Adamantanemethylamine,α-methyl-

Adamantanemethylamine,α-methyl-
Compound Structure:
Synonyms: Rimantadine;13392-28-4;1-(1-Adamantyl)ethanamine;Rimantadinum;Rimantadina;1-Rimantadine;1-(adamantan-1-yl)ethan-1-amine;alpha-Methyl-1-adamantanemethylamine;Remantadine;alpha-Methyladamantanemethylamine;1-(1-Adamantyl)ethylamine
Compound ID: NMPC-557
PubChem ID:

5071

Molecular Formula: C12H21N
Canonical SMILES: CC(C12CC3CC(C1)CC(C3)C2)N
InChIKey: UBCHPRBFMUDMNC-UHFFFAOYSA-N
About the compound:

Rimantadine is an antiviral drug used to treat and, in some cases, prevent influenza A virus infection. Here are some key details about rimantadine: Mechanism of Action: Rimantadine is classified as an Influenza A M2 Protein Inhibitor. Its primary mechanism of action is to inhibit the M2 protein of the influenza A virus. This inhibition interferes with the virus's ability to replicate and spread within the host. Medical Use: Rimantadine is administered orally and is used to treat influenzavirus A infection. It is most effective when taken within one to two days of the onset of influenza symptoms. Rimantadine can help shorten the duration of the illness and reduce the severity of symptoms, including fever. Comparison with Amantadine: Rimantadine and amantadine are both derivatives of adamantane and have similar mechanisms of action. However, rimantadine is often considered more effective than amantadine in mitigating influenza symptoms, and patients treated with rimantadine tend to experience fewer symptoms. FDA Approval: Rimantadine was approved by the Food and Drug Administration (FDA) in 1994 for medical use. Resistance: It's important to note that seasonal H3N2 and 2009 pandemic flu samples have shown resistance to rimantadine. Due to this resistance, rimantadine is no longer recommended for the treatment of the flu in some cases. Overall, rimantadine is an antiviral agent that can be effective in the prophylaxis and treatment of influenza A virus infection when used appropriately and when the virus is not resistant to it.

Properties:

Chemical and Physical Properties

Property Name

Property Value

Molecular Weight

179.30 g/mol

XLogP3-AA

2.6

Hydrogen Bond Donor Count

1

Hydrogen Bond Acceptor Count

1

Rotatable Bond Count

1

Exact Mass

179.167399674 g/mol

Monoisotopic Mass

179.167399674 g/mol

Topological Polar Surface Area

26²

Heavy Atom Count

13

Formal Charge

0

Complexity

180

Isotope Atom Count

0

Defined Atom Stereocenter Count

0

Undefined Atom Stereocenter Count

1

Defined Bond Stereocenter Count

0

Undefined Bond Stereocenter Count

0

Covalently-Bonded Unit Count

1

Compound Is Canonicalized

Yes

Physical Description

Solid

Meting Point

>300 °C

Solubility 

Hydrochloride salt freely soluble (50 mg/ml at 20 °C)

Source: PubChem

Source Species: Rauvolfia vomitoria
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