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51-43-4 molecular structure
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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 and InChIs

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

Cite this record

CBID:550 http://www.chembase.cn/molecule-550.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
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
CAS Number
51-43-4
EC Number
200-098-7
MDL Number
MFCD00002204
Beilstein Number
2368277
Merck Index
143619
PubChem SID
46509097
24894545
160964013
24845246
PubChem CID
5816
CHEBI ID
28918
ATC CODE
S01EA01
R03AA01
B02BC09
C01CA24
R01AA14
A01AD01
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

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 9.69426  H Acceptors
H Donor LogD (pH = 5.5) -2.8488538 
LogD (pH = 7.4) -1.6309718  Log P -0.42952928 
Molar Refractivity 49.2303 cm3 Polarizability 19.213377 Å3
Polar Surface Area 72.72 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P -0.82  LOG S -0.99 
Solubility (Water) 1.86e+01 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
0.18 mg/mL at 20 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)] expand Show data source
Aqueous HCl expand Show data source
DMSO expand Show data source
Apperance
White Solid expand Show data source
Melting Point
~215 °C (dec.) expand Show data source
> 200°C (dec.) expand Show data source
211-212; 215 expand Show data source
215 °C (dec.)(lit.) expand Show data source
216-219°C expand Show data source
Vapor Pressure
2.93 x 10-15 mm Hg at 25 °C (calc). expand Show data source
Optical Rotation
[α]20/D -52±2°, c = 5% in 5% HCl expand Show data source
-52 (c=1 in 0.6N HCl) expand Show data source
Hydrophobicity(logP)
-0.685 expand Show data source
-1.37 [HANSCH,C & LEO,AJ (1985)] expand Show data source
Storage Condition
-20°C expand Show data source
-20°C Freezer expand Show data source
2-8°C expand Show data source
Storage Warning
Air & Light Sensitive expand Show data source
RTECS
DO2625000 expand Show data source
European Hazard Symbols
Toxic Toxic (T) expand Show data source
UN Number
2811 expand Show data source
UN2811 expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Hazard Class
6.1 expand Show data source
Packing Group
2 expand Show data source
II expand Show data source
Australian Hazchem
2XE expand Show data source
Risk Statements
23/24/25 expand Show data source
R:25 expand Show data source
Safety Statements
27-36/37-45 expand Show data source
36/37/39-45 expand Show data source
S:28-36/37/39-45-53 expand Show data source
EU Classification
T2 expand Show data source
EU Hazard Identification Number
6.1B expand Show data source
Emergency Response Guidebook(ERG) Number
154 expand Show data source
TSCA Listed
expand Show data source
GHS Pictograms
GHS06 expand Show data source
GHS Signal Word
Danger expand Show data source
GHS Hazard statements
H300-H310-H330 expand Show data source
H301-H310-H331 expand Show data source
GHS Precautionary statements
P260-P301+P310-P304+P340-P320-P330-P361-P405-P501A expand Show data source
P261-P280-P301 + P310-P302 + P350-P310 expand Show data source
Personal Protective Equipment
Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges expand Show data source
RID/ADR
UN 2811 6.1/PG 2 expand Show data source
Storage Temperature
2-8°C expand Show data source
Admin Routes
IV, IM, endotracheal, IC expand Show data source
Bioavailability
Nil (oral) expand Show data source
Excretion
Urine expand Show data source
Half Life
2 minutes expand Show data source
Metabolism
adrenergic synapse (MAO and COMT) expand Show data source
Legal Status
POM (UK) expand Show data source
Rx-only (US) expand Show data source
S4 (Australia) expand Show data source
Pregnancy Category
A (Australia) expand Show data source
C (US) expand Show data source
Gene Information
rat ... Adra1a(29412), Adra2a(25083), Adrb1(24925), Adrb2(24176), Drd1a(24316), Drd2(24318) expand Show data source
Purity
≥97.0% (NT) expand Show data source
95% expand Show data source
98+% expand Show data source
Grade
Ph Eur expand Show data source
USP expand Show data source
Salt Data
Free Base expand Show data source
Certificate of Analysis
Download expand Show data source
Download expand Show data source
Download expand Show data source
Ignition Residue
≤0.1% expand Show data source
Loss on Drying
≤1% loss on drying expand Show data source
Pharmacopeia
testing & handling conforms to Pharmacopeia expand Show data source
Linear Formula
(HO)2C6H3CH(OH)CH2NHCH3 expand Show data source

DETAILS

DETAILS

MP Biomedicals MP Biomedicals DrugBank DrugBank Selleck Chemicals Selleck Chemicals Wikipedia Wikipedia Sigma Aldrich Sigma Aldrich TRC TRC
MP Biomedicals - 02151065 external link
Metabolite of norepinephrine.
DrugBank - DB00668 external link
Item Information
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 external link
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 external link
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 external link
Biochem/physiol Actions
Adrenoceptor agonist.
Sigma Aldrich - 02252 external link
Biochem/physiol Actions
Adrenoceptor agonist.
Sigma Aldrich - 02250 external link
Biochem/physiol Actions
Adrenoceptor agonist.
Toronto Research Chemicals - E588580 external link
Endogenous catcholamine with combined α-and β-agonist activity. Principal sympathomimetic hormone produced by the adrenal medulla. Bronchodilator; cardiostimulant; mydriatic; antiglaucoma.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • 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)
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PATENTS

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