[2-(diphenylmethoxy)ethyl]dimethylamine

• ChemBase ID: 946
• Molecular Formular: C17H21NO
• Molecular Mass: 255.35474
• Monoisotopic Mass: 255.1623143
• SMILES: O(C(c1ccccc1)c1ccccc1)CCN(C)C
• Canonical SMILES: CN(CCOC(c1ccccc1)c1ccccc1)C
• 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
• InChIKey: ZZVUWRFHKOJYTH-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [2-(diphenylmethoxy)ethyl]dimethylamine
• IUPAC Traditional name: diphenhydramine
• Brand Name: Aleryl; Alledryl; Aller-Med; Allerdryl; Allergan B; Allergeval; Allergical; Allergin; Allergina; Allergival; Allermax Caplets; Ambodryl; Amidryl; Antistominum; Antitussive; Antomin; Automin; Bagodryl; Banophen; Banophen Caplets; Baramine; Beldin; Belix; Ben-Allergin; Bena; Benachlor; Benadrin; Benadryl; Benadryl Allergy; Benadryl Preservative Free; Benapon; Benodin; Benodine; Benylan; Benylin; Benzantine; Benzhydramine; Benzhydraminum; Benzhydril; Benzhydroamina; Benzhydryl; Betramin; Compoz; Dabylen; Debendrin; Dermistina; Dermodrin; Desentol; Diabenyl; Diabylen; Dibendrin; Dibenil; Dibondrin; Difedryl; Difenhydramin; Difenidramina; Dihidral; Dimedrol; Dimedryl; Diphantine; Diphen; Diphen Cough; Diphenhist; Diphenhist Captabs; Dormarex 2; Dryistan; Drylistan; Dylamon; Etanautine; Genahist; Histaxin; Hyadrine; Hydramine; Hyrexin; Ibiodral; Medidryl; Mephadryl; Nausen; Nervine Nighttime Sleep-Aid; Novamina; Nytol Quickcaps; Nytol Quickgels; Probedryl; Restamin; Rigidil; Rigidyl; Siladryl; Silphen; Sleep-Eze D; Sleep-Eze D Extra Strength; Sominex; Soverin; Syntedril; Syntodril; Torinal; Twilite Caplets; Unisom Sleepgels Maximum Strength; Vena; Vicks Formula 44; Benadryl, Unisom, Sominex
• Synonyms: Diphenhydramine Base; Diphenhydramine Hcl; Diphenhydramine Salicylate; Diphenylhydramine; Diphenhydramine; N-[2-(BENZHYDRYLOXY)ETHYL]-N,N-DIMETHYLAMINE; BENADRYL HYDROCHLORIDE

Database IDs

• CAS Number: 147-24-0; 58-73-1
• PubChem SID: 46505484; 160964409
• PubChem CID: 3100
• CHEBI ID: 4636
• ATC CODE: D04AA32; D04AA33; R06AA02
• CHEMBL: 657
• Chemspider ID: 2989
• DrugBank ID: DB01075
• IUPHAR ligand ID: 1224
• KEGG ID: D00669
• Unique Ingredient Identifier: 8GTS82S83M
• Wikipedia Title: Diphenhydramine
• Medline Plus: a682539

CALCULATED PROPERTIES

JChem

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 0.52368176
• LogD (pH = 7.4): 2.174247
• Log P: 3.6519072
• Molar Refractivity: 79.927 cm^3
• Polarizability: 31.40543 Å^3
• Polar Surface Area: 12.47 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 3.44
• LOG S: -3.53
• Solubility (Water): 7.52e-02 g/l

PROPERTIES

Physical Property

• Solubility: 3.06 mg/mL at 37 oC [BEILSTEIN]
• Hydrophobicity(logP): 3.27 [HANSCH,C ET AL. (1995)]

Pharmacology Properties

• Admin Routes: Oral, parenteral (IM), parenteral (IV), topical, suppository
• Bioavailability: 40-60%
• Excretion: 94% through the urine, 6% through feces
• Half Life: 8 hours (children); 9 to 12 hours (adults); 17 hours (elderly)
• Metabolism: Various cytochrome P450 liver enzymes: CYP2D6 (80%), 3A4 (10%)
• Protein Bound: 98-99%
• Legal Status: Over the counter
• Pregnancy Category: A (Australia); B (US)

DETAILS

MP Biomedicals - 05213472

MP Biomedicals Rare Chemical collection

DrugBank - DB01075

• Drug Groups: approved
• Description: A histamine H1 antagonist used as an antiemetic, antitussive, for dermatoses and pruritus, for hypersensitivity reactions, as a hypnotic, an antiparkinson, and as an ingredient in common cold preparations. It has some undesired antimuscarinic and sedative effects.
• Indication: For the treatment of symptoms associated with Vertigo/Meniere's disease, nausea and vomiting, motion sickness and insect bite.
• Pharmacology: Diphenhydramine is an antihistamine of the ethanolamine class. Ethanolamine antihistamines have significant antimuscarinic activity and produce marked sedation in most patients. In addition to the usual allergic symptoms, the drug also treats irritant cough and nausea, vomiting, and vertigo associated with motion sickness. It also is used commonly to treat drug-induced extrapyramidal symptoms as well as to treat mild cases of Parkinson's disease. Rather than preventing the release of histamine, as do cromolyn and nedocromil, diphenhydramine competes with free histamine for binding at HA-receptor sites. Diphenhydramine competitively antagonizes the effects of histamine on HA-receptors in the GI tract, uterus, large blood vessels, and bronchial muscle. Ethanolamine derivatives have greater anticholinergic activity than do other antihistamines, which probably accounts for the antidyskinetic action of diphenhydramine. This anticholinergic action appears to be due to a central antimuscarinic effect, which also may be responsible for its antiemetic effects, although the exact mechanism is unknown.
• Toxicity: LD₅₀=500 mg/kg (orally in rats). Considerable overdosage can lead to myocardial infarction (heart attack), serious ventricular dysrhythmias, coma and death.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic and renal
• Absorption: Quickly absorbed with maximum activity occurring in approximately one hour.
• Half Life: 1-4 hours
• Protein Binding: 98 to 99%
• Elimination: Little, if any, is excreted unchanged in the urine; most appears as the degradation products of metabolic transformation in the liver, which are almost completely excreted within 24 hours.
• References: Raphael GD, Angello JT, Wu MM, Druce HM: Efficacy of diphenhydramine vs desloratadine and placebo in patients with moderate-to-severe seasonal allergic rhinitis. Ann Allergy Asthma Immunol. 2006 Apr;96(4):606-14. [Pubmed]
• External Links: Wikipedia; RxList; Drugs.com

DrugBank - DB06975

Drug information: experimental

REFERENCES

• Raphael GD, Angello JT, Wu MM, Druce HM: Efficacy of diphenhydramine vs desloratadine and placebo in patients with moderate-to-severe seasonal allergic rhinitis. Ann Allergy Asthma Immunol. 2006 Apr;96(4):606-14. Pubmed