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Substance Name: Diphenhydramine [INN:BAN:JAN]
RN: 58-73-1
UNII: 8GTS82S83M
InChIKey: ZZVUWRFHKOJYTH-UHFFFAOYSA-N

Note

  • 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.

Molecular Formula

  • C17-H21-N-O

Molecular Weight

  • 255.359
 

Classification Codes

  • Anesthetics
  • Anesthetics, Local
  • Anti-Allergic Agents
  • Antiemetics
  • Autonomic Agents
  • Central Nervous System Agents
  • Central Nervous System Depressants
  • Drug / Therapeutic Agent
  • Gastrointestinal Agents
  • Histamine Agents
  • Histamine Antagonists
  • Histamine H1 Antagonists
  • Human Data
  • Hypnotics and Sedatives
  • Mutation Data
  • Neurotransmitter Agents
  • Peripheral Nervous System Agents
  • Reproductive Effect
  • Sensory System Agents
  • Sleep Aids, Pharmaceutical

Names and Synonyms

Name of Substance

  • Diphenhydramine
  • Diphenhydramine [INN:BAN:JAN]

MeSH Heading

  • Diphenhydramine

Synonyms

  • 2-(Benzhydryloxy)-N,N-dimethylethylamine
  • 2-(Diphenylmethoxy)-N,N-dimethylethylamine
  • 4-10-00-00125 (Beilstein Handbook Reference)
  • Alledryl
  • Allergical
  • alpha-(2-Dimethylaminoethoxy)diphenylmethane
  • Amidryl
  • Antistominum
  • Antomin
  • Automin
  • Bagodryl
  • Baramine
  • Benachlor
  • Benadrin
  • Benapon
  • Benodin
  • Benodine
  • Benylan
  • Benzantine
  • Benzhydramine
  • Benzhydraminum
  • Benzhydril
  • Benzhydroamina
  • beta-Dimethylamino-aethyl-benzhydryl-aether
  • beta-Dimethylamino-aethyl-benzhydryl-aether [German]
  • beta-Dimethylaminoethanol diphenylmethyl ether
  • beta-Dimethylaminoethylbenzhydrylether
  • Betramin
  • BRN 1914136
  • CCRIS 1959
  • Dabylen
  • Debendrin
  • Dermistina
  • Dermodrin
  • Desentol
  • Diabenyl
  • Diabylen
  • Dibondrin
  • Difedryl
  • Difenhidramina
  • Difenhidramina [INN-Spanish]
  • Difenhydramin
  • Difenidramina
  • Difenidramina [Italian]
  • Dihidral
  • Dimedrol base
  • Diphantine
  • Diphenhydramine
  • Diphenhydraminum
  • Diphenhydraminum [INN-Latin]
  • Drylistan
  • Dylamon
  • EC 200-396-7
  • EINECS 200-396-7
  • Etanautine
  • Ethanamine, 2-(diphenylmethoxy)-N,N-dimethyl-
  • Ethylamine, N,N-dimethyl-2-(diphenylmethoxy)-
  • FAR 90X2
  • Histaxin
  • HSDB 3066
  • Hyadrine
  • Ibiodral
  • Medidryl
  • Mephadryl
  • N-(2-(Diphenylmethoxy)ethyl)-N,N-dimethylamine
  • N-(Benzhydryloksy-etylo)dwumetyloamina
  • N-(Benzhydryloksy-etylo)dwumetyloamina [Polish]
  • Nausen
  • Novamina
  • O-Benzhydryldimethylaminoethanol
  • PM 255
  • Probedryl
  • Rigidyl
  • S51
  • Syntedril
  • UNII-8GTS82S83M

Systematic Names

  • Diphenhydramine
  • Ethanamine, 2-(diphenylmethoxy)-N,N-dimethyl-
  • Ethylamine, 2-(diphenylmethoxy)-N,N-dimethyl-

Registry Numbers

CAS Registry Number

  • 58-73-1

FDA UNII

  • 8GTS82S83M

Related Registry Numbers

  • 147-24-0 (hydrochloride)
  • 88637-37-0 (citrate (1:1))

System Generated Number

  • 0000058731

Structure Descriptors

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

InChIKey

ZZVUWRFHKOJYTH-UHFFFAOYSA-N

Smiles

C(c1ccccc1)(c1ccccc1)OCCN(C)C

Toxicity

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 (0.714mg/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 (0.793mg/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.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 168 deg C   EXP
pKa Dissociation Constant 8.98 (none)   EXP
log P (octanol-water) 3.27 (none)   EXP
Water Solubility 3060 mg/L 37 EXP
Vapor Pressure 3.70E-05 mm Hg 25 EST
Henry's Law Constant 3.70E-09 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 1.27E-10 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.