DL-Carnitine
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Basic information
- CAS
406-76-8- Standard SMILES
C[N+](C)(C)CC(O)CC(=O)[O-]- InChIKey
PHIQHXFUZVPYII-UHFFFAOYSA-N- Molecular formula
- C7H15NO3
- Average molar mass
- 161.2 g/mol
- Monoisotopic mass
- 161.10519334
Overview
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.
Names & identifiers
- Preferred name
- DL-Carnitine
- IUPAC
- 3-hydroxy-4-(trimethylazaniumyl)butanoate
- English name
- DL-Carnitine
- Molecular formula
- C7H15NO3
- Molecular weight
- 161.2
Names & synonyms
DL-CarnitineCarnitineCarnitina3-hydroxy-4-(trimethylazaniumyl)butanoateD,L-carnitineS7UI8SM58ANSC-757390CHEBI:17126(3-Carboxy-2-hydroxypropyl)trimethylammonium hydroxide inner saltCarnitinumCHEBI:3424(3-carboxy-2-hydroxypropyl)-trimethylazanium
Show more names
CardiogenCarrierCardiogen peptideCarnumMiocorC00487NovaineExcitineCARNITINCarnicor
Carnitine dl-RefChem:574690(3-carboxy-2-hydroxypropyl)trimethylazanium206-976-6406-76-8461-06-33-hydroxy-4-(trimethylammonio)butanoateCarnitine DL-form
Database identifiers
- CAS
406-76-8、541-15-1- PubChem CID
- 288
- DTXSID
DTXSID3022744- ChEMBL
CHEMBL172513- ChEBI
Properties
Computed structural propertiesFilling in
- XLogP
- -0.2
- Topological polar surface area
- 60.4 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 3
- Heavy atoms
- 11
- Formal charge
- 0
- Complexity
- 134
Experimental & physicochemical properties
Cosmetics
Cosmetic ingredients (Carnitine) -> CIR (Cosmetic Ingredient Review)
Cleansing; Foam boosting
Dietary IngredientsCarnitine
Collision Cross Section131.39 Ų [M]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physicochemical properties
- Melting point
- 197 · 197-198 °C (decomp)
- storage temp.
- -20 °C · Store at -20°C
- solubility
- 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
- FDA UNII
- 7 UI8SM58A · S7UI8SM58A
- Symbol(GHS)
- 7 · GHS07
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Hazard information
Regulatory InformationCarnitine: Does not have an individual approval but may be used under an appropriate group standard
Toxicology
Exposure RoutesIntravenous, Oral.
Absolute bioavailability is 15% (tablets or solution).
Time to maximum plasma concentration was found to be 3.3 hours.
Toxicity Summary
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).
Safety data
Chemistry & industry
Pharmacology
Metabolism/Metabolites
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.
Uses & manufacturing
Uses
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
Applications
UsesDL-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.
Upstream & downstream products
Related reactions
45 records
Compound notes
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