Diphenhydramine citrateProduct ingredient for Diphenhydramine

Name
Diphenhydramine citrate
Drug (Active Moiety)
Diphenhydramine

Diphenhydramine, also known commercially as Benadryl, is a first generation antihistamine that is used primarily for the treatment of seasonal allergies. However, it also has antiemetic, antitussive, hypnotic, and antiparkinson properties. 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. While its use in in allergies has largely fallen out of favour due to this sedative effect, diphenhydramine has been repurposed for use within many OTC (over the counter) cough-and-cold medications that have been marketed for "night time" use.

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
DBSALT001461
Structure
Thumb
Synonyms
Not Available
UNII
4OD433S209
CAS Number
88637-37-0
Weight
Average: 447.484
Monoisotopic: 447.189316898
Chemical Formula
C23H29NO8
InChI Key
SPCKHVPPRJWQRZ-UHFFFAOYSA-N
InChI
InChI=1S/C17H21NO.C6H8O7/c1-18(2)13-14-19-17(15-9-5-3-6-10-15)16-11-7-4-8-12-16;7-3(8)1-6(13,5(11)12)2-4(9)10/h3-12,17H,13-14H2,1-2H3;13H,1-2H2,(H,7,8)(H,9,10)(H,11,12)
IUPAC Name
2-hydroxypropane-1,2,3-tricarboxylic acid; [2-(diphenylmethoxy)ethyl]dimethylamine
SMILES
OC(=O)CC(O)(CC(O)=O)C(O)=O.CN(C)CCOC(C1=CC=CC=C1)C1=CC=CC=C1
External Links
ChemSpider
152357
ChEMBL
CHEMBL1201089
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 Count11ChemAxon
Refractivity79.93 m3·mol-1ChemAxon
Polarizability29.99 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon