ナルセイン
4-[2-(2-ヒドロキシ-1-ナフチル)-2-ソジオスルホヒドラジノ]ベンゼンスルホン酸ナトリウム · 6-[[6-[2-(ジメチルアミノ)エチル]-4-メトキシ-1,3-ベンゾジオキソール-5-イル]アセチル]-2,3-ジメトキシ安息香酸 · ナルセイン · 6-(2-{6-[2-(ジメチルアミノ)エチル]-4-メトキシ-2H-1,3-ベンゾジオキソール-5-イル}アセチル)-2,3-ジメトキシ安息香酸 · ナトリウム 4-{[(2-ヒドロキシナフタレン-1-イル)[(ソジオオキシ)スルホニル]アミノ]アミノ}ベンゼン-1-スルホナート · NARCEINE · NARCEIN · CI 15511
識別子と物理属性
| CAS No. | 131-28-2 |
|---|---|
| 分子式 | C23H27NO8 |
| 平均分子量 | 445.5 g/mol |
| 単同位体質量 | 445.17366682 g/mol |
| SMILES | COc1ccc(C(=O)Cc2c(CCN(C)C)cc3c(c2OC)OCO3)c(C(=O)O)c1OC |
| InChIKey | DEXMFYZAHXMZNM-UHFFFAOYSA-N |
| PubChem CID | 8564 |
| ChEMBL | CHEMBL486305 |
| ChEBI | CHEBI:7480 |
| EC No. | 205-021-0 |
| DTXSID | DTXSID40156833 |
| 現地名 | ナルセイン |
化学・物理的性質
| XLogP | 0.5 |
|---|---|
| 極性表面積 | 104 |
| 水素結合供与体数 | 1 |
| 水素結合受容体数 | 9 |
| 回転可能結合数 | 10 |
| 重原子数 | 32 |
| 形式電荷 | 0 |
| 複雑度 | 643 |
| 医薬品 | DEA NFLIS-Drug Category -> Narcotics |
| 溶解度 | 0.78 mg/mL at 13 °C579.1mg/L(15℃) |
| 融点 | 145 °C138°mp 176° |
| Physical Description | Solid |
| 沸点 | 555.14°C (rough estimate) |
| 密度 | 1.3285 (rough estimate) |
| 屈折率 | 1.5614 (estimate) |
| pKa（酸解離定数） | pKb (20°) = 10.7, pKa = 9.3 |
| CAS データベース | 131-28-2 |
安全性と法規制
| GHS 分類 | WarningH302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 13 reports by companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Hazard Classes and Categories | Acute Tox. 4 (100%) |
用途
解説
ナルセイン．アヘン中に0.1～0.5％ 含有されるアルカロイド．単離が困難なので，(±)-ナルコチンより合成される．融点145 ℃(無水和物)，176 ℃(水和物)．pKa 9.3，pKb 10.7(20 ℃)．熱エタノールに易溶，酸性あるいはアルカリ性の水に可溶．エチルエステル(エチルナルセイン)塩酸塩は麻酔作用をもち，鎮痛，鎮咳薬として用いられる．
説明
An alkaloid of opium (Papaver somniferum) was first isolated by Pelletier in 1832 but not characterized until some years later by Couerbe and Anderson, the latter assigning to it the formula C23H2909N which was accepted until Freund showed that it contains H20 of crystallization. The base remains in the mother liquors after removal of the major alkaloids. It forms slender, colourless needles or prisms of the trihydrate, m.p. 170°C. It is optically inactive and dissolves readily in alkalies forming metallic derivatives. It behaves as a weak, monoacidic base forming well-crystallized salts. The hydrochloride crystallizes with 5.5 H20 from cold, dilute HCI, or as the trihydrate from hot solutions. From MeOH it yields crystals with 1 mole of solvent, m.p. 190-2°C. The aurichloride forms reddish-yellow needles, m.p. 130°C and the picrate has m.p. 195°C. With chlorine water, followed by the addition of ammonia, it gives a characteristic blood-red colour while with dilute iodine solution, the solid alkaloid develops a blue colour. With ethyl nitrite, narceine forms an oximino derivative which, on exhaustive methylation, furnishes trimethylamine, hemipinic acid and 2-cyano-3- methoxy-4: s-methylenedioxy-1-vinylbenzene.
製法・合成法
純化方法
Recrystallise Narcein from water (as trihydrate). The styphnate has m 185-189o (from EtOH), and the picrate has m 200o (from EtOH). [Beilstein 19 H 370, 19 I 797, 19 II 386, 19 IV 4382.]