Diphenhydramine

Base Information

• Chemical Name: Diphenhydramine
• CAS No.: 58-73-1
• Deprecated CAS: 2226543-89-9
• Molecular Formula: C17H21NO
• Molecular Weight: 255.36
• Hs Code.: 2922199090
• European Community (EC) Number: 200-396-7
• NSC Number: 665800
• UNII: 8GTS82S83M
• DSSTox Substance ID: DTXSID4022949
• Nikkaji Number: J1.390K
• Wikipedia: Diphenhydramine
• Wikidata: Q413486
• NCI Thesaurus Code: C61728
• RXCUI: 3498
• Pharos Ligand ID: LYU23YRCSQTR
• Metabolomics Workbench ID: 37934
• ChEMBL ID: CHEMBL657
• Mol file: 58-73-1.mol

Synonyms:2-Diphenylmethoxy-N,N-dimethylethylamine;Allerdryl;Benadryl;Benhydramin;Benylin;Benzhydramine;Citrate, Diphenhydramine;Dimedrol;Diphenhydramine;Diphenhydramine Citrate;Diphenhydramine Citrate (1:1);Diphenhydramine Hydrochloride;Diphenylhydramin;Diphenylhydramine;Dormin;Hydrochloride, Diphenhydramine

Chemical Property of Diphenhydramine

Chemical Property:

• Appearance/Colour: clear light yellow liquid
• Melting Point: 167-172 °C
• Refractive Index: 1.5450 to 1.5490
• Boiling Point: 343.734 °C at 760 mmHg
• PKA: pKa 9.1 (Uncertain)
• Flash Point: 101.53 °C
• PSA: 12.47000
• Density: 1.025 g/cm³
• LogP: 3.35420
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 6
• Exact Mass: 255.162314293
• Heavy Atom Count: 19
• Complexity: 211

Purity/Quality:

99%+ ^*data from raw suppliers

Diphenhydramine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Drug Classes: Antihistamines
• Canonical SMILES: CN(C)CCOC(C1=CC=CC=C1)C2=CC=CC=C2
• Recent ClinicalTrials: Inotuzumab Ozogamicin for Children With MRD Positive CD22+ Lymphoblastic Leukemia
• Recent EU Clinical Trials: Ketamine for the treatment of depressive and negative symptoms in patients with schizophrenia: a randomized controlled cross-over pilot study.
• Recent NIPH Clinical Trials: Research on effect of hay fever drugs on brain functions
• Description: Diphenhydramine is one of the main representatives of antihistamine drugs that block H1 receptors. Besides antihistamine activity, diphenhydramine exhibits a local anesthetic effect, relaxes smooth muscle, and has sedative and soporific action.
• Uses: Diphenhydramine also reduces muscle rigidity and general stiffness, and has a relatively minor effect on tremors. Diphenhydramine is used for symptoms of allergies, for treating hives, hay fever, serum sickness, and other allergic illnesses, and also as a sedative and soporific drug as an independent as well as in combination with other drugs. Synonyms of this drug are dimedrol, benadryl, allergina, valdren, and many others. Antihistaminic.
• Therapeutic Function: Antihistaminic

Technology Process of Diphenhydramine

There total 25 articles about Diphenhydramine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

2-(N,N-dimethylamino)ethanol (108-01-0) + 1,1-Diphenylmethanol (91-01-0) → 2-diphenylmethoxy-N,N-dimethylethanamine (58-73-1)

Guidance literature:

With di(n-butyl)tin oxide; 3-methyl-1-propylimidazolium bromide; In neat (no solvent); for 8h; Reagent/catalyst; Reflux;

Reference yield: 93.0%

2-(N,N-dimethylamino)ethanol (108-01-0) + diphenylchloromethane (90-99-3) → 2-diphenylmethoxy-N,N-dimethylethanamine (58-73-1)

Guidance literature:

With sodium hydroxide; In water; at 175 ℃; for 0.266667h; under 12929 Torr;

DOI:10.1039/c3sc50859e

Reference yield: 92.0%

1,1-Diphenylmethanol (91-01-0) + 2-(dimethylamino)ethyl chloride (107-99-3) → 2-diphenylmethoxy-N,N-dimethylethanamine (58-73-1)

Guidance literature:

With sodium hydride; In benzene; 1. room temperature, 90 min; 2. 60 deg C, 30 min;

DOI:10.1135/cccc19842649

upstream raw materials:

2-(N,N-dimethylamino)ethanol

1,1-Diphenylmethanol

2-(Diphenylmethoxy)-N,N-dimethylacetamid

1,1'-[(2-chloroethoxy)methylene]bis-benzene

Downstream raw materials:

(2-benzhydryloxy-ethyl)-benzyloxycarbonylmethyl-dimethyl-ammonium; chloride

3-dimethylamino-1,1-diphenyl-propan-1-ol

Diphenhydramine-N-oxide

(2-Benzhydryloxy-ethyl)-dimethyl-(2-methyl-acryloyloxymethyl)-ammonium; chloride

Refernces

• 1、 Loren, Bradley P.,Wleklinski, Michael,Koswara, Andy,Yammine, Kathryn,Hu, Yanyang,Nagy, Zoltan K.,Thompson, David H.,Cooks, R. Graham. "Mass spectrometric directed system for the continuous-flow synthesis and purification of diphenhydramine". . p. 4363 - 4370. Retrieved 2017.
• 2、 Xu, Yangsen,Zhang, Zhaofei,Qiu, Chuntian,Chen, Shaoqin,Ling, Xiang,Su, Chenliang. "Photocatalytic Water-Splitting Coupled with Alkanol Oxidation for Selective N-alkylation Reactions over Carbon Nitride". . p. 582 - 589. Retrieved 2020/12/09.
• 3、 Steiner, Sebastian,Wolf, Jakob,Glatzel, Stefan,Andreou, Anna,Granda, Jaros?aw M.,Keenan, Graham,Hinkley, Trevor,Aragon-Camarasa, Gerardo,Kitson, Philip J.,Angelone, Davide,Cronin, Leroy. "Organic synthesis in a modular robotic system driven by a chemical programming language". . . Retrieved 2018/12/14.