O-Acetyl-L-carnitine hydrochloride Chemical Properties

Melting point:

194 °C (dec.)(lit.)

alpha 

-29 º (c=1, H2O)

refractive index 

-28 ° (C=1, H2O)

storage temp. 

2-8°C

solubility 

H₂O: 100 mg/mL

form 

powder

color 

white

optical activity

[α]25/D 28°, c = 2 in H2O(lit.)

Water Solubility 

soluble

Sensitive 

Hygroscopic

Merck 

14,84

BRN 

4340103

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-;/s3

InChIKey

JATPLOXBFFRHDN-DDWIOCJRSA-N

SMILES

C([N+](C)(C)C)[C@H](OC(=O)C)CC(=O)O.[Cl-] |&1:5,r|

LogP

-4.149 (est)

CAS DataBase Reference

5080-50-2(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36-37/39

WGK Germany 

3

F 

3-9

HS Code 

29239000

MSDS

• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich

O-Acetyl-L-carnitine hydrochloride Usage And Synthesis

Description

Levacecarnine hydrochloride is a nootropic agent structurally related to the natural substance L-carnitine. It is reported to be useful in the treatment of cognition disorders in the elderly, perhaps due to its weak cholinergic properties.

Description

Acetyl-L-carnitine is an acetylated form of the essential mitochondrial metabolite L-carnitine that is catabolized by plasma esterases into carnitine. 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.

Chemical Properties

Crystallline powder

Originator

Sigma-Tau (Italy)

Uses

O-Acetyl-L-carnitine hydrochloride is used as a cholinergic agonist that stimulates neuronal response to serotonin and acetylcholine. Acetylcarnitine has antinociceptive activity that may be mediated by enhanced activity of muscarinic cholinergic receptors or mGlu2 glutamate receptors.

Uses

Acetyl-L-Carnitine (ALC) is an important dietary supplement. ALC is a natural substance, present in the human body, especially in muscles, in the brain, and in the male testicles. ALC is the acetylated, high-energy form of L-Carnitine.

Uses

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.

brand name

NICETILE; BRANICEN

General Description

Acetyl-L-carnitine (ALC/ALCAR), a quasi-vitamin is a metabolite of carnitine, present in mammalian plasma and tissues. It is the acetylated form of L-carnitine (LC). ALCAR is used as a dietary supplement. It is present at high level in the hypothalamus.

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].

Purification Methods

Recrystallise the chloride from isopropanol. Dry it over P2O5 under high vacuum. The S-betaine crystallises from EtOH/Et2O with m 145o(dec) and is hygroscopic; it has [] D -19.5o (c 6, H2O). [Krimberg & Wittandt Biochem Z 251 231 1932, Strack et al. Z Physiol Chem 238 191 1936, Beilstein 4 III 1630, 1632.]

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.

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