Diphenhydramine hydrochlorideProduct ingredient for Diphenhydramine

Name
Diphenhydramine hydrochloride
Drug Entry
Diphenhydramine

Diphenhydramine - perhaps known most commonly as its brand name formulation Benadryl - is a first-generation H1 receptor antihistamine that is used extensively for the treatment of seasonal allergies, insect bites and stings, and rashes 9,10,11,17. However, it also has antiemetic, antitussive, hypnotic, and antiparkinson properties 11,16. As histamine receptors exist both peripherally and in the central nervous system, diphenhydramine has been shown to cause sedation due to its competitive antagonism of histamine H1 receptors within the central nervous system 9,10,11,17,5. While its use in allergy therapy can sometimes fall out of favor due to its sedative effect, diphenhydramine has been repurposed for use within many non-prescription over-the-counter sleep aids and cough-and-cold medications that have been marketed for "night time" use 9,12,13.

Diphenhydramine is also used in combination with 8-chlorotheophylline as the anti-nausea drug Dimenhydrinate where it is utilized primarily for its antagonism of H1 histamine receptors within the vestibular system 4.

Diphenhydramine has also been shown to be implicated in a number of neurotransmitter systems that affect behaviour including dopamine, norepinephrine, serotonin, acetylcholine, and opioid 3. As a result, diphenhydramine is being investigated for its anxiolytic and anti-depressant properties.

Accession Number
DBSALT000056
Structure
Synonyms
Diphenhydramine HCl
UNII
TC2D6JAD40
CAS Number
147-24-0
Weight
Average: 291.816
Monoisotopic: 291.138992038
Chemical Formula
C17H22ClNO
InChI Key
PCHPORCSPXIHLZ-UHFFFAOYSA-N
InChI
InChI=1S/C17H21NO.ClH/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;1H
IUPAC Name
[2-(diphenylmethoxy)ethyl]dimethylamine hydrochloride
SMILES
Cl.CN(C)CCOC(C1=CC=CC=C1)C1=CC=CC=C1
KEGG Compound
C07784
PubChem Compound
8980
ChemSpider
8632
ChEBI
4637
ChEMBL
CHEMBL1620
Wikipedia
Diphenhydramine
Predicted Properties
PropertyValueSource
Water Solubility0.0752 mg/mLALOGPS
logP3.44ALOGPS
logP3.65Chemaxon
logS-3.5ALOGPS
pKa (Strongest Basic)8.87Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count2Chemaxon
Hydrogen Donor Count0Chemaxon
Polar Surface Area12.47 Å2Chemaxon
Rotatable Bond Count6Chemaxon
Refractivity79.93 m3·mol-1Chemaxon
Polarizability29.88 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleYesChemaxon
MDDR-like RuleNoChemaxon