ContaminantDB: Amantadine

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (9)XML

Record Information

Version

1.0

Creation Date

2009-07-05 03:00:16 UTC

Update Date

2026-05-14 16:52:42 UTC

Accession Number

CHEM002086

Identification

Common Name

Amantadine

Class

Small Molecule

Description

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. [PubChem]

Contaminant Sources

EAFUS Chemicals
HMDB Contaminants - Urine
HPV EPA Chemicals
STOFF IDENT Compounds
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Amine
Analgesic, Non-Narcotic
Antiparkinson Agent
Antiviral Agent
Dopamine Agent
Drug
Human Neurotoxin
Metabolite
Organic Compound
PMT
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1-Adamantanamine	ChEBI
1-Adamantylamine	ChEBI
1-Aminoadamantane	ChEBI
Amantadina	ChEBI
Amantadinum	ChEBI
Amantidine	ChEBI
Aminoadamantane	ChEBI
Tricyclo[3.3.1.1(3,7)]decan-1-amine	ChEBI
Tricyclo[3.3.1.1(3,7)]decan-1-ylamine	ChEBI
Tricyclo[3.3.1.1(3,7)]decane-1-amine	ChEBI
Viregyt	ChEBI
Virosol	ChEBI
Adamantamine	HMDB
Adamantanamine	HMDB
Adamantylamine	HMDB
Amantadine base	HMDB
Amantadine HCL	HMDB
Amantadine hydrochloride	HMDB
AL, amantadin	HMDB
Adekin	HMDB
Alliance brand OF amantadine hydrochloride	HMDB
Aman	HMDB
Amanta-sulfate-azu	HMDB
AmantaHCIAZU	HMDB
Amantadin al	HMDB
Amantadin neuraxpharm	HMDB
Amantadin ratiopharm	HMDB
Amantadin-neuraxpharm	HMDB
Amantadina juventus	HMDB
Amantadinratiopharm	HMDB
Desitin brand OF amantadine hydrochloride	HMDB
Infecto-flu	HMDB
Krewel brand OF amantadine hydrochloride	HMDB
Merz brand OF amantadine sulfate	HMDB
Novartis brand OF amantadine hydrochloride	HMDB
PMSAmantadine	HMDB
Solvay brand OF amantadine hydrochloride	HMDB
Stada brand OF amantadine hydrochloride	HMDB
Symmetrel	HMDB
Tregor	HMDB
AbZ brand OF amantadine hydrochloride	HMDB
Aliud brand OF amantadine sulfate	HMDB
Amanta-hci-azu	HMDB
Amantadina llorente	HMDB
Azupharma brand OF amantadine hydrochloride	HMDB
Azupharma brand OF amantadine sulfate	HMDB
Cerebramed	HMDB
Gen amantadine	HMDB
GenAmantadine	HMDB
Hexal brand OF amantadine sulfate	HMDB
Infecto flu	HMDB
Infectopharm brand OF amantadine hydrochloride	HMDB
Neuro hexal brand OF amantadine sulfate	HMDB
PMS-Amantadine	HMDB
Pharmascience brand OF amantadine hydrochloride	HMDB
Symadine	HMDB
Thiemann brand OF amantadine hydrochloride	HMDB
AZU, amantadin	HMDB
Amanta	HMDB
Amanta hci azu	HMDB
Amantadin stada	HMDB
Amantadin-ratiopharm	HMDB
Gen-amantadine	HMDB
Genpharm brand OF amantadine hydrochloride	HMDB
Hormosan brand OF amantadine sulfate	HMDB
Hydrochloride, amantadine	HMDB
Juventus, amantadina	HMDB
Mantadix	HMDB
Stada brand OF amantadine sulfate	HMDB
Stada, amantadin	HMDB
Sulfate, amantadine	HMDB
1 Aminoadamantane	HMDB
Amanta sulfate azu	HMDB
Amantasulfateazu	HMDB
Amantadin azu	HMDB
Amantadine sulfate	HMDB
Amantadinneuraxpharm	HMDB
Amixx	HMDB
Ciba geigy brand OF amantadine hydrochloride	HMDB
Ciba-geigy brand OF amantadine hydrochloride	HMDB
Du pont brand OF amantadine hydrochloride	HMDB
Endantadine	HMDB
endo Brand OF amantadine hydrochloride	HMDB
InfectoFlu	HMDB
Infex	HMDB
Juventus brand OF amantadine hydrochloride	HMDB
Llorente brand OF amantadine hydrochloride	HMDB
Llorente, amantadina	HMDB
Midantan	HMDB
Orion brand OF amantadine hydrochloride	HMDB
PMS Amantadine	HMDB
Wiregyt	HMDB
Neuraxpharm brand OF amantadine sulfate	HMDB
Ratiopharm brand OF amantadine hydrochloride	HMDB

Chemical Formula

C₁₀H₁₇N

Average Molecular Mass

151.249 g/mol

Monoisotopic Mass

151.136 g/mol

CAS Registry Number

768-94-5

IUPAC Name

adamantan-1-amine

Traditional Name

amantadine

SMILES

NC12CC3CC(CC(C3)C1)C2

InChI Identifier

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

InChI Key

DKNWSYNQZKUICI-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as monoalkylamines. These are organic compounds containing an primary aliphatic amine group.

Kingdom

Organic compounds

Super Class

Organic nitrogen compounds

Class

Organonitrogen compounds

Sub Class

Amines

Direct Parent

Monoalkylamines

Alternative Parents

Substituents

Organopnictogen compound
Hydrocarbon derivative
Primary aliphatic amine
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

adamantanes (CHEBI:2618 )
primary aliphatic amine (CHEBI:2618 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Biological Roles

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

Hexakistetrahedral crystals by sublimation (4).

Experimental Properties

Property	Value
Melting Point	180-192°C
Boiling Point	Not Available
Solubility	6290 mg/L (freely soluble)

Predicted Properties

Property	Value	Source
Water Solubility	0.085 g/L	ALOGPS
logP	2.53	ALOGPS
logP	1.47	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Basic)	10.71	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	26.02 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	45.54 m³·mol⁻¹	ChemAxon
Polarizability	17.92 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-014i-1910000000-c4908efe87e5cdf2ba74	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-014i-1910000000-8b7366cc494bf757bb81	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-01b9-6910000000-e6fd5b29f51169a772e5	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-014i-1910000000-c4908efe87e5cdf2ba74	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-014i-1910000000-8b7366cc494bf757bb81	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-01b9-6910000000-e6fd5b29f51169a772e5	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0udi-0900000000-ffe93d952abd2a39e06e	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-0f79-0900000000-b3511c6e5de6fce544c6	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-0f79-0900000000-ca740a06e33d4850b211	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-000i-0900000000-f1084780a2940c5afd1b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-000i-0900000000-a083f7fdcbb679c2996a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-000i-2900000000-496b35f0cfba5aa930ed	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-000i-7900000000-e37809d5efe023b0382d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0udi-0900000000-1a8aac6647f0187ebdf9	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-000i-0900000000-88a4152a7398da21333c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-000i-1900000000-76e73b05fc9ac0bdc170	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-002u-9600000000-048cdcfd022184f574b6	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-004l-9000000000-8bc5ffed5487b0edffaf	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0udi-0900000000-4aa7b04aaac47d693e8d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0udr-0900000000-815d4b207b027466d755	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-000i-0900000000-7ce8af9197b4d35ecffd	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-000i-0900000000-278de51184b1c34ed88f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-000i-0900000000-1a9620db53d99baf9c05	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-000i-0900000000-1a9620db53d99baf9c05	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-0f79-1900000000-f49f767b2078c543faad	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-0f79-0900000000-ca740a06e33d4850b211	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udr-0900000000-9de5310f392d5fea9404	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udr-0900000000-8549fa2798ea74b6bfe9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-0900000000-1bbfc183d3445dfb5be9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0900000000-1da79c1934401c0e75b1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-0900000000-500c2b80938b31be9d7c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0udi-0900000000-6af1e4d2eb8132df1cf9	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0006-9100000000-44ff981fd5fa6c48df97	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Inhalation. Amantadine is well absorbed orally from the gastrointestinal tract.

Mechanism of Toxicity

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.

Metabolism

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 (1). 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.

Toxicity Values

LD50: 800 mg/kg (Oral, Rat) LD50: 700 mg/kg (Oral, Mouse)

Lethal Dose

The lowest reported acute lethal dose was 2 grams.

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

For 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 (1).

Minimum Risk Level

Not Available

Health Effects

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 (2).

Symptoms

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.

Treatment

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. (3)

Concentrations

Not Available

External Links

DrugBank ID

DB00915

HMDB ID

HMDB0015051

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID