4-[(1R)-1-hydroxy-2-(methylamino)ethyl]benzene-1,2-diol

• ChemBase编号: 550
• 分子式: C9H13NO3
• 平均质量: 183.20442
• 单一同位素质量: 183.08954328
• SMILES: O[C@H](c1cc(O)c(O)cc1)CNC
• Canonical SMILES: CNC[C@@H](c1ccc(c(c1)O)O)O
• InChI: InChI=1S/C9H13NO3/c1-10-5-9(13)6-2-3-7(11)8(12)4-6/h2-4,9-13H,5H2,1H3/t9-/m0/s1
• InChIKey: UCTWMZQNUQWSLP-VIFPVBQESA-N

名称和登记号

名称

• IUPAC标准名: 4-[(1R)-1-hydroxy-2-(methylamino)ethyl]benzene-1,2-diol
• IUPAC传统名: epinephrine
• 商标名: ADROP; Adnephrine; Adrenal; Adrenalin-Medihaler; Adrenamine; Adrenan; Adrenapax; Adrenasol; Adrenatrate; Adrenine; Adrenodis; Adrenohorma; Adrenor; Adrenosan; Adrenutol; Adrin; Adrine; Aktamin; Ana-Guard; Antiasthmatique; Asmatane Mist; Asthma Meter Mist; Asthma-Nefrin; Asthmahaler Mist; Asthmanefrin; Astmahalin; Astminhal; Balmadren; Bernarenin; Biorenine; Bosmin; Brevirenin; Bronkaid; Bronkaid Mist; Bronkaid Suspension Mist; Chelafrin; Citanest Forte; Corisol; Drenamist; Duranest; Dylephrin; Epi EZ Pen Jr; Epifrin; Epiglaufrin; Epipen; Epipen Auto-Injector; Epipen EZ Pen; Epipen Jr.; Epipen Jr. Auto-Injector; Epirenamine; Epirenan; Epirenin; Epitrate; Eppy; Esphygmogenina; Exadrin; Glaucon; Glaucosan; Glauposine; Glycirenan; Haemostasin; Haemostatin; Hektalin; Hemisine; Hemostasin; Hemostatin; Hypernephrin; Hyporenin; IOP; Intranefrin; Iontocaine; Isoptoepinal; Kidoline; Levonor; Levorenen; Levorenin; Levorenine; Lidocaton; Lyophrin; Medihaler-Epi; Metanephrin; Micronefrin; Mucidrina; Myosthenine; Mytrate; Nephridine; Nephron; Nieraline; Nor-Epirenan; Norartrinal; Paranephrin; Primatene Mist; Renagladin; Renaglandin; Renaglandulin; Renaleptine; Renalina; Renoform; Renostypricin; Renostypticin; Renostyptin; Scurenaline; Septocaine; Simplene; Sindrenina; Soladren; Sphygmogenin; Stryptirenal; Styptirenal; Supracapsulin; Supradin; Supranefran; Supranephrane; Supranephrine; Supranol; Suprarenaline; Suprarenin; Suprel; Surenine; Surrenine; Sus-Phrine; Susphrine; Sympathin E; Sympathin I; Takamina; Takamine; Tokamina; Tolansin; Tolax; Tolcil; Tolhart; Tonogen; Twinject; Vaponefrin; Vasoconstrictine; Vasodrine; Vasoton; Vasotonin
• 别名: (R)-(-)-3,4-二羟基-α-(甲基氨基)苯甲醇; 副肾素; L-肾上腺素; 副肾碱; (-)-肾上腺素; L-肾上腺素; Adrenalina; Adrenalin; Adrenalin Chloride; Adrenaline; Adrenalinum; D-Adrenaline; D-Epifrin; D-Epinephrine; Epinefrin [Czech]; Epinefrina [INN-Spanish]; Epinephran; Epinephrine Bitartrate; Epinephrinum [INN-Latin]; L-Adrenalin; L-Adrenaline; L-Adrenaline Base; L-Epinephine; L-Epinephrine; L-Epirenamine; Levoepinephrine; Levoadrenaline; Racepinefrinum [inn-latin]; Racepinephrine; Racepinefrine; Racepinefrina [inn-spanish]; ADR Adrenaline; Epinephrine; Adnephrine; L-Adrenaline; (-)-Epinephrine; 4-[(1R)-1-Hydroxy-2-(methylamino)ethyl]-1,2-benzenediol; (R)-Epinephrine; Renoform; Renostypticin; Adrenal; 4-[(1R)-1-hydroxy-2-(methylamino)ethyl]benzene-1,2-diol; L-Adrenaline; (R)-(-)-3,4-Dihydroxy-α-(methylaminomethyl)benzyl alcohol; L-(-)-EPINEPHRINE; (-)-Adrenalin; (R)-(-)-3,4-Dihydroxy-α-(methylaminomethyl)benzyl alcohol

登记号

• CAS号: 51-43-4
• EC号: 200-098-7
• MDL号: MFCD00002204
• Beilstein号: 2368277
• 默克索引号: 143619
• PubChem SID: 24894545; 24845246; 46509097; 160964013
• PubChem CID: 5816
• CHEBI ID: 28918
• ATC码: R01AA14; A01AD01; R03AA01; B02BC09; C01CA24; S01EA01
• CHEMBL: 679
• Chemspider ID: 5611
• DrugBank ID: DB00668
• IUPHAR配体索引: 479
• KEGG ID: D00095
• 美国药典/FDA物质标识码: YKH834O4BH
• 维基百科标题: Epinephrine
• Medline Plus: a603002

理论计算性质

JChem

• Acid pKa: 9.69426
• 质子受体: 4
• 质子供体: 4
• LogD (pH = 5.5): -2.8488538
• LogD (pH = 7.4): -1.6309718
• Log P: -0.42952928
• 摩尔折射率: 49.2303 cm^3
• 极化性: 19.213377 Å^3
• 极化表面积: 72.72 Å^2
• 可自由旋转的化学键: 3
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: -0.82
• LOG S: -0.99
• 溶解度: 1.86e+01 g/l

分子性质

理化性质

• 溶解度: 0.18 mg/mL at 20 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]; Aqueous HCl; DMSO
• 外观: White Solid
• 熔点: ~215 °C (dec.); > 200°C (dec.); 211-212; 215; 215 °C (dec.)(lit.); 216-219°C
• 蒸汽压: 2.93 x 10-15 mm Hg at 25 °C (calc).
• 比旋光度: [α]20/D -52±2°, c = 5% in 5% HCl; -52 (c=1 in 0.6N HCl)
• 疏水性(logP): -0.685; -1.37 [HANSCH,C & LEO,AJ (1985)]

安全信息

• 保存条件: -20°C; -20°C Freezer; 2-8°C
• 保存注意事项: Air & Light Sensitive
• RTECS编号: DO2625000
• 欧盟危险性物质标志: 有毒(Toxic) (T)
• 联合国危险货物编号: 2811; UN2811
• 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): 2; II
• 澳大利亚Hazchem: 2XE
• 危险公开号: 23/24/25; R:25
• 安全公开号: 27-36/37-45; 36/37/39-45; S:28-36/37/39-45-53
• 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: 154
• TSCA收录: 是
• GHS危险品标识: GHS06
• GHS警示词: Danger
• GHS危险声明: H300-H310-H330; H301-H310-H331
• GHS警示性声明: P260-P301+P310-P304+P340-P320-P330-P361-P405-P501A; P261-P280-P301 + P310-P302 + P350-P310
• 个人保护装置: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 2
• 保存温度: 2-8°C

药理学性质

• 给药途径: IV, IM, endotracheal, IC
• 生物利用度: Nil (oral)
• 排泄: Urine
• 半衰期: 2 minutes
• 代谢: adrenergic synapse (MAO and COMT)
• 法定药品分级: POM (UK); Rx-only (US); S4 (Australia)
• 妊娠期药物分类: A (Australia); C (US)
• 相关基因信息: rat ... Adra1a(29412), Adra2a(25083), Adrb1(24925), Adrb2(24176), Drd1a(24316), Drd2(24318)

产品相关信息

• 纯度: ≥97.0% (NT); 95%; 98+%
• 级别: Ph Eur; USP
• 成盐信息: Free Base
• 燃烧残渣: ≤0.1%
• 干燥失重: ≤1% loss on drying
• 药典: testing & handling conforms to Pharmacopeia
• 线性分子式: (HO)2C6H3CH(OH)CH2NHCH3

详细说明

MP Biomedicals - 02151065

Metabolite of norepinephrine.

DrugBank - DB00668

• Drug Groups: approved
• Description: The active sympathomimetic hormone from the adrenal medulla in most species. It stimulates both the alpha- and beta- adrenergic systems, causes systemic vasoconstriction and gastrointestinal relaxation, stimulates the heart, and dilates bronchi and cerebral vessels. It is used in asthma and cardiac failure and to delay absorption of local anesthetics. [PubChem]
• Indication: Used to treat anaphylaxis and sepsis. Also one of the body's main adrenergic neurotransmitters.
• Pharmacology: Epinephrine is indicated for intravenous injection in treatment of acute hypersensitivity, treatment of acute asthmatic attacks to relieve bronchospasm, and treatment and prophylaxis of cardiac arrest and attacks of transitory atrioventricular heart block with syncopal seizures (Stokes-Adams Syndrome). The actions of epinephrine resemble the effects of stimulation of adrenergic nerves. To a variable degree it acts on both alpha and beta receptor sites of sympathetic effector cells. Its most prominent actions are on the beta receptors of the heart, vascular and other smooth muscle. When given by rapid intravenous injection, it produces a rapid rise in blood pressure, mainly systolic, by (1) direct stimulation of cardiac muscle which increases the strength of ventricular contraction, (2) increasing the heart rate and (3) constriction of the arterioles in the skin, mucosa and splanchnic areas of the circulation. When given by slow intravenous injection, epinephrine usually produces only a moderate rise in systolic and a fall in diastolic pressure. Although some increase in pulse pressure occurs, there is usually no great elevation in mean blood pressure. Accordingly, the compensatory reflex mechanisms that come into play with a pronounced increase in blood pressure do not antagonize the direct cardiac actions of epinephrine as much as with catecholamines that have a predominant action on alpha receptors.
• Toxicity: Skin, LD₅₀ = 62 mg/kg (rat)
• Affected Organisms: Humans and other mammals
• Biotransformation: Epinephrine is rapidly inactivated in the body and is degraded by enzymes in the liver and other tissues. The larger portion of injected doses is excreted in the urine as inactivated compounds and the remainder either partly unchanged or conjugated. The drug becomes fixed in the tissues and is inactivated chiefly by enzymatic transformation to metanephrine or normetanephrine either of which is subsequently conjugated and excreted in the urine in the form of sulfates and glucuronides. Either sequence results in the formation of 3-methoxy-4-hydroxy-mandelic acid which also is detectable in the urine. Main metabolic enzymes include MAO and COMT
• Absorption: Usually this vasodilator effect of the drug on the circulation predominates so that the modest rise in systolic pressure which follows slow injection or absorption is mainly the result of direct cardiac stimulation and increase in cardiac output.
• Half Life: 2 minutes
• Elimination: Renal
• References: Yamashima T: Jokichi Takamine (1854-1922), the samurai chemist, and his work on adrenalin. J Med Biogr. 2003 May;11(2):95-102. [Pubmed] ; Bennett MR: One hundred years of adrenaline: the discovery of autoreceptors. Clin Auton Res. 1999 Jun;9(3):145-59. [Pubmed]
• External Links: Wikipedia; RxList; Drugs.com

Selleck Chemicals - S2522

Research Area: Metabolic Disease
Biological Activity:
L-Adrenaline (Epinephrine) belongs to a group of the compounds known as catecholamines, which play an important role in the regulation of physiological process in living organisms. The antioxidant activity and antioxidant mechanism of L-adrenaline was clarified using various in vitro antioxidant assays. L-adrenaline inhibited 74.2% lipid peroxidation of a linoleic acid emulsion at 30 μg/ml concentration. On the other hand, butylated hydroxyanisole (BHA), butylated hydroxytoluene (BHT), alpha-tocopherol and trolox displayed 83.3, 82.1, 68.1 and 81.3% inhibition on the peroxidation of linoleic acid emulsion at the same concentration, respectively. BHA, BHT, alpha-tocopherol and trolox were used as reference antioxidants and radical scavenger compounds. L-adrenaline had effective in vitro antioxidant and radical scavenging activity. [1]

Sigma Aldrich - E4250

Biochem/physiol Actions
肾上腺素能受体激动剂。
包装
1, 5, 10 g in glass bottle
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. E4250.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Sigma Aldrich - 94986

Biochem/physiol Actions
肾上腺素能受体激动剂。

Sigma Aldrich - 02252

Biochem/physiol Actions
肾上腺素能受体激动剂。

Sigma Aldrich - 02250

Biochem/physiol Actions
肾上腺素能受体激动剂。

Toronto Research Chemicals - E588580

Endogenous catcholamine with combined α-and β-agonist activity. Principal sympathomimetic hormone produced by the adrenal medulla. Bronchodilator; cardiostimulant; mydriatic; antiglaucoma.

参考文献

• Yamashima T: Jokichi Takamine (1854-1922), the samurai chemist, and his work on adrenalin. J Med Biogr. 2003 May;11(2):95-102. Pubmed
• Bennett MR: One hundred years of adrenaline: the discovery of autoreceptors. Clin Auton Res. 1999 Jun;9(3):145-59. Pubmed
• Pohorecky, L.A., et al.: Pharmacol. Rev., 23, (1964)
• Hebert, P., et al.: J. Emerg. Med., 9, 487 (1964)
• McLean-Tooke, et al.: Br. Med. J., 327, 1332 (1964)
• Malmejac, et al.: Physiol. Rev., 44, 186 (1964)