File:Carnitine.svg · Wikimedia Commons · See Wikimedia Commons
carnitine
Sign in to saveAlso known as D,L-carnitine
Carnitine is a quaternary ammonium compound involved in metabolism in most mammals, plants, and some bacteria. In support of energy metabolism, carnitine transports long-chain fatty acids from the cytosol into mitochondria to be oxidized for free energy production, and also participates in removing products of metabolism from cells. Given its key metabolic roles, carnitine is concentrated in tissues like skeletal and cardiac muscle that metabolize fatty acids as an energy source. Generally individuals, including strict vegetarians, synthesize enough L-carnitine in vivo.
Key facts
- Drug.Verifiedfields
- changed
- Drug.Watchedfields
- changed
- Drug.verifiedrevid
- 460019989
- Drug.IUPAC_name
- 3-hydroxy-4-(trimethylazaniumyl)butanoate
- Drug.image
- Carnitine.svg
- Drug.image_class
- skin-invert-image
- Drug.width
- 180
- Drug.image2
- Carnitine-3D-structure.png
- Drug.image_class2
- bg-transparent
- Drug.pregnancy_US
- B
- Drug.legal_US
- OTC
- Drug.routes_of_administration
- Oral, intravenous
- Drug.bioavailability
- <10%
- Drug.protein_bound
- None
- Drug.metabolism
- slightly
- Drug.excretion
- Urine (>95%)
- Drug.index2_label
- R-(-)-
- Drug.CAS_number
- 406-76-8
via Wikipedia infobox
Chemical data
- Formula
- C7H15NO3
- Molecular weight
- 161.2 g/mol
- IUPAC name
- 3-hydroxy-4-(trimethylazaniumyl)butanoate
- SMILES
- C[N+](C)(C)CC(CC(=O)[O-])O
- InChIKey
- PHIQHXFUZVPYII-UHFFFAOYSA-N
- XLogP
- -0.2
- Polar surface area
- 60.4 Ų
- H-bond donors
- 1
- H-bond acceptors
- 3
- Formal charge
- 0
via PubChem
Research
23,775 papers- Carnitine Inborn Errors of Metabolism.Molecules (Basel, Switzerland) · 2019
- Carnitine.Annual review of nutrition · 1983
- Metabolomic profiling reveals amino acid and carnitine alterations as metabolic signatures in psoriasis.Theranostics · 2021
- L-carnitine's role in KAATSU training- induced neuromuscular fatigue.Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie · 2020
- Dialysis-related carnitine disorder.Seminars in dialysis · 2006
via PubMed
Wikidata facts
- Mass
- 161.105193
Show 5 more facts
- Commons category
- Carnitine
- chemical formula
- C₇H₁₅NO₃
- canonical SMILES
- C[N+](C)(C)CC(CC(=O)[O-])O
- stylized name
- levOCARNitine
- isomeric SMILES
- C[N+](C)(C)C[C@H](O)CC([O-])=O
Sources (6)
via Wikidata · CC0
~18 min read
Article
27 sectionsContents
- Biological role
- Biochemistry
- Chemical properties
- Biosynthesis and metabolism
- Physiological effects in humans
- Biosynthesis in eukaryotes
- Fatty acid transport
- Acetyl-CoA stabilization
- Tissue distribution of carnitine-biosynthetic enzymes in humans
- Carnitine shuttle system
- Regulation of fatty acid β oxidation
- Balance
- Inhibition
- Activation
- Transcription factors
- Metabolic defects of fatty acid oxidation
- Deficiency
- Supplementation
- Pharmacokinetics
- Evidence
- Male fertility
- Diseases
- Sources
- Drug interactions and adverse effects
- History
- See also
- References
Carnitine is a quaternary ammonium compound involved in metabolism in most mammals, plants, and some bacteria. In support of energy metabolism, carnitine transports long-chain fatty acids from the cytosol into mitochondria to be oxidized for free energy production, and also participates in removing products of metabolism from cells. Given its key metabolic roles, carnitine is concentrated in tissues like skeletal and cardiac muscle that metabolize fatty acids as an energy source. Generally individuals, including strict vegetarians, synthesize enough L-carnitine in vivo.
Carnitine exists as one of two stereoisomers: the two enantiomers -carnitine (S-(+)-) and -carnitine (R-(−)-). Both are biologically active, but only -carnitine naturally occurs in animals, and -carnitine is toxic as it inhibits the activity of the -form. At room temperature, pure carnitine is a whiteish powder, and a water-soluble zwitterion with relatively low toxicity. Derived from amino acids, carnitine was first extracted from meat extracts in 1905, leading to its name from Latin, "caro/carnis" or flesh.