DL-Carnitine hydrochloride

Names

[ CAS No. ]:
461-05-2

[ Name ]:
DL-Carnitine hydrochloride

[Synonym ]:
DL-Carnitine Hydrochloride
3-Carboxy-2-hydroxy-N,N,N-trimethyl-1-propanaminium chloride
3-Hydroxy-4-(trimethylammonio)butanoate hydrochloride
EINECS 207-309-1
UNII:F64264D63N
Vitamin BT Hydrochloride
Carnitine chloride
3-Hydroxy-4-(trimethylammonio)butyrate Hydrochloride
carnitine hydrochloride
MFCD00011904
3-Carboxy-2-hydroxy-N,N,N-trimethyl-1-propanaminium, inner salt, hydrochloride (1:1)
1-Propanaminium, 3-carboxy-2-hydroxy-N,N,N-trimethyl-, chloride (1:1)
3-Carboxy-2-hydroxy-N,N,N-trimethylpropan-1-aminium chloride
QV1YQ1K1&1&1 &&Anhydro HCl
(±)-Carnitine (chloride)

Biological Activity

[Description]:

(±)-Carnitine chloride exists in two isomers, known as D and L. L-carnitine plays an essential role in the β-oxidation of fatty acids and also shows antioxidant, and anti-inflammatory activities.

[Related Catalog]:

Signaling Pathways >> Others >> Others

Research Areas >> Metabolic Disease

Natural Products >> Others

[In Vitro]

The main role of L-carnitine is to shuttle long-chain fatty acids across the inner mitochondrial membrane. After L-carnitine and acyl-CoA become acyl-carnitine by activation of carnitine palmitoyl transferase (CPT)-I, the transported acyl-carnitine is changed into acyl-CoA by CPT-II in the mitochondria matrix. Palmitoyl-CoA-induced mitochondrial respiration is increased by L-carnitine treatment, and then is accelerated by the presence of ADP. This acceleration is induced by treatment with L-carnitine in a concentration-dependent manner, and is saturated at 5 mM L-carnitine[1]. Pretreatment with L-carnitine augments Nrf2 nuclear translocation, DNA binding activity and heme oxygenase-1 (HO-1) expression in H2O2-treated HL7702 cells. L-carnitine protects HL7702 cells against H2O2-induced cell damage through Akt-mediated activation of Nrf2 signaling pathway[2].

[In Vivo]

L-carnitine is found to down-regulate the ubiquitin proteasome pathway and increase IGF-1 concentrations in animal models. L-carnitine administration for 2 weeks of hindlimb suspension alleviates the decrease in weight and fiber size in the soleus muscle. In addition, L-carnitine suppresses atrogin-1 mRNA expression, which has been reported to play a pivotal role in muscle atrophy[3]. Simultaneous treatment with L-carnitine attenuates the renal fibrosis (which correlated with a reduction of plasma TGF-β1 levels) and the pro-oxidative and proinflammatory status reported in L-NAME groups, with a concomitant increase in the expression of PPAR-γ[4].

[Kinase Assay]

Mitochondria (0.6 mg protein/mL) are incubated in 2.5 mM Hepes (pH7.4) containing 225 mM mannitol, 75 mM sucrose and 100 μM ethylene glycol tetraacetic acid (EGTA) with or without 5 mM L-carnitine at 25°C. To measure oxygen uptake, 10 min after inorganic phosphate (Pi) 4 mM are added, the mitochondria are treated with palmitoyl-CoA (50 μM) and then ADP is added (200 μM). Oligomycin (5 μM) and rotenone (10 μM) are added 3-4 min after the ADP treatment. HPG (0-10 mM), which can specifically inhibit carnitine palmitoyl transferase (CPT)-I activity in the mitochondria, is added in the Hepes medium before incubation of the mitochondria[1].

[Animal admin]

Rats: After 1 week of acclimatization, rats are randomly assigned to a hindlimb suspension group, hindlimb suspension with L-carnitine administration group, and a pair-fed group. The L-carnitine group are administered a 1250 mg L-carnitine/kg dissolved in distilled water orally using a sonde. The body weight is measured every morning at 09:00 and L-carnitine solution is ingested every morning at 10:00. The experiment is conducted for 14 days[3].

[References]

[1]. Oyanagi E, et al. Protective action of L-carnitine on cardiac mitochondrial function and structure against fatty acidstress. Biochem Biophys Res Commun. 2011 Aug 19;412(1):61-7.

[2]. Li J, et al. l-carnitine protects human hepatocytes from oxidative stress-induced toxicity through Akt-mediated activation of Nrf2 signaling pathway. Can J Physiol Pharmacol. 2016 May;94(5):517-25.

[3]. Jang J, et al. l-Carnitine supplement reduces skeletal muscle atrophy induced by prolonged hindlimb suspension in rats. Appl Physiol Nutr Metab. 2016 Dec;41(12):1240-1247.

[4]. Zambrano S, et al. L-carnitine attenuates the development of kidney fibrosis in hypertensive rats by upregulating PPAR-γ. Am J Hypertens. 2014 Mar;27(3):460-70.

[Related Small Molecules]

Chemical & Physical Properties

[ Melting Point ]:
190-205ºC

[ Molecular Formula ]:
C₇H₁₆ClNO₃

[ Molecular Weight ]:
197.660

[ Exact Mass ]:
197.081863

[ PSA ]:
57.53000

[ Water Solubility ]:
SOLUBLE

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: BP2979140

CHEMICAL NAME :: Ammonium, (3-carboxy-2-hydroxypropyl)trimethyl-, chloride, (+-)-

CAS REGISTRY NUMBER :: 461-05-2

LAST UPDATED :: 199701

DATA ITEMS CITED :: 3

MOLECULAR FORMULA :: C7-H16-N-O3.Cl

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 10 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: ABMGAJ Acta Biologica et Medica Germanica. (Berlin, Ger. Dem. Rep.) V.1-41, 1958-82. For publisher information, see BBIADT. Volume(issue)/page/year: 3,28,1959

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 6 gm/kg

TOXIC EFFECTS :: Behavioral - convulsions or effect on seizure threshold Behavioral - fluid intake Lungs, Thorax, or Respiration - cyanosis

REFERENCE :: ABMGAJ Acta Biologica et Medica Germanica. (Berlin, Ger. Dem. Rep.) V.1-41, 1958-82. For publisher information, see BBIADT. Volume(issue)/page/year: 3,28,1959

Safety Information

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Gloves

[ Hazard Codes ]:
Xi:Irritant

[ Risk Phrases ]:
R36/37/38

[ Safety Phrases ]:
S26-S37/39

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
BP2979140

[ HS Code ]:
2923900090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2923900090

[ Summary ]:
2923900090 other quaternary ammonium salts and hydroxides。Supervision conditions:None。VAT:17.0%。Tax rebate rate:9.0%。MFN tariff:6.5%。General tariff:30.0%

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Related Compounds

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