ContaminantDB: Doxylamine

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (3)XML

Record Information

Version

1.0

Creation Date

2014-08-30 21:03:25 UTC

Update Date

2016-11-09 01:09:09 UTC

Accession Number

CHEM003511

Identification

Common Name

Doxylamine

Class

Small Molecule

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]

Contaminant Sources

FooDB Chemicals
STOFF IDENT Compounds
T3DB toxins

Contaminant Type

Amine
Antiemetic
Drug
Ether
Food Toxin
Histamine H1 Antagonist
Organic Compound
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2-(alpha-(2-(Dimethylamino)ethoxy)-alpha-methylbenzyl)pyridine	ChEBI
2-Dimethylaminoethoxyphenylmethyl-2-picoline	ChEBI
Dossilamina	ChEBI
Doxilamina	ChEBI
Doxilminio	ChEBI
Doxylaminum	ChEBI
N,N-Dimethyl-2-(1-phenyl-1-(2-pyridinyl)ethoxy)ethanamine	ChEBI
Phenyl-2-pyridylmethyl-beta-N,N-dimethylaminoethyl ether	ChEBI
2-(a-(2-(Dimethylamino)ethoxy)-a-methylbenzyl)pyridine	Generator
2-(Α-(2-(dimethylamino)ethoxy)-α-methylbenzyl)pyridine	Generator
Phenyl-2-pyridylmethyl-b-N,N-dimethylaminoethyl ether	Generator
Phenyl-2-pyridylmethyl-β-N,N-dimethylaminoethyl ether	Generator
Doxylamine hydrogen succinate	HMDB
Alsadorm	HMDB
Decapryn	HMDB
Decapryn succinate	HMDB
Doxylamine succinate	HMDB
Doxylamine succinate (1:1)	HMDB
Mereprine	HMDB

Chemical Formula

C₁₇H₂₂N₂O

Average Molecular Mass

270.369 g/mol

Monoisotopic Mass

270.173 g/mol

CAS Registry Number

469-21-6

IUPAC Name

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

Traditional Name

doxylamine

SMILES

CN(C)CCOC(C)(C1=CC=CC=C1)C1=CC=CC=N1

InChI Identifier

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

InChI Key

HCFDWZZGGLSKEP-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as benzylethers. These are aromatic ethers with the general formula ROCR' (R = alkyl, aryl; R'=benzene).

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzylethers

Direct Parent

Benzylethers

Alternative Parents

Substituents

Benzylether
Pyridine
Heteroaromatic compound
Tertiary amine
Tertiary aliphatic amine
Azacycle
Organoheterocyclic compound
Ether
Dialkyl ether
Amine
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

tertiary amine (CHEBI:51380 )
pyridines (CHEBI:51380 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Biological Roles

Chemical Roles

Not Available

Physical Properties

State

Liquid

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	< 25 °C
Boiling Point	139 °C at 5.00E-01 mm Hg
Solubility	1 g/ml (succinate salt)

Predicted Properties

Property	Value	Source
Water Solubility	0.54 g/L	ALOGPS
logP	2.9	ALOGPS
logP	2.96	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Basic)	8.87	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	25.36 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	82.24 m³·mol⁻¹	ChemAxon
Polarizability	31.09 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a59-7900000000-24e4f3f90dbbb5862928	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0040-0956300000-af11cf85a674e7db3735	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-001i-0910000000-b3cb895f045d519f2bf3	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-00kb-5597500000-8495062a84b32e776f33	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-0292-0940000000-f369442eba5344b3ecb4	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-001i-1920000000-07b98b36c7ef5d9ad048	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-001i-0900000000-1ae1143763892a7aac22	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-001i-0900000000-460d58a5bb6a5eb5f55b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-0159-0900000000-34dc5c06413efae437da	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-014i-0900000000-8a5f15b863b7129c1288	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-014i-0900000000-072ffba5139b7324d27a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-00lr-0900000000-fdf3fc57eff19bfe8fd8	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-001i-0900000000-4bd3999ccd0a2246f1bf	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 15V, Positive	splash10-001i-1920000000-1fbd7581ebf1730dac6d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-0159-1900000000-37f4e915e528d2466b80	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 45V, Positive	splash10-001i-0900000000-a056c64c9344a9559905	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 60V, Positive	splash10-0159-0900000000-0ab3cbbe5a34cba77313	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 90V, Positive	splash10-014i-0900000000-1a3a34606ccd3aa3009c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 75V, Positive	splash10-014i-0900000000-07c546b389aa80244f62	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-1190000000-e7b1a3b0a0368fc310df	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00e9-5790000000-7402b4fd77afe325c64b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00di-9510000000-b9439d5014a66b7857ec	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-1290000000-1725573962a3041ca617	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014j-1690000000-44de19831bffecc1c412	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-009t-5900000000-caa39da176327be2a9c2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00kb-0960000000-a2cc3fcbeb38ca35de58	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0ab9-9200000000-5a71de62862f9881c2a1	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Readily absorbed via the gastrointestinal tract.

Mechanism of Toxicity

Like other antihistamines, doxylamine acts by competitively inhibiting histamine at H1 receptors. It also has substantial sedative and anticholinergic effects.

Metabolism

Hepatic. Half Life: 10 hours

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

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.

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Signs of overdose include wheezing, tightness in the chest, fever, itching, bad cough, blue skin color, fits, swelling of face, lips, tongue, or throat.

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

DB00366

HMDB ID

HMDB0001936

FooDB ID

FDB022751

Phenol Explorer ID