The Primary Vitamers: Nicotinic Acid and Nicotinamide
Vitamin B3 primarily exists as nicotinic acid and nicotinamide, which are called vitamers. Both share a central pyridine ring structure. They differ in the chemical group attached at the third position of this ring.
Nicotinic Acid
- Chemical Formula: C6H5NO2
- Structure: Has a carboxyl group (-COOH) on the pyridine ring.
- Use: Can lower cholesterol at high doses but may cause skin flushing.
Nicotinamide (Niacinamide)
- Chemical Formula: C6H6N2O
- Structure: Has a carboxamide group (-CONH2) on the pyridine ring.
- Use: Used in supplements and does not typically cause flushing.
Beyond the Vitamers: The Coenzyme Forms
In the body, nicotinic acid and nicotinamide are converted into the active coenzymes NAD and NADP, which are vital for cellular functions.
- NAD+ and NADP+: These are electron acceptors in metabolism. They include nicotinamide linked to a ribose sugar and an adenosine diphosphate (ADP) group.
- NADP+ includes an extra phosphate group compared to NAD+, altering its role.
- NADH and NADPH: These are the reduced forms, carrying electrons for building reactions.
The Body's Own Production Line: Tryptophan Conversion
The body can synthesize niacin in the liver from the amino acid tryptophan. This conversion is not very efficient, requiring about 60 mg of tryptophan per 1 mg of niacin and also needing sufficient riboflavin, pyridoxine, and iron.
Comparison of Niacin Vitamers
| Feature | Nicotinic Acid | Nicotinamide | NAD/NADP |
|---|---|---|---|
| Core Structure | Pyridine ring + carboxyl group | Pyridine ring + carboxamide group | Nicotinamide + adenosine + phosphate groups |
| Pharmacological Use | Used in high doses to treat dyslipidemia by improving cholesterol levels. | Primarily for nutritional supplementation and treating deficiencies without causing flushing. | The active coenzyme forms are used for cellular redox reactions. |
| Side Effects | Can cause a “niacin flush,” characterized by redness, burning, and tingling. | Generally does not cause skin flushing when taken as a supplement. | High doses can cause liver toxicity; otherwise, side effects are from the precursor forms. |
| Primary Function | Precursor to NAD and NADP. Modulates lipid metabolism at high doses. | Precursor to NAD and NADP. Less impactful on lipid levels than nicotinic acid. | Coenzymes for over 400 enzymes involved in metabolic processes. |
A List of Key Food Sources
To get enough niacin, include these foods in your diet:
- Poultry: Good sources of niacin and tryptophan.
- Fish: Excellent sources like tuna and salmon.
- Red Meat: Provides niacin and tryptophan.
- Legumes: Lentils and peanuts contain niacin and tryptophan.
- Nuts and Seeds: Examples include peanuts and sunflower seeds.
- Fortified Grains: Found in many breads and cereals.
- Eggs and Dairy: Provide protein with tryptophan.
Conclusion
Vitamin B3 is a group of compounds, mainly nicotinic acid and nicotinamide, based on a pyridine ring. These are precursors to the essential coenzymes NAD and NADP, critical for energy metabolism and other processes. The body can also make niacin from tryptophan, though this is limited. This composition makes vitamin B3 vital for health. More information can be found on the Linus Pauling Institute website.