Adapromine

Adapromine is an antiviral drug of the adamantane group related to amantadine (1-aminoadamantane), rimantadine (1-(1-aminoethyl)adamantane), and memantine (1-amino-3,5-dimethyladamantane) that is marketed in Russia for the treatment and prevention of influenza.^[1][2][3][4] It is an alkyl analogue of rimantadine and is similar to rimantadine in its antiviral activity but possesses a broader spectrum of action, being effective against influenza viruses of both type A and B.^[1][2][5] Strains of type A influenza virus with resistance to adapromine and rimantadine and the related drug deitiforine were encountered in Mongolia and the Soviet Union in the 1980s.^[6][7]

Adapromine

Clinical data
Other names	JP-62, MK-3
Routes of administration	Oral
Legal status
Legal status	In general: ℞ (Prescription only)
Identifiers
IUPAC name 1-(Adamantan-1-yl)propan-1-amine
CAS Number	60196-90-9
PubChem CID	547499
ChemSpider	476539
CompTox Dashboard (EPA)	DTXSID70975615
Chemical and physical data
Formula	C13H23N
Molar mass	193.334 g·mol−1
3D model (JSmol)	Interactive image
SMILES CCC(C12CC3CC(C1)CC(C3)C2)N

Electroencephalography (EEG) studies of animals suggest that adapromine and related adamantanes including amantadine, bromantane (1-amino-2-bromophenyladamantane), and memantine have psychostimulant-like and possibly antidepressant-like effects, and that these effects may be mediated via catecholaminergic processes.^{[8][9][10][11]} These psychostimulant effects differ qualitatively from those of conventional psychostimulants like amphetamine however, and the adamantane derivatives have been described contrarily as "adaptogens" and as "actoprotectors".^[12]

In 2004, it was discovered that amantadine and memantine bind to and act as agonists of the σ₁ receptor (K_i = 7.44 μM and 2.60 μM, respectively) and that activation of the σ₁ receptor is involved in the dopaminergic effects of amantadine at therapeutically relevant concentrations.^[13] These findings might also extend to the other adamantanes such as adapromine, rimantadine, and bromantane and could explain the psychostimulant-like effects of this family of compounds.^[13]

Synthesis

The first synthesis of adapromine was disclosed in patents by DuPont published in 1967.^[14]

1-Adamantanecarboxylic acid, as its acid chloride, is treated with a cadmium-modified Grignard reagent, which gives the ketone (6). Oxime formation with hydroxylamine, followed by reduction using lithium aluminium hydride yields adapromine.^[14][15]

See also

• Tromantadine
• List of Russian drugs