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

HPLC Separation of Pyridoxine and Doxylamine on Primesep S Column

Condition

Column Primesep S, 4.6x150 mm, 5 µm, 100A
Mobile Phase MeCN/H2O
Buffer AmFm pH 3.0- 100 mM
Flow Rate 1.0 ml/min
Detection UV 270 nm,  MS- compatible mobile phase

Description

Class of Compounds Hydrophobic, Drug
Analyzing Compounds Pyridoxine,  Doxylamine


Application Analytes:

Doxylamine
Pyridoxine
Vitamin B6 (Pyridoxine)

HPLC Separation of Pyridoxine and Doxylamine on Obelisc R Column
HPLC Separation of Pyridoxine and Doxylamine on Obelisc R Column_1233

Condition

Column Obelisc R, 4.6x150 mm, 5 µm, 100A
Mobile Phase MeCN/H2O - 30/70%
Buffer AmAc pH 4.0. gradient from 10 to 60 mM in 6 min, 4 min hold
Flow Rate 1.0 ml/min
Detection UV 270 nm,  MS- compatible mobile phase

Description

Class of Compounds Hydrophobic, Drug
Analyzing Compounds Pyridoxine,  Doxylamine


Application Analytes:

Doxylamine
Pyridoxine

HPLC Separation of NyQuil Active Ingredients on Primesep AP Column
Separation type: Liquid Chromatography HILIC

HPLC.cloud View on hplc.cloud



High Performance Liquid Chromatography (HPLC) Method for Analysis of Acetaminophen, Dextromethorphan, Pseudoephedrine, Doxylamine
Nyquil is a combination of medicines used to treat headaches, fever, body aches, cough, runny nose, sneezing, and sore throat caused by allergies, the common cold, or the flu. Nyquil contains the active ingredients acetaminophen, dextromethorphan HBr, doxylamine succinate, and sometimes, phenylephrine HCl. Acetaminophen is a pain reliever and fever reducer. Dextromethorphan is a cough suppressant. It affects the cough reflex in the brain that triggers coughing. Doxylamine is an antihistamine that reduces the effects of the natural chemical histamine in the body. Histamine can produce symptoms of sneezing, itching, watery eyes, and runny nose. Pseudoephedrine is used to relieve nasal congestion caused by colds, allergies, and hay fever. It is also used to temporarily relieve sinus congestion and pressure. All active compounds of Nyquil can be separated in HPLC on a Primesep AP mixed-mode column. The analytical method uses acetonitrile (ACN) gradient and water with sulfuric acid (H2SO4) as buffer and UV detected at 210 nm.
 

Condition

Column Primesep AP, 4.6x150 mm, 5 µm, 100A
Mobile Phase Gradient MeCN - 90-60%, 10 min
Buffer H2SO4 - 0.4%
Flow Rate 1.0 ml/min
Detection UV, 210 nm
 

Description

Class of Compounds Drug, Basic, Hydrophobic, Ionizable
Analyzing Compounds Acetaminophen, Dextromethorphan, Pseudoephedrine, Doxylamine
 

Application Analytes:

Acetaminophen (Paracetamol)
Dextromethorphan
Dextromethorphan hydrobromide
Doxylamine
Pseudoephedrine (PSE)