Skip Navigation
ChemIDplus LiteBrowseAdvanced

Substance Name: Amantadine hydrochloride [USAN:USP:JAN]
RN: 665-66-7
UNII: M6Q1EO9TD0
InChIKey: WOLHOYHSEKDWQH-UHFFFAOYSA-N

Notes

  • An antiviral that is used in the prophylactic or symptomatic treatment of influenza A. It is also used as an antiparkinsonian agent, to treat extrapyramidal reactions, and for postherpetic neuralgia. The mechanisms of its effects in movement disorders are not well understood but probably reflect an increase in synthesis and release of dopamine, with perhaps some inhibition of dopamine uptake.

    See CDC 2009 H1N1 Flu (Swine Flu) Antiviral Drugs at CDC Antiviral Drugs
  • See CDC 2009 H1N1 Flu (Swine Flu) Antiviral Drugs at CDC Antiviral Drugs

Molecular Formula

  • C10-H17-N.Cl-H

Molecular Weight

  • 187.7122
 

Classification Codes

  • Antiviral
  • Antiviral (COVID-19)
  • Drug / Therapeutic Agent
  • Human Data
  • Reproductive Effect

Names and Synonyms

Name of Substance

  • Amantadine hydrochloride [USAN:USP:JAN]

Synonyms

  • 1-Adamantanamine hydrochloride
  • 1-Adamantylamine hydrochloride
  • 1-Aminoadamantane hydrochloride
  • 1-Aminoadamantene hydrochloride
  • Adamantanamine hydrochloride
  • Adamantine hydrochloride
  • Adamantylamine hydrochloride
  • ADS-5102
  • AI3-52211
  • Amantadine HCl
  • Amantadine hydrochloride
  • Amantan
  • Amazolon
  • Aminoadamantane hydrochloride
  • EC 211-560-2
  • EINECS 211-560-2
  • EXP 105-1
  • EXP-105-1
  • GP 38026
  • Influenol
  • Midantan
  • Midantane
  • Mydantane
  • NSC 83653
  • Symadine
  • Symmetrel
  • Trivaline
  • UNII-M6Q1EO9TD0
  • Virasol
  • Viregyt
  • Virofral
  • Virosol

Systematic Names

  • 1-Adamantanamine, hydrochloride
  • Amantadine hydrochloride
  • Tricyclo(3.3.1.1(sup 3,7))decan-1-amine, hydrochloride (9CI)
  • Tricyclo(3.3.1.13,7)decan-1-amine, hydrochloride
  • Tricyclo(3.3.1.13,7)decan-1-amine, hydrochloride (1:1)

Superlist Name

  • Amantadine hydrochloride

Registry Numbers

CAS Registry Number

  • 665-66-7

FDA UNII

  • M6Q1EO9TD0

Other Registry Number

  • 13878-11-0

Related Registry Number

  • 768-94-5 (Parent)

System Generated Number

  • 0000665667

Molecular Formulas

Molecular Formula

  • C10-H17-N.Cl-H

Molecular Formula Fragments

  • C10-H17-N
  • Cl-H
  • COMPONENT

Structure Descriptors

InChI

InChI=1S/C10H17N.ClH/c11-10-4-7-1-8(5-10)3-9(2-7)6-10;/h7-9H,1-6,11H2;1H

InChIKey

WOLHOYHSEKDWQH-UHFFFAOYSA-N

Smiles

Cl.NC12CC3CC(CC(C3)C1)C2

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD50 intravenous 37mg/kg (37mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BEHAVIORAL: TREMOR
Toxicology and Applied Pharmacology. Vol. 15, Pg. 642, 1969.
guinea pig LD50 oral 360mg/kg (360mg/kg) BEHAVIORAL: TREMOR

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
Toxicology and Applied Pharmacology. Vol. 15, Pg. 642, 1969.
man LDLo oral 28571ug/kg (28.571mg/kg) LUNGS, THORAX, OR RESPIRATION: ACUTE PULMONARY EDEMA

BEHAVIORAL: TOXIC PSYCHOSIS

BLOOD: HEMORRHAGE
American Journal of Psychiatry. Vol. 145, Pg. 267, 1988.
man LDLo oral 286mg/kg (286mg/kg) BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"

BEHAVIORAL: TOXIC PSYCHOSIS

BEHAVIORAL: EXCITEMENT
American Journal of Psychiatry. Vol. 145, Pg. 267, 1988.
man TDLo oral 13mg/kg/5D-I (13mg/kg) BEHAVIORAL: EUPHORIA

BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"
American Journal of Psychiatry. Vol. 143, Pg. 1170, 1985.
man TDLo oral 24mg/kg/1D-I (24mg/kg) BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"

BEHAVIORAL: EXCITEMENT
Annals of Emergency Medicine. Vol. 19, Pg. 668, 1990.
mouse LD50 intraperitoneal 198mg/kg (198mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 19, Pg. 164, 1988.
mouse LD50 intravenous 95mg/kg (95mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 19, Pg. 164, 1988.
mouse LD50 oral 700mg/kg (700mg/kg) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: TREMOR
Toxicology and Applied Pharmacology. Vol. 15, Pg. 642, 1969.
mouse LD50 subcutaneous 290mg/kg (290mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 19, Pg. 164, 1988.
rat LD50 intraperitoneal 150mg/kg (150mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES

BEHAVIORAL: TREMOR
Toxicology and Applied Pharmacology. Vol. 15, Pg. 642, 1969.
rat LD50 intravenous 90mg/kg (90mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 19, Pg. 164, 1988.
rat LD50 oral 800mg/kg (800mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 19, Pg. 164, 1988.
rat LD50 subcutaneous 500mg/kg (500mg/kg)   Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 13, Pg. 1269, 1971.
women LDLo oral 50mg/kg (50mg/kg) BEHAVIORAL: COMA

CARDIAC: PULSE RATE

CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP
American Journal of Medicine. Vol. 77, Pg. 388, 1984.