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Merck
CN

02252

(−)-Epinephrine

tested according to USP

Synonym(s):

(−)-Adrenalin, (R)-(−)-3,4-Dihydroxy-α-(methylaminomethyl)benzyl alcohol, L-Adrenaline, L-Epinephrine

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About This Item

Linear Formula:
(HO)2C6H3CH(OH)CH2NHCH3
CAS Number:
51-43-4
Molecular Weight:
183.20
EC Number:
200-098-7
UNSPSC Code:
12352200
PubChem Substance ID:
24845246
Beilstein/REAXYS Number:
2368277
MDL number:
MFCD00002204

Key Documents

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InChI key

UCTWMZQNUQWSLP-VIFPVBQESA-N

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

SMILES string

CNC[C@H](O)c1ccc(O)c(O)c1

agency

tested according to USP

mp

215 °C (dec.) (lit.)

solubility

H2O: very slightly soluble, NaOH: very soluble, acetone: insoluble, alcohol: very slightly soluble, chloroform: insoluble, diethyl ether: insoluble, oil: insoluble, potassium hydroxide solution: very soluble

application(s)

pharmaceutical (small molecule)

storage temp.

2-8°C

Gene Information

rat ... Adra1a(29412), Adra2a(25083), Adrb1(24925), Adrb2(24176), Drd1a(24316), Drd2(24318)

Application

(-)-Epinephrine was used in fertilization medium for rinsing Cumulus-oocyte complexes (COC) during in vitro maturation.

Biochem/physiol Actions

(-)-Epinephrine enhances the IL-6 secretion and bioactivity from isolated perfused rat liver (IPRL).
Adrenoceptor agonist.

Preparation Note

(-)-Epinephrine readily dissolves in aqueous solutions of mineral acids, KOH and NaOH. It is very slightly soluble in water and alcohol but is insoluble in chloroform, ether, acetone, oils as well as in aqueous solutions of ammonia and the alkali carbonates.

pictograms

Skull and crossbones
GHS06

signalword

Danger

Hazard Classifications

Acute Tox. 2 Dermal - Acute Tox. 3 Inhalation - Acute Tox. 3 Oral

Storage Class

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

Regulatory Information

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J Liao et al.
The American journal of physiology, 268(4 Pt 2), R896-R901 (1995-04-01)
A bidirectional communication exists between the nervous system and the immune system. Evidence has accumulated suggesting that cytokines-immune peptides influence sympathetic neuronal survival and that cytokines can promote the secretion of catecholamines. Using an isolated perfused rat liver (IPRL) preparation
C Wrenzycki et al.
Human reproduction (Oxford, England), 16(5), 893-901 (2001-05-02)
Assisted reproduction technologies have made great progress during the last 15 years in most mammalian species, including humans. Growing evidence indicates that bovine pre-implantation development is a superior model for investigating early human development than the mouse. The purpose of
Popchai Ngamskulrungroj et al.
PloS one, 6(1), e16076-e16076 (2011-01-21)
Human and animal cryptococcosis due to an unusual molecular type of Cryptococcus gattii (VGII) emerged recently on Vancouver Island, Canada. Unlike C. neoformans, C. gattii causes disease mainly in immunocompetent hosts, despite producing a similar suite of virulence determinants. To
Mark M Kushnir et al.
Clinical chemistry, 52(8), 1559-1567 (2006-06-17)
Congenital adrenal hyperplasia is a group of autosomal recessive disorders caused by a deficiency of 1 of 4 enzymes required for the synthesis of glucocorticoids, mineralocorticoids, and sex hormones. Analysis of 11-deoxycortisol (11DC), 17-hydroxyprogesterone (17OHP), 17-hydroxypregnenolone (17OHPr), and pregnenolone (Pr)
Michael B Levy et al.
Annals of allergy, asthma & immunology : official publication of the American College of Allergy, Asthma, & Immunology, 112(1), 58-63 (2013-12-18)
Avoidance strategies in patients with cow's milk allergy occasionally fail to protect these patients from inadvertent exposures, leading to life-threatening reactions. To assess the safety and efficacy of milk oral immunotherapy as an alternative therapeutic strategy. Patients (n = 280
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