147-24-0 Usage
Uses
Used in Pharmaceutical Industry:
Diphenhydramine hydrochloride is used as an antihistamine for treating allergy and cold symptoms such as sneezing, runny nose, watery eyes, urticaria (hives), skin rash, and pruritus (itchy skin). It is also used for its anticholinergic (drying) and sedative effects, allergic conjunctivitis due to foods, mild uncomplicated allergic skin manifestations of urticaria and angioedema, amelioration of allergic reactions to blood or plasma, dermatographism, anaphylactic reactions adjunctive to epinephrine and other standard measures, active and prophylactic treatment of motion sickness, parkinsonism, as an antiemetic, with local anesthetic properties, in preparations for the relief of cough, and in the prevention and treatment of radiation sickness, nausea, and vomiting.
Used in Cosmetic Industry:
Diphenhydramine hydrochloride is used as an ingredient in some cosmetic products for its anti-inflammatory and soothing properties, particularly in formulations targeting skin conditions like eczema, dermatitis, and other skin irritations.
Used in Veterinary Medicine:
Diphenhydramine hydrochloride is used as a veterinary drug for treating allergic reactions, motion sickness, and as a sedative in animals.
Used in Research and Development:
Diphenhydramine hydrochloride is utilized in research for studying the effects of histamine on various physiological processes and the development of new antihistamine drugs.
Clinical Pharmacology
Diphenhydramine hydrochloride is an antihistamine with anticholinergic (drying) and sedative side effects. Antihistamines appear to compete with histamine for cell receptor sites on effector cells. Diphenhydramine hydrochloride in the injectable form has a rapid onset of action. Diphenhydramine hydrochloride is widely distributed throughout the body, including the CNS. A portion of the drug is excreted unchanged in the urine, while the rest is metabolized via the liver. Detailed information on the pharmacokinetics of Diphenhydramine Hydrochloride Injection is not available.
Indications and Usage
Diphenhydramine hydrochloride in the injectable form is effective in adults and pediatric patients, other than premature infants and neonates, for the following conditions when diphenhydramine hydrochloride in the oral form is impractical.
antihistaminic: For amelioration of allergic reactions to blood or plasma, in anaphylaxis as an adjunct to epinephrine and other standard measures after the acute symptoms have been controlled, and for other uncomplicated allergic conditions of the immediate type when oral therapy is impossible or contraindicated.
Motion Sickness: For active treatment of motion sickness.
Antiparkinsonism: For use in parkinsonism, when oral therapy is impossible or contraindicated, as follows: parkinsonism in the elderly who are unable to tolerate more potent agents; mild cases of parkinsonism in other age groups, and in other cases of parkinsonism in combination with centrally acting anticholinergic agents.
Drug overdose
Antihistamine overdosage reactions may vary from central nervous system depression to stimulation. Stimulation is particularly likely in pediatric patients. Atropine-like signs and symptoms; dry mouth; fixed, dilated pupils; flushing; and gastrointestinal symptoms may also occur. Stimulants should not be used. Vasopressors may be used to treat hypotension.
Contraindications
Use in Neonates or Premature Infants: This drug should not be used in neonates or premature infants.
Use in Nursing Mothers: Because of the higher risk of antihistamines for infants generally, and for neonates and prematures in particular, antihistamine therapy is contraindicated in nursing mothers.
Use as a Local Anesthetic: Because of the risk of local necrosis, this drug should not be used as a local anesthetic.
Antihistamines are also contraindicated in the following conditions: Hyper sensitivity to diphenhydramine hydrochloride and other antihistamines of similar chemical structure.
Originator
Benadryl,Parke Davis,US,1946
Preparation
Diphenhydramine Hydrochloride synthesis is a four-step sequence starting with a Grignard reaction. Synthesis of Diphenhydramine Hydrochloride 6.A) modified synthetic route to diphenhydramine hydrochloride.B) Sequence of unit operations required for the synthesis. The dotted boxes denote the four stages of the synthesis. DMAE: dimethylaminoethanol.Organic synthesis in a modular robotic system driven by a chemical programming language
Therapeutic Function
Antihistaminic
Air & Water Reactions
Water soluble. Aqueous solutions are acidic.
Reactivity Profile
N-(2-Diphenylmethoxyethyl)-N,N-dimethylamine hydrochloride gives acidic solutions in water. Neutralizes bases. May react with strong oxidizing and strong reducing agents. May catalyze organic reactions. Slowly darkens on exposure to light.
Health Hazard
Potentially. If taken in large quantities, diphenhydramine can cause severe agitation and confusion, fever, skin flushing, problems with vision, dry mouth, dry eyes, and inability to sweat. Overdoses can lead to high heart rates, abnormal heart rhythms, seizures, and death.If given to elderly patients, diphenhydramine can cause confusion and agitation. Because of this, diphenhydramine is not recommended in elderly patients for insomnia or treatment for the common cold; though it should still be given in cases of allergic reaction.
Biological Activity
Diphenhydramine (DPH) is a first generation antihistamine that is a potent antagonist of the histamine H1 receptor (Ki = 11.7 nM using human recombinant receptors). DPH readily crosses the blood-brain barrier and produces diverse cognitive and psychomotor effects. DPH also antagonizes muscarinic cholinergic receptors (Kis = 100 to 260 nM for M1-M5), increasing the range of central nervous system effects and applications.
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.
Biochem/physiol Actions
Diphenhydramine hydrochloride (DPH) is an antihistaminic agent that relieves symptoms of hypersensitive reactions. It exhibits antimuscarinic and marked sedative effects. DPH is also used to prevent nausea, vomiting and vertigo of various causes. In addition, it acts as a potential therapeutic for insomnia.
Safety Profile
Poison by ingestion,
subcutaneous, intravenous, and
intraperitoneal routes. Human systemic
effects by ingestion or skin contact:
arrhythmias, ataxia, blood pressure
elevation, convulsions, distorted
perceptions, eye effects, and hallucinations.
Experimental teratogenic and reproductive
effects. Questionable carcinogen with
experimental tumorigenic data. When heated
to decomposition it emits very toxic fumes
of NO, and HCl. See also ESTERS and
ETHERS.
Veterinary Drugs and Treatments
In veterinary medicine, diphenhydramine is used principally for its
antihistaminic
effects, but also for other pharmacologic actions. Its
sedative effects can be of benefit
in treating the agitation (pruritus,
etc.) associated with allergic responses. It has also been used for
treatment and prevention of motion sickness and as an antiemetic
in small animals. It has been suggested for use as adjunctive treatment
of aseptic laminitis in cattle and it may be useful as an adjunctive
treatment for feline pancreatitis. For other suggested uses, refer
to the Dosage section below.
Check Digit Verification of cas no
The CAS Registry Mumber 147-24-0 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,4 and 7 respectively; the second part has 2 digits, 2 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 147-24:
(5*1)+(4*4)+(3*7)+(2*2)+(1*4)=50
50 % 10 = 0
So 147-24-0 is a valid CAS Registry Number.
InChI:InChI=1/C17H21NO.2ClH/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;2*1H
147-24-0Relevant articles and documents
On-demand continuous-flow production of pharmaceuticals in a compact, reconfigurable system
Adamo, Andrea,Beingessner, Rachel L.,Behnam, Mohsen,Chen, Jie,Jamison, Timothy F.,Jensen, Klavs F.,Monbaliu, Jean-Christophe M.,Myerson, Allan S.,Revalor, Eve M.,Snead, David R.,Stelzer, Torsten,Weeranoppanant, Nopphon,Wong, Shin Yee,Zhang, Ping
, p. 61 - 67 (2016)
Pharmaceutical manufacturing typically uses batch processing at multiple locations. Disadvantages of this approach include long production times and the potential for supply chain disruptions. As a preliminary demonstration of an alternative approach, we report here the continuous-flow synthesis and formulation of active pharmaceutical ingredients in a compact, reconfigurable manufacturing platform. Continuous end-to-end synthesis in the refrigerator-sized [1.0 meter (width) × 0.7 meter (length) × 1.8 meter (height)] system produces sufficient quantities per day to supply hundreds to thousands of oral or topical liquid doses of diphenhydramine hydrochloride, lidocaine hydrochloride, diazepam, and fluoxetine hydrochloride that meet U.S. Pharmacopeia standards. Underlying this flexible plug-and-play approach are substantial enabling advances in continuous-flow synthesis, complex multistep sequence telescoping, reaction engineering equipment, and real-time formulation.
End-to-end continuous flow synthesis and purification of diphenhydramine hydrochloride featuring atom economy, in-line separation, and flow of molten ammonium salts
Snead, David R.,Jamison, Timothy F.
, p. 2822 - 2827 (2013)
A continuous end-to-end synthesis and purification of diphenhydramine hydrochloride featuring atom economy and waste minimization is described. Combining a 1:1 molar ratio of the two starting material streams (chlorodiphenylmethane and N,N-dimethylaminoethanol) in the absence of additional solvent at high temperature gives the target compound directly as a molten salt (ionic liquid above 168 °C) in high yield. This represents the first example of continuous active pharmaceutical ingredient (API) production in this manner. Six of the twelve principles of green chemistry as defined by the American Chemical Society are achieved, most prominently waste minimization and atom economy.
Organic synthesis in a modular robotic system driven by a chemical programming language
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
, (2018/12/14)
The synthesis of complex organic compounds is largely a manual process that is often incompletely documented. To address these shortcomings, we developed an abstraction that maps commonly reported methodological instructions into discrete steps amenable to automation. These unit operations were implemented in a modular robotic platform by using a chemical programming language that formalizes and controls the assembly of the molecules. We validated the concept by directing the automated system to synthesize three pharmaceutical compounds, diphenhydramine hydrochloride, rufinamide, and sildenafil, without any human intervention. Yields and purities of products and intermediates were comparable to or better than those achieved manually. The syntheses are captured as digital code that can be published, versioned, and transferred flexibly between platforms with no modification, thereby greatly enhancing reproducibility and reliable access to complex molecules.
Method for preparing toluene benzyl phenyl substituted compound
-
Paragraph 0028; 0029; 0030; 0031, (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.
