Compound Summary

General Compound Information

Diphenhydramine

Description
Diphenhydramine is an ether that is the benzhydryl ether of 2-(dimethylamino)ethanol. It is a H1-receptor antagonist used as a antipruritic and antitussive drug. It has a role as a H1-receptor antagonist, an antiemetic, a sedative, an anti-allergic agent, a muscarinic antagonist, an antiparkinson drug, an antipruritic drug, a local anaesthetic, an antidyskinesia agent, an antitussive and a oneirogen. It is an ether and a tertiary amino compound.
Synonyms
diphenhydramine;  58-73-1;  Benadryl;  2-(Benzhydryloxy)-N,N-dimethylethanamine;  Benzhydramine;
FlavorDB ID
20
PUBCHEM ID
Molecular Weight
255.35
Molecular Formula
C17H21NO
Openeye Can Smiles
CN(C)CCOC(C1=CC=CC=C1)C2=CC=CC=C2
IUPAC Inchikey
ZZVUWRFHKOJYTH-UHFFFAOYSA-N
Compound Classification
  • ClassyFire Ontology
Compound Quality
Quality information of this compound is not available!
Compound Toxicity and Food Additive Safety (OFAS)
Toxicity Summary
Link to the Distributed Structure-Searchable Toxicity (DSSTox) Database
Overdose is expected to result in effects similar to the adverse effects that are ordinarily associated with the use of diphenhydramine, including drowsiness, hyperpyrexia, and anticholinergic effects, among others [L5266, L5269, L5281, L5287, F3394]. Additional symptoms during overdose may include mydriasis, fever, flushing, agitation, tremor, dystonic reactions, hallucinations and ECG changes [L5287]. Large overdose may cause rhabdomyolysis, convulsions, delirium, toxic psychosis, arrhythmias, coma and cardiovascular collapse [L5287]. Moreover, with higher doses, and particularly in children, symptoms of CNS excitation including hallucinations and convulsions may appear; with massive doses, coma or cardiovascular collapse may follow [F3394]. Although diphenhydramine has been in widespread use for many years without ill consequence, it is known to cross the placenta and has been detected in breast milk [F3394]. This medication should therefore only be used when the potential benefit of treatment to the mother exceeds any possible hazards to the developing fetus or suckling infant [F3394]. Pharmacokinetic studies indicate no major differences in the distribution or elimination of diphenhydramine compared to younger adults [F3394]. Nevertheless, diphenhydramine should be used with caution in the elderly, who are more likely to experience adverse effects [L5287]. Avoid use in elderly patients with confusion [L5287]. The results of a review on the use of diphenhydramine in renal failure suggest that in moderate to severe renal failure, the dose interval should be extended by a period dependent on Glomerular filtration rate (GFR) [F3394]. After intravenous administration of 0.8 mg/kg diphenhydramine, a prolonged half-life was noted in patients with chronic liver disease which correlated with the severity of the disease [F3394]. However, the mean plasma clearance and apparent volume of distribution were not significantly affected [F3394]. LD50=500 mg/kg (orally in rats). Considerable overdosage can lead to myocardial infarction (heart attack), serious ventricular dysrhythmias, coma and death.
Source: DrugBank or Hazardous Substances Data Bank (HSDB)
Receptors
Receptor REFERENCE EC50 [µM] Effective Concentration [µM]
TAS2R14 details Activated
TAS2R40 details Activated
Consensus Spectra
Spectrum Type Spectrum View Description Polarity
Experimental GCMS view GCMS positive
Experimental LCMS view LCMS_Positive positive