Citrulline

Citrulline is a non-essential amino acid, which means that the body can produce it even if it is not obtained from the diet. It plays a significant role in several biological processes, particularly in the urea cycle, where it helps in the elimination of ammonia from the body. The chemical properties and relevant information about citrulline can be summarized as follows:

Chemical Properties and Structure

• Chemical Formula: Citrulline has the chemical formula C6H13N3O3[1][2].
• Molecular Weight: The molecular weight of citrulline is 175.1857 g/mol[1].
• IUPAC Name: The IUPAC name for citrulline is (2S)-2-amino-5-(carbamoylamino)pentanoic acid[1][2].
• CAS Number: The CAS number for citrulline is 372-75-8[1][2].
• InChI Key: The InChI Key for citrulline is RHGKLRLOHDJJDR-BYPYZUCNSA-N[1][2].
• SMILES: The SMILES representation is NC@@HC(O)=O[1][2].

Classification and Taxonomy

• Citrulline belongs to the class of organic compounds known as L-alpha-amino acids, which are alpha amino acids that have the L-configuration of the alpha-carbon atom[1][2].
• It is a key intermediate in the urea cycle, which is the pathway by which mammals excrete ammonia[4][5].
• Citrulline is also produced from arginine as a by-product of the reaction catalyzed by the NOS family[2][5].

Biological Role and Health Implications

• Citrulline is involved in the production of nitric oxide in the body, which helps arteries relax and improves blood flow[3].
• It is converted by the kidneys into another amino acid, L-arginine, and nitric oxide, which are important for heart and blood vessel health, and may also boost the immune system[3].
• Citrulline supplements may help lower blood pressure in people with elevated blood pressure and ease symptoms of mild-to-moderate erectile dysfunction (ED)[3].
• It has potential benefits for treating or preventing diseases related to blood vessel problems, such as slow wound healing due to diabetes, and may improve muscle protein levels and prevent malnourishment in the elderly[3].
• Some research suggests that citrulline may be helpful for conditions like Parkinson's disease and certain dementias, although these are early human studies[3].
• Citrulline is sometimes used by athletes to improve performance, but research shows it does not help well-trained athletes perform better[3].

Usage and Dosage

• Citrulline is available as a dietary supplement, often in powder form, and is used for various health conditions such as Alzheimer's disease, dementia, fatigue, muscle weakness, sickle cell disease, erectile dysfunction, high blood pressure, and diabetes[8].
• The suggested dosage for L-citrulline depends on the condition being treated or prevented and can be up to 6 grams a day for up to 16 days[3].
• Optimal doses of L-citrulline have not been set for any condition, and the quality and active ingredients in supplements may vary widely[3].

Safety and Interactions

• There are no reported side effects of L-citrulline, but it may affect the way certain drugs work in the body[3].
• It should not be taken with nitrates for heart disease or ED drugs, as it may cause a dangerous drop in blood pressure[3].
• Caution is advised when taking L-citrulline with blood pressure medication[3].
• It is not recommended for use during pregnancy or breastfeeding, and it is important to inform a healthcare provider about any supplements being taken[3].

In summary, citrulline is an amino acid with a variety of roles in the body, particularly in the urea cycle and in the production of nitric oxide. It has potential health benefits, especially for cardiovascular health and certain metabolic conditions, and is available as a supplement. However, its use should be approached with caution, especially when taken with other medications.

Citations:

[1] http://exposome-explorer.iarc.fr/compounds/1583

[2] https://go.drugbank.com/drugs/DB00155

[3] https://www.webmd.com/vitamins-and-supplements/l-citrulline-uses-and-risks

[4] https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI%3A16349

[5] https://pubchem.ncbi.nlm.nih.gov/compound/Citrulline

[6] https://pubchem.ncbi.nlm.nih.gov/compound/DL-Citrulline

[7] https://www.sciencedirect.com/topics/biochemistry-genetics-and-molecular-biology/citrulline

[8] https://www.chemicalbook.com/ChemicalProductProperty_EN_CB6423883.htm