Adamantan-1-amine

Names

[ CAS No. ]:
768-94-5

[ Name ]:
Adamantan-1-amine

[Synonym ]:
1-Adamantanamine
EXP 105-1
1-Amantadine
(3s,5s,7s)-adamantan-1-amine
adamantan-1-amine
tricyclo[3.3.1.13,7]decan-1-amine
Symmetrel
TCMDC-125869
Tricyclo[3.3.1.1]decan-1-amine
SYMADINE
1-Adamantylamine
Mydantane
(3s,5s,7s)-1-Adamantanamine
adamantylamine
EINECS 212-201-2
Amantadine
1-Aminotricyclo[3.3.1.13,7]decane
Adamantanamine
1-aminoadamantine
adamantyl amine
tricyclo[3.3.1.1]décan-1-amine
Trivaline
Pk-merz
Amazolon
1-Aminodiamantane
1-adamantaneamine
1-aminoadamantane
MFCD00074732
Aminoadamantane
Mantadine
Tricyclo[3.3.1.1^3,7]decan-1-amine
Virofral
1-aminoadamantan
Tricyclo[3.3.1.1]decan-1-amin
Virasol
Amantadine Base
Influenol
1-Adamantanamine (8CI)
Adamantamine

Biological Activity

[Description]:

Amantadine (1-Adamantanamine) is an antiviral agent with activity against influenza A viruses. Amantadine blocks the proton flow through the M2 ion channel (M2 proton channel of influenza A) and thus prevents the release of viral RNA into the cytoplasm of the infected cells. Amantadine is an antiparkinsonian agent[1][2].

[Related Catalog]:

Signaling Pathways >> Anti-infection >> Influenza Virus

Research Areas >> Infection

[References]

[1]. Suzuki H, et al. Emergence of amantadine-resistant influenza A viruses: epidemiological study. J Infect Chemother. 2003;9(3):195-200.

[2]. Hubsher G, et al. Amantadine: the journey from fighting flu to treating Parkinson disease. Neurology. 2012;78(14):1096-1099.

Chemical & Physical Properties

[ Density]:
1.1±0.1 g/cm3

[ Boiling Point ]:
225.7±8.0 °C at 760 mmHg

[ Melting Point ]:
206-208 °C(lit.)

[ Molecular Formula ]:
C₁₀H₁₇N

[ Molecular Weight ]:
151.249

[ Flash Point ]:
96.0±9.7 °C

[ Exact Mass ]:
151.136093

[ PSA ]:
26.02000

[ LogP ]:
2.22

[ Vapour Pressure ]:
0.1±0.4 mmHg at 25°C

[ Index of Refraction ]:
1.558

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: YD1925000

CHEMICAL NAME :: Tricyclo(3.3.1.1(sup 3,7))decan-1-amine

CAS REGISTRY NUMBER :: 768-94-5

LAST UPDATED :: 199706

DATA ITEMS CITED :: 8

MOLECULAR FORMULA :: C10-H17-N

MOLECULAR WEIGHT :: 151.28

WISWESSER LINE NOTATION :: L66 B6 A B- C 1B ITJ BZ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 900 mg/kg

TOXIC EFFECTS :: Behavioral - tremor Behavioral - convulsions or effect on seizure threshold

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 223 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 700 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 245 mg/kg

TOXIC EFFECTS :: Behavioral - tremor Behavioral - ataxia

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Bird - quail

DOSE/DURATION :: >316 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

MUTATION DATA

TYPE OF TEST :: DNA adduct

TEST SYSTEM :: Bacteria - Escherichia coli

DOSE/DURATION :: 10 umol/L

REFERENCE :: MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 89,95,1981

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H302-H315-H319-H335

[ Precautionary Statements ]:
P261-P305 + P351 + P338

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Gloves

[ Hazard Codes ]:
Xi:Irritant

[ Risk Phrases ]:
R22;R36/37/38

[ Safety Phrases ]:
S26-S36

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
YD1925000

Precursor & DownStream

Precursor

DownStream

Articles

Differential effects of viroporin inhibitors against feline infectious peritonitis virus serotypes I and II.

Arch. Virol. 160(5) , 1163-70, (2015)

Feline infectious peritonitis virus (FIP virus: FIPV), a feline coronavirus of the family Coronaviridae, causes a fatal disease called FIP in wild and domestic cat species. The genome of coronaviruses...

CDDP supramolecular micelles fabricated from adamantine terminated mPEG and β-cyclodextrin based seven-armed poly (L-glutamic acid)/CDDP complexes.

Colloids Surf. B Biointerfaces 105 , 31-6, (2013)

This research is aimed to develop a nano-sized supramolecular micelle delivery system of cis-dichlorodiammine platinum (II) (CDDP) in order to achieve the passive tumor targeting. Firstly, star-shaped...

A primary fish gill cell culture model to assess pharmaceutical uptake and efflux: evidence for passive and facilitated transport.

Aquat. Toxicol. 159 , 127-37, (2015)

The gill is the principle site of xenobiotic transfer to and from the aqueous environment. To replace, refine or reduce (3Rs) the large numbers of fish used in in vivo uptake studies an effective in v...