ChemicalBook > CAS DataBase List > Diphenhydramine

Diphenhydramine

Product Name
Diphenhydramine
CAS No.
58-73-1
Chemical Name
Diphenhydramine
Synonyms
Benadryl;Benzhydryl;Dimedrol;DIPHENHYDRAMINE BASE;Benzhydril;Etanautine;Benzhydramine;Difenidramina;DiMenhydraMine;2-(Diphenylmethoxy)-N,N-dimethylethylamine
CBNumber
CB6196202
Molecular Formula
C17H21NO
Formula Weight
255.35
MOL File
58-73-1.mol
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Diphenhydramine Property

Melting point:
167-172°C
Boiling point:
bp2.0 150-165°
Density 
0.9889 (rough estimate)
refractive index 
1.5450 to 1.5490
storage temp. 
Keep in dark place,Inert atmosphere,Room temperature
solubility 
Chloroform (Slightly), Methanol (Slightly)
form 
Oil
pka
pKa 9.1 (Uncertain)
color 
Oil
Merck 
14,3309
BCS Class
1
CAS DataBase Reference
58-73-1(CAS DataBase Reference)
NIST Chemistry Reference
Ethylamine, 2-diphenylmethoxy-n,n-dimethyl-(58-73-1)
EPA Substance Registry System
Ethanamine, 2-(diphenylmethoxy)-N,N-dimethyl- (58-73-1)
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Safety

RTECS 
KR6825000
HS Code 
2922.19.7000
Hazardous Substances Data
58-73-1(Hazardous Substances Data)
Toxicity
LD50 oral in rat: 390mg/kg
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P321Specific treatment (see … on this label).

P330Rinse mouth.

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P362Take off contaminated clothing and wash before reuse.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

TCI Chemical
Product number
D4744
Product name
Diphenhydramine
Purity
>98.0%(GC)(T)
Packaging
5g
Price
$46
Updated
2024/03/01
TCI Chemical
Product number
D4744
Product name
Diphenhydramine
Purity
>98.0%(GC)(T)
Packaging
25g
Price
$132
Updated
2024/03/01
TRC
Product number
D487128
Product name
Diphenhydramine
Packaging
10g
Price
$435
Updated
2021/12/16
Usbiological
Product number
470664
Product name
Diphenhydramine
Packaging
1mg
Price
$453
Updated
2021/12/16
Usbiological
Product number
470663
Product name
Diphenhydramine
Packaging
1mg
Price
$453
Updated
2021/12/16
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Diphenhydramine Chemical Properties,Usage,Production

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.

Originator

Benadryl,Parke Davis,US,1946

Uses

Diphenhydramine also reduces muscle rigidity and general stiffness, and has a relatively minor effect on tremors.

Uses

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.

Uses

Antihistaminic.

Definition

ChEBI: 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.

Manufacturing Process

As described in US Patent 2,421,714: (a) benzhydryl
omide is first prepared as follows: 840 parts by weight of diphenylmethane is heated to 130°C with stirring. In the presence of a 200 watt electric light 6 inches from the flask, 880 parts of
omine is added slowly. Liberation of H
occurs and addition requires 1 hour and 45 minutes. The temperature is maintained at 130°C for an additional 30 minutes. A fine stream of air is blown in to remove H
and
2 while the reaction mixture cools. Benzene (180 parts) is added and the solution used immediately in (b) below.
If pure benzhydryl
omide is desired the above reaction mixture is dissolved in ether, washed with water, sodium carbonate solution and finally with water. The ether is removed, benzene added and distilled off and the benzhydryl
omide distilled in vacuo. Yield 85%.
(b) 490 parts β-dimethylaminoethanol and 530 parts of anhydrous sodium carbonate are heated to 110°C with stirring. The addition of the benzenebenzhydryl
omide mixture is then begun. The temperature is raised to 120°- 125°C. As reaction takes place carbon dioxide is evolved, the addition requires1? hours. The mixture is kept at 125°C for 5 hours additional time. After cooling, 3,000 parts of water is added and the mixture stirred until the inorganic salts are dissolved. The mixture is transferred to a large separatory funnel and 1,500 parts of ether added. The ether solution is washed several times with water and then the ether layer extracted with 1 to 4 hydrochloric acid. The acid solution is treated with 30 parts of Darco and 30 parts Filter-Cel and filtered.
The free base is liberated from the acid solution with 20% sodium hydroxide solution and taken up in ether. The ether layer is washed with water, saturated with NaCl and then shaken with solid potassium hydroxide. The ether is removed by distillation, 200 parts of benzene added and distilled off. The residue is distilled in vacuo and the fraction 150°-165°C/2 mm is collected and amounts to 433 parts. The hydrochloride salt is prepared by dissolving the free base in anhydrous ether and slowly adding an alcoholic solution of hydrogen chloride. The solid is recrystallized from absolute alcohol-ether mixture or isopropanol-ether mixture and has a MP of 161-162°C.

Therapeutic Function

Antihistaminic

Trade name

Benadryl (Parke-Davis)

Contact allergens

This antihistaminic drug with sedative properties is mainly sold over the counter. It can be used both topically (treatment of pruritis) and orally for its antiallergic, antiemetic, sedative, and anticough properties. Allergic or photoallergic contact dermatitis and fixeddrug eruption seem to be rare.

Safety Profile

Deadly human poison by an unspecified route. Poison by ingestion, intravenous, intraperitoneal, and subcutaneous routes. Experimental reproductive effects. Human systemic effects by ingestion: somnolence, alteration of operant conditioning, changes in psychophysiological tests. Human mutation data reported. When heated to decomposition it emits toxic fumes of NO,. See also ETHERS.

Synthesis

Diphenhydramine, 2-diphenylmethoxy-N,N-dimethylamine (10.2.5), is synthesized by the esterification of 2-dimethylaminoethanol with benzhydrylbromide [35¨C37].

Environmental Fate

Diphenhydramine is fairly stable in the environment although it does undergo photodegradation. Conjugates of diphenhydramine such as diphenhydramine-N-glucuronide may be converted back to the parent compound, diphenhydramine, through enzymatic cleavage during sewage treatment process. Diphenhydramine is removed poorly through wastewater treatment processes and is found in significant concentrations in aquatic organisms downstream from such plants.
Diphenhydramine has significant risk for bioaccumulation, particularly in water downstream from wastewater and sewage treatment facilities.

Solubility in water

One gram of diphenhydramine is soluble in 1 mL of water, 2 mL of ethanol, 2 mL of chloroform, or 50 mL of acetone; the compound is very slightly soluble in benzene or ether.

Toxicity evaluation

The toxicity of antihistamines is related to their anticholinergic (antimuscarinic), antihistamine, and serotonergic activation. The action of acetylcholine at the muscarinic receptors is blocked, resulting in signs and symptoms of anticholinergic poisoning. Diphenhydramine may produce direct toxicity unrelated to its anticholinergic properties including inhibition of cardiac fast sodium channels and at higher concentrations, the drug may inhibit potassium channels, which can result in QT prolongation. Diphenhydramine also blocks the reuptake of serotonin and has been reported to cause serotonin syndrome in some individuals during overdose. The action of diphenhydramine at H-1 receptors causes sedation.

Diphenhydramine Preparation Products And Raw materials

Raw materials

Benzyl alcohol 2-Chloroethanol Dimethylamine

Preparation Products

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View Lastest Price from Diphenhydramine manufacturers

Baoji Guokang Bio-Technology Co., Ltd.
Product
Diphenhydramine 58-73-1
Price
US $56.00/KG
Min. Order
1KG
Purity
98%
Supply Ability
1-1000kg
Release date
2021-06-07
Hebei Yanxi Chemical Co., Ltd.
Product
Diphenhydramine 58-73-1
Price
US $50.00/kg
Min. Order
1kg
Purity
0.99
Supply Ability
10000
Release date
2023-10-09
Wuhan Senwayer Century Chemical Co.,Ltd
Product
Diphenhydramine 58-73-1
Price
US $70.00/kg
Min. Order
1kg
Purity
99% HPLC
Supply Ability
20 tons
Release date
2022-10-13

58-73-1, DiphenhydramineRelated Search:

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