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L(-)-Carnitine(CAS No. 541-15-1)

L(-)-Carnitine C7H15NO3 (cas 541-15-1) Molecular Structure

541-15-1 Structure

Identification and Related Records

【CAS Registry number】
Vitamin BT
Ammonium, (3-carboxy-2-hydroxypropyl)trimethyl-, hydroxide, inner salt, L- (8CI)
1-Propanaminium, 3-carboxy-2-hydroxy-N,N,N-trimethyl-, inner salt, (2R)-
Ammonium, (3-carboxy-2-hydroxypropyl)trimethyl-, hydroxide,inner salt
Levocarnitine (USP)
L-Carnitine Base(Usp29)
Carnitor (TN)
Carniking 50
1-Propanaminium,3-carboxy-2-hydroxy-N,N,- N-trimethyl-,inner salt,(2R)-
L-Carnitine EP/USP
L-Carnitine Base (Vitamine BT)
L-Carnitine base USP
【Molecular Formula】
C7H15NO3 (Products with the same molecular formula)
【Molecular Weight】
【Canonical SMILES】
【Isomers smiles】
【MOL File】

Chemical and Physical Properties

white crystalline powder
【Melting Point】
【Refractive Index】
-32 ° (C=1, H2O)
-31 o (C=10, H2O)
2500 g/L (20℃)
2500 g/L (20 °C)
White, crystalline, hygroscopic powder
【HS Code】
【Storage temp】
【Spectral properties】
The specific optical rotation is between -29 and -32
【Computed Properties】
Molecular Weight:161.1989 [g/mol]
Molecular Formula:C7H15NO3
H-Bond Donor:1
H-Bond Acceptor:3
Rotatable Bond Count:3
Exact Mass:161.105193
MonoIsotopic Mass:161.105193
Topological Polar Surface Area:60.4
Heavy Atom Count:11
Formal Charge:0
Isotope Atom Count:0
Defined Atom Stereocenter Count:1
Undefined Atom Stereocenter Count:0
Defined Bond Stereocenter Count:0
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1
Feature 3D Acceptor Count:3
Feature 3D Donor Count:1
Feature 3D Anion Count:1
Feature 3D Cation Count:1
Effective Rotor Count:4
Conformer Sampling RMSD:0.6
CID Conformer Count:5

Safety and Handling

【Hazard Codes】
【Risk Statements】
【Safety Statements 】
【Hazard Note】

Hazard Codes: IrritantXi
Risk Statements: 36/37/38?
R36/37/38: Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36-37/39?
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.?
S36: Wear suitable protective clothing.?
S37/39: Wear suitable gloves and eye/face protection.
WGK Germany: 3
RTECS: BP2980000
F: 3-10
Hazard Note: Irritant
HS Code: 29239000?

Levocarnitine oral solution USP: 100 mg/mL (Carnitor). Levocarnitine tablets USP: 330 mg (Carnitor). Levocarnitine injection: 200 mg/mL (Carnitor).
L-carnitine is avail in a few forms: oral L-carnitine ... iv L-carnitine, acetyl-L-carnitine, propionyl-L-carnitine. The avail salts ... are L-carnitine HCL, L-carnitine tartrate and L-carnitine fumarate ... /Supplied in/ capsules, injection, liquid, solution, tablets, wafer
Trade names: Carnitor ... Carnitine-300 ... Carni Fuel ... Mega L-Carnitine ... Maximal Burner Carnitine ... Proxeed ...
【Exposure Standards and Regulations】
Since 1994, dietary supplements have been regulated under the Dietary Supplement Health and Education Act (DSHEA). The DSHEA requires no proof of safety for dietary supplements on the market prior to October 15, 1994. Labeling requirements for such supplements allow warnings and dosage recommendations as well as substantiated "structure or function" claims. All claims must prominently note that they have not been evaluated by the FDA, and they must bear the statement "This product is not intended to diagnose, treat, cure, or prevent any disease".

In animals, carnitine is biosynthesized primarily in the liver and kidneys from the amino acids lysine or methionine.Carnitine transports long-chain acyl groups from fatty acids into the mitochondrial matrix. L-Carnitine (CAS NO.541-15-1) products and supplements are not allowed to be imported into Canada (Health Canada).?It is stable under normal temperatures and pressures, and it?absorbs moisture or water from the air.?It should avoid the condition like incompatible materials, exposure to moist air or water. while, it is incompatibilities with other materials strong oxidizing agents. Its hazardous decomposition products are carbon monoxide, oxides of nitrogen oxides, carbon monoxide, carbon dioxide.?And its hazardous polymerization will not occur.

【Octanol/Water Partition Coefficient】
log Kow = -5.48 (est)
【Disposal Methods】
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Use and Manufacturing

【Use and Manufacturing】
Methods of Manufacturing

Enantioselective synthesis from glycerol
Essential cofactor of fatty acid metabolism; required for the transport of fatty acids through the inner mitochondrial membrane. Synthetized primarily in the liver and kidney; highest concentrations found in heart and skeletal muscle. Dietary source

Biomedical Effects and Toxicity

【Pharmacological Action】
- A group of water-soluble vitamins, some of which are COENZYMES.
【Therapeutic Uses】
Levocarnitine is indicated for treatment of primary systemic carnitine deficiency, a genetic impairment of normal biosynthesis or utilization of levocarnitine from dietary sources, or for the treatment of secondary carnitine deficiency resulting from an inborn error of metabolism. /Included in US product labeling/
Parenteral levocarnitine is indicated for the prevention and treatment of carnitine deficiency in patients with end-stage renal disease supported on hemodialysis. /Included in US product labeling/
Levocarnitine oral solution is used for the prevention and treatment of carnitine deficiency secondary to valproic acid toxicity. /NOT included in US product labeling/
L-Carnitine, acetyl-L-carnitine, and/or propionyl-L-carnitine may be used for replacement therapy to restore normal carnitine concn and/or a normal nonesterified-to-esterified carnitine ratio ... For primary and some secondary carnitine deficiencies ... L-carnitine is used for replacement therapy.
L-Carnitine is approved as a pharmaceutical by the US FDA for treatment of primary systemic carnitine deficiency, and for acute and chronic treatment of patients with inborn errors of metabolism that result in secondary carnitine deficiency (eg, medium-chain acyl-CoA dehydrogenase deficiency, glutaric aciduria, Type 2 diabetes, methylmalonic aciduria, and propionic acidemia) ... /and/ for prevention and treatment of carnitine deficiency in patients with end-stage renal disease who are undergoing dialysis.
/EXPL THER/ L-carnitine ... or placebo was administered to 120 patients with hepatic encephalopathy for 60 days. Fasting serum ammonia levels were significantly lower at 30 and 60 days compared to baseline and placebo. Mental function was also significantly improved by L-carnitine, as measured by NCT-A, an accepted psychometric test for mental status in cirrhotic patients ...
/EXPL THER/ L-carnitine is believed to be a peripheral antagonist of thyroid hormone activity in some tissues. A randomized, double-blind, placebo-controlled, six-month trial reported ... daily doses of L-carnitine prevented and reversed hyperthyroidism-related symptoms, including exerting a beneficial effect on bone mineralization.
/EXPL THER/ Carnitine insufficiency is responsible for various co-morbid conditions in maintenance hemodialysis (MHD) patients. L-carnitine supplementation is expected to improve the quality of life (QoL) of patients on MHD. ... This was a single (patient) blind, randomized, placebo-controlled clinical trial conducted on patients on MHD attending hemodialysis unit of the study center. ... Twenty patients on MHD suffering from hemodialysis-related symptoms were randomly assigned to receive intravenous L-carnitine 20 mg/kg or placebo after every dialysis session for 8 weeks. SF36 (Short Form with 36 questions) score for QoL, laboratory investigations and dialysis related symptoms were recorded at baseline and after 8 weeks. Improvement in QoL, laboratory parameters and dialysis related symptoms in the two groups after 8 weeks was compared. ... L-carnitine supplementation increased total SF36 score by 18.29 +/- 12.71 (95% CI: 10.41 to 26) while placebo resulted in reduction in total SF36 score by 6.4 +/- 16.39 (95% CI: -16.59 to 3.73). L-carnitine also resulted in significant increase in hemoglobin and serum albumin and decrease in serum creatinine as compared to placebo. More patients were relieved of dialysis related symptoms in L-carnitine group. ... [Rathod R et al; Indian J Med Sci 60 (4): 143-53 (2006)]
【Biomedical Effects and Toxicity】
L-Carnitine is a naturally occurring compound that facilitates the transport of fatty acids into mitochondria for beta-oxidation. ... In humans, the endogenous carnitine pool, which comprises free L-carnitine and a range of short-, medium- and long-chain esters, is maintained by absorption of L-carnitine from dietary sources, biosynthesis within the body and extensive renal tubular reabsorption from glomerular filtrate. In addition, carrier-mediated transport ensures high tissue-to-plasma concentration ratios in tissues that depend critically on fatty acid oxidation. The absorption of L-carnitine after oral administration occurs partly via carrier-mediated transport and partly by passive diffusion. After oral doses of 1-6 g, the absolute bioavailability is 5-18%. In contrast, the bioavailability of dietary L-carnitine may be as high as 75%. Therefore, pharmacological or supplemental doses of L-carnitine are absorbed less efficiently than the relatively smaller amounts present within a normal diet. L-Carnitine and its short-chain esters do not bind to plasma proteins and, although blood cells contain L-carnitine, the rate of distribution between erythrocytes and plasma is extremely slow in whole blood. After iv administration, the initial distribution volume of L-carnitine is typically about 0.2-0.3 L/kg, which corresponds to extracellular fluid volume. There are at least three distinct pharmacokinetic compartments for L-carnitine, with the slowest equilibrating pool comprising skeletal and cardiac muscle. L-Carnitine is eliminated from the body mainly via urinary excretion. Under baseline conditions, the renal clearance of L-carnitine (1-3 mL/min) is substantially less than glomerular filtration rate (GFR), indicating extensive (98-99%) tubular reabsorption. The threshold concentration for tubular reabsorption (above which the fractional reabsorption begins to decline) is about 40-60 umol/L, which is similar to the endogenous plasma L-carnitine level. Therefore, the renal clearance of L-carnitine increases after exogenous administration, approaching GFR after high iv doses. ... [Evans AM et al; Clin Pharmacokinet 42 (11): 941-67 (2003)] PubMed Abstract
In mammals, the carnitine pool consists of nonesterified L-carnitine and many acylcarnitine esters. Of these esters, acetyl-L-carnitine is quantitatively and functionally the most significant. Carnitine homeostasis is maintained by absorption from diet, a modest rate of synthesis, and efficient renal reabsorption. Dietary L-carnitine is absorbed by active and passive transfer across enterocyte membranes. Bioavailability of dietary L-carnitine is 54-87% and is dependent on the amount of L-carnitine in the meal. Absorption of L-carnitine dietary supplements (0.5-6 g) is primarily passive; bioavailability is 14-18% of dose. Unabsorbed L-carnitine is mostly degraded by microorganisms in the large intestine. Circulating L-carnitine is distributed to two kinetically defined compartments: one large and slow-turnover (presumably muscle), and another relatively small and rapid-turnover (presumably liver, kidney, and other tissues). At normal dietary L-carnitine intake, whole-body turnover time in humans is 38-119 hr. In vitro experiments suggest that acetyl-L-carnitine is partially hydrolyzed in enterocytes during absorption. In vivo, circulating acetyl-L-carnitine concentration was increased 43% after oral acetyl-L-carnitine supplements of 2 g/day, indicating that acetyl-L-carnitine is absorbed at least partially without hydrolysis. After single-dose intravenous administration (0.5 g), acetyl-L-carnitine is rapidly, but not completely hydrolyzed, and acetyl-L-carnitine and L-carnitine concentrations return to baseline within 12 h. At normal circulating l-carnitine concentrations, renal l-carnitine reabsorption is highly efficient (90-99% of filtered load; clearance, 1-3 mL/min), but displays saturation kinetics. Thus, as circulating L-carnitine concentration increases (as after high-dose intravenous or oral administration of L-carnitine), efficiency of reabsorption decreases and clearance increases, resulting in rapid decline of circulating L-carnitine concentration to baseline. Elimination kinetics for acetyl-L-carnitine are similar to those for L-carnitine. There is evidence for renal tubular secretion of both L-carnitine and acetyl-L-carnitine. ... [Rebouche CJ; Ann N Y Acad Sci 1033:30-41 (2004)] PubMed Abstract
The pharmacokinetics of L-carnitine and its metabolites were investigated in 7 healthy subjects following the oral administration of 0, 0.5, 1, and 2 g 3 times a day for 7 days. Mean plasma concentrations of L-carnitine across an 8-hour dose interval increased significantly (P PubMed Abstract
Evidence indicates L-carnitine is absorbed in the intestine by a combination of active transport and passive diffusion. Reports of bioavailability following an oral dose have varied substantially, with estimates as low as 16 to 18% and as high as 54 to 87% ... The mucosal absorption of carnitine appears to be saturated at about a 2-g dose. Max blood concn is reached approx 3.5 hr after an oral dose and slowly decr, with a half-life of about 15 hr. Elimination of carnitine occurs primarily through the kidneys. The heart, skeletal muscle, liver, kidneys, and epididymis have specific transport systems for carnitine that concentrate carnitine within these tissues. Despite evidence indicating incr levels of free carnitine and carnitine metabolites in the blood and urine following an oral dose, no significant change in RBC carnitine levels was noted in healthy subjects, suggesting either a slow repletion of tissue stores of carnitine following an oral dose or a low capability to transport carnitine into tissues under normal conditions.
L-carnitine and acetyl-L-carnitine (ALC) are administered orally or intravenously and are then absorbed in the jejunum by simple diffusion. Transport into cellular tissue is via an active transport mechanism, with studies showing plasma concentrations of ALC and L-carnitine reaching an equilibrium via carnitine acetyl-transferase activity. Both iv and oral administration result in a corresponding increase in cerebrospinal fluid (CSF) concentrations of ALC, indicating it readily crosses the blood-brain barrier ... The rate of clearance increases with the plasma concentration of these substances.
... Acetyl-L-carnitine ... is better absorbed from the small intestine than L-carnitine and more efficiently crosses the blood-brain barrier (ie, gets into brain tissue).
Evidence ... indicates that L-carnitine is actively transported from the small intestinal lumen into enterocytes. However ... intracellular L-carnitine in the intestinal mucosa does not cross serosal membranes by an active transport mechanism. Absorption of dietary L-carnitine and L-carnitine supplements appears to occur primarily by passive diffusion ... The bioavail of dietary supplements (0.6 to 4 g/day) is 15 to 20%. Unabsorbed L-carnitine is degraded by micro-organisms in the large intestine. Major metabolites identified are trimethylamine oxide in urine and gamma-butyrobetaine in feces.
L-Carnitine and acylcarnitine esters are present in all tissues. In most tissues and cells, they are present in higher concn than in the circulation ... In human skeletal muscle and liver, respectively, nonesterified L-carnitine is concn 76-fold and 50-fold from that in serum ... L-carnitine and acetyl-L-carnitine are concn in most tissues via the high-affinity, Na+-dependent organic cation transporter OCTN2. Kt for L-carnitine binding is 3 to 5 uM; OCTN2 binds acetyl-L-carnitine and propionyl-L-carnitine with comparable affinity. This protein is highly expressed in heart, placenta, skeletal muscle, kidney, pancreas, testis, and epididymis and weakly expressed in brain, lung, and liver. L-Carnitine entry into the liver occurs via a low-affinity (Kt = 5mM) transporter, probably distinct from OCTN2. Several other L-carnitine transporters have been identified, incl OCTN1, OCTN3, and ATB (0,+).
Circulating L-carnitine concn are maintained at a fairly constant level of around 50 uM, predominantly through efficient reabsorption by the kidney. At a filtered load of 50 umol/L, the efficiency of L-carnitine and acylcarnitine ester reabsorption is 90 to 98%. However, as the filtered load of L-carnitine incr, as, eg after consumption of a dietary supplement or after iv infusion, the efficiency of reabsorption declines rapidly ... Clearance of acylcarnitine esters is often higher than that of nonesterified L-carnitine. Experimental studies have shown that in rats and humans, kidneys are able to synthesize acetyl-L-carnitine from L-carnitine and either acetoacetate or beta-hydroxybutyrate, and that L-carnitine, acetyl-L-carnitine, and gamma-butyrobetaine (also synthesized in human kidneys) are secreted from mucosal cells into tubular lumen ... by the sodium-dependent L-carnitine transporter ...
About 60 to 75% of L-carnitine from food is absorbed. The percentage absorbed from supplements appears to be lower. In one study only 20% of a 2-g dose of L-carnitine was found to be absorbed following ingestion ... Following the admin of a dose of L-carnitine of 1980 mg twice daily, the max plasma concn level (Cmax) was 80 nmol/mL, and the time to max concn (Tmax) occurred at 3.3 hr. the bioavail of oral L-carnitine is ca 15%. L-Carnitine is not bound to plasma protein or albumin.
Five normal adult male volunteers, admin a dose of ((3)H-methyl)-L-carnitine following 15 days of a high-carnitine diet and additional L-carnitine supplement, excreted 58 to 65% of admin radioactive dose in 5 to 11 days in the urine and feces. Max concn of ((3)-H-methyl)L-carnitine in serum occurred from 2.0 to 4.5 hr after radioactive L-carnitine admin. Major metabolites found were trimethyl N-oxide, primarily in urine (8 to 49% of the admin dose) and (3)H-gamma-butyrobetaine, primarily in feces (0.44% to 45% of the admin dose). Fecal excretion of total L-carnitine was less than 1% of total L-carnitine excretion. After attainment of steady state following 4 days of oral admin of ca 2000 mg twice a day of L-carnitine, urinary excretion of L carnitine was ca 9% of the orally admin dose. Approx 95% of filtered L-carnitine is reabsorbed in healthy humans. Hypothyroidism decr the urinary excretion of L-carnitine, while hyperthyroidism incr it. Following absorption from intestine, ca 25% of L-carnitine may be acylated in the intestinal mucosa. Orally admin L-carnitine and its acylated metabolite are distributed to most tissues of the body.

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