Adapromine

{{Short description|Chemical compound}}

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| IUPAC_name = 1-(Adamantan-1-yl)propan-1-amine

| image = Adapromine.svg

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| legal_status = Rx-only

| routes_of_administration = Oral

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| CAS_number = 60196-90-9

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| PubChem = 547499

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| ChemSpiderID = 476539

| C=13 | H=23 | N=1

| smiles = CCC(C12CC3CC(C1)CC(C3)C2)N

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| synonyms = JP-62, MK-3

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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.{{cite journal| vauthors = Spasov AA, Khamidova TV, Bugaeva LI, Morozov IS |title=Adamantane derivatives: Pharmacological and toxicological properties (review)|journal=Pharmaceutical Chemistry Journal|volume=34|issue=1|year=2000|pages=1–7|issn=0091-150X|doi=10.1007/BF02524549|s2cid=41620120}}{{cite journal| vauthors = Lavrova LN, Indulen MK, Ryazantseva GM, Korytnyi VS, Yashunskii VG |title=Synthesis and biological activity of some 1-hydroxy-3-aminoalkyladamantanes and their derivatives|journal=Pharmaceutical Chemistry Journal|volume=24|issue=1|year=1990|pages=35–39|issn=0091-150X|doi=10.1007/BF00769383|s2cid=8544357}}{{cite journal| vauthors = Gavrilova NA, Frolenko TA, Semichenko ES, Suboch GA |title=Synthesis of naphtho[1,2-d]imidazoles containing an adamantyl fragment|journal=Russian Journal of Organic Chemistry|volume=46|issue=5|year=2010|pages=777–778|issn=1070-4280|doi=10.1134/S1070428010050349|s2cid=94469430}}{{cite journal| vauthors = Rodionov VN, Sklyarova AS, Shamota TV, Schreiner PR, Fokin AA |title=Selective reductive dimerization of homocubane series oximes|journal=Russian Journal of Organic Chemistry|volume=47|issue=11|year=2011|pages=1695–1702|issn=1070-4280|doi=10.1134/S1070428011110078|s2cid=94472143}} 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.{{cite journal| vauthors = Leneva IA, Glushkov RG, Gus'kova TA |title=Drugs for chemotherapy and prophylaxis of influenza: Mechanisms, efficacy, and safety (a review)|journal=Pharmaceutical Chemistry Journal|volume=38|issue=11|year=2004|pages=590–596|issn=0091-150X|doi=10.1007/s11094-005-0036-9|s2cid=9442971}} 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.{{cite journal | vauthors = Kozeletskaia KN, Grinbaum EB, Zhamsrangiĭn M, Burmistrova VV, Kiselev OI | title = [The isolation and study of the properties of current influenza A viruses (H1N1) with a natural resistance to remantadine] | language = ru | journal = Voprosy Virusologii | volume = 35 | issue = 4 | pages = 289–293 | year = 1990 | pmid = 1701588 }}{{cite journal | vauthors = Kozeletskaia KN, Karginov VA, Kiseleva OI, Mishin VP, Grinbaum EB, Burmistrova VV | title = [The origin of resistance to chemicals of naturally occurring isolates of influenza A virus] | language = ru | journal = Vestnik Rossiiskoi Akademii Meditsinskikh Nauk | issue = 9 | pages = 36–41 | year = 1995 | pmid = 7580412 }}

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.{{cite journal | vauthors = Krapivin SV, Sergeeva SA, Morozov IS | title = [A spectral analysis of the effect of adapromine on brain bioelectrical activity] | language = ru | journal = Eksperimental'naia i Klinicheskaia Farmakologiia | volume = 55 | issue = 3 | pages = 6–8 | year = 1992 | pmid = 1458170 }}{{cite journal| vauthors = Krapivin SV, Sergeeva SA, Morozov IS |title=Comparative analysis of the effects of adapromine, midantane, and bromantane on bioelectrical activity of rat brain|journal=Bulletin of Experimental Biology and Medicine|volume=125|issue=2|year=1998|pages=151–155|issn=0007-4888|doi=10.1007/BF02496845|s2cid=21940190}}{{cite journal | vauthors = Krapivin SV, Voronina TA | title = [Comparative quantitative pharmacological-EEG analysis of the effects of psychostimulants] | language = ru | journal = Vestnik Rossiiskoi Akademii Meditsinskikh Nauk | issue = 6 | pages = 7–16 | year = 1995 | pmid = 7627000 }}{{cite journal| vauthors = Krapivin SV, Sergeeva SA, Morozov IS, Dulpe IU |title=Spectral analysis of the effect of midantane on bioelectrical activity of the rat brain|journal=Bulletin of Experimental Biology and Medicine|volume=112|issue=1|year=1991|pages=975–978|issn=0007-4888|doi=10.1007/BF00841147|s2cid=22469427}} 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".{{cite journal| vauthors = Morozov IS, Ivanova IA, Lukicheva TA |journal=Pharmaceutical Chemistry Journal|volume=35|issue=5|year=2001|pages=235–238|issn=0091-150X|doi=10.1023/A:1011905302667|title=Actoprotector and Adaptogen Properties of Adamantane Derivatives (A Review)|s2cid=29475883}}

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.{{cite journal | vauthors = Peeters M, Romieu P, Maurice T, Su TP, Maloteaux JM, Hermans E | title = Involvement of the sigma 1 receptor in the modulation of dopaminergic transmission by amantadine | journal = The European Journal of Neuroscience | volume = 19 | issue = 8 | pages = 2212–2220 | date = April 2004 | pmid = 15090047 | doi = 10.1111/j.0953-816X.2004.03297.x | s2cid = 19479968 }} 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.