5080-50-2 Usage
Description
O-Acetyl-L-carnitine hydrochloride, also known as Levacecarnine hydrochloride, is a nootropic agent structurally related to the natural substance L-carnitine. It is a metabolite of carnitine, present in mammalian plasma and tissues, and is the acetylated form of L-carnitine (LC). O-Acetyl-L-carnitine hydrochloride is a crystalline powder and is used as a dietary supplement. It is present at high levels in the hypothalamus and is known by the brand names NICETILE and BRANICEN.
Uses
Used in Pharmaceutical Industry:
O-Acetyl-L-carnitine hydrochloride is used as a cholinergic agonist for stimulating neuronal response to serotonin and acetylcholine. It has antinociceptive activity that may be mediated by enhanced activity of muscarinic cholinergic receptors or mGlu2 glutamate receptors.
Used in Dietary Supplements:
O-Acetyl-L-carnitine hydrochloride is used as an important dietary supplement, particularly in the form of Acetyl-L-Carnitine (ALC). ALC is a natural substance present in the human body, especially in muscles, the brain, and the male testicles. It is the acetylated, high-energy form of L-Carnitine.
Used in Analytical Chemistry:
O-Acetyl-L-carnitine hydrochloride may be used as a precursor for the preparation of O-Acetyl-L-carnitine, which in turn may be used as an analytical reference standard for the determination of the analyte in biological samples by hydrophilic interaction liquid chromatography-tandem mass spectrometry (HILIC-MS/MS) technique.
Used in Treatment of Cognition Disorders:
Levacecarnine hydrochloride, a form of O-Acetyl-L-carnitine hydrochloride, is reported to be useful in the treatment of cognition disorders in the elderly, perhaps due to its weak cholinergic properties.
Used in Mitochondrial Function and Fatty Acid Oxidation:
Acetyl-L-carnitine facilitates the uptake of acetyl-CoA into mitochondria during fatty acid oxidation, enhances acetylcholine production, and stimulates protein and membrane phospholipid synthesis. In vivo, acetyl-L-carnitine (100 mg/kg) increases mGlu2/3 receptor protein levels and mechanical pain thresholds in a mouse model of chronic inflammatory pain induced by complete Freund's adjuvant.
Originator
Sigma-Tau (Italy)
Biochem/physiol Actions
Acetyl L-carnitine (ALC) plays a vital role in intermediary metabolism and in improving female fertility. The oxidative and metabolic status of the female reproductive system is controlled by ALC. ALC possesses cholinomimetic and anti-inflammatory effects. It controls γ-amino butyric acid (GABA) system. ALC is capable of modifying the rate of glucose usage in the brain. It also possesses a neuroprotective role in the developing brain.
in vitro
the expression of tumor antigen ca-125 in ovarian cancer cells was not affected by alcar. comparing to the control, the growth of skov-3 cells was remarkably decreased when incubated with alcar. the proliferation of skov-3 cells was decreased slightly but significantly when cells were incubated at higher alcar concentrations. in addition, alcar had no effect on the expression of the nerve growth factor receptors on skov-3 or ovcar-3 ovarian cancer cells [1].
in vivo
male flinders sensitive line (fsl) rats and male cd1 mice, exposed to model genetic and environmentally induced depression, respectively, were injected intraperitoneally with alcar 100 mg/kg for 21 days. alcar, as a long-lasting and rapid antidepressant, functioned via the epigenetic regulation of type 2 metabotropic glutamate (mglu2) receptors in fsl rats and in mice. additionally, alcar raised the transcription of grm2 gene encoding for the mglu2 receptor via increasing the levels of acetylated h3k27 bound to the grm2 promoter and gaining the acetylation of nf-kb-p65 subunit. [2].
references
[1]. engle, d., belisle, j., gubbels, j., petrie, s., hutson, p., kushner, d., & patankar, m. effect of acetyl-l-carnitine on ovarian cancer cells' proliferation, nerve growth factor receptor (trk-a and p75) expression, and the cytotoxic potential of paclitaxel and carboplatin. gynecologic oncology. 2009; 112(3): 631-636. [2]. nasca, c., xenos, d., barone, y., caruso, a., scaccianoce, s., & matrisciano, f. et al. l-acetylcarnitine causes rapid antidepressant effects through the epigenetic induction of mglu2 receptors. proceedings of the national academy of sciences. 2013; 110(12): 4804-4809.
Check Digit Verification of cas no
The CAS Registry Mumber 5080-50-2 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 5,0,8 and 0 respectively; the second part has 2 digits, 5 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 5080-50:
(6*5)+(5*0)+(4*8)+(3*0)+(2*5)+(1*0)=72
72 % 10 = 2
So 5080-50-2 is a valid CAS Registry Number.
InChI:InChI=1/C9H17NO4.ClH/c1-7(11)14-8(5-9(12)13)6-10(2,3)4;/h8H,5-6H2,1-4H3;1H/t8-;/m1./s1
5080-50-2Relevant articles and documents
Enzyme-Catalyzed Synthesis of L-Acetylcarnitine and Citric Acid Using Acetyl Coenzyme A Recycling
Patel, Smita S.,Conlon, Hugh D.,Walt, David R.
, p. 2842 - 2844 (1986)
-
A chloride process for the preparation of acetyl L-carnitine
-
Paragraph 0059; 0060; 0061; 0062, (2016/10/31)
The invention relates to the field of medical preparations and particularly discloses a method for preparing acetyl levocarnitine hydrochloride. The method comprises the following steps: mixing levocarnitine with glacial acetic acid, dripping acetyl chloride to react, adding a first solvent at a low temperature after the reaction is completed to crystallize, filtering and drying the precipitate to obtain a crude product of the acetyl levocarnitine hydrochloride; and adding a second solvent into the crude product, heating, dripping a third solvent, filtering after the solid is dissolved, slowly cooling the filtrate to the room temperature, crystallizing at a low temperature, filtering and drying the precipitate to obtain a finished product of the acetyl levocarnitine hydrochloride. The method disclosed by the invention has the advantages that various appropriate organic solvents are combined to be used in a certain order to separate and purify the acetyl levocarnitine hydrochloride, both the contents of an impurity A and the unreacted levocarnitine raw material are reduced to be lower than 0.05% and the purity of the prepared finished product of the acetyl levocarnitine hydrochloride is up to more than 99.90%.
Synthesis of carnitine benzyl esters as prodrugs
Gong, Xiao-Wei,Li, Jin-Pei,Wu, Ji-Feng,Li, Xun,Zhai, Hai-Min,Feng, Bo,Xu, Wen-Fang,Tang, Wei
experimental part, p. 327 - 330 (2009/05/30)
The introduction of C-2 acyl groups and a benzyl ester onto L-carnitine generated a series of carnitine benzyl esters as prodrug with improved liposolubility, stability and bioavailability.