Diphenhydramine

Diphenhydramine
Clinical data
Pronunciation	/ˌdaɪfɛnˈhaɪdrəmiːn/
Trade names	Benadryl, Unisom, Nytol, others
AHFS/Drugs.com	Monograph
MedlinePlus	a682539
License data	US DailyMed: Diphenhydramine;
Pregnancy; category	AU: A;
Dependence; liability	Low–moderate
Routes of; administration	By mouth, intramuscular, intravenous, topical, rectal
Drug class	first-generation antihistamine (ethanolamine), anticholinergic, hallucinogen (deliriant)
ATC code	D04AA32 (WHO) D04AA33 (WHO), R06AA02 (WHO);
Legal status
Legal status	AU: S2 (Pharmacy medicine); CA: OTC; UK: P (Pharmacy medicines); US: OTC; UN: Unscheduled;
Pharmacokinetic data
Bioavailability	40–60%
Protein binding	98–99%
Metabolism	Liver (CYP2D6, others)
Elimination half-life	Range: 2.4–13.5 h
Excretion	Urine: 94%; Feces: 6%
Identifiers
	IUPAC name 2-(diphenylmethoxy)-N,N-dimethylethanamine;
CAS Number	58-73-1 ;
PubChem CID	3100;
IUPHAR/BPS	1224;
DrugBank	DB01075 ;
ChemSpider	2989 ;
UNII	8GTS82S83M;
KEGG	D00300 ;
ChEBI	CHEBI:4636 ;
ChEMBL	ChEMBL657 ;
CompTox Dashboard (EPA)	DTXSID4022949 ;
ECHA InfoCard	100.000.360
Chemical and physical data
Formula	C17H21NO
Molar mass	255.361 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O(CCN(C)C)C(c1ccccc1)c2ccccc2;
	InChI InChI=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 ; Key:ZZVUWRFHKOJYTH-UHFFFAOYSA-N ;
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Diphenhydramine (DPH) is an antihistamine and sedative mainly used to treat allergies, insomnia, and symptoms of the common cold. It is also less commonly used for tremors in parkinsonism, and nausea. It is taken by mouth, injected into a vein, injected into a muscle, or applied to the skin. Maximal effect is typically around two hours after a dose, and effects can last for up to seven hours.

Common side effects include sleepiness, poor coordination and an upset stomach. Its use is not recommended in young children or the elderly. There is no clear risk of harm when used during pregnancy; however, use during breastfeeding is not recommended. It is a first-generation H₁-antihistamine and it works by blocking certain effects of histamine, which produces its antihistamine and sedative effects. Diphenhydramine is also a potent anticholinergic, which means it also works as a deliriant at much higher than recommended doses as a result. Its sedative and deliriant effects have led to some cases of recreational use.

Diphenhydramine was first developed by George Rieveschl and came into commercial use in 1946. It is available as a generic medication. It is sold under the brand name Benadryl, among others. In 2021, it was the 242nd most commonly prescribed medication in the United States, with more than 1 million prescriptions.

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