DL-Carnitine hydrochloride

Modify Date: 2024-01-02 09:50:30

DL-Carnitine hydrochloride Structure
DL-Carnitine hydrochloride structure
 Common Name DL-Carnitine hydrochloride
CAS Number 461-05-2 Molecular Weight 197.660
Density N/A Boiling Point N/A
Molecular Formula C7H16ClNO3 Melting Point 190-205ºC
MSDS USA Flash Point N/A

 Use of DL-Carnitine hydrochloride


(±)-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.

 Names

Name carnitinamide chloride
Synonym More Synonyms

 DL-Carnitine hydrochloride 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
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.

 Chemical & Physical Properties

Melting Point 190-205ºC
Molecular Formula C7H16ClNO3
Molecular Weight 197.660
Exact Mass 197.081863
PSA 57.53000
Water Solubility SOLUBLE

 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

4-chloroacetoacetanilide structure

4-chloroacetoac...

CAS#:39082-00-3

Anilinium chloride structure

Anilinium chloride

CAS#:142-04-1

~%

DL-Carnitine hydrochloride Structure

DL-Carnitine hy...

CAS#:461-05-2

Literature: Lonza Ltd. Patent: US3969406 A1, 1976 ;

 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%

 Articles7

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Carnitine transporter CT2 (SLC22A16) is over-expressed in acute myeloid leukemia (AML) and target knockdown reduces growth and viability of AML cells.

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 Synonyms

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)
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