Miscellaneous Organic Molecules with Isotopical Substitutions

Applications Cinnamic Acid-13C3 is the labelled analogue of Cinnamic Acid which is rac-form of trans-Cinnamic Acid (P336185) that is used in the synthesis of amides and esters through coupling reactions involving carboxylic acids and amines and N-methylation of amides and O-methylation of carboxylic acids. References Kunishima, M. et al.: Tetrahedron, 55, 13159 (1999); Xia, Q. et al.: Org. Lett., 15, 3326 (2013);

Applications Pyruvic Acid-13C3 is labelled Pyruvic acid (P998900).Pyruvic acid is an Intermediate in sugar metabolism and in enzymatic carbohydrate degradation (alcoholic fermentation) where it is converted to acetaldehyde and CO2 by carboxylase. In muscle, Pyruvic acid (derived from glycogen) is reduced to lactic acid during exertion, which is reoxidized and partially retransformed to glycogen during rest. The liver can convert Pyruvic acid to alanine by amination. References Wenzel, A., et al.: J. Neurosci., 21, 53 (2001); Martinez., et al.: Development, 6, 851 (2002); Nakayama, K., et al.: J. Biochem., 146, 757 (2009); Tanaka, T., et al.: J. Pharmacol. Sci., 109, 24 (2009)

Applications Labelled (R)-enantiomer of Metoprolol. An antihypertensive, though up to 380 times less potent than the (S)-enantiomer. References Toda, N., et al.: J. Pharm. Exp. Ther., 207, 311 (1978),

Stability Hygroscopic Applications α2-Adrenoceptor agonist related structurally to Clonidine. Used in treatment of opioid withdrawal symptoms; antihypertensive. 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 Velly, J., et al.: J. Pharmacol., 8, 351 (1977), Jarrot, B., et al.: Biochem. Pharmacol., 28, 141 (1979), Birch, P., at al.: Brit. J. Pharmacol., 68, 107 (1980),

Applications Palmitoyl-L-carnitine-d3 Hydrochloride is labelled Palmitoyl-L-carnitine Hydrochloride (P155050), a long-chain fatty ester of carnitine which is accumulated and released into the circulation, in fatty-acid oxidation defects. Pattern of Lauroyl-L-carnitine can be diagnostic for a number of ß-oxidation defects. References Ventura, F., et al.: Clinica Chimica Acta, 281, 1 (1999); Pourfarzam, M., et al.: Clinical Chem,, 40, 2267 (1994); Schaefer, J., et al.: Pediatric Res., 37, 354 (1995)

Applications Isotope labelled Arachidonoyl-L-carnitine, a biomarker in early diagnoses for cardiovascular diseases and diabetes. References Guasch-Ferre, M. et al.: Am. J. Clin. Nutr., 103, 1408 (2016);

Stability Hygroscopic Applications A isotopically labelled metabolite of Losartan, a nonpeptide angiotensin II AT1-receptor antagonist. References Pieter, B.M.W.M., et al.: Hypertension, Supp. III, 18, 5, (1991), Chang, L.L., et al.: J. Med. Chem., 36, 2558 (1993)

Applications Labelled Iloperidone. Combined dopamine (D2) and serotonin (5HT2) receptor antagonist. Antipsychotic. 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 Sainati, S.M., et al.: J. Clin. Pharmacol., 35, 713 (1995), Szewczak, M.R., et al.: J. Pharmacol. Exp. Ther., 274, 1404 (1995), Kongsamut, S., et al.: Eur. J. Pharmacol., 317, 417 (1996)

Applications 2,3,5-Trimethylpyrazine-d10 is a useful isotopically labeled compound

Applications Serotonin reuptake inhibitor. Antidepressant; antiobsessional agent. 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 Peters, M.D., et al.: Clin. Pharm., 9, 165 (1990), Adamczyk, M., et al.: Ther. Drug Monit., 17, 371 (1995), Poolsup, N., et al.: J. Clin. Pharm. Ther., 25, 197 (2000), Bose, D., et al.: J. Pharmacol. Toxicol. Methods, 52, 323 (2005),

Stability Hygroscopic Applications Isotope labelled (5S,5’S)-Dihydroxy Lysinonorleucine, a collagen reducible crosslink agent. References Mizikova, I. et al.: FEBS J., 285, 3056 (2018);

Stability Hygroscopic Applications A histamine H2-receptor antagonist which inhibits gastric acid secretion. Antiulcerative. References Bradshaw, J., et al.: Brit. J. Pharmacol., 66, 464 (1979), Berstad, A., et al.: Scand. J. Gastroenterol, 15, 637 (1980), Hohnjec, M., et al.: Anal. Profiles Drug Subs., 15, 533 (1986),

Applications A labelled Florfenicol (F405750) intermediate as antibacterial agent. References Kim, E, et al.: Microbiol. Immunol., 40, 665, (1996), Keyes, K., et al.: Antimicrob. Agents Chemother., 44, 421 (2000),

Stability Hygroscopic, Moisture Sensitive Applications Labelled Sodium Borohydride used as a reagent used to prepare α,α-dideutero-β-amino acids. Sodium Borohydride-d4 is also used to prepare amine-stabilized, deuterated borane-THF. E0 References Todd, R.C. et al.: Tetrahedron Lett., 48, 2335 (2007); Synthesis, 4013, (2006);

Applications Labelled analogue of L-Aspartic Acid, a non-essential amino acid found in food sources. Aspartic Acid is one of the 20 proteinogenic amino acids; the building blocks of proteins. Its conjugate base L-aspartate is an excitatory neurotransmitter in the central nervous system. References Ager, D.J. et al.: J. Mol. Catal. Enzym., 11, 199 (2001); Velisek, J. et al.: Cze. J. Food. Sci., 24, 1 (2006); Nagahama, M. et al.: Cell Tiss. Res., 318, 483 (2004);

Applications δ-Valerolactam-d4 is a labeled analog of δ-Valerolactam (V091440), which is a useful synthetic intermediate. It is an intermediate used to synthesize Cenicriviroc (C256550), an experimental drug candidate for the treatment of HIV infection. It is also a starting material for a new route to hexahydrojulolidines, using intramolecular 1,4-cycloaddition. References Potts, K., et al. J. Org. Chem., 58, 5040 (1993); Klibanov, O., et al.: Curr. Opinion Invest. Drugs, 11, 940 (2010);

Applications Labelled Trenbolone (T719000). Controlled substance (anabolic steroid). References Schanzer, W., et al.: Clin. Chem., 42, 1001 (1996), Kicman, A., et al.: Br. J. Pharmacol., 154, 502 (2008), Fragkaki, A., et al.: Steroids, 74, 172 (2009),

Applications PyroPyronaridine-13C2 , d4 Tetraphosphate Salt is the labeled analogue of Pyronaridine (P997640), an antimalarial drug. References Lee, D.W., et. al.: B. Kor. Chem. Soc., 35, 521 (2014)

Applications Pomalidomide-d4 is the labeled anaxlogue of Pomalidomide (P688200), a thalidomide derivative, a potent inhibitor of TNF-α production. It is an antiinflammatory and antitumor agent used in the treatment of multiple myeloma. References Ruchelman, A. et al.: Bioorg. Med. Chem. Lett., 23, 360 (2013); Latif, T. et al.: Exp. Hematol. Oncol., 1, 27 (2012); Man, H. et al.: Bioorg. Med. Chem. Lett., 13, 3415 (2003); Muller, G. et al.: Bioorg. Med. Chem. Lett., 9, 1625 (1999)

Applications N-Nitrosocytisine-d4 is the isotope labelled intermediate in the synthesis of Cytisine (C998500), an alkaloid that occurs naturally in various plants. Cytisine was shown to act as ligands for neuronal nicotine receptors and exhibits various pharmacological activities. N-substituted cytisines, have found to have the analgesic, antihypertensive and inotropic activities. References Boido, C. C., et al.: Farmaco, 58, 265 (2003);

Applications A labelled metabolite of 7-Ethoxycoumarin and Coumarin. Useful as a pharmacokinetic standard in metabolic studies. References Blankson, E., et al.: Biochem. Pharmacol., 42, 1241 (1991), Steensma, A., et al.: Xenobiotica, 24, 893 (1994), Fisher, R., et al.: Toxicol. Methods, 5, 99 (1995), Ekins, S., et al.: Drug Metab. Dispos., 24, 990 (1996)

Applications Isotope labelled Cytisine, toxic priniciple in seed of Laburnum anagyroides and other Leguminosae. A neuronal nicotinic acetylcholine agonist. 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 Barlow, R.D., et al.: Brit. J. Pharmacol., 35, 161 (1969), Jensen, A.A., et al.: J. Med. Chem., 48, 15, 4705(2005),

Applications Triphenyl Phosphate-13C6 is the isotope labelled analog of Triphenyl Phosphate (T808990). Triphenyl Phosphate is used in the insecticidal composition and also acts as a flame retardant. Triphenyl phosphate is also added to some nail polishes as a replacement for the plasticizer Dibutyl Phthalate (D429495). Diphenyl Phosphate (D492000), a metabolite of triphenyl phosphate increased sharply in the urine of women 10-14 hours after they painted their nails with polish containing triphenyl phosphate. 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 Stumpf, N., et al.: J. Econ. Entomol., 94, 1577 (2001); Ay, R., et al.: J. Pest. Sci., 78, 139 (2005); Kang, C., et al.: J. Appl. Entomol., 130, 377 (2006); Xia, X. et al.: J. Elec. Soc., 159, A1834 (2012); Chem. and Eng. News P.19, Oct 26, 2015

Stability Hygroscopic Applications A nonsedating type histamine H1-receptor antagonist. A major metabolite of Hydroxyzine. Pharmacological activity resides primarily in the (R)-isomer. Antihystaminic. References De Vos, C., et al.: Ann. Allergy, 59, 278 (1987), Juhlin, L., et al.: J. Allergy Clin. Immunol., 80, 599 (1987), Fadel, R., et al.: Clin. Allergy, 17, 373 (1987), Gengo, F.M., et al.: Clin. Pharmacol. Ther., 42, 265 (1987)

Applications Labelled DL-Serine is used in the synthesis of novel tryptoline derivatives as IDO (indoleamine 2,3-Deoxygenase) inhibitors, for potential use in Alzheimer’s treatment. References Tanaka, M. et al.: Bioorg. Med. Chem., 21, 1159 (2013);

Applications N-Methyl-d3-N-nitroso-p-toluenesulfonamide is the labeled version of Diazald; Diazomethane precursor. References Takizawa, et al.: J. Pharm. Soc. Jpn., 70, 490 (1950)

Applications Labelled 4-Octylphenol Monoethoxylate (O293770). 4-Nonylphenol ethoxylates (NPEOs) and 4-octylphenol ethoxylates (OPEOs) are widely used as nonionic surfactants. References Ahel, M., et al.: Anal. Chem., 57, 1577 (1985), Ball, H., et al.: Environ. Sci. Technol., 23, 951 (1989),

Applications Deuterated Raloxifene, a nonsteroidal, selective estrogen receptor modulator (SERM). Antiosteoporotic. References Jone, C.D., et al.: J. Med. Chem., 27, 1057 (1984), Buelke-Sam, J., et al.: Reprod. Toxicol., 12, 217 (1998),