Diphenhydramine Hydrochloride

Iupac Name：2-benzhydryloxy-N,N-dimethylethanamine;hydrochloride

Molecular Weight：291.81568

Modify Date.: 2022-10-31 01:59

Introduction: Diphenhydramine hydrochloride is an antihistamine drug having the chemical name 2-(Diphenylmethoxy)- N,N-dimethylethylamine hydrochloride. It occurs as a white, crystalline powder, is freely soluble in water and alcohol and has a molecular weight of 291.82.The molecular formula is C17H21NO·HCl and the structural formula is as follows: View more+

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1. Names and Identifiers

1.1 Name: Diphenhydramine Hydrochloride
1.2 Synonyms: 2-(Benzhydryloxy)-N,N-dimethylethanamine hydrochloride 2-(Benzhydryloxy)-N,N-dimethylethylamine Hydrochloride 2-(Benzhydryloxy)-N,N-dimethylethylamine, hydrochloride 2-(diphénylméthoxy)-N,N-diméthyléthanamine chlorhydrate 2-(Diphenylmethoxy)-N,N-dimethylethanamine hydrochloride 2-(Diphenylmethoxy)-N,N-dimethylethanamine hydrochloride (1:1) 2-(Diphenylmethoxy)-N,N-dimethylethanaminhydrochlorid 2-(diphenylmethoxy)-n,n-dimethyl-ethanaminhydrochloride 2-(diphenylmethoxy)-n,n-dimethyl-ethylaminhydrochloride 2-benzhydryloxy-N,N-dimethylethanamine,hydrochloride 2-Diphenylmethoxy-N,N-dimethylet 2-Diphenylmethoxy-N,N-dimethylethanamine hydrochloride 2-Diphenylmethoxy-N,N-dimethylethylamine Hydrochloride a-(2-Dimethylaminoethoxy)diphenylmethane Hydrochloride Actifed Allergina alpha-Hydroxydiphenylmethane-beta-dimethylaminoethyl ether hydrochloride alpha-hydroxydiphenylmethane-beta-dimethylaminoethyletherhydrochloride Ambenyl BAX b-Dimethylaminoethyl Benzhydryl Ether Hydrochloride Benacine Benadryl Benzhydramine HCl benzhydramine hydrochloride EINECS 205-687-2 Ethanamine, 2- (diphenylmethoxy)-N,N-dimethyl-, hydrochloride Ethanamine, 2-(diphenylmethoxy)-N,N-dimethyl-, hydrochloride (1:1) Ethylamine, 2- (diphenylmethoxy)-N,N-dimethyl-, hydrochloride Ethylamine, N,N-dimethyl-2-(diphenylmethoxy)-, hydrochloride MFCD00012479 N-(2-Diphenylmethoxyethyl)-N,N-Dimethylamine Hydrochloride N,N-Dimethyl-2-(diphenylmethoxy)-ethylamine hydrochloride Sedopretten Β-Dimethylaminoethyl benzhydryl ether hydrochloride

1.3 CAS No.: 147-24-0

1.4 CID: 8980

1.5 EINECS(EC#): 205-687-2

1.6 Molecular Formula: C17H22ClNO (isomer)

1.7 Inchi: InChI=1S/C17H21NO.ClH/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;1H

1.8 InChIkey: PCHPORCSPXIHLZ-UHFFFAOYSA-N

1.9 Canonical Smiles: CN(C)CCOC(C1=CC=CC=C1)C2=CC=CC=C2.Cl

1.10 Isomers Smiles: CN(C)CCOC(C1=CC=CC=C1)C2=CC=CC=C2.Cl

2. Properties

2.1 Density: 1.024

2.1 Melting point: 168-172℃

2.1 Boiling point: 343.7 °C at 760 mmHg

2.1 Refractive index: 1.5800 (estimate)

2.1 Flash Point: 101.5 °C

2.1 Precise Quality: 291.13900

2.1 PSA: 12.47000

2.1 logP: 4.15620

2.1 Solubility: 1000 g/L

2.2 Appearance: White Crystalline powder

2.3 Storage: Light Sensitive. Ambient temperatures.

2.4 Chemical Properties: White or almost white, crystalline powder.

2.5 Color/Form: Powder

2.6 Contact Allergens: This antihistaminic drug with sedative properties ismainly 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 fixeddrugeruption seem to be rare.

2.7 PH: pH(100g/L, 25℃) 4.0～5.5

2.8 Water Solubility: 1000 g/L

2.9 Spectral Properties: Intense mass spectral peaks: 58 m/z, 73 m/z, 152 m/z, 165 m/z, 255 m/z

2.10 Stability: Stable, but slowly darkens upon exposure to light. Incompatible with strong oxidizing agents.

2.11 StorageTemp: 2-8°C

3. Use and Manufacturing

3.1 Definition: ChEBI: The hydrochloride salt of diphenhydramine.

3.2 General Description: Diphenhydramine hydrochloride, 2-(diphenylmethoxy)- N,N-dimethylethanamine hydrochloride (Benadryl), is an oily, lipid-soluble free base available as the bitter-tasting hydrochloride salt, which is a stable, white crystalline powder soluble in water (1:1), alcohol (1:2) and chloroform (1:2). The salt has a pKa value of 9, and a 1% aqueous solution has a pH of about 5. In addition to antihistaminic action, diphenhydramine exhibits antidyskinetic, antiemetic, antitussive and antimuscarinic, and sedative properties.As an antihistaminic agent, diphenhydramine is recommended in various allergic conditions and, to a lesser as an antitussive and Parkinsonism drug. It is also used in OTC sleep-aid products. It is administered either orally or parenterally in the treatment of urticaria, seasonal rhinitis (hay fever), and some dermatoses.

3.3 Usage: Diphenhydramine hydrochloride is used as an antihistamine and for its antieholinergie (drying) and sedative effects; for allergic conjunctivitis due to foods; for mild,uncomplicated allergic skin manifestations of urticaria and angioedema; for amelioration of allergic reactions to blood or plasma; fordermatographism; in therapy for anaphylaetie reactions adjunctive to epinephrine and other standard measures after the acutemanifestations have been controlled; for active and prophylactie treatment of motion sickness; for parkinsonism; an antiemetic; haslocal anesthetic properties; in preparations for the relief of cough; in the prevention and treatment of radiation sickness, nausea andvomiting; for treatment of allergie cheilitis and stomatitis.

4. Safety and Handling

4.1 Symbol: GHS07

4.1 Hazard Codes: Xn

4.1 Signal Word: Warning

4.1 Risk Statements: R22

4.1 Safety Statements: 36

4.1 Exposure Standards and Regulations: Manufacturers, packers, and distributors of drug and drug products for human use are responsible for complying with the labeling, certification, and usage requirements as prescribed by the Federal Food, Drug, and Cosmetic Act, as amended (secs 201-902, 52 Stat. 1040 et seq., as amended; 21 U.S.C. 321-392).

4.2 Fire Hazard: Flash point data for N-(2-Diphenylmethoxyethyl)-N,N-dimethylamine hydrochloride are not available; however, N-(2-Diphenylmethoxyethyl)-N,N-dimethylamine hydrochloride is probably combustible.

4.3 Hazard Declaration: H302

4.3 DisposalMethods: SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

4.4 RIDADR: 2811

4.4 Safety Profile: Poison by ingestion,subcutaneous, intravenous, andintraperitoneal routes. Human systemiceffects by ingestion or skin contact:arrhythmias, ataxia, blood pressureelevation, convulsions, distortedperceptions, eye effects, and hallucinations.Experimental teratogenic and reproductiveeffects. Questionable carcinogen withexperimental tumorigenic data. When heatedto decomposition it emits very toxic fumesof NO, and HCl. See also ESTERS andETHERS.

4.5 Caution Statement: P210-P260-P280-P301 + P310-P311

4.5 Formulations/Preparations: HYDROCHLORIDE...BAX, BENADRYL, BENOCTEN, BENZEHIST, DABYLEN, DOLESTAN, FELBEN, FENYLHIST, HALBMOND, ROHYDRA, SEDOPRETTEN, VALDRENE, WEHYDRYL. /HYDROCHLORIDE/
CAPSULES, 25 & 50 MG; INJECTION (SYRINGES & AMPULS); ELIXIR, 50 MG (SINGLE ADULT DOSES). /HYDROCHLORIDE, FROM TABLE/

4.6 WGK Germany: 3

4.6 RTECS: KR7000000

4.6 Report: Reported in NTP Carcinogenesis Studies (feed); Equivocal Evidence: rat NTPTR* ?? National Toxicology Program Technical Report Series. (Research Triangle Park, NC 27709) No. 206- NTP-TR-355 (1989). ; (feed); No Evidence: mouse NTPTR* ?? National Toxicology Program Technical Report Series. (Research Triangle Park, NC 27709) No. 206- NTP-TR-355 (1989). .

4.7 Safety: 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_x and HCl.
Hazard Codes:?Xn
Risk Statements: 22?
R22:Harmful if swallowed.
Safety Statements: 36?
S36:Wear suitable protective clothing.
RIDADR: 2811
WGK Germany: 3
RTECS of Benzantin hydrochloride? (CAS NO.147-24-0): KR7000000

4.8 Specification: ? Benzantin hydrochloride (CAS NO.147-24-0), its Synonyms are Diphenhydramine hydrochloride ; 2-(Benzhydryloxy)-N,N-dimethylethylamine hydrochloride ; 2-(Diphenylmethoxy)-N,N-dimethylethylamine hydrochloride ; Allergan ; Allergival ; Benzhydramine hydrochloride ; Benzhydrol, beta-dimethylaminoethyl ether hydrochloride . It is white crystalline powder.

4.9 Toxicity

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
child	TDLo	oral	12500ug/kg (12.5mg/kg)	BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD CARDIAC: ARRHYTHMIAS (INCLUDING CHANGES IN CONDUCTION)	Journal of Pediatrics. Vol. 90, Pg. 1017, 1977.
child	TDLo	skin	60mg/kg/6H-I (60mg/kg)	SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS" BEHAVIORAL: ATAXIA	Clinical Pediatrics Vol. 25, Pg. 163, 1986.
dog	LD50	intravenous	24mg/kg (24mg/kg)	BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD BEHAVIORAL: EXCITEMENT	Journal of Pharmacology and Experimental Therapeutics. Vol. 89, Pg. 227, 1947.
guinea pig	LD50	intraperitoneal	75mg/kg (75mg/kg)	?	Journal of Pharmacology and Experimental Therapeutics. Vol. 83, Pg. 120, 1945.
guinea pig	LD50	oral	280mg/kg (280mg/kg)	?	Journal of Allergy. Vol. 27, Pg. 57, 1956.
guinea pig	LD50	subcutaneous	40mg/kg (40mg/kg)	BEHAVIORAL: TREMOR BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD	Journal of Pharmacology and Experimental Therapeutics. Vol. 113, Pg. 72, 1955.
hamster	LD50	intravenous	18mg/kg (18mg/kg)	BEHAVIORAL: TREMOR BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD BEHAVIORAL: EXCITEMENT	Journal of Pharmacology and Experimental Therapeutics. Vol. 97, Pg. 371, 1949.
mammal (species unspecified)	LD50	intraperitoneal	80mg/kg (80mg/kg)	?	Arzneimittel-Forschung. Drug Research. Vol. 3, Pg. 328, 1953.
man	TDLo	oral	10714ug/kg (10.714mg/kg)	AUTONOMIC NERVOUS SYSTEM: PARASYMPATHOLYTIC BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS" VASCULAR: BP ELEVATION NOT CHARACTERIZED IN AUTONOMIC SECTION	American Journal of Emergency Medicine. Vol. 4, Pg. 369, 1986.
mouse	LD50	intraperitoneal	56mg/kg (56mg/kg)	BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD BEHAVIORAL: EXCITEMENT	Journal of Pharmacology and Experimental Therapeutics. Vol. 112, Pg. 318, 1954.
mouse	LD50	intravenous	20mg/kg (20mg/kg)	BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY) BEHAVIORAL: ATAXIA	Arzneimittel-Forschung. Drug Research. Vol. 5, Pg. 72, 1955.
mouse	LD50	oral	164mg/kg (164mg/kg)	?	Drugs in Japan Vol. -, Pg. 550, 1995.
mouse	LD50	subcutaneous	99200ug/kg (99.2mg/kg)	BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD SKIN AND APPENDAGES (SKIN): HAIR: OTHER	Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. Vol. 54, Pg. 33, 1958.
pigeon	LD50	intramuscular	63mg/kg (63mg/kg)	GASTROINTESTINAL: NAUSEA OR VOMITING	Journal of the American Pharmaceutical Association, Scientific Edition. Vol. 46, Pg. 140, 1957.
rabbit	LD50	intravenous	10mg/kg (10mg/kg)	BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD LUNGS, THORAX, OR RESPIRATION: DYSPNEA BEHAVIORAL: EXCITEMENT	Federation Proceedings, Federation of American Societies for Experimental Biology. Vol. 4, Pg. 150, 1945.
rat	LD50	intraperitoneal	82mg/kg (82mg/kg)	?	Journal of Pharmacology and Experimental Therapeutics. Vol. 102, Pg. 250, 1951.
rat	LD50	intravenous	35mg/kg (35mg/kg)	BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX) LUNGS, THORAX, OR RESPIRATION: DYSPNEA BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD	Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 12, Pg. 2769, 1984.
rat	LD50	oral	500mg/kg (500mg/kg)	?	Drugs in Japan Vol. 6, Pg. 334, 1982.
rat	LD50	subcutaneous	201mg/kg (201mg/kg)	?	Yakugaku Zasshi. Journal of Pharmacy. Vol. 81, Pg. 261, 1961.
women	TDLo	oral	83mg/kg (83mg/kg)	BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD BEHAVIORAL: COMA CARDIAC: ARRHYTHMIAS (INCLUDING CHANGES IN CONDUCTION)	Critical Care Medicine. Vol. 16, Pg. 1161, 1988.

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5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Acute toxicity - Oral, Category 4

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Warning
Hazard statement(s)	H302 Harmful if swallowed
Precautionary statement(s)
Prevention	P264 Wash ... thoroughly after handling. P270 Do not eat, drink or smoke when using this product.
Response	P301+P312 IF SWALLOWED: Call a POISON CENTER/doctor/\u2026if you feel unwell. P330 Rinse mouth.
Storage	none
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

6. NMR Spectrum

Predict 1H proton NMR

IR : KBr disc

IR : nujol mull

Raman : 4880 A,200 M,powder

Mass

7. Synthesis Route

147-24-0Total: 3 Synthesis Route

90-99-3 125 Suppliers

147-24-0 329 Suppliers

Literatures:
Recueil des Travaux Chimiques des Pays-Bas, , vol. 71, p. 431
Yield: null

17616-20-5

147-24-0 329 Suppliers

Literatures:
Recueil des Travaux Chimiques des Pays-Bas, , vol. 71, p. 431
Yield: null

108-01-0 153 Suppliers

90-99-3 125 Suppliers

147-24-0 329 Suppliers

2498-25-1 4 Suppliers

Literatures:
Snead, David R.; Jamison, Timothy F. Chemical Science, 2013 , vol. 4, # 7 p. 2822 - 2827
Yield: null

8. Precursor and Product

precursor:

17616-20-5

90-99-3

108-01-0

product :

91-01-0

90-99-3

108-01-0

9. Other Information

9.0 Merck: 14,3309

9.1 Description: Diphenhydramine hydrochloride is an antihistamine drug having the chemical name 2-(Diphenylmethoxy)- N,N-dimethylethylamine hydrochloride. It occurs as a white, crystalline powder, is freely soluble in water and alcohol and has a molecular weight of 291.82.
The molecular formula is C17H21NO·HCl and the structural formula is as follows:

Diphenhydramine hydrochloride in the parenteral form is a sterile, pyrogen-free solution available in a concentration of 50 mg of diphenhydramine hydrochloride per mL. The solutions for parenteral use have been adjusted to a pH between 5.0 and 6.0 with either sodium hydroxide or hydrochloric acid and contains 0.1 mg/mL benzethonium chloride as a germicidal agent.

9.2 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.

9.3 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.

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9.4 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.

9.5 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.

9.6 Description: Diphenhydramine (DPH) is a first generation antihistamine that is a potent antagonist of the histamine H₁ receptor (K_i = 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 (K_is = 100 to 260 nM for M₁-M₅), increasing the range of central nervous system effects and applications. This product is also available as an analytical reference standard (Item No. 22489).

9.7 Chemical Properties: White or almost white, crystalline powder.

9.8 Originator: Benadryl,Parke Davis,US,1946

9.9 Uses: Diphenhydramine hydrochloride is used as an antihistamine and for its antieholinergie (drying) and sedative effects; for allergic conjunctivitis due to foods; for mild, uncomplicated allergic skin manifestations of urticaria and angioedema; for amelioration of allergic reactions to blood or plasma; for dermatographism; in therapy for anaphylaetie reactions adjunctive to epinephrine and other standard measures after the acute manifestations have been controlled; for active and prophylactie treatment of motion sickness; for parkinsonism; an antiemetic; has local anesthetic properties; in preparations for the relief of cough; in the prevention and treatment of radiation sickness, nausea and vomiting; for treatment of allergie cheilitis and stomatitis.

9.10 Uses: Diphenhydramine is a H1-histamine receptor antagonist. Diphenhydramine is categorized as an antihistaminic; sedative, hypnotic.

9.11 Uses: antihistamine, sedative, treatment of allergic

9.12 Uses: A histamine H1-receptor antagonist.

9.13 Uses: H1-Histamine receptor antagonist. Antihistaminic; sedative, hypnotic

9.14 Definition: ChEBI: The hydrochloride salt of diphenhydramine.

9.15 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.

9.16 Usage: A histamine H1 receptor antagonistDiphenhydramine hydrochloride acts as a sodium channel blocker. It is used as a histamine H1-receptor antagonist. Further, it is used as a sedative, hypnotic, antiemetic, antitussive and pruritus. It is employed in the treatment of allergic conditions. In addition to this, it is used as an active ingredient in common cold preparations.

9.17 Brand name: Benadryl (Parke-Davis).

9.18 Therapeutic Function: Antihistaminic

9.19 General Description: Diphenhydramine hydrochloride, 2-(diphenylmethoxy)- N,N-dimethylethanamine hydrochloride (Benadryl), is an oily, lipid-soluble free base available as the bitter-tasting hydrochloride salt, which is a stable, white crystalline powder soluble in water (1:1), alcohol (1:2) and chloroform (1:2). The salt has a pKa value of 9, and a 1% aqueous solution has a pH of about 5.
In addition to antihistaminic action, diphenhydramine exhibits antidyskinetic, antiemetic, antitussive and antimuscarinic, and sedative properties.As an antihistaminic agent, diphenhydramine is recommended in various allergic conditions and, to a lesser as an antitussive and Parkinsonism drug. It is also used in OTC sleep-aid products. It is administered either orally or parenterally in the treatment of urticaria, seasonal rhinitis (hay fever), and some dermatoses.

9.20 General Description: White or almost-white crystalline powder. Odorless with a bitter numbing taste. pH (5% aqueous solution) 4-6.

9.21 Air & Water Reactions: Water soluble. Aqueous solutions are acidic.

9.22 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.

9.23 Fire Hazard: Flash point data for N-(2-Diphenylmethoxyethyl)-N,N-dimethylamine hydrochloride are not available; however, N-(2-Diphenylmethoxyethyl)-N,N-dimethylamine hydrochloride is probably combustible.

9.24 Biological Activity: H 1 receptor antagonist. Antihistamine.

9.25 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.

9.26 Biochem/physiol Actions: H1 histamine receptor antagonistDiphenhydramine 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.

9.27 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.

9.28 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.

10. Computational chemical data

Molecular Weight: 291.81568g/mol
Molecular Formula: C₁₇H₂₂ClNO
Compound Is Canonicalized: True
XLogP3-AA: null
Exact Mass: 291.1389920
Monoisotopic Mass: 291.1389920
Complexity: 211
Rotatable Bond Count: 6
Hydrogen Bond Donor Count: 1
Hydrogen Bond Acceptor Count: 2
Topological Polar Surface Area: 12.5
Heavy Atom Count: 20
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 2
CACTVS Substructure Key Fingerprint: AAADceB6IAAEAAAAAAAAAAAAAAAAAAAAAAAwYAAAAAAAAAABQAAAHgAAAAAADBThmAYyAIMABACAAiBCAAACAAAgAAAIiAAICIgKJiKAMRiDMAAkwAEYqAeAwOAOAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==

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