(3R)-3-hydroxy-4-(trimethylazaniumyl)butanoate

• ChemBase ID: 465
• Molecular Formular: C7H15NO3
• Molecular Mass: 161.1989
• Monoisotopic Mass: 161.10519335
• 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

NAMES AND DATABASE IDS

Names

• 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

Database IDs

• CAS Number: 541-15-1
• EC Number: 208-768-0
• MDL Number: MFCD00038747
• Beilstein Number: 4292315
• PubChem SID: 160963928; 24892238; 46505864
• PubChem CID: 10917

CALCULATED PROPERTIES

JChem

• Acid pKa: 4.1961756
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): -4.134386
• LogD (pH = 7.4): -4.1171994
• Log P: -4.887506
• Molar Refractivity: 63.4853 cm^3
• Polarizability: 16.164734 Å^3
• Polar Surface Area: 60.36 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -2.9
• LOG S: -1.6
• Solubility (Water): 5.33e+00 g/l

PROPERTIES

Physical Property

• Solubility: 2500 mg/mL; H2O: soluble0.1 g/mL at 20 °C, clear, colorless
• Melting Point: 197-212 °C(lit.)
• Optical Rotation: [α]20/D -31±1°, c = 10% in H2O

Safety Information

• Storage Condition: -20°C
• RTECS: BP2980000
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: -20°C; 2-8°C

Product Information

• Purity: ~98%; ≥98%; ≥99.0% (NT)
• Salt Data: Free Base
• Ignition Residue: ≤0.1% (as SO4)
• Cation Traces: Ca: ≤10 mg/kg; Cd: ≤5 mg/kg; Co: ≤5 mg/kg; Cr: ≤5 mg/kg; Cu: ≤5 mg/kg; Fe: ≤5 mg/kg; K: ≤50 mg/kg; Mg: ≤5 mg/kg; Mn: ≤5 mg/kg; Na: ≤100 mg/kg; Ni: ≤5 mg/kg; Pb: ≤5 mg/kg; Zn: ≤5 mg/kg
• Biological Source: synthetic
• Loss on Drying: ≤0.1% loss on drying
• Linear Formula: (CH3)3N+CH2CH(OH)CH2COO-

DETAILS

DrugBank - DB00583

• 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

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

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

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

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

• 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