Showing Compound Doxylamine (FDB022751)

Record Information

Version

1.0

Creation date

2011-09-21 00:19:03 UTC

Update date

2018-05-28 18:33:55 UTC

Primary ID

FDB022751

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Doxylamine

Description

Doxylamine is a sedating antihistamine that can be used by itself as a short-term sleep aid, in combination with other drugs as a night-time cold and allergy relief. It is a member of the ethanolamine class of antihistamines and has anti-allergy power superior to almost every other antihistamine on the market, with the exception of diphenhydramine (Benadryl). It is also the most effective over-the-counter sedative available in North America, and more sedating than some prescription hypnotics. In a study, it was found that doxylamine succinate is possibly more effective than the barbiturate, phenobarbital for use as a sedative. For this reason, doxylamine has sometimes been used off label in a manner similar to diphenhydramine for the reduction of anxiety symptoms; Doxylamine succinate is used by itself as a short-term sleep aid, in combination with other drugs as a night-time cold and allergy relief drug, and a preparation is prescribed in combination with Vitamin B6 (pyridoxine) to prevent morning sickness in pregnant women. In Commonwealth countries, doxylamine is available prepared with paracetamol/acetaminophen and codeine under the brand name Syndol or Mersyndol, as treatment for tension headache and other types of pain, or as a general OTC sleep-aid branded as Somnil, Donormyl, DSozile and Restavit containing Doxylamine Succinate only. [HMDB]

CAS Number

562-10-7

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	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
2-(a-(2-(dimethylamino)Ethoxy)-a-methylbenzyl)pyridine	Generator
2-(alpha-(2-(dimethylamino)Ethoxy)-alpha-methylbenzyl)pyridine	ChEBI
2-(α-(2-(dimethylamino)ethoxy)-α-methylbenzyl)pyridine	Generator
Decapryn (TN)	hmdb

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	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C17H22N2O

IUPAC name

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

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

Isomeric SMILES

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

Average Molecular Weight

270.3694

Monoisotopic Molecular Weight

270.173213336

Classification

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 )

Ontology

Industrial application:

Drug

Pharmaceutical industry:

Pharmaceutical

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-0ab9-9200000000-5a71de62862f9881c2a1	2014-09-20	View Spectrum
Predicted GC-MS	Doxylamine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0a59-7900000000-24e4f3f90dbbb5862928	Spectrum
Predicted GC-MS	Doxylamine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0040-0956300000-af11cf85a674e7db3735	2012-07-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-001i-0910000000-b3cb895f045d519f2bf3	2012-07-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-00kb-5597500000-8495062a84b32e776f33	2012-07-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-0292-0940000000-f369442eba5344b3ecb4	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-001i-1920000000-07b98b36c7ef5d9ad048	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-001i-0900000000-1ae1143763892a7aac22	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-001i-0900000000-460d58a5bb6a5eb5f55b	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-0159-0900000000-34dc5c06413efae437da	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-014i-0900000000-8a5f15b863b7129c1288	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-014i-0900000000-072ffba5139b7324d27a	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - , positive	splash10-00lr-0900000000-fdf3fc57eff19bfe8fd8	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-001i-0900000000-4bd3999ccd0a2246f1bf	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 15V, Positive	splash10-001i-1920000000-1fbd7581ebf1730dac6d	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-0159-1900000000-37f4e915e528d2466b80	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 45V, Positive	splash10-001i-0900000000-a056c64c9344a9559905	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 60V, Positive	splash10-0159-0900000000-0ab3cbbe5a34cba77313	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 90V, Positive	splash10-014i-0900000000-1a3a34606ccd3aa3009c	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 75V, Positive	splash10-014i-0900000000-07c546b389aa80244f62	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-1190000000-e7b1a3b0a0368fc310df	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00e9-5790000000-7402b4fd77afe325c64b	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00di-9510000000-b9439d5014a66b7857ec	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-1290000000-1725573962a3041ca617	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014j-1690000000-44de19831bffecc1c412	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-009t-5900000000-caa39da176327be2a9c2	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00kb-0960000000-a2cc3fcbeb38ca35de58	2021-09-22	View Spectrum

NMR

Type	Description		View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)		Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)		Spectrum