Norephedrine

Base Information

• Chemical Name: Norephedrine
• CAS No.: 14838-15-4
• Deprecated CAS: 753492-51-2,134-60-1,36393-57-4
• Molecular Formula: C9H13NO
• Molecular Weight: 151.208
• European Community (EC) Number: 238-900-2,211-850-9,628-077-1
• NSC Number: 9920
• UNII: 7875H6443P
• DSSTox Substance ID: DTXSID4023466,DTXSID301313960
• Nikkaji Number: J81.939E
• Wikipedia: Phenylpropanolamine
• Wikidata: Q413147
• NCI Thesaurus Code: C29364
• Metabolomics Workbench ID: 37947
• ChEMBL ID: CHEMBL2092846
• Mol file: 14838-15-4.mol

Synonyms:Dexatrim;Hydrochloride, Phenylpropanolamine;Norephedrine;Phenylpropanolamine;Phenylpropanolamine Hydrochloride;Prolamine;Propagest;Triaminic DM

 This product is a nationally controlled contraband, and the Lookchem platform doesn't provide relevant sales information.

Chemical Property of Norephedrine

Chemical Property:

• Melting Point: 101-101.5°
• Refractive Index: 1.5380 (estimate)
• Boiling Point: 288.143 °C at 760 mmHg
• PKA: pKa 9.19(H2O,t =25±0.5,I=0.01)(Approximate)
• Flash Point: 128.065 °C
• PSA: 46.25000
• Density: 1.072 g/cm³
• LogP: 1.76750
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 151.099714038
• Heavy Atom Count: 11
• Complexity: 110

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C(C1=CC=CC=C1)O)N
• Isomeric SMILES: C[C@H]([C@H](C1=CC=CC=C1)O)N
• Description: Phenylpropanolamine (PPA) is a mixed-acting sympathomimetic amine similar to ephedrine. Its primary mechanism of action is through direct a-adrenergic agonism, but there is also indirect stimulation of norepinephrine release. In November 2000, the US Food and Drug Administration (FDA) Nonprescription Drugs Advisory Committee determined that there is a significant association between PPA and hemorrhagic stroke and recommended that PPA not be considered safe for over-thecounter use. At this time, a letter was issued to manufacturers requesting voluntary removal of PPA from their products. Later, in 2005, the FDA published a Tentative Final Monograph for PPA-containing products proposing Category II status (not generally recognized as safe and effective). To date, no Final Monograph has been released; however, all manufacturers have removed PPA from their products.
• Uses: Norephedrine, also called Phenylpropanolamine (PPA), is a synthetic form of the ephedrine alkaloid. Used in treatment of urinary incontinence in dogs and cats; decongestant nasal. After reports of the occurrence of intracranial hemorrhage and other adverse effects, including several deaths, PPA is no longer sold in USA and Canada. The central nervous excitement PPA was used as a nasal decongestant and as an anorectic. Studies have shown benefit in humans for urinary incontinence, and PPA is still used in veterinary medicine for this purpose.

Technology Process of Norephedrine

There total 54 articles about Norephedrine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

(+/-)-cis-4-methyl-5-phenyloxazolidin-2-one (39663-75-7) → u-2-amino-1-phenylpropan-1-ol (14838-15-4,58550-13-3,757124-50-8)

Guidance literature:

With N-(2-Aminoethyl)aminomethyl polystyrene; In tetrahydrofuran; at 60 ℃;

DOI:10.1016/S0040-4039(01)02218-3

Reference yield: 59.0%

2-(hydroxyamino)-1-phenylpropan-1-one hydrochloride → u-2-amino-1-phenylpropan-1-ol (14838-15-4,58550-13-3,757124-50-8)

Guidance literature:

2-(hydroxyamino)-1-phenylpropan-1-one hydrochloride; With methanol; sodium tetrahydroborate; at 0 ℃; for 3h;

With hydrogenchloride; acetic acid; zinc; at 0 - 20 ℃; for 72h;

DOI:10.1039/d0gc04395h

Reference yield:

methyl magnesium iodide (917-64-6) → (1S,2R)-(+)-norphedrine (37577-28-9,58550-13-3,757124-50-8) + u-2-amino-1-phenylpropan-1-ol (14838-15-4,58550-13-3,757124-50-8)

Guidance literature:

With diethyl ether; anschliessend mit wss. Schwefelsaeure und Hydroxylamin dann mit Natrium-Amalgam und wss. Essigsaeure;

upstream raw materials:

(E)-2-(hydroxyimino)-1-phenylpropan-1-one

2-nitro-1-phenylpropan-1-ol

3-chloro-1-phenyl-propane-1,2-dione-2-oxime

3-hydroxy-1-phenyl-2-(2-phenylhydrazono)propan-1-one

Downstream raw materials:

(+/-)-N-methylephedrine

cis-4-methyl-5-phenyl-oxazolidine

(1RS,2SR)-2-amino-1-phenyl-propan-1-ol; formate

(1R,2S)-norephedrine

Refernces

• 1、 Corrado, Maria L.,Knaus, Tanja,Mutti, Francesco G.. "Regio- and stereoselective multi-enzymatic aminohydroxylation of β-methylstyrene using dioxygen, ammonia and formate". supporting information. p. 6246 - 6251. Retrieved 2019/12/03.
• 2、 Legnani, Luca,Morandi, Bill. "Direct catalytic synthesis of unprotected 2-amino-1-phenylethanols from alkenes by using iron(II) phthalocyanine". supporting information. p. 2248 - 2251. Retrieved 2016/02/18.