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147-24-0

Basic Information
CAS No.: 147-24-0
Name: Diphenhydramine hydrochloride
Molecular Structure:
Molecular Structure of 147-24-0 (Diphenhydramine hydrochloride)
Formula: C17H21NO.HCl
Molecular Weight: 291.85
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;
EINECS: 205-687-2
Density: 1.024 g/cm3
Melting Point: 168-172 °C
Boiling Point: 343.7 °C at 760 mmHg
Flash Point: 101.5 °C
Solubility: 1000 g/L in water
Appearance: White crystalline powder
Hazard Symbols: HarmfulXn
Risk Codes: 22
Safety: 36
Transport Information:
PSA: 12.47000
LogP: 4.15620
Synthetic route
17616-20-5

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

147-24-0

diphenhydramine hydrochloride

90-99-3

diphenylchloromethane

147-24-0

diphenhydramine hydrochloride

108-01-0

2-(N,N-dimethylamino)ethanol

90-99-3

diphenylchloromethane

A

147-24-0

diphenhydramine hydrochloride

B

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.;
108-01-0

2-(N,N-dimethylamino)ethanol

90-99-3

diphenylchloromethane

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
58-73-1

2-diphenylmethoxy-N,N-dimethylethanamine

147-24-0

diphenhydramine hydrochloride

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

bromobenzene

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
108-01-0

2-(N,N-dimethylamino)ethanol

776-74-9

Bromodiphenylmethane

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℃;
100-52-7

benzaldehyde

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
91-01-0

1,1-Diphenylmethanol

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
147-24-0

diphenhydramine hydrochloride

31121-93-4

sodium 2-(4-isobutylphenyl)propionate

diphenhydraminium ibuprofenate

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

diphenhydramine hydrochloride

577-11-7

sodium docusate

diphenhydraminium docusate

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

diphenhydramine hydrochloride

A

108-01-0

2-(N,N-dimethylamino)ethanol

B

91-01-0

1,1-Diphenylmethanol

C

90-99-3

diphenylchloromethane

Conditions
ConditionsYield
With diclazuril In chloroform-d1 Product distribution;
147-24-0

diphenhydramine hydrochloride

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 molybdate

147-24-0

diphenhydramine hydrochloride

(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;
147-24-0

diphenhydramine hydrochloride

617-45-8

aspartic Acid

diphenhydramine aspartic acid salt

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

diphenhydramine hydrochloride

91-01-0

1,1-Diphenylmethanol

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

diphenhydramine hydrochloride

A

64-18-6

formic acid

B

471-47-6

oxamic acid

C

144-62-7

oxalic acid

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

saccharin sodium salt

147-24-0

diphenhydramine hydrochloride

diphenhydramine saccharinate

Conditions
ConditionsYield
In water Cooling;

saccharin sodium salt hydrate

147-24-0

diphenhydramine hydrochloride

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
55589-62-3

potassium acesulfame

147-24-0

diphenhydramine hydrochloride

diphenhydramine acesulfame

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

diphenhydramine hydrochloride

3922-74-5

Diphenhydramine-N-oxide

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

diphenhydramine hydrochloride

A

119-61-9

benzophenone

B

101-81-5

Diphenylmethane

Conditions
ConditionsYield
With dolomite In water at 4℃; for 1.25h; Kinetics; Reagent/catalyst; Solvent; Irradiation; Inert atmosphere;
Raw Materials
90-99-3
108-01-0
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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). .

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.