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

• ChemBase ID: 550
• Molecular Formular: C9H13NO3
• Molecular Mass: 183.20442
• Monoisotopic Mass: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-[(1R)-1-hydroxy-2-(methylamino)ethyl]benzene-1,2-diol
• IUPAC Traditional name: epinephrine
• Brand Name: 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
• Synonyms: 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; (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

Database IDs

• CAS Number: 51-43-4
• EC Number: 200-098-7
• MDL Number: MFCD00002204
• Beilstein Number: 2368277
• Merck Index: 143619
• PubChem SID: 24845246; 24894545; 46509097; 160964013
• PubChem CID: 5816
• CHEBI ID: 28918
• ATC CODE: R03AA01; R01AA14; A01AD01; B02BC09; C01CA24; S01EA01
• CHEMBL: 679
• Chemspider ID: 5611
• DrugBank ID: DB00668
• IUPHAR ligand ID: 479
• KEGG ID: D00095
• Unique Ingredient Identifier: YKH834O4BH
• Wikipedia Title: Epinephrine
• Medline Plus: a603002

CALCULATED PROPERTIES

JChem

• Acid pKa: 9.69426
• H Acceptors: 4
• H Donor: 4
• LogD (pH = 5.5): -2.8488538
• LogD (pH = 7.4): -1.6309718
• Log P: -0.42952928
• Molar Refractivity: 49.2303 cm^3
• Polarizability: 19.213377 Å^3
• Polar Surface Area: 72.72 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -0.82
• LOG S: -0.99
• Solubility (Water): 1.86e+01 g/l

PROPERTIES

Physical Property

• Solubility: 0.18 mg/mL at 20 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]; Aqueous HCl; DMSO
• Apperance: White Solid
• Melting Point: ~215 °C (dec.); > 200°C (dec.); 211-212; 215; 215 °C (dec.)(lit.); 216-219°C
• Vapor Pressure: 2.93 x 10-15 mm Hg at 25 °C (calc).
• Optical Rotation: [α]20/D -52±2°, c = 5% in 5% HCl; -52 (c=1 in 0.6N HCl)
• Hydrophobicity(logP): -0.685; -1.37 [HANSCH,C & LEO,AJ (1985)]

Safety Information

• Storage Condition: -20°C; -20°C Freezer; 2-8°C
• Storage Warning: Air & Light Sensitive
• RTECS: DO2625000
• European Hazard Symbols: Toxic (T)
• UN Number: 2811; UN2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 2; II
• Australian Hazchem: 2XE
• Risk Statements: 23/24/25; R:25
• Safety Statements: 27-36/37-45; 36/37/39-45; S:28-36/37/39-45-53
• EU Classification: T2
• EU Hazard Identification Number: 6.1B
• Emergency Response Guidebook(ERG) Number: 154
• TSCA Listed: 是
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H300-H310-H330; H301-H310-H331
• GHS Precautionary statements: P260-P301+P310-P304+P340-P320-P330-P361-P405-P501A; P261-P280-P301 + P310-P302 + P350-P310
• Personal Protective Equipment: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 2
• Storage Temperature: 2-8°C

Pharmacology Properties

• Admin Routes: IV, IM, endotracheal, IC
• Bioavailability: Nil (oral)
• Excretion: Urine
• Half Life: 2 minutes
• Metabolism: adrenergic synapse (MAO and COMT)
• Legal Status: POM (UK); Rx-only (US); S4 (Australia)
• Pregnancy Category: A (Australia); C (US)
• Gene Information: rat ... Adra1a(29412), Adra2a(25083), Adrb1(24925), Adrb2(24176), Drd1a(24316), Drd2(24318)

Product Information

• Purity: ≥97.0% (NT); 95%; 98+%
• Grade: Ph Eur; USP
• Salt Data: Free Base
• Ignition Residue: ≤0.1%
• Loss on Drying: ≤1% loss on drying
• Pharmacopeia: testing & handling conforms to Pharmacopeia
• Linear Formula: (HO)2C6H3CH(OH)CH2NHCH3

DETAILS

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
Adrenoceptor agonist.

Sigma Aldrich - 02252

Biochem/physiol Actions
Adrenoceptor agonist.

Sigma Aldrich - 02250

Biochem/physiol Actions
Adrenoceptor agonist.

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.

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
• 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)