Diphenhydramine salicylateProduct ingredient for Diphenhydramine

Name
Diphenhydramine salicylate
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
DBSALT000057
Structure
Thumb
Synonyms
Not Available
UNII
707L3YC54L
CAS Number
7491-10-3
Weight
Average: 393.4755
Monoisotopic: 393.194008357
Chemical Formula
C24H27NO4
InChI Key
RTSZUSOHOIFYSY-UHFFFAOYSA-N
InChI
InChI=1S/C17H21NO.C7H6O3/c1-18(2)13-14-19-17(15-9-5-3-6-10-15)16-11-7-4-8-12-16;8-6-4-2-1-3-5(6)7(9)10/h3-12,17H,13-14H2,1-2H3;1-4,8H,(H,9,10)
IUPAC Name
2-hydroxybenzoic acid; [2-(diphenylmethoxy)ethyl]dimethylamine
SMILES
OC(=O)C1=CC=CC=C1O.CN(C)CCOC(C1=CC=CC=C1)C1=CC=CC=C1
External Links
KEGG Compound
C14015
PubChem Compound
24098
ChemSpider
22528
ChEBI
34720
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 Count7ChemAxon
Refractivity79.93 m3·mol-1ChemAxon
Polarizability29.88 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon