ethyl 1-methyl-4-phenylpiperidine-4-carboxylate

• ChemBase编号: 337
• 分子式: C15H21NO2
• 平均质量: 247.33274
• 单一同位素质量: 247.15722892
• SMILES: O(C(=O)C1(CCN(CC1)C)c1ccccc1)CC
• Canonical SMILES: CCOC(=O)C1(CCN(CC1)C)c1ccccc1
• InChI: InChI=1S/C15H21NO2/c1-3-18-14(17)15(9-11-16(2)12-10-15)13-7-5-4-6-8-13/h4-8H,3,9-12H2,1-2H3
• InChIKey: XADCESSVHJOZHK-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: ethyl 1-methyl-4-phenylpiperidine-4-carboxylate
• IUPAC传统名: meperidine
• 商标名: Centralgin; Demarol; Demerol; Dispadol; Dolantin; Dolcontral; Dolosal; Dolsin; Isonipecaine; Lidol; Lydol; Meperidine Hcl; Meperidol; Methyl phenylpiperidine carbonic acid ethyl ester; Nemerol; Operidine; Petantin; Pethanol; Pethidin; Pethidine; Pethidineter; Petydyna; Phetidine; Piperosal; Pipersal; Piridosal
• 别名: 哌替啶 溶液; Meperidine; Meperidine solution

登记号

• CAS号: 57-42-1
• MDL号: MFCD00057376
• PubChem SID: 160963800; 24882043; 46506899
• PubChem CID: 4058

理论计算性质

JChem

• 质子受体: 2
• 质子供体: 0
• LogD (pH = 5.5): -0.14636338
• LogD (pH = 7.4): 1.627321
• Log P: 2.4558003
• 摩尔折射率: 72.4837 cm^3
• 极化性: 28.46522 Å^3
• 极化表面积: 29.54 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: -2.35
• 溶解度: 1.11e+00 g/l

分子性质

理化性质

• 溶解度: 3220 mg/L
• 闪点: 11 °C; 51.8 °F
• 疏水性(logP): 2.6

安全信息

• 欧盟危险性物质标志: 易燃性(Flammable) (F); 有毒(Toxic) (T)
• 联合国危险货物编号: 1230
• 德国WGK号: 1
• 联合国危险货物等级: 3
• 联合国危险货物包装类别(PG): 2
• 危险公开号: 11-23/24/25-39/23/24/25
• 安全公开号: 16-36/37-45
• GHS危险品标识: GHS02; GHS06; GHS08
• GHS警示词: Danger
• GHS危险声明: H225-H301 + H311 + H331-H370
• GHS警示性声明: P210-P260-P280-P301 + P310-P311
• RID/ADR: UN 1230 3/PG 2
• 毒品管制信息: kontrollierte Droge in Deutschlandregulated under CDSA - not available from Sigma-Aldrich Canada
• 保存温度: -20°C

药理学性质

• 相关基因信息: human ... OPRD1(4985), OPRK1(4986), OPRM1(4988)rat ... Oprm1(25601), Slc6a3(24898), Slc6a4(25553)

产品相关信息

• 浓度: 1 mg/mL in methanol
• 级别: drug standard
• Empirical Formula (Hill Notation): C15H21NO2

详细说明

DrugBank - DB00454

• Drug Groups: approved
• Description: A narcotic analgesic that can be used for the relief of most types of moderate to severe pain, including postoperative pain and the pain of labor. Prolonged use may lead to dependence of the morphine type; withdrawal symptoms appear more rapidly than with morphine and are of shorter duration. [PubChem]
• Indication: Used to control moderate to severe pain.
• Pharmacology: Meperidine is a synthetic opiate agonist belonging to the phenylpiperidine class. Meperidine may produce less smooth muscle spasm, constipation, and depression of the cough reflex than equivalent doses of morphine. The onset of action is lightly more rapid than with morphine, and the duration of action is slightly shorter. The chemical structure of meperidine is similar to local anesthetics. Meperidine is recommended for relief of moderate to severe acute pain and has the unique ability to interrupt postoperative shivering and shaking chills induced by amphotericin B. Meperidine has also been used for intravenous regional anesthesia, peripheral nerve blocks and intraarticular, epidural and spinal analgesia. Meperidine is considered a second-line agent for the treatment of acute pain.
• Affected Organisms: Humans and other mammals
• Biotransformation: Meperidine is metabolized in the liver by hydrolysis to meperidinic acid followed by partial conjugation with glucuronic acid. Meperidine also undergoes N-demethylation to normeperidine, which then undergoes hydrolysis and partial conjugation. Normeperidine is about half as potent as meperidine, but it has twice the CNS stimulation effects.
• Absorption: The oral bioavailability of meperidine in patients with normal hepatic function is 50-60% due to extensive first-pass metabolism. Bioavailability increases to 80-90% in patients with hepatic impairment (e.g. liver cirrhosis). Meperidine is less than half as effective when administered orally compared to parenteral administration. One study reported that 80-85% of the drug administered intramuscularly was absorbed within 6 hours of intragluteal injection in health adults; however, inter-individual variation and patient-specific variable appear to cause considerable variations in absorption upon IM injection.
• Half Life: Initial distribution phase (t_{1/2 α}) = 2-11 minutes; terminal elimination phase (t_{1/2 β}) = 3-5 hours. In patients with hepatic dysfunction (e.g. liver cirrhosis or active viral hepatitis) the t_{1/2 β} is prolonged to 7-11 hours.
• Protein Binding: 60-80% bound to plasma proteins, primarily albumin and α₁-acid glycoprotein. The presence of cirrhosis or active viral hepatitis does not appear to affect the extent of protein binding.
• Elimination: Excreted in the urine. The proportion of drug that is excreted unchanged or as metabolites is dependent on pH. When urine pH is uncontrolled, 5-30% of the meperidine dose is excreted as normeperidine and approximately 5% is excreted unchanged. Meperidine and normeperidine are found in acidic urine, while the free and conjugated forms of meperidinic and normperidinic acids are found in alkaline urine.
• Distribution: Meperidine crosses the placenta and is distributed into breast milk.
• External Links: Wikipedia; RxList; Drugs.com