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Norephedrine

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Also known as: 154-41-6, 2-amino-1-phenylpropan-1-ol hydrochloride, 2-amino-1-phenyl-1-propanol hydrochloride, Dl-phenylpropanolamine hydrochloride, Dl-norephedrine hydrochloride, 3198-15-0

Molecular Formula

C₉H₁₄ClNO

Molecular Weight

187.66 g/mol

InChI Key

DYWNLSQWJMTVGJ-UHFFFAOYSA-N

A sympathomimetic that acts mainly by causing release of NOREPINEPHRINE but also has direct agonist activity at some adrenergic receptors. It is most commonly used as a nasal vasoconstrictor and an appetite depressant.

1 2D Structure

Norephedrine

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

2-amino-1-phenylpropan-1-ol;hydrochloride

2.1.2 InChI

InChI=1S/C9H13NO.ClH/c1-7(10)9(11)8-5-3-2-4-6-8;/h2-7,9,11H,10H2,1H3;1H

2.1.3 InChI Key

DYWNLSQWJMTVGJ-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CC(C(C1=CC=CC=C1)O)N.Cl

2.2 Synonyms

2.2.1 MeSH Synonyms

1. Dexatrim

2. Hydrochloride, Phenylpropanolamine

3. Norephedrine

4. Phenylpropanolamine

5. Prolamine

6. Propagest

7. Triaminic Dm

2.2.2 Depositor-Supplied Synonyms

1. 154-41-6

2. 2-amino-1-phenylpropan-1-ol Hydrochloride

3. 2-amino-1-phenyl-1-propanol Hydrochloride

4. Dl-phenylpropanolamine Hydrochloride

5. Dl-norephedrine Hydrochloride

6. 3198-15-0

7. Norephedrine Hydrochloride

8. 40626-29-7

9. Prestwick_388

10. (+)-norephedrine Hydrochloride

11. Norephedrine Hcl

12. D-(+)-norephedrine Hydrochloride

13. 2-amino-1-phenylpropan-1-ol;hydrochloride

14. Phenylpropanolamine Chloride

15. Schembl4011782

16. Chembl1200695

17. Dtxsid6027185

18. Phenyl Propanolamine Hydrochloride

19. Akos027320395

20. Benzenemethanol, .alpha.-[(1s)-1-aminoethyl]-, Hydrochloride, (.alpha.r)-

21. 53631-70-2

22. Db-045612

23. Db-048135

24. Db-049620

25. P0742

26. Dl-erythro-2-amino-1-phenyl-1-propanol Hydrochloride

27. Benzenemethanol, .alpha.-[(1r)-1-aminoethyl]-, Hydrochloride (1:1), (.alpha.s)-rel-

2.3 Create Date

2005-03-27

3 Chemical and Physical Properties

Molecular Formula	C₉H₁₄ClNO
Molecular Weight	187.66 g/mol
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	2
Rotatable Bond Count	2
Exact Mass	187.0763918 g/mol
Monoisotopic Mass	187.0763918 g/mol
Topological Polar Surface Area	46.2 Å²
Heavy Atom Count	12
Formal Charge	0
Complexity	110
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	2
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	2

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.)

Nasal Decongestants

Drugs designed to treat inflammation of the nasal passages, generally the result of an infection (more often than not the common cold) or an allergy related condition, e.g., hay fever. The inflammation involves swelling of the mucous membrane that lines the nasal passages and results in inordinate mucus production. The primary class of nasal decongestants are vasoconstrictor agents. (From PharmAssist, The Family Guide to Health and Medicine, 1993) (See all compounds classified as Nasal Decongestants.)

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.)

Appetite Depressants

Agents that are used to suppress appetite. (See all compounds classified as Appetite Depressants.)