サリチルアミド
サリチルアミド · パニタール · サラミド · サミド · o-ヒドロキシベンズアミド · 2-ヒドロキシベンズアミド · アルギアミダ · アケット
識別子と物理属性
| CAS No. | 65-45-2 |
|---|---|
| 分子式 | C7H7NO2 |
| 平均分子量 | 137.14 g/mol |
| 単同位体質量 | 137.04767846 g/mol |
| SMILES | NC(=O)c1ccccc1O |
| InChIKey | SKZKKFZAGNVIMN-UHFFFAOYSA-N |
| PubChem CID | 5147 |
| ChEMBL | CHEMBL27577 |
| ChEBI | CHEBI:32114 |
| EC No. | 200-609-3 |
| DTXSID | DTXSID3021726 |
| 現地名 | サリチルアミド |
化学・物理的性質
| XLogP | 1.3 |
|---|---|
| 極性表面積 | 63.3 |
| 水素結合供与体数 | 2 |
| 水素結合受容体数 | 2 |
| 回転可能結合数 | 1 |
| 重原子数 | 10 |
| 形式電荷 | 0 |
| 複雑度 | 136 |
| 医薬品 | DEA NFLIS-Drug Category -> AnalgesicsPharmaceuticals -> Listed in ZINC15 |
| 化粧品 | Keratolytic |
| pH | ABOUT 5 @ 28 °C (AQ SOLN) |
| SpringerMaterials Properties | Chemical shift |
| LogP（分配係数） | Log Kow = 1.281.280 |
| 味 | SOMEWHAT BITTER |
| 密度 | 1.175 at 284 °F (NTP, 1992) - Denser than waterwill sink1.175 @ 140 °C/4 °C1,175 g/cm3 |
| Color/Form | WHITE OR SLIGHTLY PINK CRYSTALLINE POWDERYELLOW LEAFLETS FROM DILUTE ALCOHOL |
| 溶解度 | less than 1 mg/mL at 68 °F (NTP, 1992)SOLUBILITY IN WATER: 0.2% @ 30 °C0.8% @ 47 °CIN GLYCEROL: 2.0% @ 5 °C5.0% @ 39 °C10.0% @ 60 °CIN PROPYLENE GLYCOL: 10.0% @ 5 °CSLIGHTLY SOL IN NAPHTHA, CARBON TETRACHLORIDEFREELY SOL IN SOLN OF ALKALIESSOL IN CHLOROFORM, ALC, ETHERメタノール: 0.1 g/mL、透明<0.1 g/100 mL で 20 ºC |
| Human Drugs | Pharmaceuticals |
| 沸点 | 518 °F at 760 mmHg (decomposes) (NTP, 1992)181.5 °C @ 14 MM HG181.50 °C. @ 760.00 mm Hg270°C |
| Decomposition | DANGEROUSWHEN HEATED TO DECOMPOSITION, IT EMITS HIGHLY TOXIC FUMES OF /NITROGEN OXIDES/.270°C |
| 融点 | 140-144 °C(lit.) |
| 屈折率 | 1.5323 (estimate) |
| 引火点 | 181°C/14mm |
| 貯蔵条件 | Inert atmosphere,Room Temperature |
| 外観・状態 | 結晶性粉末 |
| pKa（酸解離定数） | pKa 8.13(H2O t = 37) (Uncertain) |
| 色 | 白い |
| 臭い | 無臭 |
| Merck | 14,8328 |
| BRN | 742439 |
| ヘンリー定数 | 2.0×104 mol/(m3Pa) at 25℃, Abraham and Jr. (2019) |
| 安定性 | 安定。光に敏感。強塩基、強酸化剤とは相容れない。 |
| 化粧品成分の機能 | 角質溶解性 |
| InChI | 1S/C7H7NO2/c8-7(10)5-3-1-2-4-6(5)9/h1-4,9H,(H2,8,10) |
| InChIKey | SKZKKFZAGNVIMN-UHFFFAOYSA-N |
| SMILES | NC(=O)c1ccccc1O |
| LogP（分配係数） | 1.280 |
| CAS データベース | 65-45-2(CAS DataBase Reference) |
| NISTの化学物質情報 | Benzamide, 2-hydroxy-(65-45-2) |
| EPAの化学物質情報 | o-Hydroxybenzamide (65-45-2) |
化学的特性
Salicylamide is a odorless white or slightly pink crystals. It is less acidic (pKa 8.2) than other salicylic acid derivatives. Although poorly soluble in water, stable solutions can be formed at pH 9 through ionization of the phenolic group.
安全性と法規制
| GHS 分類 | WarningH302 (99.3%): Harmful if swallowed [Warning Acute toxicity, oral]P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, 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 851 reports by companies from 17 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.DangerH302: Harmful if swallowed [Warning Acute toxicity, oral] |
|---|---|
| 規制情報 | Chemical: Benzamide, 2-hydroxy-Status: Active Update: 21-03-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/2210Salicylamide: Does not have an individual approval but may be used under an appropriate group standard |
| 火災危険 | Flash point data for this chemical are not availablehowever, it is probably combustible. (NTP, 1992) |
| 健康有害性 | SYMPTOMS: Symptoms of exposure to this compound include dizziness, drowsiness, nausea, vomiting, epigastric distress, allergic reactions and blood dyscrasias. It can cause central nervous depression, hypotension and respiratory arrest. This compound may greatly potentiate the hepatic toxicity of acetaminophen. It may also cause hyperpnea, renal failure, prolonged bleeding time, a mild burning pain in the mouth, throat and abdomen, lethargy, tinnitus hearing loss, excitability, delirium, fever, sweating, dehydration, incoordination, restlessness, ecchymoses, coma, convulsions, cyanosis, oliguria, uremia, pulmonary edema, gastric ulcer, weight loss and mental deterioration. Other symptoms may include skin eruptions, headache, difficulty in hearing, dimness of vision, lassitude and hyperventilation. |
| 反応性グループ | Amides and Imides |
| Reactivity Profile | 2-HYDROXYBENZAMIDE is an amide. Amides/imides react with azo and diazo compounds to generate toxic gases. Flammable gases are formed by the reaction of organic amides/imides with strong reducing agents. Amides are very weak bases (weaker than water). Imides are less basic yet and in fact react with strong bases to form salts. That is, they can react as acids. Mixing amides with dehydrating agents such as P2O5 or SOCl2 generates the corresponding nitrile. The combustion of these compounds generates mixed oxides of nitrogen (NOx). This chemical may be sensitive to prolonged exposure to light. (NTP, 1992) |
用途
解説
サリチルアミド (英: Salicylamide) とは、白色の結晶または結晶性粉末の芳香族化合物です。 IUPAC名は、2-ヒドロキシベンズアミド (英: 2-hydroxybenzamide) 、また別名としてo-ヒドロキシベンズアミド (英: o-hydroxybenzamide) とも呼ばれます。 化学式はC7H7NO2で表され、分子量は137.14です。なお、CAS登録番号は65-45-2です。 サリチルアミドは、サリチル酸メチルにアンモニアを作用させる、求核置換反応によるアミド化によって得られます。
用途
解熱?鎮痛?抗炎症剤
用途
薬理・生理作用研究用、有機合成原料。
説明
Salicylamide is less acidic (pKa 8.2) than other salicylic acid derivatives. Although poorly soluble in water, stable solutions can be formed at pH 9 through ionization of the phenolic group. It is absorbed from the GI tract on oral administration and is rapidly metabolized to inactive metabolites by intestinal mucosa, but not by hydrolysis. Activity appears to reside in the intact molecule. It is approximately 40 to 55% plasma protein bound, and it competes with other salicylates and acetaminophen for glucuronide conjugation, decreasing the extent of conjugation of these other drugs.
使用
salicylamide is an analgesic, fungicide, and anti-inflammatory ingredient used to soothe the skin. It is an aromatic amide.
一般的な説明
Salicylamide, o-hydroxybenzamide, is a derivative of salicylicacid that is fairly stable to heat, light, and moisture. Itreportedly exerts a moderately quicker and deeper analgesiceffect than aspirin because of quicker CNS penetration. Its metabolismdiffers from aspirin, because it is not metabolized tosalicylic acid but rather excreted exclusively as the ether glucuronideor sulfate. Thus, as a result of lack of contributionfrom salicylic acid, it has a lower analgesic and antipyretic efficacythan that of aspirin. However, it can be used in place ofsalicylates for patients with a demonstrated sensitivity to salicylates.It is also excreted much more rapidly than other salicylates,which accounts for its lower toxicity. It is available inseveral nonprescription products, in combination with acetaminophenand phenyltoloxamine (e.g., Rid-A Pain compound,Cetazone T, Dolorex, Ed-Flex, Lobac) or with aspirin,acetaminophen, and caffeine (e.g., Saleto, BC Powder).
使用用途
サリチルアミドは、非ステロイド性抗炎症薬の1種で、発熱や腫れ、痛みなどを軽減する薬物です。解熱作用、鎮痛作用はアスピリンと同様の効能があります。 経口投与の非ステロイド性抗炎症薬として多くの一般用医薬品に使用されてきましたが、現在では使われることは稀です。処方箋が必要な風邪薬であるPL顆粒にも、成分の1つとしてサリチルアミドが使用されています。しかし、一般市販薬とは成分の配合比率が異なります。 非ステロイド系抗炎症薬は、体内で生成される痛みを感じさせ、発熱、炎症を起こす物質 (プロスタグランジン) の生成を抑制します。プロスタグランジン生成阻害効果により、痛みの緩和、炎症を抑えることが可能ですが、痛みや発熱、腫れなどの発生原因自体を治すことはできません。
製法・合成法
純化方法
Crystallise the amide from water or repeatedly from CHCl3 [Nishiya et al. J Am Chem Soc 108 3880 1986]. [Beilstein 10 IV 169.] The anilide [87-17-2] M 213.2, m 135o crystallises from H2O. [Beilstein 12 H 500, 12 I 268, 12 II 256, 12 944.]