L-Carnitine base
[CAS# 541-15-1]

Identification

• Classification: API >> Digestive system medication >> Digestive drug
• Name: L-Carnitine base
• Synonyms: 3-Hydroxy-4-(trimethylammonio)butanoate; Vitamin BT; L(-)-Carnitine
• Molecular Formula: C₇H₁₅NO₃
• Molecular Weight: 161.20
• CAS Registry Number: 541-15-1
• EC Number: 208-768-0
• SMILES: C[N+](C)(C)C[C@@H](CC(=O)[O-])O

Properties

• Melting point: 208-212 °C
• alpha: -31 ° (c=10, H2O)
• Water solubility: 2500 g/L (20 °C)

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319
• Safety Statements: P264-P264+P265-P280-P302+P352-P305+P351+P338-P321-P332+P317-P337+P317-P362+P364

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Specific target organ toxicity - single exposure	STOT SE	3	H336

Discovery and Applications

L-Carnitine base is a quaternary ammonium compound with the chemical formula C7H15NO3. It is a naturally occurring substance synthesized in the human body from the amino acids lysine and methionine. L-Carnitine plays a vital role in the metabolism of fatty acids, facilitating their transport into the mitochondria for energy production. Its discovery can be traced back to the 1900s when it was first isolated from meat extracts, hence its name derived from the Latin word "carnis," meaning flesh. Since its identification, L-carnitine has garnered significant attention for its potential health benefits and applications.

The initial isolation of L-carnitine was achieved by Russian chemist S. M. Gulewitsch and his colleague A. A. Krimberg in 1905, who extracted it from the muscle tissue of animals. Over the following decades, researchers explored the biochemical pathways of L-carnitine, elucidating its crucial role in fatty acid metabolism. In the 1960s, studies began to highlight its significance in enhancing exercise performance and weight management, marking the beginning of its popularity as a dietary supplement.

L-carnitine is primarily known for its role in energy metabolism. It acts as a carrier molecule that transports long-chain fatty acids across the inner mitochondrial membrane, where they are oxidized to produce adenosine triphosphate (ATP), the primary energy currency of the cell. This function has led to extensive research on L-carnitine's potential benefits in improving physical performance, particularly in endurance sports. Athletes often supplement with L-carnitine to enhance fat oxidation and delay the onset of fatigue during prolonged exercise, although the evidence on its efficacy remains mixed.

In addition to its performance-enhancing properties, L-carnitine has been studied for its potential therapeutic applications in various health conditions. One of the most notable uses is in the treatment of carnitine deficiency, a rare genetic disorder that impairs the body's ability to produce or transport L-carnitine, leading to severe metabolic disturbances. Supplementation with L-carnitine can effectively restore normal energy metabolism and alleviate symptoms in affected individuals.

L-carnitine has also been investigated for its potential benefits in cardiovascular health. Some studies suggest that L-carnitine supplementation may improve exercise capacity in patients with coronary artery disease and heart failure, potentially enhancing the heart's ability to utilize fatty acids as a source of energy. Additionally, L-carnitine has been explored for its role in reducing inflammation and oxidative stress, which are associated with various cardiovascular conditions.

Beyond its applications in exercise and cardiovascular health, L-carnitine has attracted attention for its potential effects on weight loss and body composition. Research has indicated that L-carnitine supplementation may promote fat loss, although results are inconsistent and further studies are necessary to establish its effectiveness as a weight management aid. Additionally, L-carnitine is being studied for its neuroprotective properties, with preliminary research suggesting it may have a role in improving cognitive function and protecting against neurodegenerative diseases.

L-carnitine is available in various forms, including L-carnitine tartrate and acetyl-L-carnitine, each with distinct properties and potential applications. The supplementation of L-carnitine is generally considered safe when taken at recommended doses, but it may cause side effects in some individuals, including gastrointestinal discomfort and nausea. As with any supplement, it is important for individuals to consult healthcare professionals before starting L-carnitine to assess its appropriateness for their specific health needs.

In summary, L-carnitine base is a crucial compound with a rich history of discovery and diverse applications in metabolism, exercise performance, cardiovascular health, and weight management. Its role in facilitating energy production and its potential therapeutic benefits continue to make it a topic of interest in the fields of nutrition and medicine.

References

2024. Assessment of the relative bioavailability between betaine and L-carnitine for Nile tilapia. Aquaculture International.
DOI: 10.1007/s10499-024-01771-2

1991. Supraphysiological dosages of vitamins and their implications in man. Cellular and Molecular Life Sciences, 47(2).
DOI: 10.1007/bf01945422

1987. Modulation by palmitoylcarnitine of protein kinase C activation. Cancer Research, 47(24).
URL: https://pubmed.ncbi.nlm.nih.gov/3479247