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Adapromine

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Adapromine
Clinical data
Other namesJP-62, MK-3
Routes of
administration		Oral
Legal status
Legal status
  • In general: ℞ (Prescription only)
Identifiers
  • 1-(Adamantan-1-yl)propan-1-amine
CAS Number
PubChem CID
ChemSpider
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC13H23N
Molar mass193.334 g·mol−1
3D model (JSmol)
  • CCC(C12CC3CC(C1)CC(C3)C2)N

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]

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 (Ki = 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

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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

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References

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  1. ^ a b Spasov AA, Khamidova TV, Bugaeva LI, Morozov IS (2000). "Adamantane derivatives: Pharmacological and toxicological properties (review)". Pharmaceutical Chemistry Journal. 34 (1): 1–7. doi:10.1007/BF02524549. ISSN 0091-150X. S2CID 41620120.
  2. ^ a b Lavrova LN, Indulen MK, Ryazantseva GM, Korytnyi VS, Yashunskii VG (1990). "Synthesis and biological activity of some 1-hydroxy-3-aminoalkyladamantanes and their derivatives". Pharmaceutical Chemistry Journal. 24 (1): 35–39. doi:10.1007/BF00769383. ISSN 0091-150X. S2CID 8544357.
  3. ^ Gavrilova NA, Frolenko TA, Semichenko ES, Suboch GA (2010). "Synthesis of naphtho[1,2-d]imidazoles containing an adamantyl fragment". Russian Journal of Organic Chemistry. 46 (5): 777–778. doi:10.1134/S1070428010050349. ISSN 1070-4280. S2CID 94469430.
  4. ^ Rodionov VN, Sklyarova AS, Shamota TV, Schreiner PR, Fokin AA (2011). "Selective reductive dimerization of homocubane series oximes". Russian Journal of Organic Chemistry. 47 (11): 1695–1702. doi:10.1134/S1070428011110078. ISSN 1070-4280. S2CID 94472143.
  5. ^ Leneva IA, Glushkov RG, Gus'kova TA (2004). "Drugs for chemotherapy and prophylaxis of influenza: Mechanisms, efficacy, and safety (a review)". Pharmaceutical Chemistry Journal. 38 (11): 590–596. doi:10.1007/s11094-005-0036-9. ISSN 0091-150X. S2CID 9442971.
  6. ^ Kozeletskaia KN, Grinbaum EB, Zhamsrangiĭn M, Burmistrova VV, Kiselev OI (1990). "[The isolation and study of the properties of current influenza A viruses (H1N1) with a natural resistance to remantadine]". Voprosy Virusologii (in Russian). 35 (4): 289–293. PMID 1701588.
  7. ^ Kozeletskaia KN, Karginov VA, Kiseleva OI, Mishin VP, Grinbaum EB, Burmistrova VV (1995). "[The origin of resistance to chemicals of naturally occurring isolates of influenza A virus]". Vestnik Rossiiskoi Akademii Meditsinskikh Nauk (in Russian) (9): 36–41. PMID 7580412.
  8. ^ Krapivin SV, Sergeeva SA, Morozov IS (1992). "[A spectral analysis of the effect of adapromine on brain bioelectrical activity]". Eksperimental'naia i Klinicheskaia Farmakologiia (in Russian). 55 (3): 6–8. PMID 1458170.
  9. ^ Krapivin SV, Sergeeva SA, Morozov IS (1998). "Comparative analysis of the effects of adapromine, midantane, and bromantane on bioelectrical activity of rat brain". Bulletin of Experimental Biology and Medicine. 125 (2): 151–155. doi:10.1007/BF02496845. ISSN 0007-4888. S2CID 21940190.
  10. ^ Krapivin SV, Voronina TA (1995). "[Comparative quantitative pharmacological-EEG analysis of the effects of psychostimulants]". Vestnik Rossiiskoi Akademii Meditsinskikh Nauk (in Russian) (6): 7–16. PMID 7627000.
  11. ^ Krapivin SV, Sergeeva SA, Morozov IS, Dulpe IU (1991). "Spectral analysis of the effect of midantane on bioelectrical activity of the rat brain". Bulletin of Experimental Biology and Medicine. 112 (1): 975–978. doi:10.1007/BF00841147. ISSN 0007-4888. S2CID 22469427.
  12. ^ Morozov IS, Ivanova IA, Lukicheva TA (2001). "Actoprotector and Adaptogen Properties of Adamantane Derivatives (A Review)". Pharmaceutical Chemistry Journal. 35 (5): 235–238. doi:10.1023/A:1011905302667. ISSN 0091-150X. S2CID 29475883.
  13. ^ a b Peeters M, Romieu P, Maurice T, Su TP, Maloteaux JM, Hermans E (April 2004). "Involvement of the sigma 1 receptor in the modulation of dopaminergic transmission by amantadine". The European Journal of Neuroscience. 19 (8): 2212–2220. doi:10.1111/j.0953-816X.2004.03297.x. PMID 15090047. S2CID 19479968.
  14. ^ a b US patent 3352912, Prichard WW, "Adamantanes and tricyclo[4. 3. 1. 1 3.8] undecanes", issued 1967-11-14, assigned to EI Du Pont de Nemours and Co 
  15. ^ Aldrich PE, Hermann EC, Meier WE, Paulshock M, Prichard WW, Snyder JA, et al. (June 1971). "Antiviral agents. 2. Structure-activity relationships of compounds related to 1-adamantanamine". Journal of Medicinal Chemistry. 14 (6): 535–543. doi:10.1021/jm00288a019. PMID 5091970.
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