Chemical Component Summary

NameN-[2-(BENZHYDRYLOXY)ETHYL]-N,N-DIMETHYLAMINE
SynonymsDIPHENHYDRAMINE; ANTISTOMINUM; BENZHYDRAMINE
Identifiers2-benzhydryloxy-N,N-dimethyl-ethanamine
FormulaC17 H21 N O
Molecular Weight255.355
TypeNON-POLYMER
Isomeric SMILESCN(C)CCOC(c1ccccc1)c2ccccc2
InChIInChI=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
InChIKeyZZVUWRFHKOJYTH-UHFFFAOYSA-N

Chemical Details

Formal Charge0
Atom Count40
Chiral Atom Count0
Bond Count41
Aromatic Bond Count12

Drug Info: DrugBank

DrugBank IDDB01075 
NameDiphenhydramine
Groups
  • investigational
  • approved
DescriptionDiphenhydramine - 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 [L5263, L5266, L5269, F3379]. However, it also has antiemetic, antitussive, hypnotic, and antiparkinson properties [L5269, F3352]. 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 [L5263, L5266, L5269, F3379, A174541]. 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 [L5263, L5281, L5287]. Diphenhydramine is also used in combination with [DB14132] as the anti-nausea drug [DB00985] where it is utilized primarily for its antagonism of H1 histamine receptors within the vestibular system [A1540]. Diphenhydramine has also been shown to be implicated in a number of neurotransmitter systems that affect behaviour including dopamine, norepinephrine, serotonin, acetylcholine, and opioid [A1539]. As a result, diphenhydramine is being investigated for its anxiolytic and anti-depressant properties.
Synonyms
  • 2-(benzhydryloxy)-N,N-dimethylethylamine
  • Diphenhydramine methylbromide
  • Diphenhydramine
  • β-dimethylaminoethyl benzhydryl ether
  • N-(2-(diphenylmethoxy)ethyl)-N,N-dimethylamine
Brand Names
  • AuroFlu Night Time Severe Cold and Cough Warming Relief
  • CounterAct PM
  • Night Time Severe Cold and Cough
  • Topcare Pain Relief PM Extra Strength
  • The Itch Eraser
IndicationDiphenhydramine is a first-generation histamine H1 receptor antagonist (H1 antihistamine) that is widely available as a non-prescription, over-the-counter (OTC) medication. As an OTC medication, diphenhydramine is typically formulated as tablets and creams indicated for use in treating sneezing, runny nose, itchy/watery eyes, itching of nose or throat, insomnia, pruritis, urticaria, insect bites/stings, allergic rashes, and nausea [L5263, L5266, L5269, F3379, A174541]. Additionally, when the use of oral diphenhydramine is impractical, there are also prescription-only formulations such as diphenhydramine injection products that are effective in adults and pediatric patients (other than premature infants and neonates) for: i) the amelioration of allergic reactions to blood or plasma, in anaphylaxis as an adjunct to epinephrine and other standard measures after acute allergic reaction symptoms have been controlled, and for other uncomplicated allergic conditions of the immediate type when oral therapy is impossible or contraindicated [F3352]; ii) the active treatment of motion sickness [F3352]; and iii) use in parkinsonism when oral therapy is impossible or contraindicated, as follows: parkinsonism in the elderly who are unable to tolerate more potent agents; mild cases of parkinsonism in other age groups, and in other cases of parkinsonism in combination with centrally acting anticholinergic agents [F3352].
Categories
  • Agents producing tachycardia
  • Amines
  • Aminoalkyl Ethers
  • Anesthetics
  • Anesthetics, Local
ATC-Code
  • D04AA32
  • R06AA02
  • D04AA33
  • R06AA52
CAS number58-73-1

Drug Targets

NameTarget SequencePharmacological ActionActions
Histamine H1 receptorMSLPNSSCLLEDKMCEGNKTTMASPQLMPLVVVLSTICLVTVGLNLLVLY...unknownantagonist
Muscarinic acetylcholine receptor M2MNNSTNSSNNSLALTSPYKTFEVVFIVLVAGSLSLVTIIGNILVMVSIKV...unknownantagonist
Prostaglandin G/H synthase 1MSRSLLLWFLLFLLLLPPLPVLLADPGAPTPVNPCCYYPCQHQGICVRFG...unknownsubstrate
Cytochrome P450 2D6MGLEALVPLAVIVAIFLLLVDLMHRRQRWAARYPPGPLPLPGLGNLLHVD...unknownsubstrate,inhibitor
Cytochrome P450 2C9MDSLVVLVLCLSCLLLLSLWRQSSGRGKLPPGPTPLPVIGNILQIGIKDI...unknownsubstrate
View More
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
Pharos CHEMBL657
PubChem 3100
ChEMBL CHEMBL657
ChEBI CHEBI:4636
CCDC/CSD FIMTAW, JEMJOA01