58-73-1 Usage
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
Different sources of media describe the Uses of 58-73-1 differently. You can refer to the following data:
1. Diphenhydramine also reduces muscle rigidity and general stiffness, and has a relatively
minor effect on tremors.
2. 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.
3. Antihistaminic.
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
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 [35–37].
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.
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.
Check Digit Verification of cas no
The CAS Registry Mumber 58-73-1 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 5 and 8 respectively; the second part has 2 digits, 7 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 58-73:
(4*5)+(3*8)+(2*7)+(1*3)=61
61 % 10 = 1
So 58-73-1 is a valid CAS Registry Number.
InChI:InChI=1/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
58-73-1Relevant articles and documents
Blackburn,Ober
, p. 245,247 (1967)
Spectrophotometric method for the determination, validation, spectroscopic and thermal analysis of diphenhydramine in pharmaceutical preparation
Ulu, Sevgi Tatar,Elmali, Fikriye Tuncel
, p. 324 - 329 (2010)
A sensitive, simple and rapid spectrophotometric method was developed for the determination of diphenhydramine in pharmaceutical preparation. The method was based on the charge-transfer complex of the drug, as n-electron donor, with 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ), as π-acceptor. The formation of this complex was also confirmed by UV-vis, FTIR and 1H NMR spectra techniques and thermal analysis. The proposed method was validated according to the ICH guidelines with respect to linearity, limit of detection, limit of quantification, accuracy, precision, recovery and robustness. The linearity range for concentrations of diphenhydramine was found to be 12.5-150 μg/mL with acceptable correlation coefficients. The detection and quantification limits were found to be 2.09 and 6.27 μg/mL, respectively. The proposed and references methods were applied to the determination of drug in syrup. This preparation were also analyzed with an reference method and statistical comparison by t- and F-tests revealed that there was no significant difference between the results of the two methods with respect to mean values and standard deviations at the 95% confidence level.
Systems and methods for synthesizing chemical products, including active pharmaceutical ingredients
-
Page/Page column 33-35, (2020/12/14)
Systems and methods for synthesizing chemical products, including active pharmaceutical ingredients, are provided. Certain of the systems and methods described herein are capable of manufacturing multiple chemical products without the need to fluidically connect or disconnect unit operations when switching from one making chemical product to making another chemical product.
Method for preparing toluene benzyl phenyl substituted compound
-
Paragraph 0024; 0025; 0026; 0027, (2018/03/26)
In order to overcome the shortcomings of the prior art, the invention provides a method for preparing a toluene benzyl phenyl substituted compound. According to the method, first a reaction substrateand an attack reagent are added in a reaction vessel and mixed; a catalyst is added to the mixture and evenly mixed; the evenly mixed material reacts for 12-48 h at 70-110 DEG C; finally, a solvent isremoved, and a product is purified, to obtain the toluene benzyl substituted compound. The reaction substrate is a compound containing a phenyl group and having at least one alpha hydrogen attached to the phenyl group; and the attack reagent is phenylboronic acid. The catalyst is a mixture of di-tert-butyl peroxide and nickel acetylacetonate. By synthesizing 2 kg of diphenhydramine hydrochloridethrough the synthetic method, the cost can be reduced by 150000 yuan.
