MedKoo Cat#: 471014 | Name: (-)-Cotinine
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

(-)-Cotinine is a major metabolite of nicotine in humans, it is a minor alkaloid found in tobacco plants

Chemical Structure

(-)-Cotinine
(-)-Cotinine
CAS#486-56-6

Theoretical Analysis

MedKoo Cat#: 471014

Name: (-)-Cotinine

CAS#: 486-56-6

Chemical Formula: C10H12N2O

Exact Mass: 176.0950

Molecular Weight: 176.22

Elemental Analysis: C, 68.16; H, 6.86; N, 15.90; O, 9.08

Price and Availability

Size Price Availability Quantity
100mg USD 350.00 2 Weeks
250mg USD 650.00 2 Weeks
500mg USD 1,050.00 2 Weeks
1g USD 1,650.00 2 Weeks
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Related CAS #
No Data
Synonym
NIH 10498; NIH10498; NIH-10498; (-)-Cotinine; S-(-)-Cotinine; (S)-Cotinine
IUPAC/Chemical Name
(S)-1-methyl-5-(pyridin-3-yl)pyrrolidin-2-one
InChi Key
UIKROCXWUNQSPJ-VIFPVBQESA-N
InChi Code
InChI=1S/C10H12N2O/c1-12-9(4-5-10(12)13)8-3-2-6-11-7-8/h2-3,6-7,9H,4-5H2,1H3/t9-/m0/s1
SMILES Code
O=C1N(C)[C@H](C2=CC=CN=C2)CC1
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
~10 mg/ml in PBS (pH 7.2); ~30 mg/ml in EtOH, DMSO, & DMF
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 176.22 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Nowak JM, Żuryń A, Grzanka A. Kotynina--metabolizm, zastosowanie jako biomarker i wpływ na organizm człowieka [Cotinine--metabolism, application as a biomarker and the effects on the organism]. Postepy Hig Med Dosw (Online). 2012 Dec 14;66:996-1005. Polish. doi: 10.5604/17322693.1024156. PMID: 23687219. 2: Kim S. Overview of Cotinine Cutoff Values for Smoking Status Classification. Int J Environ Res Public Health. 2016 Dec 14;13(12):1236. doi: 10.3390/ijerph13121236. PMID: 27983665; PMCID: PMC5201377. 3: Takeda N. [Cotinine]. Nihon Rinsho. 1999 Sep;57 Suppl:471-7. Japanese. PMID: 10543157. 4: Echeverria V, Zeitlin R. Cotinine: a potential new therapeutic agent against Alzheimer's disease. CNS Neurosci Ther. 2012 Jul;18(7):517-23. doi: 10.1111/j.1755-5949.2012.00317.x. Epub 2012 Apr 25. PMID: 22530628; PMCID: PMC6493450. 5: Ding ZM, Gao Y, Sentir AM, Tan X. Self-Administration of Cotinine in Wistar Rats: Comparisons to Nicotine. J Pharmacol Exp Ther. 2021 Mar;376(3):338-347. doi: 10.1124/jpet.120.000367. Epub 2020 Dec 23. PMID: 33361363; PMCID: PMC7883011. 6: Merianos AL, Jandarov RA, Mahabee-Gittens EM. High Cotinine and Healthcare Utilization Disparities Among Low-Income Children. Am J Prev Med. 2021 Feb;60(2):267-275. doi: 10.1016/j.amepre.2020.06.018. Epub 2020 Oct 29. PMID: 33131989; PMCID: PMC7854767. 7: Benowitz NL. Cotinine as a biomarker of environmental tobacco smoke exposure. Epidemiol Rev. 1996;18(2):188-204. doi: 10.1093/oxfordjournals.epirev.a017925. PMID: 9021312. 8: Echeverria V, Barreto GE, Avila-Rodriguezc M, Tarasov VV, Aliev G. Is VEGF a Key Target of Cotinine and Other Potential Therapies Against Alzheimer Disease? Curr Alzheimer Res. 2017;14(11):1155-1163. doi: 10.2174/1567205014666170329113007. PMID: 28356047. 9: Cheng J, Mi P, Li Y, Lu Y, Sun F. Melatonin prevents oocyte deterioration due to cotinine exposure in mice†. Biol Reprod. 2022 Aug 9;107(2):635-649. doi: 10.1093/biolre/ioac043. PMID: 35191979. 10: Zhao L, Zhao Z, Zhang K, Zhang X, Xu S, Liu J, Liu B, Hong Q, Qiu J, He J. Cotinine Hydroxylase CotA Initiates Biodegradation of Wastewater Micropollutant Cotinine in Nocardioides sp. Strain JQ2195. Appl Environ Microbiol. 2021 Aug 26;87(18):e0092321. doi: 10.1128/AEM.00923-21. Epub 2021 Aug 26. PMID: 34232707; PMCID: PMC8388815. 11: Buccafusco JJ, Terry AV Jr. The potential role of cotinine in the cognitive and neuroprotective actions of nicotine. Life Sci. 2003 May 16;72(26):2931-42. doi: 10.1016/s0024-3205(03)00226-1. PMID: 12706481. 12: Pérez-Martín H, Lidón-Moyano C, González-Marrón A, Fu M, Pérez-Ortuño R, Ballbè M, Martín-Sánchez JC, Pascual JA, Fernández E, Martínez-Sánchez JM. Changes in the salivary cotinine cut-offs to discriminate smokers and non- smokers before and after Spanish smoke-free legislation. Cancer Epidemiol. 2022 Oct;80:102226. doi: 10.1016/j.canep.2022.102226. Epub 2022 Jul 22. PMID: 35878525. 13: Lidón-Moyano C, Fu M, Pérez-Ortuño R, Ballbè M, Garcia E, Martín-Sánchez JC, Pascual JA, Fernández E, Martínez-Sánchez JM. Third-hand exposure at homes: Assessment using salivary cotinine. Environ Res. 2021 May;196:110393. doi: 10.1016/j.envres.2020.110393. Epub 2020 Oct 28. PMID: 33129855. 14: Alasmari F, Alasmari AF, Elzayat E, Alotaibi MM, Alotaibi FM, Attwa MW, Alanazi FK, Abdelgadir EH, Ahmad SR, Alqahtani F, Al-Rejaie SS, Alshammari MA. Nicotine and cotinine quantification after a 4-week inhalation of electronic cigarette vapors in male and female mice using UPLC-MS/MS. Saudi Med J. 2022 Jul;43(7):678-686. doi: 10.15537/smj.2022.43.7.20220142. PMID: 35830983; PMCID: PMC9749686. 15: Yusuf KK, Wilson R, Mbah A, Sappenfield W, King LM, Salihu HM. Maternal Cotinine Levels and Red Blood Cell Folate Concentrations in the Periconceptual Period. South Med J. 2020 Apr;113(4):156-163. doi: 10.14423/SMJ.0000000000001083. PMID: 32239227. 16: Diken OE, Unculu S, Karnak D, Cağlayan O, Göçmen JS, Kayacan O. Cotinine levels in serum and bronchoalveolar lavage fluid. Southeast Asian J Trop Med Public Health. 2010 Sep;41(5):1252-7. PMID: 21073047. 17: West O, Hajek P, McRobbie H. Systematic review of the relationship between the 3-hydroxycotinine/cotinine ratio and cigarette dependence. Psychopharmacology (Berl). 2011 Nov;218(2):313-22. doi: 10.1007/s00213-011-2341-1. Epub 2011 May 20. PMID: 21597990. 18: Dziuda MR, Grzybowski A. Kotynina--biomarker ekspozycji na dym tytoniowy [Cotinine--the biomarker of exposure to tobacco smoke]. Przegl Lek. 1999;56(2):161-3. Polish. PMID: 10375952. 19: Idle JR. Titrating exposure to tobacco smoke using cotinine--a minefield of misunderstandings. J Clin Epidemiol. 1990;43(4):313-7. doi: 10.1016/0895-4356(90)90117-8. PMID: 2182786. 20: Bramer SL, Kallungal BA. Clinical considerations in study designs that use cotinine as a biomarker. Biomarkers. 2003 May-Aug;8(3-4):187-203. doi: 10.1080/13547500310012545. PMID: 12944172.