Marvin  03060623042D          

 13 13  0  0  1  0            999 V2000
   -1.3740   -0.7298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6595   -1.1423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0550   -0.7298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0550    0.0952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6595    0.5077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3740    0.0952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0885   -1.1423    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0885    0.5077    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7694    0.5077    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4839    0.0952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7694    1.3327    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1984    0.5077    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9128    0.0952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  6  1  2  0  0  0  0
  7  1  1  0  0  0  0
  3  2  2  0  0  0  0
  4  3  1  0  0  0  0
  5  4  2  0  0  0  0
  9  4  1  0  0  0  0
  6  5  1  0  0  0  0
  8  6  1  0  0  0  0
 10  9  1  0  0  0  0
  9 11  1  1  0  0  0
 12 10  1  0  0  0  0
 13 12  1  0  0  0  0
M  END
> <ID>
CHEBI:28918

> <NAME>
(R)-adrenaline

> <DEFINITION>
The R-enantiomer of adrenaline. It is a hormone secreted by the adrenal glands resulting in the 'fight-or-flight' response.

> <STAR>
3

> <SECONDARY_ID>
CHEBI:1942; CHEBI:23928

> <SYNONYM>
levoepinephrine; L-Adrenaline; Epinephrin; adrenaline; adrenaline; Adrenalin; 4-[(1R)-1-Hydroxy-2-(methylamino)ethyl]-1,2-benzenediol; 4-[(1R)-1-Hydroxy-2-(methylamino)ethyl]-1,2-benzenediol; (R)-(-)-Epirenamine; (R)-(-)-Epinephrine; (R)-(-)-Adrenaline; (R)-(-)-Adnephrine; (R)-(-)-adrenaline; (-)-adrenaline; (-)-3,4-dihydroxy-alpha-((methylamino)methyl)benzyl alcohol; (-)-(R)-epinephrine

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

> <INN>
epinephrinum; epinephrine; epinephrine; epinefrina

> <BRAND_NAME>
Primatene; Epipen JR; Epipen; Epipen; Adrenalin

> <FORMULA>
C9H13NO3

> <MASS>
183.20440

> <MONOISOTOPIC_MASS>
183.08954

> <CHARGE>
0

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

> <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

> <BEILSTEIN_REGISTRY_NUMBER>
2368277

> <CAS_REGISTRY_NUMBER>
51-43-4

> <REAXYS_REGISTRY_NUMBER>
2368277

> <CHEMIDPLUS>
51-43-4

> <DRUGBANK_ACCESSION>
DB00668

> <KEGG_COMPOUND_ACCESSION>
C00788

> <KEGG_DRUG_ACCESSION>
D00095

> <KNAPSACK_ACCESSION>
C00029643

> <METACYC_ACCESSION>
L-EPINEPHRINE

> <NIST_CHEMISTRY_WEBBOOK>
51-43-4

> <WIKIPEDIA_ACCESSION>
Epinephrine

> <PUBMED_CITATION>
18325983; 21963816; 22115931; 22405854; 22425731; 22429969; 22569014; 22623754; 22826982; 22895980; 22898765; 22905594; 22940899; 23066296; 23130169; 23164182; 23185846; 29438107

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