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

• ChemBase编号: 465
• 分子式: C7H15NO3
• 平均质量: 161.1989
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: (3R)-3-hydroxy-4-(trimethylazaniumyl)butanoate
• IUPAC传统名: L-carnitine
• 商标名: Carnitor; Karnitin; Nicetile
• 别名: 左旋肉毒碱; 维生素 BT; L-肉毒碱 内盐; (-)-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

登记号

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

理论计算性质

JChem

• Acid pKa: 4.1961756
• 质子受体: 3
• 质子供体: 1
• LogD (pH = 5.5): -4.134386
• LogD (pH = 7.4): -4.1171994
• Log P: -4.887506
• 摩尔折射率: 63.4853 cm^3
• 极化性: 16.164734 Å^3
• 极化表面积: 60.36 Å^2
• 可自由旋转的化学键: 4
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: -2.9
• LOG S: -1.6
• 溶解度: 5.33e+00 g/l

分子性质

理化性质

• 溶解度: 2500 mg/mL; H2O: soluble0.1 g/mL at 20 °C, clear, colorless
• 熔点: 197-212 °C(lit.)
• 比旋光度: [α]20/D -31±1°, c = 10% in H2O

安全信息

• 保存条件: -20°C
• RTECS编号: BP2980000
• 欧盟危险性物质标志: 刺激性(Irritant) (Xi)
• 德国WGK号: 3
• 危险公开号: 36/37/38
• 安全公开号: 26-36
• GHS危险品标识: GHS07
• GHS警示词: Warning
• GHS危险声明: H315-H319-H335
• GHS警示性声明: P261-P305 + P351 + P338
• 个人保护装置: dust mask type N95 (US), Eyeshields, Gloves
• 保存温度: -20°C; 2-8°C

产品相关信息

• 纯度: ~98%; ≥98%; ≥99.0% (NT)
• 成盐信息: Free Base
• 燃烧残渣: ≤0.1% (as SO4)
• 痕量阳离子: 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
• 生物来源: synthetic
• 干燥失重: ≤0.1% loss on drying
• 线性分子式: (CH3)3N+CH2CH(OH)CH2COO-

详细说明

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
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。
Other Notes
Review. Carnitine and its role in fatty acid metabolism1

参考文献

• 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