Showing Compound Diphenhydramine (FDB022744)

Record Information

Version

1.0

Creation date

2011-09-21 00:18:57 UTC

Update date

2018-05-28 18:33:54 UTC

Primary ID

FDB022744

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Diphenhydramine

Description

A histamine H1 antagonist used as an antiemetic, antitussive, for dermatoses and pruritus, for hypersensitivity reactions, as a hypnotic, an antiparkinson, and as an ingredient in common cold preparations. It has some undesired antimuscarinic and sedative effects. -- Pubchem; Pseudoephedrine is a phenethylamine, and an isomer of ephedrine. Pseudoephedrine is the International Nonproprietary Name (INN) of the (1S,2S)- diastereomer of ephedrine (which has 1R,2S- configuration). Other names are (+)-pseudoephedrine and D-pseudoephedrine (Reynolds, 1989). The enantiomer (-)-(1R,2R)-Pseudoephedrine has fewer side-effects, fewer central nervous system (CNS) stimulatory effects, does not reduce to d-methamphetamine, yet retains its efficacy as a decongestant.[citation needed] However, the patent holder for (-)-Pseudoephedrine (Pfizer/Warner-Lambert) has not yet sought or received government approval for its sale to the public.(US Patent 6,495,529); Treatment for urinary incontinence is an unlabeled use for these medications. Unlabeled use means doctors can use the medication to treat a condition other than that for which it was first approved by the U.S. Food and Drug Administration (FDA). These medications are approved by the FDA for the treatment of nasal congestion caused by colds or allergies. However it has also been successful in treating stress incontinence by increasing the pressure (tension) exerted by the muscles of the bladder neck and the urethra, which helps retain the urine within the bladder.; Despite being one of the oldest antihistamines on the market, it is by and large the most effective antihistamine available, either by prescription or over-the-counter, and has been shown to exceed the effectiveness of even the latest prescription drugs. Consequently, it is frequently used when an allergic reaction requires fast, effective reversal of the (often dangerous) effects of a massive histamine release. However, it is not always the drug of choice for treating allergies. Like many other first generation antihistamines, is also a potent anticholinergic agent. This leads to profound drowsiness as a very common side-effect, along with the possibilities of motor impairment (ataxia), dry mouth and throat, flushed skin, rapid or irregular heartbeat (tachycardia), blurred vision at near point due to lack of accommodation (cycloplegia), abnormal sensitivity to bright light (photophobia), pupil dilatation, urinary retention, constipation, difficulty concentrating, short-term memory loss, visual disturbances, hallucinations, confusion, erectile dysfunction, and delirium. -- Wikipedia [HMDB]

CAS Number

147-24-0

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Show entries

Search:

Synonym	Source
2-(Benzhydryloxy)-N,N-dimethylethylamine	ChEBI
2-Diphenylmethoxy-N,N-demthylethanamine	ChEBI
2-Diphenylmethoxy-N,N-dimethylethylamine	HMDB
a-(2-Dimethylaminoethoxy)diphenylmethane	Generator
Alledryl	HMDB
Allerdryl	HMDB
Allergan	HMDB
Allergina	HMDB
alpha-(2-Dimethylaminoethoxy)diphenylmethane	ChEBI
b-Dimethylaminoethanol diphenylmethyl ether	Generator

Showing 1 to 10 of 46 entries

Predicted Properties

Property	Value	Source
Water Solubility	0.075 g/L	ALOGPS
logP	3.44	ALOGPS
logP	3.65	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Basic)	8.87	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	12.47 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	79.93 m³·mol⁻¹	ChemAxon
Polarizability	29.86 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

C17H21NO

IUPAC name

[2-(diphenylmethoxy)ethyl]dimethylamine

InChI Identifier

InChI=1S/C17H21NO/c1-18(2)13-14-19-17(15-9-5-3-6-10-15)16-11-7-4-8-12-16/h3-12,17H,13-14H2,1-2H3

InChI Key

ZZVUWRFHKOJYTH-UHFFFAOYSA-N

Isomeric SMILES

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

Average Molecular Weight

255.3547

Monoisotopic Molecular Weight

255.162314299

Classification

Description

Belongs to the class of organic compounds known as diphenylmethanes. Diphenylmethanes are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Diphenylmethanes

Direct Parent

Diphenylmethanes

Alternative Parents

Substituents

Diphenylmethane
Benzylether
Tertiary aliphatic amine
Tertiary amine
Ether
Dialkyl ether
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Amine
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

tertiary amino compound (CHEBI:4636 )
ether (CHEBI:4636 )
a small molecule (CPD-10890 )

Ontology

Physiological effect

Health effect:

Health condition:

Coma

Cardiac disorders:

Myocardial infarction

Ingestion

Biological location:

Subcellular:

Biofluid and excreta:

Blood

Role

Industrial application:

Drug

Pharmaceutical industry:

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Show entries

Search:

Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-0a4i-9200000000-b9014c8fc8ccbba24163	2014-09-20	View Spectrum
GC-MS	Diphenhydramine, non-derivatized, GC-MS Spectrum	splash10-0a4i-9100000000-7b9eb1f702c76f6b6062	Spectrum
GC-MS	Diphenhydramine, non-derivatized, GC-MS Spectrum	splash10-0a4i-9100000000-7b9eb1f702c76f6b6062	Spectrum
Predicted GC-MS	Diphenhydramine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-066r-6900000000-84b4a2c53eae448ca1bd	Spectrum
Predicted GC-MS	Diphenhydramine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Diphenhydramine, 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, N/A (Annotated)	splash10-0006-0090000000-a71e531b49571f09ab25	2012-07-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)	splash10-00kk-0980000000-cce91896f34562beeffa	2012-07-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)	splash10-001i-1900000000-4c29bd5e0eab94596eaa	2012-07-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (Unknown) , Positive	splash10-0a4i-9100000000-ab642e8f86de11af896c	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-000t-0910000000-3576ca5ec77ab87354ec	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-014i-0900000000-0ccd6de9ca58593fd490	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-014i-0900000000-3568aae4c27ffe333c0e	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-014i-0900000000-22e0c745355c836f1535	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-014i-0900000000-6bb69a66a343440c64f8	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-014i-0900000000-1b87d83415d22bb17f1b	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-0gb9-0900000000-50251362d768cd1b1c4f	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-0gb9-0900000000-9f37a733a05f5b01d313	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-014i-0900000000-7d73b95ed09ea2d72260	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-0gb9-2900000000-1666a8ab5a6d81c0bd01	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-014i-0900000000-3f31841d858381760f03	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-014i-0900000000-de872e048c7e12cef490	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-014i-0900000000-de872e048c7e12cef490	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - , positive	splash10-014i-0900000000-789a4a3fe118d5bf2456	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - , positive	splash10-014i-2900000000-8ef94659f614b9ff24ca	2017-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-1190000000-b33f7871c289d81b8648	2017-07-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0ab9-6690000000-814b7cb7faf094058c00	2017-07-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00xr-9500000000-98351e9c274a79fda2d0	2017-07-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-1290000000-3911d08f3498d2ef857f	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0ue9-4890000000-3d0fdfdee0fffe9f228f	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0059-9500000000-41b5f1e1a6122e43b285	2017-07-26	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