichlorophenylamino)-4-trifluoromethylpyrimidine-5-carboxylic Acid is used to prepare a selective CB2 receptor agonist for the treatment of inflammatory pain. References Giblin, G., et al.: J. Med. Chem., 50, 2597 (2007)

AM251: potent CB1 blocker (IC50: 8 nM), 306x CB2 selective; GPR55 activator (EC50: 39 nM).

Stability Light Sensitive Applications Cannabigerorcin acts as a potential fungicide for use as a crop protection agent. Synthetic cannabinoid. Antimicrobial. References Eisohly, H. et al : J. Pharm. Sci., 71, 1319 (2012); Tanaka, H. et al.: Forens. Sci. Int., 106, 135 (1999);

Applications Labelled 4-Methoxytetrahydropyran-4-carboxylic Acid (M265540). 4-Methoxytetrahydropyran-4-carboxylic Acid is used in the preparation of imidazole derivatives as modulators of cannabinoid receptors CB2. References Cialdai, C., et al.: Eur. J. Pharmacol., 549, 140 (2006); Fedi, V., et al.: J. Med. Chem., 50, 4793 (2007); Giuliani, S., et al.: Drugs Future, 33, 111 (2008); Meini, S., et al.: J. Pharm. Exp. Ther., 329, 486 (2009);

Applications Acetaminophen Glutathione Disodium Salt is a metabolite of Acetaminophen (A161220), an analgesic and antipyretic agent used as a pain reliever to treat headache, muscle aches, and arthritis (1,2,3,4). References (1) Chen, C., et al.: Xenobiotica, 30, 1019 (2000) (2) Ikeda, H., et al.: Biochem. J., 364, 563 (2002) (3) Aleksunes, L., et al.: Toxicol. Sci., 83, 44 (2005) (4) Elsby, R., et al.: J. Biol. Chem., 278, 22243 (2003)

Applications 5-Chloro-1-Indanone is used as a reagent in the synthesis of novel tricyclic pyrazoles as CB1 and CB2 cannabinoid receptors. Also used in he synthesis of heteroarylmethylidene cubstituted compounds as selective inhibitors of aldosterone synthase. References Ulmschneider, S. et al.: J. Med. Chem., 48, 1563 (2005); Ulmschneider, S. et al.: J. Med. Chem., 48, 1563 (2005);

Cannabidiol analytical standard provided with w/w absolute assay, to be used for quantitative titration.

Pregnenolone acetate inhibits CB1 receptors, blocking THC effects and shielding the brain from cannabis intoxication.

β-Caryophyllene ((-)-(E)-Caryophyllene) acts as an CB2 receptor agonist.

GW 833972A: selective CB2 agonist; reduces neural depolarization and citric acid cough in animals.

Applications Pyridin-3-ylacetaldehyde Bisulfate Adduct is the bisulfate form of Pyridin-3-ylacetaldehyde Sodium Salt (P991755), which is used in the synthesis of CB1/CB2 agonist that can be applied to the treatment of chronic pain. Used in the synthesis of 3-Substituted quinoline derivatives. References Cheng, Y. et al.: Bioorg. Med. Chem. Lett., 22, 1619 (2012); Maguire, M. et al.: J. Med. Chem., 37, 2129 (1994);

Applications Acetaminophen Dimer-d6 is deuterium labeled Acetaminophen Dimer (A161235). Acetaminophen Dimer is an oxidatively couple dimer of Acetaminaphen (A161220), an analgesic and antipyretic agent used as a pain reliever to treat headache, muscle aches, and arthritis (1). Acetaminophen Dimer along with other p-acetamidophenol analogs were used to determine peroxidase activities (2,3). References (1) McGill, M. R. and Jaeschke, H. Pharm Res. 30, 2174 (2013)(2) Potter, D.W. et al.: Mol. Pharmacol., 29, 155 (1986)(3) Shiga, M. et al.: Anal. Sci., 11, 195 (1995)

Stability Light Sensitive Applications Isocaryophyllene is an Z- isomer of β-Caryophyllene (C184725). β-Caryophyllene is one of the chemical compounds that contributes to the spiciness of black pepper. β-Caryophyllene was shown to selectively bind to the cannabinoid receptor type-2 (CB2) and to exert significant cannabimimetic antiinflammatory effects in mice. References Kaul, P.N., et al.: J. Sci. Food Agric., 83, 53 (2003); Singh, G., et al.: J. Agric. Food Chem., 54, 174 (2006);

Applications (S)-2-Benzylaziridine is a reagent for the synthesis of renin inhibitors, taurine and cannabinoid type 2 (CB2) receptor agonists. References Kaltenbronn, J. S., et al.: J. Med. Chem 33, 838 (1990); Hu, L., et al.: J. Org. Chem. 72, 4543 (2007); Matsushima, Y., et al.: Jpn. Kokai Tokkyo Koho  JP 2012072067 A 20120412 (2012)

AM-2232 (UNII-40KCH8YIKP) is a potent and unselective agonist of the cannabinoid receptors.

OMDM-6 is a dual agonist of TRPV1(EC50 = 75 nM) and CB1 (Ki = 3.2 μM). OMDM-6 inhibits anandamide cellular uptake with a Ki of 7.0 μM.

(R)-Monlunabant ((R)-MRI-1891) serves as a CB1 receptor antagonist utilized in obesity and metabolic disease research [1].

Monlunabant ((S)-MRI-1891), a solid dispersion compound, functions as an inhibitor of the cannabinoid CB1 receptor [1].

Delta8-THC acetate (Delta8-tetrahydrocannabinol) is a psychoactive cannabinoid that binds to the cannabinoid receptor 1 (CB1 receptor) and exhibits anti-nausea, appetite-stimulating, and anti-inflammatory effects. It may also offer neuroprotective benefits and has potential applications in research on anxiety and depression.

2'-Hydroxydaidzein is an isoflavonoid phytonutrient found in plant species, when a natural compound. 2'-Hydroxydaidzein has antioxidant activity, driven mainly by o-hydrogen bond dissociation enthalpy (BDE) and hydrogen atom transfer (HAT) mechanisms. 2'-Hydroxydaidzein inhibits chemical mediators in inflammatory cells and may be of value in the treatment and prevention of inflammatory diseases associated with excessive chemical mediator production. It may have a role in the treatment and prevention of central and peripheral inflammatory diseases associated with excessive chemical mediator production. 2'-Hydroxydaidzein inhibited the release of neutrophils and formyl-Met-Leu-Phe/cytochalasin B (fMLP/CB) in rats, with IC(50) values of 2.8+/-0.1 and 5.9+/-1.4 microM, respectively.

Applications O-Arachidonoyl ethanolamine hydrochloride is a partial agonist at CB1 receptor and a full agonist at CB2 receptor. O-Arachidonoyl ethanolamine hydrochloride can be isolated from constituent of human and rat brain. It can be used to prepare antimicrobial arachidonic acid derivative. References Kvasenkov, O. I. RU 2171610 C2 20010810 (2001); Sharir, H., et al.: J Neuroimmune Pharmacol. 7, 856 (2012)

Applications (1-Pentyl-1H-indol-3-yl)(2,2,3,3-tetramethylcyclopropyl)methanone is an Indol-3-ylcycloalkyl Ketone with high affinity for the CB2 cannabinoid receptor. Tetramethylcyclopropyl group was found to lead to high affinity CB2 agonists. Synthetic Cannabinoids References Malan, T., et al.: Curr. Opin. Pharmacol., 3, 62 (2003), Cabral, G., et al.: J. Leukocyte Biol., 78, 1192 (2005), Beltramo, M., et al.: Eur. J. Neurosci., 23, 1530 (2006), Dziadulewicz, E., et al.: J. Med. Chem., 50, 3851 (2007),

Polyphenol

Compound 38-S is an orally active CB1R/AMPK modulator with a K i of 0.81 nM and an IC50 of 3.9 nM for CB1R.

Applications S-Methyl-d3-thioacetaminophen is deuterium labeled S-Methyl-3-thioacetaminophen (M330610), a metabolite of Acetaminophen (A161220). Acetaminophen is an analgesic and antipyretic agent used as a pain reliever to treat headache, muscle aches, and arthritis (1,2,3). References (1) McGill, M. R. and Jaeschke, H. Pharm Res. 30, 2174 (2013)(2) Fairbrother, J.E., et al.: Anal. Profiles Drug Subs., 3, 1 (1974) (3) Hinson, J.A., et al.: Rev. Biochem. Toxicol., 2, 103 (1980)

Olorinab (APD 371) (APD 371) is a highly potent, selective and fully efficacious cannabinoid receptor type 2 (CB2) agonist. With an EC50 of 6.2 nM for hCB2.

CB2 receptor agonist 2 (ZINC72105556): potent, Ki=8.5 nM, high selectivity for CB2.

Stability Hygroscopic Applications Quercetin 3-Sulfate Potassium Salt is an metabolite of Quercetin (Q509500), a mitochondrial ATPase and phosphodiesterase inhibitor with potential anticancer activities. References El-Mousallami, A.M.D., et al.: Natural. Prod. Sci., 6, 193 (2000); Haraguchi, H. et al.: J. Natural. Prod., 59, 443 (1996);

Applications Cannflavin B is a prenylated flavone which can be isolated from the cannabinoid free ethanolic extract of Cannabis sativa L. References Barrett, M. L., Experientia, 42, 452-3, (1986)

CB2R/FAAH modulator-2 (compound 26) is a dual modulator targeting at CB2R and FAAH.

Applications FUB-AMB is an analogue of AB-PINACA (A109000) which is a cannabimimetic indazole derivative and has been identified as a designer drug in illegal products.Synthetic Cannabinoids References Uchiyama, N., et al.: Forensic Toxicol., 31, 93 (2013)

Applications Labelled analogue of a cannabimimetic indole derivative that acts as both a cannabinoid receptor CB1 and CB2 agonist. References Huffman J.W. et al.: Bioorg. Med. Chem. Lett., 15, 4110 (2005); De Freitas, G.B.L. et al.: Eur. J. Med. Chem., 44, 2482 (2009); Tuccinardi, T. et al.: J. Med. Chem., 49, 984 (2006);

Cannabigerol is a high affinity α±2-adrenergic receptor agonist, moderate affinity 5-HT1A receptor antagonist, and low affinity CB1 receptor antagonist ; also

ML192 (CID1434953) is a selective GPR55 ligand antagonist.

Applications An N-1 alkyl indole cannabinoid receptor agonist. The N-1 alkyl chain length of cannabimimetic indoles influences CB1 and CB2 receptor binding. References D'Ambra, T., et al.: J. Med. Chem., 35, 124 (1992), Cheng, Y., et al.: Biochem. Pharmacol., 22, 3099 (1973), Pertwee, R., et al.: Eur. J. Pharmacol., 284, 241 (1995),

Applications (Z)-2-Nonen-1-ol is an intermediate in the synthesis of Falcarinol (F101100), a covalent cannabinoid CB1 receptor antagonist and induces pro-allergic effects in skin. References Czepa, A., et al.: J. Agric. Food Chem., 52, 4508 (2004), Radulovic, N., et al.: Chem. Nat. Compds., 44, 390 (2008),

Oxygen-heterocyclic compound

Polyphenol

(±)-Cannabichromene is a major non-psychotropic phytocannabinoid that inhibits endocannabinoid inactivation and activates the TRPA1.

Applications Labelled JWH-200 (M723765). An analgesic compound which acts as a partial agonist at both the CB1 and CB2 cannabinoid receptors. References Compton, D., et al.: J. Pharmacol. Exper. Ther., 263, 1118 (1992), Tetko, I., et al.: J. Med. Chem., 44, 2411 (2001), Huffman, J., et al.: Bioorg. Med. Chem., 11, 539 (2003),

Applications 3-Cysteinylacetaminophen-D5 (major), Trifluoroacetic Acid Salt is deuterium labeled 3-Cysteinylacetaminophen Trifluoroacetic Acid Salt (C994750), which is a metabolite of Acetaminophen (A161220), an analgesic and antipyretic agent used as a pain reliever to treat headache, muscle aches, and arthritis (1,2,3).Minimum isotopic incorporation d-3, no d-0 present. A representative lot has 64% isotopic incorporation at the 6-position, 89% at the 4-position. References (1) McGill, M. R. and Jaeschke, H. Pharm Res. 30, 2174 (2013)(2) Fairbrother, J.E., et al.: Anal. Profiles Drug Subs., 3, 1 (1974) (3) Hinson, J.A., et al.: Rev. Biochem. Toxicol., 2, 103 (1980)

rel-(1R,2S)-8-Bromo-1-(3-bromo-4-hydroxy-5-methoxyphenyl)-1,2-dihydro-7-hydroxy-N2,N3-bis[2-(4-hydroxyphenyl)ethyl]-6-methoxy-2,3-naphthalenedicarboxamide is a synthetic chemical compound, which is derived through targeted organic synthesis and structural optimization efforts. Its source lies in advanced laboratory methodologies designed to enhance specific pharmacological properties. The mode of action is expected to involve selective interaction with particular molecular targets, potentially modulating distinct pathways related to cellular function or signaling processes. This compound is currently under investigation for its potential applications in therapeutic settings, where it might offer novel approaches to modulating disease mechanisms. Specifically, its structure suggests possible utility in addressing oxidative stress, inflammatory pathways, or hormonal signaling, although detailed biological studies will be necessary to confirm these roles. Furthermore, its unique structure and functional groups could serve as a prototype for developing more refined analogs aimed at achieving greater efficacy and specificity in disease treatment regimens. Rigorous preclinical and clinical evaluations are essential to uncover its full utility and therapeutic potential within the scientific and medical communities.

NESS 0327 is a high selectivity antagonist of the cannabinoid CB1 receptor. NESS 0327 is more than 60,000-fold selective for the CB1 receptor.

SCH-336: potent, selective CB2 agonist (Ki=1.8 nM, EC50=2 nM), orally active, 100x CB2 vs. CB1 preference, reduces leukocyte migration and eosinophilia.