1-Methylnicotinamide

Last updated
1-Methylnicotinamide
1-Methylnicotinamide.svg
Names
Preferred IUPAC name
3-Carbamoyl-1-methylpyridin-1-ium
Other names
Trigonellamide; N1-Methylnicotinamide; NMN
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
PubChem CID
UNII
  • C[N+]1=CC=CC(=C1)C(=O)N
Properties
C7H9N2O+
Molar mass 137.161 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

1-Methylnicotinamide (1-MNA,trigonellamide) is a prototypic organic cation. [1] 1-Methylnicotinamide is the methylated amide of Nicotinamide (niacinamide, vitamin B3).

Contents

1-Methylnicotinamide is an endogenic substance that is produced in the liver when Nicotinamide is metabolized. It is a typical substance secreted in the kidney. It participates in the nicotinamide salvage pathway within the NAD+ (nicotinamide adenine dinucleotide) metabolic pathway, thereby contributing to optimizing NAD+ levels. [2]

Occurrence

To date, the highest natural concentration of 1-methylnicotinamide has been found in the alga Undaria pinnatifida (3.2 mg/100 g of dried algae) and green tea leaves (3 mg/100 g of product). Other products with notable 1-MNA content include celery (1.6 mg/100 g of product), Chinese black mushrooms (shiitake, 1.3 mg/100 g), and fermented soybeans (natto, 1.0 mg/100 g). [3]

Biosynthesis

1-Methylnicotinamide can be produced in the liver by nicotinamide N-methyltransferase (NNMT). The reaction takes place during the metabolism of NAD+ (nicotinamide adenine dinucleotide). NNMT is also present in brain tissue, adipose tissue, muscle tissue, kidneys, and skin. [4] [5]

NNMT (nicotinamide N-methyltransferase) is an enzyme that in humans is encoded by the NNMT gene. [6] NNMT catalyzes the methylation of nicotinamide and similar compounds using the methyl donor S-adenosyl methionine (SAM-e) to produce S-adenosyl-L-homocysteine (SAH) and 1-methylnicotinamide. [7] NNMT is highly expressed in the human liver. [7]

Role in the body

Scientific research highlights numerous therapeutic and health-promoting properties of 1-MNA, including vascular protective, [8] [9] anticoagulant, [10] anti-atherosclerotic, [11] anti-inflammatory, [12] [13] [14] neuroprotective, [15] and endurance-enhancing effects. [16]

Vascular Protective Effects

1-MNA exerts beneficial effects on blood vessels through its action on the vascular endothelium. It improves the bioavailability of nitric oxide (NO), which is crucial for vasodilation, and regulates the activity of endothelial nitric oxide synthase (eNOS), the enzyme responsible for NO synthesis. [8] [9]

These effects have been demonstrated in both in vivo and in vitro studies. Oral administration of 1-MNA has been shown to increase the diameter of the brachial artery (as measured by flow-mediated dilation, FMD) and stimulate NO release from human endothelial cells in both healthy individuals and those with hypercholesterolemia increased. [9]

Additionally, in cases of vascular dysfunction (e.g., hypertriglyceridemia or diabetes), 1-MNA restored normal NO-dependent vasodilation. [8] By increasing NO bioavailability, 1-MNA may counteract endothelial dysfunction, support endothelial regeneration, and improve vascular function, particularly in the context of cardiovascular risk. [8] [9]

Anticoagulant Effects

1-Methylnicotinamide is an endogenous activator of prostacyclin synthesis and can therefore regulate thrombolytic[ check spelling ] and inflammatory processes in the cardiovascular system. [8] It inhibits platelet-dependent thrombosis through a mechanism involving [10] cyclooxygenase-2 and prostacyclin and increases nitric oxide bioavailability in the endothelium. [9] [7] Endogenous prostacyclin (PGI2) plays a critical role in preventing platelet aggregation and thrombus formation. A deficiency in PGI2 can lead to increased platelet aggregation and arterial thrombi.

Anti-atherosclerotic and Anti-inflammatory Effects

1-MNA exhibits anti-atherosclerotic and anti-inflammatory properties by improving the prostacyclin- and NO-dependent secretory function of the vascular endothelium, inhibiting platelet activation, reducing inflammation within atherosclerotic plaques, and lowering systemic inflammation and TNF-α levels. [11]

The anti-inflammatory effects of 1-MNA are linked to its ability to stimulate endogenous PGI2 secretion and reduce IL-4 and TNF-α levels. [12] These effects are mediated by endothelial mechanisms rather than a direct impact on immune cell function, ensuring that the body’s immune response is not weakened. [13] [14]

NAD+ Optimization

1-MNA is an inhibitor of nicotinamide N-methyltransferase (NNMT). By inhibiting NNMT activity, it regulates NAD+ biosynthesis via the nicotinamide salvage pathway, the primary route for NAD+ synthesis in mammals. By participating in this pathway, 1-MNA optimizes NAD+ levels. [2]

Impact on SIRT1

Research published in Nature Medicine indicates that 1-MNA enhances SIRT1 expression and stability. [17] SIRT1 is an enzyme associated with longevity.

Studies using the nematode Caenorhabditis elegans indicate that 1-MNA supplementation may extend lifespan. These studies also link 1-MNA to SIRT1. [18]

Neuroprotective Effects

Animal experiments with diabetic rats have shown that 1-methylnicotinamide positively effects degenerative changes in the brain, allowing cognitive performance to be maintained longer. [19] It also prevents depressive behavior with efficacy comparable to the common antidepressant fluoxetine. This effect is attributed to the reduction of neuroinflammation, pro-inflammatory cytokines (IL-6, TNF-α), and increased expression of BDNF (brain-derived neurotrophic factor), a protein supporting neuron survival and growth. [20]

The neuroprotective effects of 1-MNA involve shielding against neurotoxins, amyloid-beta plaques in the brain, neuroinflammatory responses, and neuronal apoptosis. It has been shown to improve memory deficits and cognitive functions, suggesting potential for treating neurodegenerative disorders. [15] [21]

Enhancement of Physical Performance

1-MNA acts as a myokine, supporting the utilization of amino acids for gluconeogenesis in the liver and stimulating lipolysis in adipose tissue, thereby providing energy for muscles. [22] Studies indicate that 1-MNA supplementation improves exercise tolerance and reduces fatigue. After one month of supplementation, post-COVID-19 patients reported improved distances in a 6-minute walk test (6MWT), with 92% of participants experiencing better outcomes compared to controls. [16]

Additional studies highlight 1-MNA’s ability to enhance physical performance by stimulating PGI2 release, protecting microcirculation, and ensuring adequate blood flow to muscle tissues. This mechanism may reduce cardiovascular risks associated with physical exertion, particularly in individuals with impaired endothelial response. [23]

Commercialization

1-MNA has been approved for use in food products in the form of 1-MNA chloride. The approval process in the European Union was successfully completed by PHARMENA SA. In 2017, the European Food Safety Authority (EFSA) confirmed the safety of 1-MNA chloride in food supplements, leading to its authorization in 2018 under EU Regulation 2018/1123. [24]

1-MNA chloride is currently used in dietary supplements. [25] Other chemical forms of 1-MNA are not currently allowed on the market as food.

Safety

The safety of 1-MNA chloride has been thoroughly evaluated by EFSA, confirming its safe use. It must meet quality parameters defined in EU Regulation 2018/1123. [24] [26]

Related Research Articles

<span class="mw-page-title-main">Inflammation</span> Physical effects resulting from activation of the immune system

Inflammation is part of the biological response of body tissues to harmful stimuli, such as pathogens, damaged cells, or irritants. The five cardinal signs are heat, pain, redness, swelling, and loss of function.

<span class="mw-page-title-main">Prostaglandin</span> Group of physiologically active lipid compounds

Prostaglandins (PG) are a group of physiologically active lipid compounds called eicosanoids that have diverse hormone-like effects in animals. Prostaglandins have been found in almost every tissue in humans and other animals. They are derived enzymatically from the fatty acid arachidonic acid. Every prostaglandin contains 20 carbon atoms, including a 5-carbon ring. They are a subclass of eicosanoids and of the prostanoid class of fatty acid derivatives.

<span class="mw-page-title-main">Vasodilation</span> Widening of blood vessels

Vasodilation, also known as vasorelaxation, is the widening of blood vessels. It results from relaxation of smooth muscle cells within the vessel walls, in particular in the large veins, large arteries, and smaller arterioles. Blood vessel walls are composed of endothelial tissue and a basal membrane lining the lumen of the vessel, concentric smooth muscle layers on top of endothelial tissue, and an adventitia over the smooth muscle layers. Relaxation of the smooth muscle layer allows the blood vessel to dilate, as it is held in a semi-constricted state by sympathetic nervous system activity. Vasodilation is the opposite of vasoconstriction, which is the narrowing of blood vessels.

<span class="mw-page-title-main">Endothelium</span> Layer of cells that line the inner surface of blood vessels

The endothelium is a single layer of squamous endothelial cells that line the interior surface of blood vessels and lymphatic vessels. The endothelium forms an interface between circulating blood or lymph in the lumen and the rest of the vessel wall.

<span class="mw-page-title-main">Prostacyclin</span> Chemical compound

Prostacyclin (also called prostaglandin I2 or PGI2) is a prostaglandin member of the eicosanoid family of lipid molecules. It inhibits platelet activation and is also an effective vasodilator.

<span class="mw-page-title-main">Endothelial dysfunction</span> Impaired function of the inner lining of blood/lymph vessels

In vascular diseases, endothelial dysfunction is a systemic pathological state of the endothelium. The main cause of endothelial dysfunction is impaired bioavailability of nitric oxide.

<span class="mw-page-title-main">Endothelin</span>

Endothelins are peptides with receptors and effects in many body organs. Endothelin constricts blood vessels and raises blood pressure. The endothelins are normally kept in balance by other mechanisms, but when overexpressed, they contribute to high blood pressure (hypertension), heart disease, and potentially other diseases.

<span class="mw-page-title-main">Thrombotic microangiopathy</span> Medical condition

Thrombotic microangiopathy (TMA) is a pathology that results in thrombosis in capillaries and arterioles, due to an endothelial injury. It may be seen in association with thrombocytopenia, anemia, purpura and kidney failure.

The epoxyeicosatrienoic acids or EETs are signaling molecules formed within various types of cells by the metabolism of arachidonic acid by a specific subset of cytochrome P450 enzymes, termed cytochrome P450 epoxygenases. They are nonclassic eicosanoids.

<span class="mw-page-title-main">Sirtuin</span> Enzyme

Sirtuins are a family of signaling proteins involved in metabolic regulation. They are ancient in animal evolution and appear to possess a highly conserved structure throughout all kingdoms of life. Chemically, sirtuins are a class of proteins that possess either mono-ADP-ribosyltransferase or deacylase activity, including deacetylase, desuccinylase, demalonylase, demyristoylase and depalmitoylase activity. The name Sir2 comes from the yeast gene 'silent mating-type information regulation 2', the gene responsible for cellular regulation in yeast.

<span class="mw-page-title-main">ICAM-1</span> Mammalian protein found in Homo sapiens

ICAM-1 also known as CD54 is a protein that in humans is encoded by the ICAM1 gene. This gene encodes a cell surface glycoprotein which is typically expressed on endothelial cells and cells of the immune system. It binds to integrins of type CD11a / CD18, or CD11b / CD18 and is also exploited by rhinovirus as a receptor for entry into respiratory epithelium.

<span class="mw-page-title-main">Nicorandil</span> Chemical compound

Nicorandil is a vasodilator drug used to treat angina.

<span class="mw-page-title-main">Thromboxane receptor</span> Mammalian protein found in Homo sapiens

The thromboxane receptor (TP) also known as the prostanoid TP receptor is a protein that in humans is encoded by the TBXA2R gene, The thromboxane receptor is one among the five classes of prostanoid receptors and was the first eicosanoid receptor cloned. The TP receptor derives its name from its preferred endogenous ligand thromboxane A2.

<span class="mw-page-title-main">Prostacyclin receptor</span> Mammalian protein found in Homo sapiens

The prostacyclin receptor, also termed the prostaglandin I2 receptor or just IP, is a receptor belonging to the prostaglandin (PG) group of receptors. IP binds to and mediates the biological actions of prostacyclin (also termed prostaglandin I2, PGI2, or when used as a drug, epoprostenol). IP is encoded in humans by the PTGIR gene. While possessing many functions as defined in animal model studies, the major clinical relevancy of IP is as a powerful vasodilator: stimulators of IP are used to treat severe and even life-threatening diseases involving pathological vasoconstriction.

<span class="mw-page-title-main">Nicotinamide phosphoribosyltransferase</span> Human protein and coding gene

Nicotinamide phosphoribosyltransferase, formerly known as pre-B-cell colony-enhancing factor 1 (PBEF1) or visfatin for its extracellular form (eNAMPT), is an enzyme that in humans is encoded by the NAMPT gene. The intracellular form of this protein (iNAMPT) is the rate-limiting enzyme in the nicotinamide adenine dinucleotide (NAD+) salvage pathway that converts nicotinamide to nicotinamide mononucleotide (NMN) which is responsible for most of the NAD+ formation in mammals. iNAMPT can also catalyze the synthesis of NMN from phosphoribosyl pyrophosphate (PRPP) when ATP is present. eNAMPT has been reported to be a cytokine (PBEF) that activates TLR4, that promotes B cell maturation, and that inhibits neutrophil apoptosis.

<span class="mw-page-title-main">NNMT</span> Protein-coding gene in humans

Nicotinamide N-methyltransferase (NNMT) is an enzyme that in humans is encoded by the NNMT gene. NNMT catalyzes the methylation of nicotinamide and similar compounds using the methyl donor S-adenosyl methionine (SAM-e) to produce S-adenosyl-L-homocysteine (SAH) and 1-methylnicotinamide.

Endothelial activation is a proinflammatory and procoagulant state of the endothelial cells lining the lumen of blood vessels. It is most characterized by an increase in interactions with white blood cells (leukocytes), and it is associated with the early states of atherosclerosis and sepsis, among others. It is also implicated in the formation of deep vein thrombosis. As a result of activation, enthothelium releases Weibel–Palade bodies.

<span class="mw-page-title-main">Nicotinamide riboside</span> Chemical compound

Nicotinamide riboside (NR, SR647) is a pyridine-nucleoside and a form of vitamin B3. It functions as a precursor to nicotinamide adenine dinucleotide, or NAD+, through a two-step and a three-step pathway.

<span class="mw-page-title-main">MIR34A</span> Non-coding RNA in the species Homo sapiens

MicroRNA 34a (miR-34a) is a microRNA that in humans is encoded by the MIR34A gene.

<span class="mw-page-title-main">12-Hydroxyheptadecatrienoic acid</span> Chemical compound

12-Hydroxyheptadecatrienoic acid (also termed 12-HHT, 12(S)-hydroxyheptadeca-5Z,8E,10E-trienoic acid, or 12(S)-HHTrE) is a 17 carbon metabolite of the 20 carbon polyunsaturated fatty acid, arachidonic acid. 12-HHT is less ambiguously termed 12-(S)-hydroxy-5Z,8E,10E-heptadecatrienoic acid to indicate the S stereoisomerism of its 12-hydroxyl residue and the Z, E, and E cis–trans isomerism of its three double bonds. 12-HHT was discovered and structurally defined in 1973 by Paulina Wlodawer, Bengt Samuelsson, and Mats Hamberg. It was identified as a product of arachidonic acid metabolism made by microsomes isolated from sheep seminal vesicle glands and by intact human platelets. 12-HHT was for many years thought to be merely a biologically inactive byproduct of prostaglandin synthesis. More recent studies, however, have attached potentially important activity to it.

References

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  17. ↑ Hong, Shangyu; Moreno-Navarrete, Jose M; Wei, Xiaojing; Kikukawa, Yusuke; Tzameli, Iphigenia; Prasad, Deepthi; Lee, Yoonjin; Asara, John M; Fernandez-Real, Jose Manuel; Maratos-Flier, Eleftheria; Pissios, Pavlos (2015). "Nicotinamide N-methyltransferase regulates hepatic nutrient metabolism through Sirt1 protein stabilization". Nature Medicine. 21 (8): 887–894. doi:10.1038/nm.3882. ISSN   1078-8956. PMC   4529375 . PMID   26168293.
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  22. ↑ Nejabati, Hamid Reza; Ghaffari-Novin, Mahsa; Fathi-Maroufi, Nazila; Faridvand, Yousef; Holmberg, Hans-Christer; Hansson, Ola; Nikanfar, Saba; Nouri, Mohammad (2022). "N1-Methylnicotinamide: Is it Time to Consider it as a Dietary Supplement for Athletes?". Current Pharmaceutical Design. 28 (10): 800–805. doi:10.2174/1381612828666220211151204. PMID   35152860.
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  24. 1 2 "Implementing regulation - 2018/1123 - EN - EUR-Lex". eur-lex.europa.eu. Retrieved 2024-12-09.
  25. ↑ "Endotelio – Molekuła przyszłości". Endotelio. Retrieved 2024-12-09.
  26. ↑ EFSA Panel on Dietetic Products, Nutrition and Allergies (NDA); Turck, Dominique; Bresson, Jean-Louis; Burlingame, Barbara; Dean, Tara; Fairweather-Tait, Susan; Heinonen, Marina; Hirsch-Ernst, Karen Ildico; Mangelsdorf, Inge; McArdle, Harry J; Naska, Androniki; Neuhäuser-Berthold, Monika; Nowicka, Grażyna; Pentieva, Kristina; Sanz, Yolanda (2017). "Safety of 1-methylnicotinamide chloride (1-MNA) as a novel food pursuant to Regulation (EC) No 258/97". EFSA Journal. 15 (10). doi:10.2903/j.efsa.2017.5001. PMC   7010160 . PMID   32625296.
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