Doxylamine

CAS Number 469-21-6
Molecular Formula C17H22N2O
Molecular Weight 270.377 g/mol
InChI Key HCFDWZZGGLSKEP-UHFFFAOYSA-N
LogP 2.50
Synonyms
  • Doxylamine
  • N,N-Dimethyl-2-[1-phenyl-1-(pyridin-2-yl)ethoxy]ethan-1-amine
  • Ethanamine, N,N-dimethyl-2-[1-phenyl-1-(2-pyridinyl)ethoxy]-
  • 469-21-6
  • 5-21-03-00508
  • Ethanamine, N,N-dimethyl-2-[1-phenyl-1-(2-pyridinyl)ethoxy]-
  • (.+-.)-Doxylamine
  • 2-[α-[2-(Dimethylamino)ethoxy]-α-methylbenzyl]pyridine
  • Donormil
  • doxilminio
  • Doxylamin
  • Pyridine, 2-[α-[2-(dimethylamino)ethoxy]-α-methylbenzyl]-
  • BRN 0230379
  • 2-(alpha-(2-(Dimethylamino)ethoxy)-alpha-methylbenzyl)pyridine
  • EINECS 207-414-2
  • NCI C60684
  • Phenyl-2-pyridylmethyl-beta-N,N-dimethylaminoethyl ether
  • Pyridine, 2-(alpha-(2-(dimethylamino)ethoxy)-alpha-methylbenzyl)-
  • Doxylaminum
  • UNII-95QB77JKPL
  • 2-Dimethylaminoethoxyphenylmethyl-2-picoline
  • Dossilamina
  • N,N-Dimethyl-2-(1-phenyl-1-(2-pyridinyl)ethoxy)ethanamine
  • Phenyl-2-pyridylmethyl-beta-N,N-dimethylaminoethyl ether

Applications:


Separation of NyQuil Active Ingredients on Primesep C
Primesep C separates the active ingredients in the over-the-counter cold medicine, NyQuil. Succinate and bromate co-elute early, but acetaminophen, pseudoephedrine, doxylamine, and dextromethorphan are baseline resolved. A combination of cation exchange, complex formation, and hydrophobic interactions separate this mixture with a mobile phase of water, acetonitrile (MeCN, ACN) and triethylamine (TEA) phosphate with UV detection at 205 nm.

Condition

Column Primesep C, 4.6x150 mm, 5 µm, 100A
Mobile Phase MeCN
Buffer TEAPh
Flow Rate 1.0 ml/min
Detection UV, 205 nm
   

Description

Class of Compounds Drug, Analgetic, Acid, Hydrophilic, Ionizable,
Analyzing Compounds Acetaminophen, Pseudoephedrine, Doxylamine, Dextromethorphan


Application Analytes:

Acetaminophen (Paracetamol)
Dextromethorphan
Doxylamine
Pseudoephedrine (PSE)

HPLC Separation of NyQuil Active Ingredients
NyQuil is a cough medication produced by Procter&Gamble. It consists of acetaminophen, pseudoephedrine, doxylamine and dextromethorphan. Most of the analytical HPLC methods include either use of ion-pairing reagent or a gradient elution. Mixed-mode chromatography allows to replace long gradient method with short isocratic method. All four compounds are well separated within 3-5 minutes. Methods can be optimized for analysis of other cough composition containing general cough suppressants and pain killers. Method is robust and being validated at several drug companies.

Condition

Column Primesep C, 4.6x50 mm, 5 µm, 100A
Mobile Phase MeCN
Buffer TEAPh
Flow Rate 1.0 ml/min
Detection UV, 210 nm
   

Description

Class of Compounds Drug, Analgetic, Acid, Hydrophilic, Ionizable,
Analyzing Compounds Acetaminophen, Pseudoephedrine, Doxylamine, Dextromethorphan


Application Analytes:

Acetaminophen (Paracetamol)
Dextromethorphan
Doxylamine
Pseudoephedrine (PSE)

HPLC Separation of Drugs
Mixed-mode chromatography allows to separate various hydrophobic and hydrophilic drugs in one HPLC method. Presence of at least two mechanism of retention allows adjust selectivity of separation by changing three parameters: amount of acetonitrile, buffer concentration and buffer pH. Seven common drugs are separated on a Primesep C trimodal HPLC column in gradient method. Method provides alternative selectivity to traditional reversed-phase chromatography. Operational range in which basic compounds are retained the most is from pH 3 to 5. At higher pH, longer retention can be achieved. Mixed-mode chromatography provides longer retention and better peak shapes for basic and acidic analytes. Method can be used in analysis of drugs and pharmaceuticals.

Condition

Column Primesep C, 4.6x150 mm, 5 µm, 100A
Mobile Phase MeCN
Buffer Formic Acid
Flow Rate 1.0 ml/min
Detection UV, 250 nm
   

Description

Class of Compounds Drug, Analgetic, Acid, Hydrophilic, Ionizable,
Analyzing Compounds Norphenylephrine, Norephedrine, Pseudoephedrine, Doxylamine, Pyrilamine, Dextromethorphan, Trimipramine


Application Analytes:

Dextromethorphan
Doxylamine
Norephedrine
Norphenylephrine
Pseudoephedrine (PSE)
Pyrilamine

Comparison of the Separation of Polar Drugs on Obelisc R and Zorbax SB-AQ


Common hydrophobic basic and hydrophilic basic drugs are separated by mixed-mode chromatography with greater selectivity and resolution than traditional reversed-phase column. Drugs are retained by combination of reversed-phase and cation-exchange mechanisms. Retention time is controlled by amount of acetonitrile, buffer concentration and buffer pH. Available detection techniques are based on buffer selection and include UV, Evaporative Light-Scattering Detector (ELSD), Corona (CAD), LC/MS, etc. This HPLC method can be adopted as general approach for analysis of drugs and pharmaceuticals.



Application Analytes:


Dextromethorphan
Doxylamine
Norephedrine
Norphenylephrine
Pseudoephedrine (PSE)
Pyrilamine