Nicotine
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MedKoo CAT#: 596512

CAS#: 54-11-5

Description: Nicotine is highly toxic alkaloid. It is the prototypical agonist at nicotinic cholinergic receptors where it dramatically stimulates neurons and ultimately blocks synaptic transmission. Nicotine is also important medically because of its presence in tobacco smoke.


Chemical Structure

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Nicotine
CAS# 54-11-5

Theoretical Analysis

MedKoo Cat#: 596512
Name: Nicotine
CAS#: 54-11-5
Chemical Formula: C10H14N2
Exact Mass: 162.12
Molecular Weight: 162.236
Elemental Analysis: C, 74.03; H, 8.70; N, 17.27

Price and Availability

Size Price Availability Quantity
250mg USD 260
1250mg USD 470
5g USD 720
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Synonym: Nicotine; L-Nicotine; NSC 5065; NSC-5065; NSC5065; Tetrahydronicotyrine, dl-; Black leaf;

IUPAC/Chemical Name: (S)-3-(1-methylpyrrolidin-2-yl)pyridine

InChi Key: SNICXCGAKADSCV-JTQLQIEISA-N

InChi Code: InChI=1S/C10H14N2/c1-12-7-3-5-10(12)9-4-2-6-11-8-9/h2,4,6,8,10H,3,5,7H2,1H3/t10-/m0/s1

SMILES Code: CN1[C@H](C2=CC=CN=C2)CCC1

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: Soluble in DMSO

Shelf Life: >2 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: 2934.99.9001

More Info:

Product Data:
Biological target: Nicotine is highly toxic alkaloid. It is the prototypical agonist at nicotinic cholinergic receptors where it dramatically stimulates neurons and ultimately blocks synaptic transmission.
In vitro activity: Nicotine decreased the expression of microRNA (miR)-296-3p, which directly targeted the 3'-untranslated region (3'-UTR) of SIRPα mRNA in macrophage. Furthermore, nicotine inhibited the phagocytic ability of macrophage by regulating the miR-296-3p-SIRPα axis. Moreover, nicotine decreased miR-296-3p expression via increasing c-Myc expression in macrophage. Reference: Anal Cell Pathol (Amst). 2023 Feb 15;2023:6306358. https://pubmed.ncbi.nlm.nih.gov/36845756/
In vivo activity: Nic (nicotine) was found to improve neuroapoptosis, enhance tyrosine hydroxylase activity, and reduce the accumulation of the phosphorylated α-synuclein in the substantia nigra and striatal regions of PD mice by TUNEL and immunohistochemical assays. Immuno-fluorescent method for labeling Iba1 and CD68 indicated that Nic remarkably alleviates the activation of microglia which represents the M1 polarization state in the mice brain under MPTP stimulation. No significant difference in the expression of p38/MAPK pathway was found in the nigrostriatal regions, while Nic could significantly inhibit the elevated p-JNK/JNK ratio and increase the declined p-ERK/ERK ratio in the substantia nigra of MPTP-exposed brains, which was further confirmed by the pretreatment of CYP2A5 inhibitor to decline the metabolic activity of Nic. Reference: Front Pharmacol. 2023 Feb 2;14:1088957. https://pubmed.ncbi.nlm.nih.gov/36817162/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMF 50.0 308.19
DMSO 30.0 184.92
Ethanol 50.0 308.19
PBS (pH 7.2) 1.0 6.16

Preparing Stock Solutions

The following data is based on the product molecular weight 162.24 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
Formulation protocol: 1. Long DD, Zhang YZ, Liu A, Shen L, Wei HR, Lou QQ, Hu SS, Chen DY, Chai XQ, Wang D. Microglia sustain anterior cingulate cortex neuronal hyperactivity in nicotine-induced pain. J Neuroinflammation. 2023 Mar 21;20(1):81. doi: 10.1186/s12974-023-02767-0. PMID: 36944965; PMCID: PMC10031886. 2. Liu Z, Wang F, Huang X, Chen Z, Zhao Y, Wang Y, Luo X, Zhao G. Nicotine Suppresses Phagocytic Ability of Macrophages by Regulating the miR-296-3p-SIRPα Axis. Anal Cell Pathol (Amst). 2023 Feb 15;2023:6306358. doi: 10.1155/2023/6306358. PMID: 36845756; PMCID: PMC9946743. 3. Ruan S, Xie J, Wang L, Guo L, Li Y, Fan W, Ji R, Gong Z, Xu Y, Mao J, Xie J. Nicotine alleviates MPTP-induced nigrostriatal damage through modulation of JNK and ERK signaling pathways in the mice model of Parkinson's disease. Front Pharmacol. 2023 Feb 2;14:1088957. doi: 10.3389/fphar.2023.1088957. PMID: 36817162; PMCID: PMC9932206. 4. Yang L, Shen J, Liu C, Kuang Z, Tang Y, Qian Z, Guan M, Yang Y, Zhan Y, Li N, Li X. Nicotine rebalances NAD+ homeostasis and improves aging-related symptoms in male mice by enhancing NAMPT activity. Nat Commun. 2023 Feb 17;14(1):900. doi: 10.1038/s41467-023-36543-8. PMID: 36797299; PMCID: PMC9935903.
In vitro protocol: 1. Long DD, Zhang YZ, Liu A, Shen L, Wei HR, Lou QQ, Hu SS, Chen DY, Chai XQ, Wang D. Microglia sustain anterior cingulate cortex neuronal hyperactivity in nicotine-induced pain. J Neuroinflammation. 2023 Mar 21;20(1):81. doi: 10.1186/s12974-023-02767-0. PMID: 36944965; PMCID: PMC10031886. 2. Liu Z, Wang F, Huang X, Chen Z, Zhao Y, Wang Y, Luo X, Zhao G. Nicotine Suppresses Phagocytic Ability of Macrophages by Regulating the miR-296-3p-SIRPα Axis. Anal Cell Pathol (Amst). 2023 Feb 15;2023:6306358. doi: 10.1155/2023/6306358. PMID: 36845756; PMCID: PMC9946743.
In vivo protocol: 1. Ruan S, Xie J, Wang L, Guo L, Li Y, Fan W, Ji R, Gong Z, Xu Y, Mao J, Xie J. Nicotine alleviates MPTP-induced nigrostriatal damage through modulation of JNK and ERK signaling pathways in the mice model of Parkinson's disease. Front Pharmacol. 2023 Feb 2;14:1088957. doi: 10.3389/fphar.2023.1088957. PMID: 36817162; PMCID: PMC9932206. 2. Yang L, Shen J, Liu C, Kuang Z, Tang Y, Qian Z, Guan M, Yang Y, Zhan Y, Li N, Li X. Nicotine rebalances NAD+ homeostasis and improves aging-related symptoms in male mice by enhancing NAMPT activity. Nat Commun. 2023 Feb 17;14(1):900. doi: 10.1038/s41467-023-36543-8. PMID: 36797299; PMCID: PMC9935903.

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1: Wollman LB, Levine RB, Fregosi RF. Developmental nicotine exposure alters glycinergic neurotransmission to hypoglossal motoneurons in neonatal rats. J Neurophysiol. 2018 May 30. doi: 10.1152/jn.00600.2017. [Epub ahead of print] PubMed PMID: 29847237.

2: Fujii N, Nishiyasu T, Sigal RJ, Boulay P, McGarr GW, Kenny GP. Aging attenuates ATP-induced, but not muscarinic and nicotinic, cutaneous vasodilation in men. Microcirculation. 2018 May 30:e12462. doi: 10.1111/micc.12462. [Epub ahead of print] PubMed PMID: 29846993.

3: Kurti M, He Y, Silver D, Giorgio M, von Lampe K, Macinko J, Ye H, Tan F, Mei V. Presence of Counterfeit Marlboro Gold Packs in Licensed Retail Stores in New York City: Evidence From Test Purchases. Nicotine Tob Res. 2018 May 26. doi: 10.1093/ntr/nty096. [Epub ahead of print] PubMed PMID: 29846723.

4: Cruz TB, McConnell R, Low BW, Unger JB, Pentz MA, Urman R, Berhane K, Chou CP, Liu F, Barrington-Trimis J. Tobacco Marketing and Subsequent Use of Cigarettes, E-cigarettes and Hookah in Adolescents. Nicotine Tob Res. 2018 May 28. doi: 10.1093/ntr/nty107. [Epub ahead of print] PubMed PMID: 29846704.

5: Ho YY, Nhu Vo T, Chu H, Luo X, Le CT. A Bayesian hierarchical model for demand curve analysis. Stat Methods Med Res. 2018 Jul;27(7):2038-2049. doi: 10.1177/0962280216673675. Epub 2016 Oct 20. PubMed PMID: 29846147.

6: Liu DH, An M, Bao BL, Ren F, Xia P. Nicotine inhibits CD24 expression in Lewis lung carcinoma cells by upregulation of RAS expression. Int J Oncol. 2018 May 22. doi: 10.3892/ijo.2018.4415. [Epub ahead of print] PubMed PMID: 29845249.

7: Motooka Y, Matsui T, Slaton RM, Umetsu R, Fukuda A, Naganuma M, Hasegawa S, Sasaoka S, Hatahira H, Iguchi K, Nakamura M. Adverse events of smoking cessation treatments (nicotine replacement therapy and non-nicotine prescription medication) and electronic cigarettes in the Food and Drug Administration Adverse Event Reporting System, 2004-2016. SAGE Open Med. 2018 May 21;6:2050312118777953. doi: 10.1177/2050312118777953. eCollection 2018. PubMed PMID: 29844912; PubMed Central PMCID: PMC5966839.

8: Behar RZ, Luo W, McWhirter KJ, Pankow JF, Talbot P. Analytical and toxicological evaluation of flavor chemicals in electronic cigarette refill fluids. Sci Rep. 2018 May 29;8(1):8288. doi: 10.1038/s41598-018-25575-6. PubMed PMID: 29844439.

9: Do EK, Prom-Wormley EC, Fuemmeler BF, Dick DM, Kendler KS, Maes HH. Associations Between Initial Subjective Experiences with Tobacco and Self-Reported Recent Use in Young Adulthood. Subst Use Misuse. 2018 May 29:1-8. doi: 10.1080/10826084.2018.1473435. [Epub ahead of print] PubMed PMID: 29843549.

10: Michelogiannakis D, Rossouw PE, Al-Shammery D, Akram Z, Khan J, Romanos GE, Javed F. Influence of nicotine on orthodontic tooth movement: A systematic review of experimental studies in rats. Arch Oral Biol. 2018 May 23;93:66-73. doi: 10.1016/j.archoralbio.2018.05.016. [Epub ahead of print] Review. PubMed PMID: 29843070.

11: Tararina MA, Xue S, Smith LC, Muellers SN, Miranda PO, Janda KD, Allen KN. Crystallography Coupled with Kinetic Analysis Provide Mechanistic Underpinnings of a Nicotine-Degrading Enzyme. Biochemistry. 2018 May 29. doi: 10.1021/acs.biochem.8b00384. [Epub ahead of print] PubMed PMID: 29812904.

12: Buckell J, Marti J, Sindelar JL. Should flavours be banned in cigarettes and e-cigarettes? Evidence on adult smokers and recent quitters from a discrete choice experiment. Tob Control. 2018 May 28. pii: tobaccocontrol-2017-054165. doi: 10.1136/tobaccocontrol-2017-054165. [Epub ahead of print] PubMed PMID: 29807947.

13: Jawad M, Eissenberg T, Salman R, Soule E, Alzoubi KH, Khabour OF, Karaoghlanian N, Baalbaki R, El Hage R, Saliba NA, Shihadeh A. Toxicant inhalation among singleton waterpipe tobacco users in natural settings. Tob Control. 2018 May 28. pii: tobaccocontrol-2017-054230. doi: 10.1136/tobaccocontrol-2017-054230. [Epub ahead of print] PubMed PMID: 29807946.

14: Staal YC, van de Nobelen S, Havermans A, Talhout R. New Tobacco and Tobacco-Related Products: Early Detection of Product Development, Marketing Strategies, and Consumer Interest. JMIR Public Health Surveill. 2018 May 28;4(2):e55. doi: 10.2196/publichealth.7359. PubMed PMID: 29807884.

15: Dautzenberg B. [Understand the tobacco industry's strategy for recruiting teens: Lessons from a 1973 marketing document]. Rev Pneumol Clin. 2018 May 25. pii: S0761-8417(18)30102-0. doi: 10.1016/j.pneumo.2018.04.006. [Epub ahead of print] French. PubMed PMID: 29807733.

16: Chen YH, Lin BJ, Hsieh TH, Kuo TT, Miller J, Chou YC, Huang EY, Hoffer BJ. Differences in Nicotine Encoding Dopamine Release between the Striatum and Shell Portion of the Nucleus Accumbens. Cell Transplant. 2018 Jan 1:963689718775382. doi: 10.1177/0963689718775382. [Epub ahead of print] PubMed PMID: 29807460.

17: Stefanovics EA, Potenza MN, Pietrzak RH. The physical and mental health burden of obesity in U.S. veterans: Results from the National Health and Resilience in Veterans Study. J Psychiatr Res. 2018 May 22;103:112-119. doi: 10.1016/j.jpsychires.2018.05.016. [Epub ahead of print] PubMed PMID: 29807318.

18: Bisong SA, Ukoh IE, Nna VU, Ebong PE. Vitamin E attenuates nicotine- and noise-induced reproductive impairment in male albino Wistar rats. Andrologia. 2018 May 28:e13050. doi: 10.1111/and.13050. [Epub ahead of print] PubMed PMID: 29806220.

19: Kassem NOF, Kassem NO, Liles S, Jackson SR, Posis AIB, Chatfield DA, Hovell MF. Levels of Urine Cotinine from Hookah Smoking and Exposure to Hookah Tobacco Secondhand Smoke in Hookah Lounges and Homes. Int J High Risk Behav Addict. 2018 Mar;7(1). pii: e67601. doi: 10.5812/ijhrba.67601. Epub 2018 Feb 19. PubMed PMID: 29805963; PubMed Central PMCID: PMC5967845.

20: Nouri-Shirazi M, Tamjidi S, Nourishirazi E, Guinet E. Combination of TLR8 and TLR4 agonists reduces the degrading effects of nicotine on DC-NK mediated effector T cell generation. Int Immunopharmacol. 2018 May 24;61:54-63. doi: 10.1016/j.intimp.2018.05.012. [Epub ahead of print] PubMed PMID: 29803914.