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Substance Name: Amantadine [INN:BAN]
RN: 768-94-5
UNII: BF4C9Z1J53
InChIKey: DKNWSYNQZKUICI-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.
  • 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

Molecular Formula

  • C10-H17-N

Molecular Weight

  • 151.251
 

Classification Codes

  • Analgesics
  • Analgesics, Non-Narcotic
  • Anti-Dyskinesia Agents
  • Anti-Infective Agents
  • Antiparkinson Agents
  • Antiviral Agents
  • Central Nervous System Agents
  • Dopamine Agents
  • Drug / Therapeutic Agent
  • Mutation Data
  • Neurotransmitter Agents
  • Peripheral Nervous System Agents
  • Sensory System Agents

Names and Synonyms

Name of Substance

  • Amantadine
  • Amantadine [INN:BAN]

MeSH Heading

  • Amantadine

Synonyms

  • 1-Adamantanamine
  • 1-Adamantylamine
  • 1-Aminoadamantane
  • 1-Aminotricyclo(3.3.1.1(sup 3,7))decane
  • Adamantanamine
  • Adamantylamine
  • Amantadina
  • Amantadina [INN-Spanish]
  • Amantadine
  • Amantadinum
  • Amantadinum [INN-Latin]
  • Aminoadamantane
  • BRN 2204333
  • EC 212-201-2
  • EINECS 212-201-2
  • Gocovri
  • HSDB 3202
  • NSC 341865
  • Pk-merz
  • Tricyclo(3.3.1.1(3,7))-decan-1-amine
  • Tricyclo(3.3.1.1(sup 3.7))decan-1-amine
  • UNII-BF4C9Z1J53

Systematic Names

  • 1-Adamantanamine (8CI)
  • Amantadine
  • Tricyclo(3.3.1.1(sup 3,7))decan-1-amine
  • Tricyclo(3.3.1.13,7)decan-1-amine

Registry Numbers

CAS Registry Number

  • 768-94-5

FDA UNII

  • BF4C9Z1J53

Other Registry Number

  • 744952-70-3

Related Registry Number

  • 665-66-7 (hydrochloride)

System Generated Number

  • 0000768945

Structure Descriptors

InChI

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

InChIKey

DKNWSYNQZKUICI-UHFFFAOYSA-N

Smiles

C1C2CC3CC1CC(C3)(C2)N

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 245mg/kg (245mg/kg) BEHAVIORAL: ATAXIA

BEHAVIORAL: TREMOR
Drugs of the Future. Vol. 5, Pg. 557, 1980.
mouse LD50 oral 700mg/kg (700mg/kg)   British UK Patent Application. Vol. #2070004,
quail LD50 oral > 316mg/kg (316mg/kg)   Ecotoxicology and Environmental Safety. Vol. 6, Pg. 149, 1982.
rat LD50 intraperitoneal 223mg/kg (223mg/kg)   British UK Patent Application. Vol. #2070004,
rat LD50 oral 900mg/kg (900mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: TREMOR
Journal de Pharmacologie. Vol. 9, Pg. 121, 1978.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 180 deg C   EXP
log P (octanol-water) 2.44 (none)   EXP
Water Solubility 6290 mg/L 25 EST
Vapor Pressure 0.132 mm Hg 25 EST
Henry's Law Constant 8.32E-06 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 4.03E-11 cm3/molecule-sec 25 EST

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