(3aS,8aR)-1,3a,8-trimethyl-1H,2H,3H,3aH,8H,8aH-pyrrolo[2,3-b]indol-5-yl N-methylcarbamate

• ChemBase编号: 856
• 分子式: C15H21N3O2
• 平均质量: 275.34614
• 单一同位素质量: 275.16337693
• SMILES: O(c1cc2[C@]3([C@H](N(CC3)C)N(c2cc1)C)C)C(=O)NC
• Canonical SMILES: CNC(=O)Oc1ccc2c(c1)[C@]1(C)CCN([C@@H]1N2C)C
• InChI: InChI=1S/C15H21N3O2/c1-15-7-8-17(3)13(15)18(4)12-6-5-10(9-11(12)15)20-14(19)16-2/h5-6,9,13H,7-8H2,1-4H3,(H,16,19)/t13-,15+/m1/s1
• InChIKey: PIJVFDBKTWXHHD-HIFRSBDPSA-N

名称和登记号

名称

• IUPAC标准名: (3aS,8aR)-1,3a,8-trimethyl-1H,2H,3H,3aH,8H,8aH-pyrrolo[2,3-b]indol-5-yl N-methylcarbamate
• IUPAC传统名: physostigmine
• 商标名: Antilirium; Esromiotin; Ezerin; Fysostigmin; Physostol
• 别名: 伊色林; 毒扁豆碱; Eserolein, Methylcarbamate; Erserine; Eserine; Eserine Salicylate; Eserine Sulfate; Isopto Eserine; Physostigmine; Physostigmine; ESERINE; Eserine; (3aS-cis)-1,2,3,3a,8,8a-Hexahydro-1,3a,8-trimethylpyrrolo[2,3-b]indol-5-ol Methylcarbamate Ester; Synapton; Cogmine; Esromiotin; MCV 4484; NIH 10421; NSC 30782

登记号

• CAS号: 57-47-6
• EC号: 200-332-8
• MDL号: MFCD00151090
• Beilstein号: 91230
• PubChem SID: 46506998; 160964319; 24869283; 24277867
• PubChem CID: 5983
• CHEBI ID: 27953
• ATC码: V03AB19; S01EB05
• CHEMBL: 94
• Chemspider ID: 5763
• DrugBank ID: DB00981
• KEGG ID: D00196
• 美国药典/FDA物质标识码: 9U1VM840SP
• 维基百科标题: Physostigmine

理论计算性质

JChem

• Acid pKa: 14.772489
• 质子受体: 3
• 质子供体: 1
• LogD (pH = 5.5): 1.1139581
• LogD (pH = 7.4): 2.170551
• Log P: 2.232533
• 摩尔折射率: 78.3968 cm^3
• 极化性: 29.907698 Å^3
• 极化表面积: 44.81 Å^2
• 可自由旋转的化学键: 2
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 1.8
• LOG S: -2.44
• 溶解度: 9.92e-01 g/l

分子性质

理化性质

• 溶解度: 7760 mg/L; DMSO; Methanol
• 外观: White Solid
• 熔点: 102-104 °C(lit.); 102-106 °C; 105-107°C; 96-98°C
• 闪点: >100 °C; >212 °F
• 比旋光度: [α]20/D -77±1°, c = 1.7% in chloroform; [α]25/D -116°, c = 1 in benzene
• 疏水性(logP): 1.7

安全信息

• 保存条件: -20°C Freezer; Room Temperature (15-30°C)
• RTECS编号: TJ2100000
• 欧盟危险性物质标志: 剧毒(Highly toxic) (T+)
• 联合国危险货物编号: 1544
• 德国WGK号: 3
• 联合国危险货物等级: 6.1
• 联合国危险货物包装类别(PG): 1; I
• 澳大利亚Hazchem: 2X
• 危险公开号: 26/28; R:26/28
• 安全公开号: 25-45; S:25-45
• 欧盟危险货物分类: T2
• 欧盟危险识别号(EUHIN): 6.1B
• 美国ERG指导号: 151
• GHS危险品标识: GHS06
• GHS警示词: Danger
• GHS危险声明: H300-H330
• GHS警示性声明: P260-P264-P284-P310
• 个人保护装置: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 1544 6.1/PG 1
• 保存温度: 2-8°C

药理学性质

• 给药途径: intravenous, intramuscular, ophthalmic
• 代谢: Major metabolite: Eseroline
• 法定药品分级: rx-only (US)
• 妊娠期药物分类: C (US)
• 相关基因信息: human ... ACHE(43), APP(351), BCHE(590)mouse ... Ache(11423), Bche(12038), Chrm1(12669)rat ... Ache(83817), Bche(65036), Chrm2(81645)

产品相关信息

• 纯度: ≥98.0% (N); ≥99% (HPLC); 99%
• Empirical Formula (Hill Notation): C15H21N3O2
• 分类: Genuine Natural Compounds

详细说明

MP Biomedicals - 02151075

Free Base
Crystalline

MP Biomedicals - 05211751

MP Biomedicals Rare Chemical collection

DrugBank - DB00981

• Drug Groups: approved
• Description: A cholinesterase inhibitor that is rapidly absorbed through membranes. It can be applied topically to the conjunctiva. It also can cross the blood-brain barrier and is used when central nervous system effects are desired, as in the treatment of severe anticholinergic toxicity. [PubChem]
• Indication: For the treatment of glaucoma, and in the treatment of severe anticholinergic toxicity.
• Pharmacology: Physostigmine is a parasympathomimetic, specifically, a reversible cholinesterase inhibitor which effectively increases the concentration of acetylcholine at the sites of cholinergic transmission. Physostigmine is used to treat glaucoma. Because it crosses the blood-brain barrier, it is also used to treat the central nervous system effects of atropine overdose and other anticholinergic drug overdoses. Physostigmine can reverse both central and peripheral anticholinergia.
• Toxicity: Side effects include increased sweating, loss of bladder control, muscle weakness, nausea, vomiting, diarrhea, or stomach cramps or pain, shortness of breath, tightness in chest, or wheezing, slow or irregular heartbeat, unusual tiredness or weakness, watering of mouth, blurred vision or change in near or distant vision, and eye pain.
• Affected Organisms: Humans and other mammals
• Biotransformation: Quickly hydrolyzed by cholinesterases
• External Links: Wikipedia; RxList; Drugs.com

Sigma Aldrich - E8375

包装
1, 5 g in glass bottle
250 mg in glass bottle
Biochem/physiol Actions
乙酰胆碱酯酶抑制剂越过血脑屏障并与乙酰胆碱酯酶形成缓慢降解的氨基甲酰酶络合物。

Sigma Aldrich - 219312

Biochem/physiol Actions
乙酰胆碱酯酶抑制剂越过血脑屏障并与乙酰胆碱酯酶形成缓慢降解的氨基甲酰酶络合物。

Sigma Aldrich - 45710

Biochem/physiol Actions
乙酰胆碱酯酶抑制剂越过血脑屏障并与乙酰胆碱酯酶形成缓慢降解的氨基甲酰酶络合物。

Toronto Research Chemicals - P398500

It is a parasympathomimetic, specifically, a reversible cholinesterase inhibitor obtained from the Calabar bean, used to treat glaucoma and delayed gastric emptying.

参考文献

• Engelhart, L., et al.: Arch. Exp. Pathol. Pharmakol., 150, 1 (1930)
• Muhtadi, F.J., et al.: Anal. Profiles Drug Subs., 18, 289 (1930)