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541-15-1 molecular structure
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(3R)-3-hydroxy-4-(trimethylazaniumyl)butanoate

ChemBase ID: 465
Molecular Formular: C7H15NO3
Molecular Mass: 161.1989
Monoisotopic Mass: 161.10519335
SMILES and InChIs

SMILES:
O[C@@H](C[N+](C)(C)C)CC(=O)[O-]
Canonical SMILES:
O[C@@H](C[N+](C)(C)C)CC(=O)[O-]
InChI:
InChI=1S/C7H15NO3/c1-8(2,3)5-6(9)4-7(10)11/h6,9H,4-5H2,1-3H3/t6-/m1/s1
InChIKey:
PHIQHXFUZVPYII-ZCFIWIBFSA-N

Cite this record

CBID:465 http://www.chembase.cn/molecule-465.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(3R)-3-hydroxy-4-(trimethylazaniumyl)butanoate
IUPAC Traditional name
L-carnitine
Brand Name
Carnitor
Karnitin
Nicetile
Synonyms
(-)-Carnitine
(S)-Carnitine
(-)-L-Carnitin
3-Carboxy-2-hydroxy-N,N,N-trimethyl-1-propanaminium
Carnitine
Vitamin BT
L-Carnitine
Levocarnitine
Carnitor
Karnitin
L-carnitine(Levocarnitine)
L-Carnitine inner salt
(-)-(R)-3-Hydroxy-4-(trimethylammonio)butyrate
左旋肉毒碱
维生素 BT
L-肉毒碱 内盐
CAS Number
541-15-1
EC Number
208-768-0
MDL Number
MFCD00038747
Beilstein Number
4292315
PubChem SID
46505864
160963928
24892238
PubChem CID
10917

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 4.1961756  H Acceptors
H Donor LogD (pH = 5.5) -4.134386 
LogD (pH = 7.4) -4.1171994  Log P -4.887506 
Molar Refractivity 63.4853 cm3 Polarizability 16.164734 Å3
Polar Surface Area 60.36 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P -2.9  LOG S -1.6 
Solubility (Water) 5.33e+00 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
2500 mg/mL expand Show data source
H2O: soluble0.1 g/mL at 20 °C, clear, colorless expand Show data source
Melting Point
197-212 °C(lit.) expand Show data source
Optical Rotation
[α]20/D -31±1°, c = 10% in H2O expand Show data source
Storage Condition
-20°C expand Show data source
RTECS
BP2980000 expand Show data source
European Hazard Symbols
Irritant Irritant (Xi) expand Show data source
MSDS Link
Download expand Show data source
German water hazard class
3 expand Show data source
Risk Statements
36/37/38 expand Show data source
Safety Statements
26-36 expand Show data source
GHS Pictograms
GHS07 expand Show data source
GHS Signal Word
Warning expand Show data source
GHS Hazard statements
H315-H319-H335 expand Show data source
GHS Precautionary statements
P261-P305 + P351 + P338 expand Show data source
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves expand Show data source
Storage Temperature
-20°C expand Show data source
2-8°C expand Show data source
Purity
~98% expand Show data source
≥98% expand Show data source
≥99.0% (NT) expand Show data source
Salt Data
Free Base expand Show data source
Ignition Residue
≤0.1% (as SO4) expand Show data source
Cation Traces
Ca: ≤10 mg/kg expand Show data source
Cd: ≤5 mg/kg expand Show data source
Co: ≤5 mg/kg expand Show data source
Cr: ≤5 mg/kg expand Show data source
Cu: ≤5 mg/kg expand Show data source
Fe: ≤5 mg/kg expand Show data source
K: ≤50 mg/kg expand Show data source
Mg: ≤5 mg/kg expand Show data source
Mn: ≤5 mg/kg expand Show data source
Na: ≤100 mg/kg expand Show data source
Ni: ≤5 mg/kg expand Show data source
Pb: ≤5 mg/kg expand Show data source
Zn: ≤5 mg/kg expand Show data source
Biological Source
synthetic expand Show data source
Loss on Drying
≤0.1% loss on drying expand Show data source
Linear Formula
(CH3)3N+CH2CH(OH)CH2COO- expand Show data source

DETAILS

DETAILS

DrugBank DrugBank Selleck Chemicals Selleck Chemicals Sigma Aldrich Sigma Aldrich
DrugBank - DB00583 external link
Item Information
Drug Groups approved
Description Constituent of striated muscle and liver. It is used therapeutically to stimulate gastric and pancreatic secretions and in the treatment of hyperlipoproteinemias. [PubChem]
Indication 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.
Pharmacology 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. Lack of carnitine can lead to liver, heart, and muscle problems. Carnitine deficiency is defined biochemically as abnormally low plasma concentrations of free carnitine, less than 20 µmol/L at one week post term and may be associated with low tissue and/or urine concentrations. Further, this condition may be associated with a plasma concentration ratio of acylcarnitine/levocarnitine greater than 0.4 or abnormally elevated concentrations of acylcarnitine in the urine. Only the L isomer of carnitine (sometimes called vitamin BT) affects lipid metabolism. The "vitamin BT" form actually contains D,L-carnitine, which competitively inhibits levocarnitine and can cause deficiency. Levocarnitine can be used therapeutically to stimulate gastric and pancreatic secretions and in the treatment of hyperlipoproteinemias.
Toxicity LD50 > 8g/kg (mouse, oral). Adverse effects include hypertension, fever, tachycardia and seizures.
Affected Organisms
Humans and other mammals
Biotransformation Major metabolites include trimethylamine N-oxide and [3H]-gamma-butyrobetaine.
Absorption Absolute bioavailability is 15% (tablets or solution).
Half Life 17.4 hours (elimination) following a single intravenous dose.
Protein Binding None
References
Olpin SE: Fatty acid oxidation defects as a cause of neuromyopathic disease in infants and adults. Clin Lab. 2005;51(5-6):289-306. [Pubmed]
Steiber A, Kerner J, Hoppel CL: Carnitine: a nutritional, biosynthetic, and functional perspective. Mol Aspects Med. 2004 Oct-Dec;25(5-6):455-73. [Pubmed]
External Links
Wikipedia
RxList
Selleck Chemicals - S2388 external link
Research Area: Metabolic Disease
Biological Activity:
L-carnitine(Levocarnitine) is constituent of striated muscle and liver.It is used therapeutically to stimulate gastric and pancreatic secretions and in the treatment of hyperlipoproteinemias.. 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. 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. [1]
Sigma Aldrich - C7393 external link
Biochem/physiol Actions
肉毒碱是一种天然存在于大多数哺乳动物组织中的季铵。它在骨骼肌和心脏中参与能量代谢调控,浓度相对较高。它可将葡萄糖代谢由糖酵解转移至糖原储存,并促进长链脂肪酸向线粒体转运,使其在线粒体氧化产生能量。
Sigma Aldrich - C0158 external link
Biochem/physiol Actions
肉毒碱是一种天然存在于大多数哺乳动物组织中的季铵。它在骨骼肌和心脏中参与能量代谢调控,浓度相对较高。它可将葡萄糖代谢由糖酵解转移至糖原储存,并促进长链脂肪酸向线粒体转运,使其在线粒体氧化产生能量。
包装
1, 5, 25, 100 g in poly bottle
Sigma Aldrich - 22018 external link
Biochem/physiol Actions
Carnitine is a quaternary amine that occurs naturally in most mammalian tissue. It is present in relatively high concentrations in skeletal muscle and heart where it is involved in regulating energy metabolism. It shifts glucose metabolism from glycolysis to glycogen storage and enhances the transport of long chain fatty acids into the mitochondria where they are oxidized for energy production.
Other Notes
Review. Carnitine and its role in fatty acid metabolism1

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Olpin SE: Fatty acid oxidation defects as a cause of neuromyopathic disease in infants and adults. Clin Lab. 2005;51(5-6):289-306. Pubmed
  • • Steiber A, Kerner J, Hoppel CL: Carnitine: a nutritional, biosynthetic, and functional perspective. Mol Aspects Med. 2004 Oct-Dec;25(5-6):455-73. Pubmed
  • • http://www.drugbank.ca/drugs/DB00583
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