(1S,5S,13R)-14-methoxy-4-(2H3)methyl-12-oxa-4-azapentacyclo[9.6.1.01,13.05,17.07,18]octadeca-7(18),8,10,14,16-pentaen-10-ol

• ChemBase编号: 175915
• 分子式: C18H19NO3
• 平均质量: 297.34836
• 单一同位素质量: 297.13649347
• SMILES: c1(c2c3c(cc1)C[C@H]1C4=CC=C([C@@H]([C@]34CCN1C)O2)OC)O
• Canonical SMILES: COC1=CC=C2[C@@]34[C@H]1Oc1c4c(C[C@@H]2N(CC3)C)ccc1O
• InChI: InChI=1S/C18H19NO3/c1-19-8-7-18-11-4-6-14(21-2)17(18)22-16-13(20)5-3-10(15(16)18)9-12(11)19/h3-6,12,17,20H,7-9H2,1-2H3/t12-,17-,18-/m0/s1
• InChIKey: ZKLXUUYLEHCAMF-IGNZVWTISA-N

名称和登记号

名称

• IUPAC标准名: (1S,5S,13R)-14-methoxy-4-(^2H₃)methyl-12-oxa-4-azapentacyclo[9.6.1.0^1,^1^3.0^5,^1^7.0^7,^1^8]octadeca-7(18),8,10,14,16-pentaen-10-ol
• IUPAC传统名: (1S,5S,13R)-14-methoxy-4-(^2H₃)methyl-12-oxa-4-azapentacyclo[9.6.1.0^1,^1^3.0^5,^1^7.0^7,^1^8]octadeca-7(18),8,10,14,16-pentaen-10-ol
• 别名: (5α)-6,7,8,14-Tetradehydro-4,5-epoxy-6-methoxy-17-methylmorphinan-3-ol; 3-O-Demethylthebaine; Oripavine-d3

登记号

• PubChem SID: 164231825
• PubChem CID: 71751337

理论计算性质

• Acid pKa: 10.070539
• 质子受体: 4
• 质子供体: 1
• LogD (pH = 5.5): -1.4085258
• LogD (pH = 7.4): 0.35481924
• Log P: 1.2523338
• 摩尔折射率: 86.1774 cm^3
• 极化性: 32.445 Å^3
• 极化表面积: 41.93 Å^2
• 可自由旋转的化学键: 1
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: Chloroform; Methanol
• 外观: Gray Solid
• 熔点: 183-187°C (dec.)

安全信息

• 保存条件: Controlled Substance, -20°C Freezer

详细说明

Toronto Research Chemicals - O675002

The major metabolite of Thebaine. Oripavine possesses an analgesic potency comparable to Morphine; it is not clinically useful due to severe toxicity and low therapeutic index. An opiate.

参考文献

• Barber, R., et al.: J. Med. Chem., 18, 1074 (1975)
• Yamazoe, Y., et al.: J. Pharmacol., 31, 433 (1975)