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2D Structure
Also known as: (-)-epinephrine bitartrate, Adrenaline bitartrate, Mls000028381, Epinephrine d-bitartrate, L-epinephrine bitartrate, Smr000058630
Molecular Formula
C13H19NO9
Molecular Weight
333.29  g/mol
InChI Key
YLXIPWWIOISBDD-FVGYRXGTSA-N

The active sympathomimetic hormone from the ADRENAL MEDULLA. 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.
1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
2,3-dihydroxybutanedioic acid;4-[(1R)-1-hydroxy-2-(methylamino)ethyl]benzene-1,2-diol
2.1.2 InChI
InChI=1S/C9H13NO3.C4H6O6/c1-10-5-9(13)6-2-3-7(11)8(12)4-6;5-1(3(7)8)2(6)4(9)10/h2-4,9-13H,5H2,1H3;1-2,5-6H,(H,7,8)(H,9,10)/t9-;/m0./s1
2.1.3 InChI Key
YLXIPWWIOISBDD-FVGYRXGTSA-N
2.1.4 Canonical SMILES
CNCC(C1=CC(=C(C=C1)O)O)O.C(C(C(=O)O)O)(C(=O)O)O
2.1.5 Isomeric SMILES
CNC[C@@H](C1=CC(=C(C=C1)O)O)O.C(C(C(=O)O)O)(C(=O)O)O
2.2 Synonyms
2.2.1 MeSH Synonyms

1. 4-(1-hydroxy-2-(methylamino)ethyl)-1,2-benzenediol

2. Acetate, Epinephrine

3. Adrenaline

4. Adrenaline Acid Tartrate

5. Adrenaline Bitartrate

6. Adrenaline Hydrochloride

7. Epifrin

8. Epinephrine

9. Epinephrine Acetate

10. Epinephrine Bitartrate

11. Epinephrine Hydrochloride

12. Epitrate

13. Lyophrin

14. Medihaler-epi

2.2.2 Depositor-Supplied Synonyms

1. (-)-epinephrine Bitartrate

2. Adrenaline Bitartrate

3. Mls000028381

4. Epinephrine D-bitartrate

5. L-epinephrine Bitartrate

6. Smr000058630

7. Adrenaline Bitartate

8. Adrenaline (as Tartrate)

9. Sr-01000075267

10. L-epinephrine Hydrogen Tartrate

11. Adrenalin Tartrate

12. Nsc-756755

13. Opera_id_1462

14. Epinephrini Hydrogenotartras

15. Lopac0_000502

16. Schembl597216

17. Chembl1256958

18. L-adrenaline Hydrogen Bitartrate

19. L-epinephrine Hydrogen Bitartrate

20. Hms2233k16

21. Hms3261f05

22. Tox21_500502

23. Akos030504417

24. Ccg-221806

25. Lp00502

26. Ncgc00093902-01

27. Ncgc00261187-01

28. A0175

29. Eu-0100502

30. E 4375

31. Sr-01000075267-1

32. Sr-01000075267-4

33. Sr-01000075267-6

2.3 Create Date
2006-06-15
3 Chemical and Physical Properties
Molecular Weight 333.29 g/mol
Molecular Formula C13H19NO9
Hydrogen Bond Donor Count8
Hydrogen Bond Acceptor Count10
Rotatable Bond Count6
Exact Mass333.10598118 g/mol
Monoisotopic Mass333.10598118 g/mol
Topological Polar Surface Area188 Ų
Heavy Atom Count23
Formal Charge0
Complexity288
Isotope Atom Count0
Defined Atom Stereocenter Count1
Undefined Atom Stereocenter Count2
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count2
4 Pharmacology and Biochemistry
4.1 MeSH Pharmacological Classification

Adrenergic alpha-Agonists

Drugs that selectively bind to and activate alpha adrenergic receptors. (See all compounds classified as Adrenergic alpha-Agonists.)


Adrenergic beta-Agonists

Drugs that selectively bind to and activate beta-adrenergic receptors. (See all compounds classified as Adrenergic beta-Agonists.)


Bronchodilator Agents

Agents that cause an increase in the expansion of a bronchus or bronchial tubes. (See all compounds classified as Bronchodilator Agents.)


Mydriatics

Agents that dilate the pupil. They may be either sympathomimetics or parasympatholytics. (See all compounds classified as Mydriatics.)


Sympathomimetics

Drugs that mimic the effects of stimulating postganglionic adrenergic sympathetic nerves. Included here are drugs that directly stimulate adrenergic receptors and drugs that act indirectly by provoking the release of adrenergic transmitters. (See all compounds classified as Sympathomimetics.)


Vasoconstrictor Agents

Drugs used to cause constriction of the blood vessels. (See all compounds classified as Vasoconstrictor Agents.)