Amantadine Hydrochloride

HCID 64150CAS 665-66-7

Basic information

Standard SMILES
Cl.NC12CC3CC(CC(C3)C1)C2
InChIKey
WOLHOYHSEKDWQH-UHFFFAOYSA-N
Molecular formula
C10H17N.ClH
Average molar mass
187.71 g/mol
Monoisotopic mass
187.11277726

Overview

Amantadine Hydrochloride can cause developmental toxicity according to state or federal government labeling requirements.

Names & identifiers

Preferred name
Amantadine Hydrochloride
IUPAC
adamantan-1-amine;hydrochloride

Names & synonyms

Amantadine hydrochloride665-66-71-Adamantanamine hydrochlorideAmantadine HCl1-Aminoadamantane hydrochlorideAdamantanamine hydrochlorideMantadix1-Adamantylamine hydrochlorideOsmolexExp-105-1LysovirMantadine
Show more names
NSC-83653M6Q1EO9TD0Tricyclo(3.3.1.1(sup 3,7))decan-1-amine, hydrochlorideNSC83653CHEBI:2619Osmolex erRefChem:54147Hydrochloride, Amantadine

Database identifiers

CAS
665-66-7
PubChem CID
64150
DTXSID
DTXSID50874031
ChEMBL
CHEMBL1569
UNII
M6Q1EO9TD0
EC Number
211-560-2

Properties

Computed structural properties

Topological polar surface area
26 Ų
Hydrogen bond donors
2
Hydrogen bond acceptors
1
Rotatable bonds
0
Heavy atoms
12

Experimental & physicochemical properties

Human Drugs · 3 items

Breast Feeding; Lactation; Milk, Human; Anti-Infective Agents; Antiparkinson Agents; Antiviral Agents; Dopamine Agents

FDA approved drugs -> Active ingredient

FDA approved drugs -> Active ingredient

Physical DescriptionDry Powder
Collision Cross Section138.6 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

Safety & regulation

GHS classification

GHS Classification · 4 items

Danger

H302 (99.5%): Harmful if swallowed [Warning Acute toxicity, oral]

P203, P260, P261, P264, P264+P265, P270, P271, P273, P280, P301+P317, P301+P330+P331, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P318, P319, P321, P330, P363, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 210 reports by companies from 11 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory Information · 5 items

Chemical: Tricyclo[3.3.1.13,7]decan-1-amine, hydrochloride

Hazard Traits - Developmental Toxicity

Tricyclo[3.3.1.13,7]decan-1-amine, hydrochloride (1:1) is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Tricyclo[3.3.1.13,7]decan-1-amine, hydrochloride (1:1) are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

REACH registered substance: Amantadine hydrochloride (EC: 211-560-2)

1-Adamantane ammonium chloride: Does not have an individual approval but may be used under an appropriate group standard

Hazard Classes and CategoriesAcute Tox. 4 (99.5%)

Toxicology

Treatment · 1 item

There is no specific antidote for an overdose of Amantadine. However, slowly administered intravenous physostigmine in 1 and 2 mg doses in an adult2 at 1- to 2-hour intervals and 0.5 mg doses in a child3 at 5- to 10-minute intervals up to a maximum of 2 mg/hour have been reported to be effective in the control of central nervous system toxicity caused by amantadine hydrochloride. For acute overdosing, general supportive measures should be employed along with immediate gastric lavage or induction of emesis. Fluids should be forced, and if necessary, given intravenously. The pH of the urine has been reported to influence the excretion rate of Amantadine. (L1744)

Health Effects · 1 item

Acute overdosage of amantadine has resulted in cardiac dysfunction (e.g., arrhythmia, tachycardia, hypertension); pulmonary edema and respiratory distress (including adult respiratory distress syndrome); renal dysfunction (e.g., increased BUN, decreased creatinine clearance, renal insufficiency); or CNS toxicity (e.g., insomnia, anxiety, psychotic reactions, lethargy, somnolence, coma). Hyperthermia also has occurred with amantadine overdosage. In addition, seizures may be exacerbated in patients with a history of a seizure disorder (A620).

Exposure RoutesInhalation. Amantadine is well absorbed orally from the gastrointestinal tract.
Toxicity Summary · 1 item

The mechanism of its antiparkinsonic effect is not fully understood, but it appears to be releasing dopamine from the nerve endings of the brain cells, together with stimulation of norepinephrine response. It also has NMDA receptor antagonistic effects. The antiviral mechanism seems to be unrelated. The drug interferes with a viral protein, M2 (an ion channel), which is needed for the viral particle to become "uncoated" once it is taken inside the cell by endocytosis.

Signs and Symptoms · 1 item

Deaths have been reported from overdose with amantadine. The lowest reported acute lethal dose was 2 grams. Drug overdose has resulted in cardiac, respiratory, renal or central nervous system toxicity. Cardiac dysfunction includes arrhythmia, tachycardia and hypertension. Pulmonary edema and respiratory distress (including ARDS) have been reported. Renal dysfunction including increased BUN, decreased creatinine clearance and renal insufficiency can occur. Central nervous system effects that have been reported include insomnia, anxiety, aggressive behavior, hypertonia, hyperkinesia, tremor, confusion, disorientation, depersonalization, fear, delirium, hallucination, psychotic reactions, lethargy, somnolence and coma. Seizures may be exacerbated in patients with prior history of seizure disorders. Hyperthermia has also been observed in cases where a drug overdose has occurred.

Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).

Chemistry & industry

Pharmacology

Metabolism/Metabolites · 1 item

No appreciable metabolism, although negligible amounts of an acetyl metabolite have been identified. Amantadine is well absorbed orally from the gastrointestinal tract. The mechanism of its antiparkinsonic effect is not fully understood, but it appears to be releasing dopamine from the nerve endings of the brain cells, together with stimulation of norepinephrine response. The antiviral mechanism seems to be unrelated. The drug interferes with a viral protein, M2 (an ion channel), which is needed for the viral particle to become "uncoated" once it is taken inside the cell by endocytosis. Metabolites are excreted in the urine (A308). Route of Elimination: It is primarily excreted unchanged in the urine by glomerular filtration and tubular secretion. Half Life: Mean half-lives ranged from 10 to 14 hours, however renal function impairment causes a severe increase in half life to 7 to 10 days.

FDA Pharmacological Classification · 4 items

AMANTADINE HCL

M2 Protein Inhibitors [MoA]; Influenza A M2 Protein Inhibitor [EPC]

AMANTADINE HYDROCHLORIDE

Influenza A M2 Protein Inhibitor [EPC]; M2 Protein Inhibitors [MoA]

MeSH Pharmacological Classification · 4 items

Agents used in the treatment of Parkinson's disease. The most commonly used drugs act on the dopaminergic system in the striatum and basal ganglia or are centrally acting muscarinic antagonists.

Agents used in the prophylaxis or therapy of VIRUS DISEASES. Some of the ways they may act include preventing viral replication by inhibiting viral DNA polymerase; binding to specific cell-surface receptors and inhibiting viral penetration or uncoating; inhibiting viral protein synthesis; or blocking late stages of virus assembly.

Any drugs that are used for their effects on dopamine receptors, on the life cycle of dopamine, or on the survival of dopaminergic neurons.

A subclass of analgesic agents that typically do not bind to OPIOID RECEPTORS and are not addictive. Many non-narcotic analgesics are offered as NONPRESCRIPTION DRUGS.

Uses & manufacturing

UsesFor the chemoprophylaxis, prophylaxis, and treatment of signs and symptoms of infection caused by various strains of influenza A virus. Also for the treatment of parkinsonism and drug-induced extrapyramidal reactions (A308).
U.S. Production2021: 250,000 - <550,000 lb
Industry UsesProcessing aids not otherwise specified
General Manufacturing Information · 2 items

All Other Basic Organic Chemical Manufacturing

Tricyclo[3.3.1.13,7]decan-1-amine, hydrochloride (1:1): ACTIVE

Related reactions

25 records

Linked notes

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