DL-Carnitine (HCID 288)

Überblick

Carnitine is an amino-acid betaine that is butanoate substituted with a hydroxy group at position C-3 and a trimethylammonium group at C-4. It has a role as a mouse metabolite and a human metabolite. It is functionally related to a butyrate. It is a conjugate base of a carnitinium.

Namen und Bezeichner

Bevorzugter Name: DL-Carnitine
IUPAC: 3-hydroxy-4-(trimethylazaniumyl)butanoate
Lokaler Name: (±)-(3-Carboxy-2-hydroxypropyl)trimethylammoniumhydroxid
Englischer Name: DL-Carnitine
Summenformel: C7H15NO3
Molmasse: 161.2

Namen und Synonyme

DL-CarnitineCarnitineCarnitina3-hydroxy-4-(trimethylazaniumyl)butanoateD,L-carnitineS7UI8SM58ANSC-757390CHEBI:17126(3-Carboxy-2-hydroxypropyl)trimethylammonium hydroxide inner saltCarnitinumCHEBI:3424(3-carboxy-2-hydroxypropyl)-trimethylazanium

Weitere Namen anzeigen

CardiogenCarrierCardiogen peptideCarnumMiocorC00487NovaineExcitineCARNITINCarnicor

Carnitine dl-RefChem:574690(3-carboxy-2-hydroxypropyl)trimethylazanium206-976-6406-76-8461-06-33-hydroxy-4-(trimethylammonio)butanoateCarnitine DL-form

Datenbank-Bezeichner

CAS: 406-76-8、541-15-1
PubChem CID: 288
DTXSID: DTXSID3022744
ChEMBL: CHEMBL172513
ChEBI: CHEBI:17126
UNII: S7UI8SM58A
EC Number: 206-976-6
Nikkaji: J1.347.334J

Eigenschaften

Berechnete Struktureigenschaften

XLogP: -0,2
Polarare Oberfläche (TPSA): 60,4 Å²
H-Brücken-Donoren: 1
H-Brücken-Akzeptoren: 3
Frei drehbare Bindungen: 3
Schwere Atome: 11
Formalladung: 0
Komplexität: 134

Experimentelle und physikochemische Eigenschaften

Cosmetics · 2 Einträge

Cosmetic ingredients (Carnitine) -> CIR (Cosmetic Ingredient Review)

Cleansing; Foam boosting

Dietary IngredientsCarnitine

Collision Cross Section131.39 Å² [M]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

Physikochemische Eigenschaften

Schmelzpunkt: 197 · 197-198 °C (decomp)
storage temp.: -20 °C · Store at -20°C
Löslichkeit: Soluble in DMSO
InChI: InChI=1S/C7H15NO3/c1-8(2,3)5-6(9)4-7(10)11/h6,9H,4-5H2,1-3H3
InChIKey: PHIQHXFUZVPYII-UHFFFAOYSA-N
SMILES: C(C(O)CC([O-])=O)[N+](C)(C)C

Sicherheit und Regulatorisches

Gefahrenhinweise

Regulatory InformationCarnitine: Does not have an individual approval but may be used under an appropriate group standard

Toxikologische Informationen

Exposure RoutesIntravenous, Oral. Absolute bioavailability is 15% (tablets or solution). Time to maximum plasma concentration was found to be 3.3 hours.

Toxicity Summary · 3 Einträge

The CIR Expert Panel concluded the following ingredients are safe in the present practices of use and concentration described in the safety assessment when formulated to be non-irritating...Carnitine...

Safe for use in cosmetics, with qualifications

Levocarnitine can be synthesised within the body from the amino acids lysine or methionine. Vitamin C (ascorbic acid) is essential to the synthesis of carnitine. Levocarnitine is a carrier molecule in the transport of long chain fatty acids across the inner mitochondrial membrane. It also exports acyl groups from subcellular organelles and from cells to urine before they accumulate to toxic concentrations. Only the L isomer of carnitine (sometimes called vitamin BT) affects lipid metabolism. Levocarnitine is handled by several proteins in different pathways including carnitine transporters, carnitine translocases, carnitine acetyltransferases and carnitine palmitoyltransferases.

Signs and SymptomsAdverse effects include hypertension, fever, tachycardia and seizures.

Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).

Toxicity DataLD<sub>50</sub> > 8g/kg (mouse, oral).

Sicherheitsdaten

Alarmwort: Warnung
Gefahrenhinweise: Code Gefahrenhinweise Gefahrenklasse Abteilung Alarmwort Symbol P-Code H302

Chemie und Industrie

Pharmakologische Informationen

Metabolism/Metabolites · 1 Eintrag

After oral administration L-carnitine which is unabsorbed is metabolized in the gastrointestinal tract by bacterial microflora. Major metabolites include trimethylamine N-oxide and [3H]-gamma-butyrobetaine. Route of Elimination: Following a single intravenous dose, 73.1 +/- 16% of the dose was excreted in the urine during the 0-24 hour interval. Post administration of oral carnitine supplements, in addition to a high carnitine diet, 58-65% of the administered radioactive dose was recovered from urine and feces in 5-11 days. Half Life: 17.4 hours (elimination) following a single intravenous dose.

Verwendung und Herstellung

Uses · 2 Einträge

CIR ingredient: Carnitine

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 such as glutaric aciduria II, methyl malonic aciduria, propionic acidemia, and medium chain fatty acylCoA dehydrogenase deficiency. Used therapeutically to stimulate gastric and pancreatic secretions and in the treatment of hyperlipoproteinemias. Parenteral levocarnitine is indicated for the prevention and treatment of carnitine deficiency in patients with end-stage renal disease.

Use ClassificationCosmetics -> Cleansing; Foam boosting

Anwendungen · 1 Eintrag

VerwendenDL-Carnitine is a Chloride salt free form of D,L-Carnitine Chloride (C184100). Carnitine is a vitamin, essential cofactor of fatty acid metabolism. It is required for the transport of fatty acids through the inner mitochondrial membrane. Synthesized primarily in the liver and kidney; highest concentrations found in heart and skeletal muscle. Dietary sources include red meat, dairy products, beans, avocado.