(1S,5R,13R,14S,17R)-10-ethoxy-4-methyl-12-oxa-4-azapentacyclo[9.6.1.01,13.05,17.07,18]octadeca-7,9,11(18),15-tetraen-14-ol

• ChemBase编号: 1265
• 分子式: C19H23NO3
• 平均质量: 313.39082
• 单一同位素质量: 313.1677936
• SMILES: O1[C@@H]2[C@]34[C@H]([C@H](N(CC3)C)Cc3c4c1c(OCC)cc3)C=C[C@@H]2O
• Canonical SMILES: CCOc1ccc2c3c1O[C@@H]1[C@@]43CCN([C@H](C2)[C@@H]4C=C[C@@H]1O)C
• InChI: InChI=1S/C19H23NO3/c1-3-22-15-7-4-11-10-13-12-5-6-14(21)18-19(12,8-9-20(13)2)16(11)17(15)23-18/h4-7,12-14,18,21H,3,8-10H2,1-2H3/t12-,13+,14-,18-,19-/m0/s1
• InChIKey: OGDVEMNWJVYAJL-LEPYJNQMSA-N

名称和登记号

名称

• IUPAC标准名: (1S,5R,13R,14S,17R)-10-ethoxy-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0^1,^1^3.0^5,^1^7.0^7,^1^8]octadeca-7,9,11(18),15-tetraen-14-ol; (1S,5R,13R,14S,17R)-10-ethoxy-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0^{1,13}.0^{5,17}.0^{7,18}]octadeca-7(18),8,10,15-tetraen-14-ol
• IUPAC传统名: ethylmorphine
• 别名: Morphine 3-ethyl ether; Ethylmorphine; Codethyline; Dionine; Ethyl morphine; Ethylmorphine

登记号

• CAS号: 76-58-4
• EC号: 200-970-7
• MDL号: MFCD00083327
• PubChem SID: 160964725; 46505092; 24894676
• PubChem CID: 5359271
• ATC码: R05DA01
• Chemspider ID: 4514250
• DrugBank ID: DB01466
• 美国药典/FDA物质标识码: RWO67D87EU
• 维基百科标题: Ethylmorphine

理论计算性质

JChem

• LogD (pH = 5.5): -1.5852752
• LogD (pH = 7.4): -0.08994477
• Log P: 1.6997592
• 摩尔折射率: 89.3533 cm^3
• 极化性: 34.45052 Å^3
• 极化表面积: 41.93 Å^2
• 可自由旋转的化学键: 2
• 里宾斯基五规则: true
• Acid pKa: 13.78274
• 质子受体: 4
• 质子供体: 1

ALOGPS 2.1

• Log P: 1.72
• LOG S: -2.57
• 溶解度: 8.35e-01 g/l

分子性质

理化性质

• 溶解度: 2.61 mg/mL at 20 oC [SEIDELL,A (1941)]

安全信息

• RTECS编号: QD0850000
• 欧盟危险性物质标志: 有害性(Harmful) (Xn)
• 德国WGK号: 3
• 危险公开号: 22
• 安全公开号: 36/37/39-45
• GHS危险品标识: GHS07
• GHS警示词: Warning
• GHS危险声明: H302
• 个人保护装置: dust mask type N95 (US), Eyeshields, Gloves
• 毒品管制信息: USDEA Schedule II; Home Office Schedule 2; stupéfiant; kontrollierte Droge in Deutschland; regulated under CDSA - not available from Sigma-Aldrich Canada
• 保存温度: 2-8°C

药理学性质

• 法定药品分级: Schedule II (Single-Entity), Schedule III (In Combination Products)

详细说明

DrugBank - DB01466

• Drug Groups: illicit; experimental
• Description: A narcotic analgesic and antitussive. It is metabolized in the liver by ethylmorphine-N-demethylase and used as an indicator of liver function. It is not marketed in the US but is approved for use in various countries around the world. In the US it is a schedule II drug (single-entity) and schedule III drug (in combination products).
• Indication: Ethylmorphine is an analgesic used for pain relief.
• Pharmacology: Ethylmorphine is metabolized by the enzyme cytochrome P450 2D6 to morphine. Morphine is a narcotic pain management agent indicated for the relief of pain in patients who require opioid analgesics for more than a few days. Morphine interacts predominantly with the opioid mu-receptor. These mu-binding sites are discretely distributed in the human brain, with high densities in the posterior amygdala, hypothalamus, thalamus, nucleus caudatus, putamen, and certain cortical areas. They are also found on the terminal axons of primary afferents within laminae I and II (substantia gelatinosa) of the spinal cord and in the spinal nucleus of the trigeminal nerve. In clinical settings, morphine exerts its principal pharmacological effect on the central nervous system and gastrointestinal tract. Its primary actions of therapeutic value are analgesia and sedation. Morphine appears to increase the patient's tolerance for pain and to decrease discomfort, although the presence of the pain itself may still be recognized. In addition to analgesia, alterations in mood, euphoria and dysphoria, and drowsiness commonly occur. Opioids also produce respiratory depression by direct action on brain stem respiratory centers.
• Affected Organisms: Humans and other mammals
• Biotransformation: After ingestion, ethylmorphine is converted to morphine in the human liver by the CYP450-isozyme CYP2D6, similarly to codeine.
• References: Aasmundstad TA, Xu BQ, Johansson I, Ripel A, Bjorneboe A, Christophersen AS, Bodd E, Morland J: Biotransformation and pharmacokinetics of ethylmorphine after a single oral dose. Br J Clin Pharmacol. 1995 Jun;39(6):611-20. [Pubmed] ; Xu BQ, Aasmundstad TA, Lillekjendlie B, Bjorneboe A, Christophersen AS, Morland J: Effects of ethanol on ethylmorphine metabolism in isolated rat hepatocytes: characterization by means of a multicompartmental model. Pharmacol Toxicol. 1997 Apr;80(4):171-81. [Pubmed]
• External Links: Wikipedia

Sigma Aldrich - E8512

Biochem/physiol Actions
Narcotic analgesic; antitussive

参考文献

• Aasmundstad TA, Xu BQ, Johansson I, Ripel A, Bjorneboe A, Christophersen AS, Bodd E, Morland J: Biotransformation and pharmacokinetics of ethylmorphine after a single oral dose. Br J Clin Pharmacol. 1995 Jun;39(6):611-20. Pubmed
• Xu BQ, Aasmundstad TA, Lillekjendlie B, Bjorneboe A, Christophersen AS, Morland J: Effects of ethanol on ethylmorphine metabolism in isolated rat hepatocytes: characterization by means of a multicompartmental model. Pharmacol Toxicol. 1997 Apr;80(4):171-81. Pubmed