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1-Adamantan-ammoniumchlorid

Amantadine Hydrochloride

HCID 64150
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Grundinformationen

CAS
665-66-7
Standard-SMILES
Cl.NC12CC3CC(CC(C3)C1)C2
InChIKey
WOLHOYHSEKDWQH-UHFFFAOYSA-N
Summenformel
C10H17N.ClH
Durchschnittliche Molmasse
187,71 g/mol
Monoisotopische Masse
187,11277726

Überblick

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

Namen und Bezeichner

Bevorzugter Name
Amantadine Hydrochloride
IUPAC
adamantan-1-amine;hydrochloride
Lokaler Name
1-Adamantan-ammoniumchlorid
Englischer Name
1-Adamantanamine hydrochloride
Summenformel
C10H18ClN
Molmasse
187.71

Namen und Synonyme

Amantadine hydrochloride665-66-71-Adamantanamine hydrochlorideAmantadine HCl1-Aminoadamantane hydrochlorideAdamantanamine hydrochlorideMantadix1-Adamantylamine hydrochlorideOsmolexExp-105-1LysovirMantadine
Weitere Namen anzeigen
symmetrel1-ADAMANTANAMINE HCLADAMANTAN-1-AMINE HYDROCHLORIDEMantadanAmantadine hydrochlorid(3s,5s,7s)-adamantan-1-amine hydrochloride
NSC-83653M6Q1EO9TD0Tricyclo(3.3.1.1(sup 3,7))decan-1-amine, hydrochlorideNSC83653CHEBI:2619Osmolex erRefChem:54147Hydrochloride, Amantadine

Datenbank-Bezeichner

CAS
665-66-7
PubChem CID
64150
DTXSID
DTXSID50874031
ChEMBL
CHEMBL1569
UNII
M6Q1EO9TD0

Eigenschaften

Berechnete Struktureigenschaften

Polarare Oberfläche (TPSA)
26 Ų
H-Brücken-Donoren
2
H-Brücken-Akzeptoren
1
Frei drehbare Bindungen
0
Schwere Atome
12
Formalladung
0
Komplexität
144

Experimentelle und physikochemische Eigenschaften

Human Drugs · 3 Einträge

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]

Physikochemische Eigenschaften

Schmelzpunkt
300 °C · >300 °C(lit.)
Siedepunkt
308.63 °C · 308.63°C (rough estimate)
Dichte
1.0276 · 1.0276 (rough estimate)
Brechungsindex
1.61 · 1.6100 (estimate)
storage temp.
30 °C · Store below +30°C.
Löslichkeit
2 O: · H2O: 50 mg/mL
Aggregatzustand
Fine Crystalline Powder
pka
10.71 · 10.71

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

GHS-Klassifizierung

GHS Classification · 4 Einträge

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.

Gefahrenhinweise

Regulatory Information · 5 Einträge

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%)

Toxikologische Informationen

Treatment · 1 Eintrag

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)

Chemie und Industrie

Pharmakologische Informationen

Metabolism/Metabolites · 1 Eintrag

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 Einträge

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 Einträge

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.

Verwendung und Herstellung

Zugehörige Reaktionen

25
Reaktionsaufzeichnung erstellen
Reaktionsgleichung von HRID 234742
HRID 234742als Eduktuspto-grants-1997_01
Reaktionsgleichung von HRID 338189
HRID 338189als Eduktuspto-grants-2014_11
Reaktionsgleichung von HRID 487117
HRID 487117als Eduktuspto-grants-1994_03
Reaktionsgleichung von HRID 606682
HRID 606682als Eduktuspto-grants-2011_03
Reaktionsgleichung von HRID 617228
HRID 617228als Eduktuspto-grants-1999_09
Reaktionsgleichung von HRID 876156
HRID 876156als Eduktuspto-grants-2015_03
Reaktionsgleichung von HRID 924562
HRID 924562als Eduktuspto-grants-2016_03
Reaktionsgleichung von HRID 926901
HRID 926901als Eduktuspto-grants-2016_03
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Weitere Aktionen
Neue NotizNeue ReaktionAnfrage stellen
EC Number
211-560-2
Farbe
White
Wasserlöslichkeit
soluble
Merck
14 · 14,374
BRN
4198854 · 4198854
Major Application
pharmaceutical (small molecule)
InChI
1S/C10H17N.ClH/c11-10-4-7-1-8(5-10)3-9(2-7)6-10;/h7-9H,1-6,11H2;1H/t7-,8+,9-,10-;
InChIKey
WOLHOYHSEKDWQH-UHFFFAOYSA-N
SMILES
Cl[H].[H][C@@]12C[C@@]3([H])C[C@@]([H])(C1)CC(N)(C2)C3
LogP
-1.64 at · -1.64 at 23℃ and pH6.3
CAS Datenbank
665 · 665-66-7(CAS DataBase Reference)
EPA chemische Informationen
Amantadine hydrochloride (665-66-7)
Health Effects · 1 Eintrag

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 Eintrag

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 Eintrag

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).
Drug Induced Liver Injury · 6 Einträge

Drug Induced Liver Injury Rank (DILIrank 2.0)

Amantadine hydrochloride

Ambiguous-DILI-concern

3

Warnings & precautions

DOI:10.1016/j.drudis.2016.02.015

Effects During Pregnancy and Lactation◉ Summary of Use during Lactation
Toxicity DataLD50: 800 mg/kg (Oral, Rat) LD50: 700 mg/kg (Oral, Mouse)

Sicherheitsdaten

wgk
3
tsca
TSCA listed
ridadr
UN 1759 8 / PGII
hs_code
29213000
RTECS-Nr.
AU4375000
risk_code
22-40-20/21/22
Toxizität
LD50 orally in mice, rats: 700, 1275 mg/kg (Vernier)
hazard_code
Xn
safety_code
22-36/37-36-35-20/21
hazard_class
IRRITANT
Speicherklasse
8A - Combustible corrosive hazardous materials
Hazard Classifications
Acute Tox. 4 Oral
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 Einträge

All Other Basic Organic Chemical Manufacturing

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

Anwendungen · 1 Eintrag

Verwenden1-Adamantanamine hydrochloride is used in the prophylactic or symptomatic treatment of influenza A. It is also used as an antiparkinsonian agent, to treat extra pyramidal reactions, and for postherpetic neuralgia. It is also used an NMDA-receptor antagoinst.

Vor- und nachgelagerte Produkte

Vorgelagerte Rohstoffe

Aluminium-nickelAmantadin3a,4,7,7a-Tetrahydro-4,7-methan-1H-indenNatriumsulfitChlorHarnstoffAluminiumchloridHydrogenchloridWasserstoffBromNatriumhydroxidCyanwasserstoffTricyclo[3.3.1.13,7]decanTricyclo[3.3.1.13.7]dec-2-ylaminhydrochlorid

Ergänzende Hinweise

DefinitionChEBI: A hydrochloride obtained by combining amantadine and hydrochloric acid in equimolar amounts.