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| 融点 | 88-90 °C | | 沸点 | 172 °C (12.7517 mmHg) | | 比重(密度) | 1.17 | | 屈折率 | 1.5600 (estimate) | | 闪点 | 172°C/13mm | | 貯蔵温度 | 2-8°C | | 溶解性 | alcohol: soluble1 gm in 5 ml | | 外見 | Crystalline Powder | | 酸解離定数(Pka) | 2.5(at 25℃) | | 色 | White | | 臭い (Odor) | odorless | | 水溶解度 | Soluble in ethanol, chloroform, ethyl ether and dilute acids. Sparingly soluble in water | | Merck | 14,1086 | | BRN | 638434 | | 安定性： | Stable. Combustible. Incompatible with strong oxidizing agents. | | InChIKey | BLFLLBZGZJTVJG-UHFFFAOYSA-N | | LogP | 1.860 | | CAS データベース | 94-09-7(CAS DataBase Reference) | | NISTの化学物質情報 | Benzoic acid, 4-amino-, ethyl ester(94-09-7) | | EPAの化学物質情報 | Benzocaine (94-09-7) |
| | 4-アミノ安息香酸 エチル Usage And Synthesis |
| 外観 | 白色〜わずかにうすい黄色, 結晶〜結晶性粉末 | | 定義 | 本品は、パラアミノ安息香酸(PABA(*))のエチルエステルであり、次の化学式で表される。
参照表示名称：ＰＡＢＡ | | 溶解性 | エタノール及びアセトンに溶け、水にほとんど溶けない。 | | 解説 | C9H11NO2(165.19)．p-アミノ安息香酸エチルは，ベンゾカイン，アネステシンともいう．p-ニトロトルエンを二クロム酸カリウムと硫酸で酸化してp-ニトロ安息香酸とし，これを亜鉛と塩酸で還元して生じたp-アミノ安息香酸を，エタノールと塩化水素でエステル化すると得られる．白色の結晶．融点89～91 ℃．無臭でやや苦味をもち，舌を麻ひさせる．エタノール，クロロホルム，エーテルに易溶，オリブ油に可溶，水に難溶．局所麻酔剤として外用する．森北出版「化学辞典（第2版） | | 用途 | 表面麻酔として作用します。 | | 用途 | 牛、羊、豚および馬の局所麻酔薬、及び魚介類の鎮静?麻酔剤 | | 用途 | 有機合成原料(医薬品、染料)。 | | 化粧品の成分用途 | 口腔ケア剤、口腔衛生剤、褪色防止剤、外用鎮痛剤 | | 効能 | 鎮痛薬, 表面麻酔薬, 鎮痒薬 | | 商品名 | アミノ安息香酸エチル (マイラン製薬) | | 説明 | Benzocaine (ethyl p-aminobenzoate) is used topically by itself or in combination with menthol or
phenol in nonprescription dosage forms such as gels, creams, ointments, lotions, aerosols, and
lozenges to relieve pain or irritation caused by such conditions as sunburn, insect bites,
toothache, teething, cold sores or canker sores in or around the mouth, and fever blisters.
Benzocaine is a lipophilic local anesthetic agent with a short duration of action.
Like most amino ester-type local anesthetics, it is easily hydrolyzed by plasma cholinesterase.
Because of its low pKa, however, it is un-ionized under most physiological conditions and, therefore, can only bind
to the lipid side of the local anesthetic receptor. It also can easily cross membranes
into systemic circulation to cause systemic toxicities. Furthermore, being a PABA derivative, it
has similar allergenic properties to procaine and is contraindicated with sulfonamide antibacterial
agents. | | 化学的特性 | Benzocaine is a white odourless needle-like crystal, slightly soluble in water and easily soluble in organic solvents. For example: ethanol, chloroform, ether, soluble in almond oil, olive oil. | | 使用 | Benzocaine is used as an anesthetic (Local and topical) that in products such as burn and sunburn remedies, hemorrhoidal creams, suppositories, creams for treatment of poison ivy, oral and gingival products, sore-throat sprays/lozenges, astringents, appetite suppressants, callus and wart remedies, athlete's-foot remedies, toothache- and denture-irritation products. | | 定義 | ChEBI: Benzocaine is a benzoate ester having 4-aminobenzoic acid as the acid component and ethanol as the alcohol component. A surface anaesthetic, it is used to suppress the gag reflex, and as a lubricant and topical anaesthetic on the larynx, mouth, nasal cavity, respiratory tract, oesophagus, rectum, urinary tract, and vagina. It has a role as a topical anaesthetic, an antipruritic drug, an allergen and a sensitiser. It is a benzoate ester and a substituted aniline. | | brand name | Americaine (Fisons); Baby
Anbesol (Whitehall-Robins). | | 生物学の機能 | Benzocaine is a PABA derivative used primarily for
topical application to skin and mucous membranes. Its
low aqueous solubility allows it to stay at the site of application
for long periods. Its minimal rate of absorption
after topical administration is associated with a low incidence
of systemic toxicity. Benzocaine is contraindicated
in patients with known sensitivity to ester-linked
anesthetics or PABA-containing compounds. | | Synthesis Reference(s) | Journal of the American Chemical Society, 71, p. 4154, 1949 DOI: 10.1021/ja01180a513
Chemical and Pharmaceutical Bulletin, 29, p. 1443, 1981 DOI: 10.1248/cpb.29.1443 | | 一般的な説明 | Benzocaine is a unique local anesthetic because it does notcontain a tertiary amine. The pKa of the aromatic amine is 3.5ensuring that benzocaine is uncharged at physiological pH.Because it is uncharged, it is not water soluble but is ideal fortopical applications. The onset of action is within 30 secondsand the duration of drug action is 10 to 15 minutes. | | Biochem/physiol Actions | Benzocaine is the ethyl ester of p-aminobenzoic acid (PABA). Benzocaine acts to inhibit the voltage-dependent sodium channels (VDSCs) on the nerve membrane, stopping the propagation of the action potential. | | 臨床応用 | Benzocaine is used for endoscopy, bronchoscopy, and topicalanesthesia. Benzocaine is available as a 20% solution topicalspray, in a 1% gel for mucous membrane application, and a14% glycerin suspension for topical use in the outer ear.Toxicity to benzocaine can occur when the topical doseexceeds 200 to 300 mg resulting in methemoglobinemia.Infants and children are more susceptible to this and methemoglobinemiahas been reported after benzocaine lubricationof endotracheal tubes and after topical administration to treata painful diaper rash. | | 安全性プロファイル | Poison by ingestion and
intraperitoneal routes. Human systemic
effects by rectal route:
methemoglobinemia/carboxyhemoglobinem
ia in infants. A skin irritant and a mild
sensitizer. Local contact may cause contact
dermatitis. Used as a topical anesthetic and
as a sun-screening agent. When heated to
decomposition it emits highly toxic fumes of
NOx. See also ETHYL ALCOHOL and
ESTERS | | 合成 | Benzocaine is the ethyl ester of 4-aminobenzoic acid (2.3.1). The classic,
optimal way of benzocaine synthesis is the reduction of the nitro group of the ethyl ester
of 4-nitrobenzoic acid to benzocaine by hydrogen, which generates directly in the reaction
medium by the reaction of iron filings with dilute acids [24¨C26]. 
| | 純化方法 | Crystallise Benzocaine from EtOH/H2O or EtOH (m 93-94o), and dry it in air. [Beilstein 14 H 422, 14 IV 1129.] | | Structure and conformation | Ethyl aminobenzoate, a para-aminobenzoate derivative (PABA) |
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