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329-65-7 molecular structure
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4-[1-hydroxy-2-(methylamino)ethyl]benzene-1,2-diol

ChemBase ID: 73260
Molecular Formular: C9H13NO3
Molecular Mass: 183.20442
Monoisotopic Mass: 183.08954328
SMILES and InChIs

SMILES:
c1(c(ccc(c1)C(CNC)O)O)O
Canonical SMILES:
CNCC(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
InChIKey:
UCTWMZQNUQWSLP-UHFFFAOYSA-N

Cite this record

CBID:73260 http://www.chembase.cn/molecule-73260.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
4-[1-hydroxy-2-(methylamino)ethyl]benzene-1,2-diol
IUPAC Traditional name
(+-)-adrenaline
DL-adrenaline
Synonyms
(±)-3,4-Dihydroxy-α-(methylaminomethyl)benzyl alcohol
(±)-Adrenalin
3,4-Dihydroxy-α-(methylaminomethyl)benzyl alcohol
DL-Adrenaline
(+/-)-3,4-Dihydroxy-α-[(methylamino)methyl]benzyl Alcohol
1-(3,4-Dihydroxy)phenyl-2-methylaminoethanol
Epirenamine
Racepinefrine
Racepinephrine
rac Epinephrine
DL-Adrenaline
3,4-Dihydroxy-α-(methylaminomethyl)benzyl alcohol
4-[1-Hydroxy-2-(methylamino)ethyl]-1,2-benzenediol
(±)-3,4-Dihydroxy-α-(methylaminomethyl)benzyl alcohol
DL-EPINEPHRINE
(±)-Epinephrine
4-(1-Hydroxy-2-(MethylaMino)ethyl)benzene-1,2-diol
(±)-3,4-二羟基-α-(甲基氨基)苯甲醇
3,4-二羟基-α-甲胺甲基苄醇
4-[1-羟基-2-(甲基氨基)乙基]-1,2-苯二酚
消旋肾上腺素
(±)-肾上腺素
CAS Number
329-65-7
EC Number
206-347-6
MDL Number
MFCD00063027
PubChem SID
24894424
162038180
PubChem CID
838

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
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 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
Aqueous Acid expand Show data source
DMSO (hot) expand Show data source
Apperance
Brown Solid expand Show data source
Melting Point
196-199°C expand Show data source
197 °C (dec.)(lit.) expand Show data source
205-210°C (dec.) expand Show data source
Storage Condition
-20°C expand Show data source
2-8°C, Store Under Nitrogen, Protect from light expand Show data source
Refrigerator expand Show data source
RTECS
DO2975000 expand Show data source
European Hazard Symbols
Toxic Toxic (T) expand Show data source
UN Number
2811 expand Show data source
MSDS Link
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
24-36/37/38 expand Show data source
R:25 expand Show data source
Safety Statements
26-36/37-45 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
GHS Pictograms
GHS06 expand Show data source
GHS Signal Word
Danger expand Show data source
GHS Hazard statements
H311-H315-H319-H335 expand Show data source
GHS Precautionary statements
P261-P280-P305 + P351 + P338-P312 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
Target
GPCR expand Show data source
Gene Information
rat ... Adra1a(29412), Adra2a(25083), Adrb1(24925), Adrb2(24176) expand Show data source
Purity
≥95% expand Show data source
95% expand Show data source
98% 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
Linear Formula
(HO)2C6H3CH(CH2NHCH3)OH expand Show data source

DETAILS

DETAILS

MP Biomedicals MP Biomedicals Selleck Chemicals Selleck Chemicals Sigma Aldrich Sigma Aldrich TRC TRC
Selleck Chemicals - S2523 external link
Biological Activity:
DL-Adrenaline is a hormone and a neurotransmitter secreted by the medulla of the adrenal glands. In medicine DL-Adrenaline is used chiefly as a stimulant in cardiac arrest, as a vasoconstrictor in shock, and as a bronchodilator and antispasmodic in bronchial asthma. DL-Adrenaline is found in small amounts in the body and is essential for maintaining cardiovascular homeostasis because of its ability to divert blood to tissues under stress. DL-Adrenaline acts by binding to a variety of adrenergic receptors. DL-Adrenaline is a nonselective agonist of all adrenergic receptors, including α1, α2, β1, β2, and β3 receptors. Epinephrine’s binding to these receptors triggers a number of metabolic changes. Binding to α-adrenergic receptors inhibits insulin secretion by the pancreas, stimulates glycogenolysis in the liver and muscle, and stimulates glycolysis in muscle. [1][2]References on DL-Adrenaline[1] http://en.wikipedia.org/wiki/Epinephrine, , [2] Am J Physiol. , 1982 Apr, 242(4):H593-601
Sigma Aldrich - E1635 external link
Biochem/physiol Actions
肾上腺受体激动剂
Sigma Aldrich - 316741 external link
Biochem/physiol Actions
Adrenoceptor agonist.
Toronto Research Chemicals - E588585 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
  • • Berecek KH et al. Am J Physiol. 1982 Apr;242(4):H593-601.
  • • Cucinotta, V., et al.: J. Pharm. Biomed. Anal., 37, 1009 (2005)
  • • Marin-Zamora, M., et al.: J. Agric. Food Chem., 55, 4569 (2005)
  • • Kao, B., et al.: J. Perinatol., 28, 205 (2005)
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PATENTS

PATENTS

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INTERNET

INTERNET

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