dimethyl({2-[1-phenyl-1-(pyridin-2-yl)ethoxy]ethyl})amine

• ChemBase ID: 250
• Molecular Formular: C17H22N2O
• Molecular Mass: 270.36938
• Monoisotopic Mass: 270.17321333
• SMILES: O(C(c1ccccc1)(c1ncccc1)C)CCN(C)C
• Canonical SMILES: CN(CCOC(c1ccccn1)(c1ccccc1)C)C
• InChI: InChI=1S/C17H22N2O/c1-17(20-14-13-19(2)3,15-9-5-4-6-10-15)16-11-7-8-12-18-16/h4-12H,13-14H2,1-3H3
• InChIKey: HCFDWZZGGLSKEP-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: dimethyl({2-[1-phenyl-1-(pyridin-2-yl)ethoxy]ethyl})amine
• IUPAC Traditional name: doxylamine
• Brand Name: Unisom
• Synonyms: Dossilamina [DCIT]; Doxilminio [INN-Spanish]; Doxylaminum [INN-Latin]; Doxylamine

Database IDs

• CAS Number: 469-21-6
• PubChem SID: 160963713; 46506354
• PubChem CID: 3162
• CHEBI ID: 51380
• ATC CODE: R06AA09
• CHEMBL: 1004
• Chemspider ID: 3050
• DrugBank ID: DB00366
• KEGG ID: D07878
• Unique Ingredient Identifier: 95QB77JKPL
• Wikipedia Title: Doxylamine
• Medline Plus: a682537

CALCULATED PROPERTIES

JChem

• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): -0.16813163
• LogD (pH = 7.4): 1.4848965
• Log P: 2.9619422
• Molar Refractivity: 82.2373 cm^3
• Polarizability: 32.315342 Å^3
• Polar Surface Area: 25.36 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.9
• LOG S: -2.7
• Solubility (Water): 5.41e-01 g/l

PROPERTIES

Physical Property

• Solubility: 1 g/ml (succinate salt)
• Hydrophobicity(logP): 2.5

Pharmacology Properties

• Admin Routes: Oral
• Bioavailability: Oral: 24.7%, Intranasal: 70.8%
• Excretion: Urine; 60% unchanged doxylamine
• Half Life: variable; 6–12 hours
• Metabolism: Hepatic
• Legal Status: OTC
• Pregnancy Category: Briggs' "A" (Compatible)

DETAILS

DrugBank - DB00366

• Drug Groups: approved
• Description: Histamine H1 antagonist with pronounced sedative properties. It is used in allergies and as an antitussive, antiemetic, and hypnotic. Doxylamine has also been administered in veterinary applications and was formerly used in parkinsonism. [PubChem]
• Indication: Used alone as a short-term sleep aid, in combination with other drugs as a night-time cold and allergy relief drug. Also used in combination with Vitamin B6 (pyridoxine) to prevent morning sickness in pregnant women.
• Pharmacology: Doxylamine is an antihistamine commonly used as a sleep aid. This drug is also used to relieve symptoms of hay fever (allergic rhinitis), hives (rash or itching), and other allergic reactions. Doxylamine is a member of the ethanolamine class of antihistamines and has anti-allergy power far superior to virtually every other antihistamine on the market, with the exception of diphenhydramine (Benadryl). It is also the most powerful over-the-counter sedative available in the United States, and more sedating than many prescription hypnotics. In a study, it was found to be superior to even the barbiturate, phenobarbital for use as a sedative. Doxylamine is also a potent anticholinergic.
• Toxicity: Signs of overdose include wheezing, tightness in the chest, fever, itching, bad cough, blue skin color, fits, swelling of face, lips, tongue, or throat.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic.
• Absorption: Readily absorbed via the gastrointestinal tract.
• Half Life: 10 hours
• External Links: Wikipedia; Drugs.com