Cannabinoïdes

Applications JWH 018 is the 18th compound synthesized in a series of more than 470 analogs and metabolites of ∆9-Tetrahydrocannabinol (THC) (T293200), the active component of marijuana. JWH 018 acts as cannabinoid receptor.Controlled substance.Synthetic Cannabinoids References Matsuda, L., et al.: Nature, 346, 561 (1990), Gerard, C., et al.: Biochem. J., 279, 129 (1991), Parkkari, T., et al.: Bioorg. Med. Chem., 14, 5252 (2006), Salo, O., et al.: J. Med. Chem., 49, 554 (2006),

OMDM-1 ((Z)-N-[(2S)-1-hydroxy-3-(4-hydroxyphenyl)propan-2-yl]octadec-9-enamide) is a selective and metabolically stable anandamide cellular uptake (ACU)

GP 1a: potent CB2 receptor agonist (EC50=7.1), 30x CB2 over CB1 preference, boosts P-ERK1/2, aids skin healing, anti-inflammatory.

Applications Labelled analogue of a cannabimimetic indole derivative that acts as a CB2 receptor agonist with weak CB2 activity. It has been shown to possess immunomodulatory effects and may be useful in the treatment of pain and inflammation. Synthetic cannabinoids References Aung, M.M. et al.: Drug Alc. Depend., 60, 133 (2000); Ghosh, S. et al.: Mol. Immunol., 43, 2169 (2006); Ehrhart, J. et al.: J. Neuroinflam., 2, 29 (2005); Romero-Sandoval, A. et al.: Anethesiol., 106, 787 (2007);

Applications A synthetic cannabimimetic indole derivative which acts as a potent and selective agonist for the cannabinoid receptor CB1. Synthetic cannabinoids References Willis P.G. et al.: J. Lab. Cpd. Radiopharmac., 46, 799 (2003);

PSNCBAM-1 (PSNCBAM 1) is a CB1 receptor negative allosteric modulator (EC50 = 0.1 μM) with hypophagic effects in vivo.

Applications 4′-Chloroacetanilide is an impurity 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) Călinescu, O., et al.: J. Chromatogr. Sci. 50(4), 335-42, (2012)(2) McGill, M. R. and Jaeschke, H. Pharm Res. 30, 2174 (2013)(3) Fairbrother, J.E., et al.: Anal. Profiles Drug Subs., 3, 1 (1974) (4) Hinson, J.A., et al.: Rev. Biochem. Toxicol., 2, 103 (1980)

Stability Temperature, Moisture, Light, and Oxygen Sensitive Applications N-Acetyl-4-benzoquinone imine-D3 is deuterium labeled N-Acetyl-4-benzoquinone Imine (A170000). 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)

Applications Rimonabant Hydrochloride is a potent and selective CB1 cannabinoid antagonist used to investigate CB receptor properties (1). Rimonabant Hydrochloride is also an anti-obesity agent (2). Not a dangerous good if item is equal to or less than 1g/ml and there is less than 100g/ml in the package References (1) Carai, M.A.M., et al.: Life Sci., 77, 2339 (2005) (2) Janiak, P., et al.: Kidney Int. 72, 1345 (2007)

Carboxylic acid with phenol function

Applications 2-Methylisoborneol solution - (CAS# 2371-42-8) is a useful research chemical compound.

COR659: suppresses alcohol/chocolate intake in rats; enhances GABAB receptor, blocks CB1 receptor.

Quinone

In the central nervous system, 2-Arachidonoylglycerol is a second endogenous cannabinoid ligand

CB2 PET Radioligand 1 (compound [18F]9) is a positron emission tomography (PET) radioligand with high affinity for the human cannabinoid receptor 2 (hCB2, Ki=7.

Applications Used in the preparation of CB1 cannabinoid receptor agonists and brain imaging agents. References Deng, H. et al; J. Med. Chem. 48, 6386 (2005)

Applications 1-Alkyl-2-aryl-4-(1-naphthoyl)pyrroles as high affinity ligands for the cannabinoid CB1 and CB2 receptors. References Reggio, P., et al.: J. Med. Chem., 41, 5177 (1998), Huffman, J., et al.: Bioorg. Med. Chem., 11, 539 (2003),

Applications AM 630 acts as a potential CB2 receptor cannabinoid antagonist with application towards human lung cancer treatment and angiogenesis induction.Synthetic Cannabinoids References Ramer, R. et al.: Mol. Canc. Ther., 12, 69 (2013); Huang, H. et al.: Hepatol., 56, 248 (2012);

Applications N-(4-Bromopheneethyl-phthalimide is a building block used in the preparation of N-phenylethylindole carboxamides for structure activity relationship study of allosteric modulators of CB1 receptor. References Piscitelli, F., et al.: J. Med. Chem., 55, 5627 (2012);

Applications Labelled JWH 19 (H296800). An N-1 alkyl indole cannabinoid receptor agonist. The N-1 alkyl chain length of cannabimimetic indoles influences CB1 and CB2 receptor binding. Not a dangerous good if item is equal to or less than 1g/ml and there is less than 100g/ml in the package 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 An analgesic chemical which acts as a cannabinoid agonist at the CB1 and CB2 receptors.Synthetic Cannabinoids References Rituparna, S., et al.: Lett. Drug Des. Discov., 6, 599 (2009), De Freitas, G., et al.: Eur. J. Med. Chem., 44, 2482 (2009),

Applications cis-2-Decen-1-ol is an intermediate in the synthesis of Falcarinol which is a covalent cannabinoid CB1 receptor antagonist and induces pro-allergic effects in skin. A natural pesticide produced by carrots and red ginseng, protecting hosts roots from various fungal diseases. It has been shown to have nutritional benefits, reducing the risk of developing specific forms of cancer. References Czepa, A., et al.: J. Agric. Food Chem., 52, 4508 (2004), Radulovic, N., et al.: Chem. Nat. Compds., 44, 390 (2008),

GW 405833 (L-768242) is an agonist of cannabinoid-2 (CB(2)) receptor-selective

Anandamide ((5Z,8Z,11Z,14Z)-N-(2-Hydroxyethyl)icosa-5,8,11,14-tetraenamide), an immune modulator, acts via not only cannabinoid receptors (CB1 and CB2) but also

exo-Tetrahydrocannabivarin (Compound 12) is an analog of Δ9,11-THC. It weakly binds to cannabinoid receptors (CB) with an IC50 of 1.4 μM. In mice, exo-Tetrahydrocannabivarin exhibits activity related to both motor function and analgesia.

Arvanil (N-Vanillylarachidonamide) is a synthetic capsaicin-amphetamine hybrid that acts as a ligand for VR1 and CB1, offering neuroprotective effects.

Applications 1-(5-Fluoropentyl)-1H-indole-3-carboxylic Acid is an intermediate in the synthesis of 5-Fluoro NNEI (F588720), which is a synthetic cannabinoid (CB) and analogue of JWH 018 (P283650). The physiological and toxicological properties of this compound are not known.Synthetic Cannabinoids

Applications A cannabinoid receptor ligand.Synthetic Cannabinoids References Huffman, J., et al.: Bioorg Med. Chem., 9, 2863 (2001), Govaerts, S., et al.: Eur. J. Pharm. Sci., 23, 233 (2004), Bosier, B., et al.: J. Neurochem., 102, 1996 (2007),

Applications 1-(3,5-Bis(benzyloxy)phenyl)pentan-2-ol is an intermediate for the synthesis of 2''-Hydroxycannabidiol (H824820), which is a metabolite of Canabidiol (C175300), a major constituents in marijuana. 2''-Hydroxycannabidiol can be used to investigate canabidiol metabolism and human liver microsomes that metabolize Canabidiol into 6α-Hydroxycannabidiol. References Jiang, R., et al.: Life Sci. 89, 165 (2011); Lander, N., et al.: Science 169, 611 (1970)

CB2R agonist 3, a potent activator of cannabinoid receptor 2 (CB2R), exhibits an EC50 value of 0.37μM, indicative of its significant role in the immune system [

Taranabant racemate is an antagonist and/or inverse agonist of the Cannabinoid-1 (CB1) receptor.

N-Arachidonyldopamine (NADA) is a selective and potent endogenous CB1 receptor agonist (Ki: 250 nM).N-Arachidonyldopamine is also a potent and selective TRPV1

Anandamide is an endogenous cannabinoid, which is a bioactive lipid mediator primarily found in the brain and peripheral organs. It is synthesized from membrane phospholipid precursors through enzymatic pathways, primarily involving the enzyme N-acyl phosphatidylethanolamine phospholipase D (NAPE-PLD). Anandamide acts as a ligand for cannabinoid receptors, mainly the CB1 receptor located in the central nervous system, and the CB2 receptor found in peripheral tissues. This compound plays a critical role in the modulation of neurotransmitter release and is involved in various physiological processes including pain, mood, appetite regulation, and memory. Additionally, anandamide's interaction with cannabinoid receptors influences synaptic plasticity and neuroprotection. Due to its far-reaching effects, anandamide is a subject of interest in pharmacological research, particularly in exploring therapeutic avenues for neurological disorders, chronic pain management, and appetite modulation. Understanding its pathways and effects at the molecular level continues to be an essential aspect of cannabinoid research, aiming to harness its potential in medical applications.

Applications KML-29 is an extremely specific monoacylglycerol lipase (MAGL) inhibitor. KML-2 should be useful to distinguish between actions of 2-arachidonoyl glycerol (an endogenous ligand of cannabinoid receptors that is deactivated by MAGL) and anandamide, another endocannabinoid. References Ueda, N. et al.: Chem. Biol., 19, 545 (2012);

Applications 4'-O-Methyl-d3 Quercetin is the labeled analogue of 4'-O-Methyl Quercetin (M326580), a major metabolite of the flavanoid Quercetin (Q509500) with antioxidant properties. It helps to protect H9c2 cardiomyoblasts against H2O2-induced oxidative stress via the modulation of PI3K/Akt and ERK1/2 signaling pathways. Not a dangerous good if item is equal to or less than 1g/ml and there is less than 100g/ml in the package References Duenas, M. et al.: Eur. Food Res. Technol., 232, 103 (2011); Ameho, C.K. et al.: J. Nutrit. Biochem., 19, 467 (2008); Angeloni, C. et al.: Biochimie, 89, 73 (2007)

Applications JWH 018 N-Pentanoic Acid β-D-Glucuronide is a metabolite of JWH 018 or 1-Pentyl-3-(1-Napthoyl)indole (P283650), which is a mildly selective agonist of the peripheral cannabinoid (CB2) receptor. References Chimalakonda, K. et al.: Anal. Chem., 83, 6381 (2011); Aung, M. et al.: Drug Alcohol Depend., 60, 133 (2000)

Impurity Paracetamol EP Impurity A Applications 2-Acetamidophenol is an impurity of Acetaminophen (A161220). Acetaminophen is an analgesic and antipyretic agent and used as a pain reliever to treat headache, muscle aches, and arthritis (1,2). 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)

Stability Hygroscopic Applications (2,4-difluorophenyl)hydrazine is a reactant in the preparation of 1a,2,5,5a-tetrahydro-1H-2,3-diaza-cyclopropa[a]pentalen-4-carboxamides as potent and selective CB2 receptor agonists. References Han, S., et. al.: Bioorg. Med. Chem. Lett., 25, 322 (2015)

AM404 is a cannabinoid reuptake inhibitor and a TRPV (1) activator with neuroprotective and anticancer activities that blocks anandamide transport.

Applications Isotope labelled JWH-007 is a novel cannabinoid receptor agonist at both the CB1 and CB2 receptors. References Pertwee, R.G., et al.: Euro. J. Pharmacol., 284, 241 (1995); Wiley, J.L., et al.: J. Pharmacol. Experiment. Therap., 285, 995 (1998);

Applications 2-[(9Z)-9-Octadecenyloxy]-1,3-propanediol, which is an endogenous cannabinoid receptor ligand. References Suhara, Y. et al.: Chem. Pharm. Bull., 48, 903 (2000);

Applications An inactive isomer of Nabilone, present often as an impurity in trans-Nabilone preparations. References Rubin, A., et al.: Clin. Pharmacol. Ther., 22, 85 (1977), Stark, P., et al.: J. Pharmacol. Exp. Ther., 214, 124 (1980), Souter, R.W., et al.: Anal. Profiles Drug Subs., 10, 499 (1981), Ward, A., Drugs, 30, 127 (1985),

2-Arachidonyl glycerol is an endogenous cannabinoid receptor agonist, which is derived from arachidonic acid present in cellular membranes. It functions as a signaling lipid and plays a critical role in the endocannabinoid system, which is a complex network of receptors and ligands involved in maintaining physiological homeostasis. Sourced primarily from membrane phospholipids, 2-Arachidonyl glycerol acts by binding to cannabinoid receptors, CB1 and CB2, located in the central and peripheral nervous systems. This binding modulates various signaling pathways, influencing processes like inflammation, pain perception, and neuroprotection. Its uses and applications are extensive in scientific research, especially in exploring mechanisms of neurodegenerative diseases, pain management, and immune response regulation. 2-Arachidonyl glycerol also serves as a vital tool for understanding the physiological roles of endocannabinoids and their potential therapeutic implications.

AM841, a high-affinity electrophilic ligand, covalently interacts with a cysteine residue in helix six, thus activating the CB1 cannabinoid receptor.

Applications 3-Methoxy Acetaminophen 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 4-Acetaminophen-d3 Sulfate is deuterium labeled metabolite of Acetaminophen (A161220), an analgesic and antipyretic agent (1,2,3). References (1) Lloyd, A., et al.: Biochim. Biophys. Acta., 52, 413 (1961) (2) Purohit, A., et al.: J. Steroid Biochem. Mol. Biol., 86, 423 (2003) (3) Winum, J., et al.: J. Med. Chem., 46, 2197 (2003)

CB2 receptor agonist 9 (Compound 33) is an orally active agonist of cannabinoid receptor 2 (CB2 receptor) with an EC50 of 16.2 nM. It inhibits the expression of TNF-α, IL-1β, and IL-6, demonstrating anti-inflammatory activity in a DSS-induced acute colitis model in mice.

SR144528 is an antagonist of the CB2 receptor (Ki = 0.6 nM) and inhibits microsomal ACAT activity (IC50 = 3.6 μM).

CID 16020046 (C390-0219) is a selective GPR55 antagonist, inhibiting GPR55 constitutive activity with IC50 of 0.15 μM in yeast.

Applications Daminozide-d4 is labelled Daminozide which is a plant growth regulator. Used as a standard for Pesticide detection, and cannabis testing. References Moriya, M., et al.: Mutation Res. Genetic Toxicol. Testing, 116, 185 (1983); Rose, N., et al.: J. Med. Chem., 55, 6639 (2012); Narayanan, V., et al.: Analusis, 21, 107 (1993)

Applications 5-fluoro SDB-005 is an analogue of SDB-005 (S210000), which shows full agonist profiles at CB1 and CB2 receptors. References Banister, S.D., et. al.: ACS Chem. Neurosci., 4, 1081 (2013)

6-Iodopravadoline (AM630) is an antagonist of CB2 (Ki: 31.2 nM). And it shows 165-fold selectivity more than CB1 receptors.

Applications A cannabimimetic indole derivative that acts as both a cannabinoid receptor CB1 and CB2 agonist. Synthetic Cannabinoids 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);

Evofolin B is a natural compound isolated from the stem bark of Zanthoxylum ailanthoides.