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Diphenhydramine

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Name

Diphenhydramine

EINECS 200-396-7
CAS No. 58-73-1 Density 1.025 g/cm3
PSA 12.47000 LogP 3.35420
Solubility N/A Melting Point 167-172 °C
Formula C17H21NO Boiling Point 343.734 °C at 760 mmHg
Molecular Weight 255.36 Flash Point 101.53 °C
Transport Information N/A Appearance clear light yellow liquid
Safety Risk Codes N/A
Molecular Structure Molecular Structure of 58-73-1 (Diphenhydramine) Hazard Symbols N/A
Synonyms

Ethanamine, 2-(diphenylmethoxy)-N,N-dimethyl-;Ethylamine,2-(diphenylmethoxy)-N,N-dimethyl- (7CI,8CI);2-(Diphenylmethoxy)-N,N-dimethylethylamine;Benzhydramine;Dimedrol base;FAR 90X2;N-[2-(Diphenylmethoxy)ethyl]-N,N-dimethylamine;O-Benzhydryldimethylaminoethanol;Probedryl;a-(2-Dimethylaminoethoxy)diphenylmethane;b-Dimethylaminoethylbenzhydrylether;N-[2-(Diphenylmethoxy)ethyl]-N,N-dimethylamine;

Article Data 39

Diphenhydramine Synthetic route

108-01-0

2-(N,N-dimethylamino)ethanol

91-01-0

1,1-Diphenylmethanol

58-73-1

2-diphenylmethoxy-N,N-dimethylethanamine

Conditions
ConditionsYield
With di(n-butyl)tin oxide; 3-methyl-1-propylimidazolium bromide In neat (no solvent) for 8h; Reagent/catalyst; Reflux;98%
108-01-0

2-(N,N-dimethylamino)ethanol

90-99-3

diphenylchloromethane

58-73-1

2-diphenylmethoxy-N,N-dimethylethanamine

Conditions
ConditionsYield
With sodium hydroxide In water at 175℃; under 12929 Torr; for 0.266667h;93%
In acetonitrile at 200℃; for 0.0833333h; Temperature;
91-01-0

1,1-Diphenylmethanol

107-99-3

2-(dimethylamino)ethyl chloride

58-73-1

2-diphenylmethoxy-N,N-dimethylethanamine

Conditions
ConditionsYield
With sodium hydride In benzene 1. room temperature, 90 min; 2. 60 deg C, 30 min;92%
67-56-1

methanol

17471-10-2

Desmethyldiphenhydramine

58-73-1

2-diphenylmethoxy-N,N-dimethylethanamine

Conditions
ConditionsYield
With aluminum (III) chloride; water In acetonitrile at 20℃; Irradiation;88%
26926-47-6

2-diphenylmethoxyethanol

124-40-3

dimethyl amine

A

58-73-1

2-diphenylmethoxy-N,N-dimethylethanamine

B

1119277-62-1

2-(dimethylamino)-3,3-diphenylpropan-1-ol

Conditions
ConditionsYield
With [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; bis[2-(diphenylphosphino)phenyl] ether In toluene at 20℃; Inert atmosphere; Reflux;A 10%
B 67%
108-01-0

2-(N,N-dimethylamino)ethanol

(E)-1-benzhydryl-3-(1,3-dimethylimidazol-2-ylidene)triazene

58-73-1

2-diphenylmethoxy-N,N-dimethylethanamine

Conditions
ConditionsYield
With toluene-4-sulfonic acid at 60℃; for 36h;35%
41858-14-4

2-(Diphenylmethoxy)-N,N-dimethylacetamid

58-73-1

2-diphenylmethoxy-N,N-dimethylethanamine

Conditions
ConditionsYield
With lithium aluminium tetrahydride; diethyl ether
32669-06-0

1,1'-[(2-chloroethoxy)methylene]bis-benzene

124-40-3

dimethyl amine

58-73-1

2-diphenylmethoxy-N,N-dimethylethanamine

108-01-0

2-(N,N-dimethylamino)ethanol

776-74-9

Bromodiphenylmethane

58-73-1

2-diphenylmethoxy-N,N-dimethylethanamine

Conditions
ConditionsYield
With sodium carbonate; benzene at 120 - 125℃;
In acetonitrile at 200℃; for 0.166667h; Temperature;
In toluene for 20h; Williamson Ether Synthesis; Reflux;
108-01-0

2-(N,N-dimethylamino)ethanol

908093-98-1

diazodiphenylmethane

58-73-1

2-diphenylmethoxy-N,N-dimethylethanamine

Conditions
ConditionsYield
With benzene

Diphenhydramine Consensus Reports

Reported in EPA TSCA Inventory.

Diphenhydramine Specification

The Diphenhydramine, with the CAS registry number 58-73-1, is also known as N-[2-(Diphenylmethoxy)ethyl]-N,N-dimethylamine. Its EINECS number is 200-396-7. This chemical's molecular formula is C17H21NO and molecular weight is 255.35. What's more, its systematic name is 2-(Diphenylmethoxy)-N,N-dimethylethanamine. Its classification codes are: (1)Anesthetics; (2)Anesthetics, local; (3)Anti-allergic agents; (4)Antiemetics; (5)Autonomic Agents; (6)Central Nervous System Agents; (7)Central Nervous System Depressants; (8)Drug / Therapeutic Agent; (9)Gastrointestinal Agents; (10)Histamine Agents; (11)Histamine Antagonists; (12)Histamine H1 antagonists; (13)Human Data; (14)Hypnotics and Sedatives; (15)Mutation data; (16)Neurotransmitter Agents; (17)Peripheral Nervous System Agents; (18)Reproductive Effect; (19)Sensory System Agents. This chemical is a first generation (typical) antihistamine used to treat a number of conditions including: allergic symptoms and itchiness, the common cold, insomnia, motion sickness, and extrapyramidal symptoms. It has a histamine H1 antagonist used as an antiemetic, antitussive, for dermatoses and pruritus, for hypersensitivity reactions, as a hypnotic, an antiparkinson, and as an ingredient in common cold preparations. It has some undesired antimuscarinic and sedative effects. 

Physical properties of Diphenhydramine are: (1)ACD/LogP: 2.997; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0.13; (4)ACD/LogD (pH 7.4): 1.63; (5)ACD/BCF (pH 5.5): 1.00; (6)ACD/BCF (pH 7.4): 4.78; (7)ACD/KOC (pH 5.5): 1.37; (8)ACD/KOC (pH 7.4): 43.56; (9)#H bond acceptors: 2; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 6; (12)Polar Surface Area: 12.47 Å2; (13)Index of Refraction: 1.551; (14)Molar Refractivity: 79.568 cm3; (15)Molar Volume: 249.226 cm3; (16)Polarizability: 31.543×10-24cm3; (17)Surface Tension: 38.67 dyne/cm; (18)Density: 1.025 g/cm3; (19)Flash Point: 101.53 °C; (20)Enthalpy of Vaporization: 58.762 kJ/mol; (21)Boiling Point: 343.734 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25°C.

Preparation: this chemical can be prepared by (2-chloro-ethyl)-dimethyl-amine and diphenylmethanol at the room temperature. This reaction will need reagent NaH and solvent benzene with the reaction time of 1.5 hours. The yield is about 92%.

Diphenhydramine can be prepared by (2-chloro-ethyl)-dimethyl-amine and diphenylmethanol at the room temperature

Uses of Diphenhydramine: it can be used to produce C22H28NO3(1+)·Cl(1-). It will need reagent acetone. The yield is about 80%.

Diphenhydramine can be used to produce C22H28NO3(1+)·Cl(1-)

You can still convert the following datas into molecular structure:
(1)SMILES: O(CCN(C)C)C(c1ccccc1)c2ccccc2
(2)Std. InChI: InChI=1S/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
(3)Std. InChIKey: ZZVUWRFHKOJYTH-UHFFFAOYSA-N

The toxicity data is as follows:  

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
guinea pig LD50 intraperitoneal 75mg/kg (75mg/kg)   Therapie. Vol. 28, Pg. 767, 1973.
guinea pig LD50 subcutaneous 56mg/kg (56mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 4, Pg. 189, 1954.
human TDLo oral 714ug/kg (.714mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: ALTERATION OF OPERANT CONDITIONING

BEHAVIORAL: CHANGES IN PSYCHOPHYSIOLOGICAL TESTS
Drug Development Research. Vol. 27, Pg. 33, 1992.
man LDLo unreported 7353ug/kg (7.353mg/kg)   "Poisoning; Toxicology, Symptoms, Treatments," 2nd ed., Arena, J.M., Springfield, IL, C.C. Thomas, 1970Vol. 2, Pg. 73, 1970.
mouse LD50 intraperitoneal 56mg/kg (56mg/kg)   Yakkyoku. Pharmacy. Vol. 34, Pg. 27, 1983.
mouse LD50 intravenous 29mg/kg (29mg/kg) BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Russian Pharmacology and Toxicology Vol. 40, Pg. 42, 1977.
mouse LD50 oral 160mg/kg (160mg/kg)   Chimica Therapeutica. Vol. 7, Pg. 224, 1972.
mouse LD50 subcutaneous 50mg/kg (50mg/kg)   Bollettino Chimico Farmaceutico. Vol. 111, Pg. 293, 1972.
rat LD50 intraperitoneal 280mg/kg (280mg/kg)   Indian Journal of Medical Research. Vol. 59, Pg. 614, 1971.
rat LD50 intravenous 42mg/kg (42mg/kg)   Drugs in Japan Vol. -, Pg. 476, 1990.
rat LD50 oral 390mg/kg (390mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)
Russian Pharmacology and Toxicology Vol. 40, Pg. 42, 1977.
rat LD50 subcutaneous 474mg/kg (474mg/kg)   Drugs in Japan Vol. -, Pg. 476, 1990.
women TDLo multiple routes 793ug/kg/1H-I (.793mg/kg) BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)

BEHAVIORAL: ATAXIA

BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"
Pharmacotherapy Vol. 14, Pg. 492, 1994.
women TDLo oral 30mg/kg (30mg/kg) BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"

CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP

VASCULAR: BP ELEVATION NOT CHARACTERIZED IN AUTONOMIC SECTION
Deutsche Medizinische Wochenschrift. Vol. 120, Pg. 1695, 1995.
women TDLo oral 82mg/kg (82mg/kg) BEHAVIORAL: MUSCLE WEAKNESS

BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"

BEHAVIORAL: COMA
Toxicology Letters. Vol. 109(Suppl,
women TDLo oral 178mg/kg (178mg/kg) CARDIAC: EKG CHANGES NOT DIAGNOSTIC OF ABOVE

VASCULAR: BP ELEVATION NOT CHARACTERIZED IN AUTONOMIC SECTION

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Annals of Emergency Medicine. Vol. 33, Pg. 104, 1999.

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