Product Name

  • Name

    Diphenhydramine hydrochloride

  • EINECS 205-687-2
  • CAS No. 147-24-0
  • Article Data5
  • CAS DataBase
  • Density 1.024 g/cm3
  • Solubility 1000 g/L in water
  • Melting Point 168-172 °C
  • Formula C17H21NO.HCl
  • Boiling Point 343.7 °C at 760 mmHg
  • Molecular Weight 291.821
  • Flash Point 101.5 °C
  • Transport Information
  • Appearance White crystalline powder
  • Safety 36
  • Risk Codes 22
  • Molecular Structure Molecular Structure of 147-24-0 (Diphenhydramine hydrochloride)
  • Hazard Symbols HarmfulXn
  • Synonyms Ethanamine,2-(diphenylmethoxy)-N,N-dimethyl-, hydrochloride (9CI);2-Diphenylmethoxy-N,N-dimethylethylamine hydrochloride;Alledryl;Allergina;Amidryl;Bagodryl;Bena;Benadrilhydrochloride;Benison;Benodine;Benzantin;Benzhydrol b-dimethylaminoethyl ether hydrochloride;Denydryl;Dibondrin;Dimedrol;Diphantine;Fenylhist;
  • PSA 12.47000
  • LogP 4.15620

Synthetic route

benzhydryl-(2-hydroxy-ethyl)-dimethyl-ammonium; chloride
17616-20-5

benzhydryl-(2-hydroxy-ethyl)-dimethyl-ammonium; chloride

diphenhydramine hydrochloride
147-24-0

diphenhydramine hydrochloride

diphenylchloromethane
90-99-3

diphenylchloromethane

diphenhydramine hydrochloride
147-24-0

diphenhydramine hydrochloride

2-(N,N-dimethylamino)ethanol
108-01-0

2-(N,N-dimethylamino)ethanol

diphenylchloromethane
90-99-3

diphenylchloromethane

A

diphenhydramine hydrochloride
147-24-0

diphenhydramine hydrochloride

B

2-(N,N-dimethylamino)ethanol hydrochloride
2498-25-1

2-(N,N-dimethylamino)ethanol hydrochloride

Conditions
ConditionsYield
With sodium hydroxide In water; isopropyl alcohol at 175℃; under 12929 Torr; for 0.266667h; Overall yield = 71 %Spectr.;
...Expand
2-(N,N-dimethylamino)ethanol
108-01-0

2-(N,N-dimethylamino)ethanol

diphenylchloromethane
90-99-3

diphenylchloromethane

diphenhydramine hydrochloride
147-24-0

diphenhydramine hydrochloride

Conditions
ConditionsYield
Stage #1: 2-(N,N-dimethylamino)ethanol; diphenylchloromethane at 180℃; for 0.25h; Flow reactor;
Stage #2: With sodium hydroxide In hexane; water at 140℃; under 12751.3 Torr; Flow reactor;
Stage #3: With hydrogenchloride In diethyl ether; hexane; water
2-diphenylmethoxy-N,N-dimethylethanamine
58-73-1

2-diphenylmethoxy-N,N-dimethylethanamine

diphenhydramine hydrochloride
147-24-0

diphenhydramine hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In ethanol at 20℃; for 1h; Time;9.6 mmol
bromobenzene
108-86-1

bromobenzene

diphenhydramine hydrochloride
147-24-0

diphenhydramine hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: magnesium / 0.67 h / Reflux; Inert atmosphere
1.2: 5 h / Reflux; Inert atmosphere
2.1: toluene / 4 h / Reflux
3.1: toluene / 20 h / Reflux
3.2: 25 °C
View Scheme
2-(N,N-dimethylamino)ethanol
108-01-0

2-(N,N-dimethylamino)ethanol

Bromodiphenylmethane
776-74-9

Bromodiphenylmethane

diphenhydramine hydrochloride
147-24-0

diphenhydramine hydrochloride

Conditions
ConditionsYield
Stage #1: 2-(N,N-dimethylamino)ethanol; Bromodiphenylmethane In toluene for 20h; Williamson Ether Synthesis; Reflux;
Stage #2: With hydrogenchloride In diethyl ether at 25℃;
benzaldehyde
100-52-7

benzaldehyde

diphenhydramine hydrochloride
147-24-0

diphenhydramine hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: magnesium / 0.67 h / Reflux; Inert atmosphere
1.2: 5 h / Reflux; Inert atmosphere
2.1: toluene / 4 h / Reflux
3.1: toluene / 20 h / Reflux
3.2: 25 °C
View Scheme
1,1-Diphenylmethanol
91-01-0

1,1-Diphenylmethanol

diphenhydramine hydrochloride
147-24-0

diphenhydramine hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: toluene / 4 h / Reflux
2.1: toluene / 20 h / Reflux
2.2: 25 °C
View Scheme
diphenhydramine hydrochloride
147-24-0

diphenhydramine hydrochloride

sodium 2-(4-isobutylphenyl)propionate
31121-93-4

sodium 2-(4-isobutylphenyl)propionate

diphenhydraminium ibuprofenate

diphenhydraminium ibuprofenate

Conditions
ConditionsYield
In water at 40℃; for 24h;79%
diphenhydramine hydrochloride
147-24-0

diphenhydramine hydrochloride

sodium docusate
577-11-7

sodium docusate

diphenhydraminium docusate

diphenhydraminium docusate

Conditions
ConditionsYield
In water at 40℃; for 24h;68%
diphenhydramine hydrochloride
147-24-0

diphenhydramine hydrochloride

A

2-(N,N-dimethylamino)ethanol
108-01-0

2-(N,N-dimethylamino)ethanol

B

1,1-Diphenylmethanol
91-01-0

1,1-Diphenylmethanol

C

diphenylchloromethane
90-99-3

diphenylchloromethane

Conditions
ConditionsYield
With diclazuril In chloroform-d1 Product distribution;
...Expand
diphenhydramine hydrochloride
147-24-0

diphenhydramine hydrochloride

2-diphenylmethoxy-N,N-dimethylethanamine
58-73-1

2-diphenylmethoxy-N,N-dimethylethanamine

Conditions
ConditionsYield
With sodium hydroxide In water
With ammonia In water for 0.0166667h;
With sodium hydroxide In water at 20℃; for 2h;
ammonium thiocyanate

ammonium thiocyanate

ammonium molybdate

ammonium molybdate

diphenhydramine hydrochloride
147-24-0

diphenhydramine hydrochloride

(2-benzhydryloxy-N,N-dimethylethaneammonium)[Mo(thiocyanate)6]

(2-benzhydryloxy-N,N-dimethylethaneammonium)[Mo(thiocyanate)6]

Conditions
ConditionsYield
With hydrogenchloride; ascorbic acid In hydrogenchloride; water mixing aq. soln. of molybdate salt, 4M aq. HCl, aq. ammonium thiocyanateand ascorbic acid, keeping for 15 min at room temp., addn. of amine der iv. in distd. water, keeping for 15 min; extn. (CH2Cl2), separation of organic phase, drying over Na2SO4, UV;
...Expand
diphenhydramine hydrochloride
147-24-0

diphenhydramine hydrochloride

aspartic Acid
617-45-8

aspartic Acid

diphenhydramine aspartic acid salt

diphenhydramine aspartic acid salt

Conditions
ConditionsYield
With sodium hydroxide In water Heating / reflux;
diphenhydramine hydrochloride
147-24-0

diphenhydramine hydrochloride

Sodium carboxymethylcellulose

Sodium carboxymethylcellulose

diphenhydramine sodium carboxymethyl cellulose salt

diphenhydramine sodium carboxymethyl cellulose salt

Conditions
ConditionsYield
In water at 75 - 80℃;
diphenhydramine hydrochloride
147-24-0

diphenhydramine hydrochloride

1,1-Diphenylmethanol
91-01-0

1,1-Diphenylmethanol

Conditions
ConditionsYield
With hydrogenchloride In methanol Reagent/catalyst;
diphenhydramine hydrochloride
147-24-0

diphenhydramine hydrochloride

A

formic acid
64-18-6

formic acid

B

oxamic acid
471-47-6

oxamic acid

C

oxalic acid
144-62-7

oxalic acid

Conditions
ConditionsYield
With water; sodium sulfate pH=7; Electrochemical reaction;
...Expand
saccharin sodium salt
128-44-9

saccharin sodium salt

diphenhydramine hydrochloride
147-24-0

diphenhydramine hydrochloride

diphenhydramine saccharinate

diphenhydramine saccharinate

Conditions
ConditionsYield
In water Cooling;
saccharin sodium salt hydrate

saccharin sodium salt hydrate

diphenhydramine hydrochloride
147-24-0

diphenhydramine hydrochloride

diphenhydramine saccharinate

diphenhydramine saccharinate

Conditions
ConditionsYield
Stage #1: saccharin sodium salt hydrate; diphenhydramine hydrochloride In water Heating;
Stage #2: In water at 20℃; for 168h;		Ca. 30 g
potassium acesulfame
55589-62-3

potassium acesulfame

diphenhydramine hydrochloride
147-24-0

diphenhydramine hydrochloride

diphenhydramine acesulfame

diphenhydramine acesulfame

Conditions
ConditionsYield
In waterCa. 30 g
diphenhydramine hydrochloride
147-24-0

diphenhydramine hydrochloride

Diphenhydramine-N-oxide
3922-74-5

Diphenhydramine-N-oxide

Conditions
ConditionsYield
With dihydrogen peroxide for 6h;
diphenhydramine hydrochloride
147-24-0

diphenhydramine hydrochloride

A

benzophenone
119-61-9

benzophenone

B

Diphenylmethane
101-81-5

Diphenylmethane

Conditions
ConditionsYield
With dolomite In water at 4℃; for 1.25h; Kinetics; Reagent/catalyst; Solvent; Irradiation; Inert atmosphere;

Diphenhydramine hydrochloride Consensus Reports

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). .

Diphenhydramine hydrochloride Specification

The Diphenhydramine hydrochloride, with the CAS registry number 147-24-0, is also known as 2-(Diphenylmethoxy)-N,N-dimethylethanaminhydrochlorid. It belongs to the product categories of Anilines, Aromatic Amines and Nitro Compounds; API Intermediates; Amines; Aromatics; Intermediates & Fine Chemicals; Pharmaceuticals; Histamine receptor. Its EINECS registry number is 205-687-2. This chemical's molecular formula is C17H22ClNO and molecular weight is 291.82. What's more, both its IUPAC name and systematic name are the same which is called 2-Benzhydryloxy-N,N-dimethylethanamine hydrochloride. This chemical should be stored in a cool, dry and well-ventilated place. It is used as histamine receptor antagonist, antihistaminic, sedative, hypnotic.

Physical properties about Diphenhydramine hydrochloride are: (1)ACD/LogP: 3.662; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0.79; (4)ACD/LogD (pH 7.4): 2.29; (5)ACD/BCF (pH 5.5): 1.00; (6)ACD/BCF (pH 7.4): 15.29; (7)ACD/KOC (pH 5.5): 3.15; (8)ACD/KOC (pH 7.4): 100.11; (9)#H bond acceptors: 2; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 6; (12)Polar Surface Area: 12.47 Å2; (13)Flash Point: 101.5 °C; (14)Enthalpy of Vaporization: 58.76 kJ/mol; (15)Boiling Point: 343.7 °C at 760 mmHg; (16)Vapour Pressure: 6.9E-05 mmHg at 25 °C.

When you are dealing with this chemical, you should be very careful. This chemical may cause damage to health. It is harmful if swallowed. Therefore, you should wear suitable protective clothing.

You can still convert the following datas into molecular structure:
(1) SMILES: Cl.O(CCN(C)C)C(c1ccccc1)c2ccccc2
(2) 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
(3) InChIKey: PCHPORCSPXIHLZ-UHFFFAOYSA-N

The toxicity data is as follows:

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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