Nicotine and Nicotine Derivatives

<p>Applications Labelled Nicotinamide, precursor of the coenzymes NAD and NADP. Nicotinamide is a water soluble vitamin (enzyme cofactor).<br>References Sharma, M., et al.: J. Chem. Pharm. Res., 2, 416 (2010); Al-Nadaf, A., et al.: Bioorg. Medi. Chem., 18, 3088 (2010);<br></p>

<p>Applications Trigonelline is an alkaloid present in coffee and fenugreek presenting phytoestrogenic activity.<br>References Folwarczna, J. et al.: Mol. Nutr. Food Res., 58, 1457 (2014);<br></p>

<p>Applications Labelled Isonicotinamide is an isomeric analogue of nicotinamide and a metabolite of isonicotinic thioamide. Isonicotinamide strongly inducde apoptosis in human acute myelomonocytic leukemia cells, HL-60.<br>References Taguchi, H.: Furi Rajik. Rin., 14, 23 (1999); Golovinski, E. et al.: Comp. Rend. Acad. Bulg. Sci., 21, 375 (1968);<br></p>

<p>Applications The (S)-metabolite of Nicotine (N412420).<br> Not a dangerous good if item is equal to or less than 1g/ml and there is less than 100g/ml in the package<br>References Armstrong, D., et al.: Chirality, 11, 82 (1999), Carmella, S., et al.: Carcinogenesis, 21, 839 (2000),<br></p>

<p>Stability Light Sensitive<br>Applications Labelled rac-Nicotine (N412420). Nicotine is an alkaloid isolated from plants. Nicotine is an active stimulant, having both addictive and carcinogenic properties. Nicotine can be absorbed through the alimentary canal, respiratory tract and intact skin. Nicotine is used in the treatment of smoking withdrawal syndrome. Nicotine has been used as an anthelmintic.<br> Not a dangerous good if item is equal to or less than 1g/ml and there is less than 100g/ml in the package<br>References Ferretti, G., et al.: J. Med. Chem., 45, 4724 (2002), Guillen, M., et al.: J. Agric. Food Chem., 53, 1093 (2005), Ramunno, A., et al.: Bioorg. Med. Chem. Lett., 15, 3237 (2005), Alburges, M., et al.: Eur. J. Pharmacol., 573, 124 (2007),<br></p>

<p>Stability Hygroscopic<br>Applications trans-3'-Hydroxy Cotinine is a metabolite of Nicotine (N412450, (S)-(-)-Nicotine).<br>References Benowitz, N., et al.: J. Pharmcol. Exp. Ther., 268, 296 (1994); Horning, E., et al.: Life Sci., 13, 1331 (1973), Desai, D., et al.: Chem. Res. Toxicol., 3, 47 (1990), Kitagawa, K., et al.: J. Biol. Chem., 276, 17830 (2001),<br></p>

<p>Stability Air Sensitive<br>Applications β-Nornicotyrine (cas# 494-98-4) is a compound useful in organic synthesis.<br>References Beckett, A., et al.: J. Pharm. Pharmacol., 24, 115 (1972), Zwickenpflug, W., et al.: Chem. Res. Toxicol., 19, 150 (2006),<br></p>

<p>Applications A potent inhibitor of gluconeogenesis.<br>References Blank, B., et al.: J. Med. Chem., 17, 1065 (1974), Memoli, K.A., Tetrahedron Letters, 37, 21, 3617 (1996)<br></p>

<p>Stability May Turn Brown on Exposure to Light or Air<br>Applications Labelled rac-Nicotine (N412420). Nicotine is an alkaloid isolated from plants. Nicotine is an active stimulant, having both addictive and carcinogenic properties. Nicotine can be absorbed through the alimentary canal, respiratory tract and intact skin. Nicotine is used in the treatment of smoking withdrawal syndrome. Nicotine has been used as an anthelmintic.<br> Not a dangerous good if item is equal to or less than 1g/ml and there is less than 100g/ml in the package<br>References Ferretti, G., et al.: J. Med. Chem., 45, 4724 (2002), Guillen, M., et al.: J. Agric. Food Chem., 53, 1093 (2005), Ramunno, A., et al.: Bioorg. Med. Chem. Lett., 15, 3237 (2005), Alburges, M., et al.: Eur. J. Pharmacol., 573, 124 (2007),<br></p>

<p>Stability Hygroscopic<br>Applications A tobacco alkaloid as risk factor of human cancer.<br> Not a dangerous good if item is equal to or less than 1g/ml and there is less than 100g/ml in the package<br>References Stepanov, I., et al.: Cancer Res., 69, 8236 (2009), Maertens, R., et al.: Chem. Res. Toxicol., 22, 1406 (2009), Gaworski, C., et al.: Toxicol., 269, 54 (2010),<br></p>

<p>Applications An amino ketone metabolite of nicotine, and precursor to NNK.<br> Not a dangerous good if item is equal to or less than 1g/ml and there is less than 100g/ml in the package<br>References Stephen S. Hect, Sharon E. Murphy, et. al. , Proc. Natl. Acad. Sci. USA, Oct. 24, 2000.<br></p>

<p>Stability Light Sensitive<br>Applications The S-enantiomer metabolite of tobacco, a specific N-nitrosamines with carcinogenic activity.<br> Not a dangerous good if item is equal to or less than 1g/ml and there is less than 100g/ml in the package<br>References Hoffmann, D., et al.: Cancer Res., 39, 2505 (1979), Hecht, S., et al.: Chem. Res. Toxicol., 11, 559 (1998), Hecht, S., et al.: Mutation. Res., 424, 127 (1999), Wang, M., et al.: Chem. Res. Toxicol., 16, 616 (2003),<br></p>

<p>Applications Labelled Nudifloramide (N925500). Nudifloramide is a metabolite of Niacin (or Nicorinic acid).<br>References Felsted, R., et al.: J. Biol. Chem., 242, 1274 (1967), Igel, M., et al.: Eur. J. Clin. Pharmacol., 57, 357 (2001), Kashyap, M., et al.: Am. J. Cardiol., 89, 672 (2002), Bottorff, M., et al.: Am. J. Cardiol., 97, 27 (2006),<br></p>

<p>Stability Hygroscopic<br>Applications (R,S)-Norcotinine-pyridyl-d4 (cas# 1020719-70-3) is a compound useful in organic synthesis.<br></p>

<p>Applications 3-Pyridylacetic Acid is a metabolite of Nicotine (N412420). 3-Pyridylacetic Acid is an antilipemic.<br>References Baer, T.A., et al.: J. Med. Chem., 16, 85 (1973); Kyerematen, G. A., et al.: Drug Metab. Dispos., 16, 125 (1988);<br></p>

<p>Stability Hygroscopic<br>Applications A labelled major metabolite of nicotine in humans. Carcinogen.<br>References Sugasawa, S., et al.: Pharma. Bull., et al.: 2, 39 (1954), Thompson, J.A., et al.: J. Chromatog., 231, 53 (1982); Seeman, J.I., et al.: J. Org. Chem., 51, 1548 (1986)<br></p>

<p>Applications A metabolite of Nicotine.<br> Not a dangerous good if item is equal to or less than 1g/ml and there is less than 100g/ml in the package<br></p>

<p>Applications 3-(4-Formylaminobutyryl)pyridine (cas# 887355-56-8) is a compound useful in organic synthesis.<br></p>

<p>Applications Labelled rac-Nicotine (N412420). Nicotine is an alkaloid isolated from plants. Nicotine is an active stimulant, having both addictive and carcinogenic properties. Nicotine can be absorbed through the alimentary canal, respiratory tract and intact skin. Nicotine is used in the treatment of smoking withdrawal syndrome. Nicotine has been used as an anthelmintic.<br> Not a dangerous good if item is equal to or less than 1g/ml and there is less than 100g/ml in the package<br>References Guillen, M., et al.: J. Agric. Food Chem., 53, 1093 (2005), Alburges, M., et al.: Eur. J. Pharmacol., 573, 124 (2007), Roy, K., et al.: Eur. J. Med. Chem., 44, 1941 (2009),<br></p>

<p>Applications Trigonelline (chloride) is an alkaloid found in plants and coffee. Trigonelline is a product of niacin metabolism that is excreted in urine.<br></p>

<p>Stability Hygroscopic<br>Applications A major metabolite of Nicotine in humans. Carcinogen.<br>References Benowitz, N., et al.: Clin. Pharmacol. Ther., 56, 483 (1994), Nakajima, M., et al.: Drug Metab. Dispos., 24, 1212 (1996), Messina, E., et al.: J. Pharmacol. Exp. Ther., 282, 1608 (1997), Oscarson, M., et al.: Hum. Mutat., 20, 275 (2002),<br></p>

<p>Applications Isotope labelled Nicotelline is a Nicotine (N412420) related metabolite with potential as an inhibitor of human cytochrome P-450 2A6.<br> Not a dangerous good if item is equal to or less than 1g/ml and there is less than 100g/ml in the package<br>References Denton, T. et al.: Biochem. Pharm., 67, 751 (2004); Gorrod, J. et al.: Anal. Det. Nic. Rel. Comp. Metab., 69, (1999);<br></p>

<p>Impurity Nicotine USP Related Compound F (3-(pyrrolidine-2-yl)pyridine)<br>Stability Light Sensitive<br>Applications (RS)-Nornicotine is a tobacco alkaloid and the major Nicotine (N412420) metabolite in brain. Nornicotine appears to activate different nAChR subtypes, has a better pharmacokinetic profile, and produces less toxicity than Nicotine. Nornicotine shows a significant analgesic activity. Nicotine USP Related Compound F (3-(pyrrolidine-2-yl)pyridine).<br>References Hecht, S., et al.: Carcinogenesis, 9, 875 (1988), Rivenson, A., et al.: Cancer Res., 48, 6912 (1988), Hoffmann, D., et al.: Chem. Res. Toxicol., 14, 767 (2001), Kool, J., et al.: J. Med. Chem., 49, 3287 (2006), Kool, J., et al.: Drug Metab. Dispos., 35, 640 (2007),<br></p>

<p>Applications (S)-Anabasine is a nicotinic receptor agonist.<br> Not a dangerous good if item is equal to or less than 1g/ml and there is less than 100g/ml in the package<br>References Keeler, R., et al.: Clin. Toxicol., 12, 49 (1978); Aceto, M., et al.: J. Med. Chem., 22, 17 (1979); Brand, J., et al.: J. Chem. Ecol., 19, 1315 (1993)<br></p>

<p>Applications N-Methylnicotinamide is a metabolite of Nicotinamide (N407750), which is a water-soluble vitamin B, incorporated within nicotinamide cofactors such as NADH and NADPH. N-Methylnicotinamide is commonly found in the human urine and is used as a biomarker to study diseases such as liver cirrhosis and type 2 diabetes.<br>References Pumpo, R., et al.: Am. J. Gastroenterol., 96, 1183 (2001); Sharma, M., et al.: J. Chem. Pharm. Res., 2, 416 (2010); Al-Nadaf, A., et al.: Bioorg. Medi. Chem., 18, 3088 (2010); Connor, S., et al.: Mol. Biosyst., 6, 909 (2010);<br></p>

<p>Applications rac-Nicotine-d3 N-β-D-Glucuronide is a labelled racemic analogue of Nicotine N-β-D-Glucuronide (N424575), a Nicotine (N412420) metabolite in rat brain. Nicotine N-β-D-Glucuronide is used as a Nicotine biomarker in rat brain.<br>References Alexandrov, K., et al.: Toxicol. Lett., 198, 63 (2010), Huang, L., et al.: J. Neurochem., 109, 826 (2009), Quik, M., et al.: Biochem. Pharmacol., 78, 677 (2009), Weems, J., et al.: Chem. Res. Toxicol., 23, 696 (2010),<br></p>

<p>Applications o-Nicotine is a Nicotine analog (N412420). o-Nicotine has high affinity for nicotinic receptor, and its ability to elicit neurotransmitter secretions make it a good candidate for treating cholinergic neurodegenerative diseases.<br> Not a dangerous good if item is equal to or less than 1g/ml and there is less than 100g/ml in the package<br>References Romano, C., et al.: Psychopharmacol., 74, 310 (1981), Wang, D., et al.: Drug Dev. Res., 45, 10 (1998),<br></p>

<p>Stability Hygroscopic<br>Applications S-(-)-Cotinine is a major metabolite of Nicotine (N412450) in humans. It is a carcinogen.This compound is a contaminant of emerging concern (CECs)<br>References Thompson, J.A., et al.: J. Chromatog., 231, 53 (1982); Seeman, J.I., et al.: J. Org. Chem., 51, 1548 (1986); Nakajima, M., et al.: Drug Metab. Dispos., 24, 1212 (1996)<br></p>

<p>Applications Nicotelline is a Nicotine (N412420) related metabolite with potential as an inhibitor of human cytochrome P-450 2A6.<br> Not a dangerous good if item is equal to or less than 1g/ml and there is less than 100g/ml in the package<br>References Denton, T. et al.: Biochem. Pharm., 67, 751 (2004); Gorrod, J. et al.: Anal. Det. Nic. Rel. Comp. Metab., 69, (1999);<br></p>

<p>Stability Hygroscopic<br>Applications A metabolite of (+/-)-Cotinine.<br>References Morselli, P.L., et al.: J. Med. Chem., 10, 1033 (1967),<br></p>

<p>Applications Labelled Isonicotinic Acid (I821760). Used in the biological study of differentiation induced by nicotinic acid, nicotinamide and isonicotinic acid in human leukemia cell lines.<br>References Zeilinger, S., et al.: J. Biol. Chem., 271, 25624 (1996), Panagiotou, G., et al.: J. Biotechnol., 118, 304 (2005),<br></p>

<p>Applications 1,4-Dihydro-1-methyl-4-oxo-3-pyridinecarboxamide-d3 is the isotope labelled analog of 1,4-Dihydro-1-methyl-4-oxo-3-pyridinecarboxamide (D453415); a compound that has been shown to be one of the potential novel biomarkers of peroxisome proliferation in the rat.<br>References Ringeissen, S., Biomarkers, 8, 240 (2003); Shibata, K., et al.: Biosci. Biotech. and Biochem., 77, 2105 (2013)<br></p>

<p>Applications N-Ethylnicotinamide is a derivative of Nicotinamide (N407750), which is a water-soluble vitamin and is part of the vitamin B group.<br>References Sharma, M., et al.: J. Chem. Pharm. Res., 2, 416 (2010), Al-Nadaf, A., et al.: Bioorg. Medi. Chem., 18, 3088 (2010),<br></p>

<p>Applications A metabolite of Nicotine. S-Enantiomer of Cotinine.<br>References Sugasawa, S., et al.: Pharma. Bull., et al.: 2, 39 (1954), Thompson, J.A., et al.: J. Chromatog., 231, 53 (1982); Seeman, J.I., et al.: J. Org. Chem., 51, 1548 (1986)<br></p>

<p>Stability Hygroscopic<br>Applications A major metabolite of Nicotine in humans. Carcinogen.<br>References Benowitz, N., et al.: Clin. Pharmacol. Ther., 56, 483 (1994), Nakajima, M., et al.: Drug Metab. Dispos., 24, 1212 (1996), Messina, E., et al.: J. Pharmacol. Exp. Ther., 282, 1608 (1997), Oscarson, M., et al.: Hum. Mutat., 20, 275 (2002),<br></p>

<p>Stability Hygroscopic<br>Applications trans-3'-Hydroxy Cotinine-d3 (Racemic Mixtures) (cas# 159956-78-2) is a compound useful in organic synthesis.<br> Not a dangerous good if item is equal to or less than 1g/ml and there is less than 100g/ml in the package<br>References Desai, D., et al.: Chem. Res. Toxicol., 3, 47 (1990)<br></p>

<p>Stability Hygroscopic<br>Applications Labelled (R,S)-Anatabine is a metabolite of Nicotine (N412420).<br> Not a dangerous good if item is equal to or less than 1g/ml and there is less than 100g/ml in the package<br>References Quan, P.M., et al.: J. Org. Chem., 30, 2769 (1965), Maciuk, A., et al.: J. Pharm. Biomed. Anal., 48, 238 (2008),<br></p>

<p>Applications rac N’-Nitrosonornicotine-d4 is present in cigarettes and patches in reduced amounts in order to facilitate the cessation of smoking. Induces down-regulation of nonmuscle myosin II affecting cell motility and wound healing.<br> Not a dangerous good if item is equal to or less than 1g/ml and there is less than 100g/ml in the package<br>References Hatsukami, D. et al.: Canc. Epid. Bio. Prev., 22, 1015 (2013); Prins, J. et al.: J. Prot. Res., 12, 1282 (2013);<br></p>

<p>Applications Sorbicillin analog. A bioactive secondary metabolites from terrestrial Streptomyces species TN262.<br>References Ma, L. et al. : J. Anitibiot. 64, 645 (2011); Elleuch, L. et al.: Appl. Biochem. Biotech. 162, 579 (2010)<br></p>

<p>Stability Hygroscopic, Light Sensitive<br>Applications (R,S)-Anatabine is a metabolite of Nicotine (N412420).<br> Not a dangerous good if item is equal to or less than 1g/ml and there is less than 100g/ml in the package<br>References Quan, P.M., et al.: J. Org. Chem., 30, 2769 (1965), Maciuk, A., et al.: J. Pharm. Biomed. Anal., 48, 238 (2008),<br></p>

<p>Stability Very Hygroscopic<br>Applications Nicotine N-β-D-Glucuronide is a Nicotine (N412420) metabolite in rat brain. Nicotine N-β-D-Glucuronide is used as a Nicotine biomarker in rat brain.<br> Not a dangerous good if item is equal to or less than 1g/ml and there is less than 100g/ml in the package<br>References Alexandrov, K., et al.: Toxicol. Lett., 198, 63 (2010), Huang, L., et al.: J. Neurochem., 109, 826 (2009), Quik, M., et al.: Biochem. Pharmacol., 78, 677 (2009), Weems, J., et al.: Chem. Res. Toxicol., 23, 696 (2010),<br></p>

<p>Applications A labelled major metabolite of nicotine in humans. Carcinogen.<br>References Sugasawa, S., et al.: Pharma. Bull., et al.: 2, 39 (1954), Thompson, J.A., et al.: J. Chromatog., 231, 53 (1982); Seeman, J.I., et al.: J. Org. Chem., 51, 1548 (1986)<br></p>

<p>Applications 2-Chloro-rac-Nicotine is a metabolite of rac-Nicotine (N412420); an active stimulant having both addictive and carcinogenic properties.<br> Not a dangerous good if item is equal to or less than 1g/ml and there is less than 100g/ml in the package<br>References Lowry, T., et al.: J. Chem. Soc., 319 (1931);<br></p>

<p>Stability Light Sensitive<br>Applications Labelled (RS)-Nornicotine (N757000). (RS)-Nornicotine is a tobacco alkaloid and the major Nicotine (N412420) metabolite in brain. Nornicotine appears to activate different nAChR subtypes, has a better pharmacokinetic profile, and produces less toxicity than Nicotine. Nornicotine shows a significant analgesic activity.<br>References Hecht, S., et al.: Carcinogenesis, 9, 875 (1988), Rivenson, A., et al.: Cancer Res., 48, 6912 (1988), Hoffmann, D., et al.: Chem. Res. Toxicol., 14, 767 (2001), Kool, J., et al.: J. Med. Chem., 49, 3287 (2006), Kool, J., et al.: Drug Metab. Dispos., 35, 640 (2007),<br></p>

<p>Applications Used in the preparation of 2-Aminodihydro[1,3]thiazines as BACE 2 inhibitors and their preparation and use in the treatment of diabetes.<br>References Denny, W., et al.: J. Med. Chem., 33, 814 (1990), Maurya, M., et al.: J. Chem. Res., 446 (1998),<br></p>

<p>Applications Glucosides of Nicotine (N412420). A representative lot was a 1:1 mixture of alpha and beta.<br></p>

<p>Stability Light Sensitive<br>Applications (±)-Nicotine-d7 (N-methyl-d3; pyridine-d4) is the labelled version of Nicotine (N412420(M)) is an alkaloid isolated from plants. Nicotine is an active stimulant, having both addictive and carcinogenic properties. Nicotine can be absorbed through the alimentary canal, respiratory tract and intact skin. Nicotine is used in the treatment of smoking withdrawal syndrome. Nicotine has been used as an anthelmintic.<br>References Ferretti, G., et al.: J. Med. Chem., 45, 4724 (2002), Guillen, M., et al.: J. Agric. Food Chem., 53, 1093 (2005), Ramunno, A., et al.: Bioorg. Med. Chem. Lett., 15, 3237 (2005), Alburges, M., et al.: Eur. J. Pharmacol., 573, 124 (2007),<br></p>

<p>Applications Nicotine analog.<br>References Yamamoto, I., et al.: Agr. Biol. Chem., 27, 446 (1963)<br></p>

<p>Applications A nicotine metabolite.<br> Not a dangerous good if item is equal to or less than 1g/ml and there is less than 100g/ml in the package<br>References Kool, J., et al.: J. Med. Chem., 49, 3287 (2006), Newman, D., et al.: J. Nat. Prod., 70, 461 (2007), Kool, J., et al.: Drug Metab. Dispos., 35, 640 (2007),<br></p>

<p>Applications (±)-Cotinine-2,4,5,6-d4 (pyridine-d4) (CAS# 350818-68-7) is a useful isotopically labeled research compound.<br></p>

<p>Stability Hygroscopic<br>Applications Nicotine-N-(4-deoxy-4,5-didehydro)-β-D-glucuronide is a possible metabolite of Nicotine (N412420).<br> Not a dangerous good if item is equal to or less than 1g/ml and there is less than 100g/ml in the package<br></p>

<p>Applications 4-Chloro-6-nitrosoresorcinol-d1 is the labeled analogue of 4-Chloro-6-nitrosoresorcinol (C374860). 4-Chloro-6-nitrosoresorcinol-d1 is an intermediate in the synthesis of 6-Hydroxy Chlorzoxazone-d2 (H825123), a labeled analogue of 6-Hydroxy Chlorzoxazone (H825120), A major metabolite of chlorzoxazone and formed by the actions of cytochrome P450IIE1.<br>References Twele, et al.: Arzneim.-Forsch., 32, 759 (1982); Peter, et al.: che. Res. Toxicol., 3, 566 (1990)<br></p>

<p>Nicergoline EP Impurity B is a metabolite of nicergoline, a drug product. It has been synthesized for use as an impurity standard for analytical and pharmacopoeia purposes. Nicergoline EP Impurity B is not found in nature and has been shown to be metabolically stable in vitro. It can be used as a reference substance for the determination of nicergoline concentrations in human plasma samples.</p>