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carnitine

File:Carnitine.svg · Wikimedia Commons · See Wikimedia Commons

EntityQ243309· pop 45· linked from 309 articles

Also 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

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 sections
Contents
  • 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.

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