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{{Short description|Chemical compound}}
{{cs1 config|name-list-style=vanc|display-authors=6}}
{{Drugbox
{{Drugbox
| Verifiedfields =
| Verifiedfields =
| Watchedfields =
| Watchedfields =
| verifiedrevid =
| verifiedrevid =
| IUPAC_name = 1-(1-Adamantyl)propan-1-amine
| IUPAC_name = 1-(Adamantan-1-yl)propan-1-amine
| image = Adapromine.svg
| image = Adapromine.svg
| width = 170
| width = 170


<!--Clinical data-->
<!--Clinical data-->
| tradename =
| tradename =
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
| pregnancy_US = <!-- A / B / C / D / X -->
| pregnancy_US = <!-- A / B / C / D / X -->
| pregnancy_category =
| pregnancy_category =
| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
| legal_CA =
| legal_CA =
| legal_UK =
| legal_UK =
| legal_US =
| legal_US =
| legal_status = Rx-only
| legal_status = Rx-only
| routes_of_administration = [[Oral administration|Oral]]
| routes_of_administration = [[Oral administration|Oral]]


<!--Pharmacokinetic data-->
<!--Pharmacokinetic data-->
| bioavailability =
| bioavailability =
| protein_bound =
| protein_bound =
| metabolism =
| metabolism =
| elimination_half-life =
| elimination_half-life =
| excretion =
| excretion =


<!--Identifiers-->
<!--Identifiers-->
| CAS_number_Ref =
| CAS_number_Ref =
| CAS_number = 60196-90-9
| CAS_number = 60196-90-9
| CAS_supplemental =
| CAS_supplemental =
| ATC_prefix =
| ATC_prefix =
| ATC_suffix =
| ATC_suffix =
| PubChem = 547499
| PubChem = 547499
| DrugBank_Ref =
| DrugBank_Ref =
| DrugBank =
| DrugBank =
| ChemSpiderID_Ref =
| ChemSpiderID_Ref =
| ChemSpiderID = 476539
| ChemSpiderID = 476539


<!--Chemical data-->
<!--Chemical data-->
| C=13 | H=23 | N=1
| C=13 | H=23 | N=1
| molecular_weight = 193.32842 g/mol
| smiles = CCC(C12CC3CC(C1)CC(C3)C2)N
| smiles = CCC(C12CC3CC(C1)CC(C3)C2)N
| StdInChI_Ref =
| StdInChI_Ref =
| StdInChI =
| StdInChI =
| StdInChIKey_Ref =
| StdInChIKey_Ref =
| StdInChIKey =
| StdInChIKey =
| synonyms = JP-62, MK-3
| synonyms = JP-62, MK-3
}}
}}


'''Adapromine''', also known as '''1-(1-aminopropyl)adamantane''', 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]].<ref name="SpasovKhamidova2000">{{cite journal|last1=Spasov|first1=A. A.|last2=Khamidova|first2=T. V.|last3=Bugaeva|first3=L. I.|last4=Morozov|first4=I. S.|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}}</ref><ref name="LavrovaIndulen1990">{{cite journal|last1=Lavrova|first1=L. N.|last2=Indulen|first2=M. K.|last3=Ryazantseva|first3=G. M.|last4=Korytnyi|first4=V. S.|last5=Yashunskii|first5=V. G.|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}}</ref><ref name="GavrilovaFrolenko2010">{{cite journal|last1=Gavrilova|first1=N. A.|last2=Frolenko|first2=T. A.|last3=Semichenko|first3=E. S.|last4=Suboch|first4=G. A.|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}}</ref><ref name="RodionovSklyarova2011">{{cite journal|last1=Rodionov|first1=V. N.|last2=Sklyarova|first2=A. S.|last3=Shamota|first3=T. V.|last4=Schreiner|first4=P. R.|last5=Fokin|first5=A. A.|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}}</ref> It is an [[alkyl]] [[structural analog|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.<ref name="SpasovKhamidova2000" /><ref name="LavrovaIndulen1990" /><ref name="LenevaGlushkov2004">{{cite journal|last1=Leneva|first1=I. A.|last2=Glushkov|first2=R. G.|last3=Gus’kova|first3=T. A.|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}}</ref> Strains of type A influenza virus with [[drug resistance|resistance]] to adapromine and rimantadine and the related drug [[deitiforine]] were encountered in [[Mongolia]] and the [[Soviet Union]] in the 1980s.<ref name="pmid1701588">{{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 = Russian | journal = Vopr. Virusol. | volume = 35 | issue = 4 | pages = 289–93 | year = 1990 | pmid = 1701588 | doi = | url = }}</ref><ref name="pmid7580412">{{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 = Russian | journal = Vestn. Akad. Med. Nauk SSSR | volume = | issue = 9 | pages = 36–41 | year = 1995 | pmid = 7580412 | doi = | url = }}</ref>
'''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]].<ref name="SpasovKhamidova2000">{{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}}</ref><ref name="LavrovaIndulen1990">{{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}}</ref><ref name="GavrilovaFrolenko2010">{{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}}</ref><ref name="RodionovSklyarova2011">{{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}}</ref> It is an [[alkyl]] [[structural analog|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.<ref name="SpasovKhamidova2000" /><ref name="LavrovaIndulen1990" /><ref name="LenevaGlushkov2004">{{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}}</ref> Strains of type A influenza virus with [[drug resistance|resistance]] to adapromine and rimantadine and the related drug [[deitiforine]] were encountered in [[Mongolia]] and the [[Soviet Union]] in the 1980s.<ref name="pmid1701588">{{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 }}</ref><ref name="pmid7580412">{{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 }}</ref>


[[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.<ref name="pmid1458170">{{cite journal | vauthors = Krapivin SV, Sergeeva SA, Morozov IS | title = [A spectral analysis of the effect of adapromine on brain bioelectrical activity] | language = Russian | journal = Eksp Klin Farmakol | volume = 55 | issue = 3 | pages = 6–8 | year = 1992 | pmid = 1458170 | doi = | url = }}</ref><ref name="KrapivinSergeeva1998">{{cite journal|last1=Krapivin|first1=S. V.|last2=Sergeeva|first2=S. A.|last3=Morozov|first3=I. S.|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}}</ref><ref name="pmid7627000">{{cite journal | vauthors = Krapivin SV, Voronina TA | title = [Comparative quantitative pharmacological-EEG analysis of the effects of psychostimulants] | language = Russian | journal = Vestn. Akad. Med. Nauk SSSR | volume = | issue = 6 | pages = 7–16 | year = 1995 | pmid = 7627000 | doi = | url = }}</ref><ref name="KrapivinSergeeva1991">{{cite journal|last1=Krapivin|first1=S. V.|last2=Sergeeva|first2=S. A.|last3=Morozov|first3=I. S.|last4=Dulpe|first4=I. U.|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}}</ref> These psychostimulant effects differ qualitatively from those of conventional psychostimulants like [[amphetamine]] however, and the adamantane derivatives have been described contrarily as "[[adaptogen]]s" and as "actoprotectors".<ref name="MorozovIvanova2001">{{cite journal|last1=Morozov|first1=I. S.|last2=Ivanova|first2=I. A.|last3=Lukicheva|first3=T. A.|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)}}</ref>
[[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.<ref name="pmid1458170">{{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 }}</ref><ref name="KrapivinSergeeva1998">{{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}}</ref><ref name="pmid7627000">{{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 }}</ref><ref name="KrapivinSergeeva1991">{{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}}</ref> These psychostimulant effects differ qualitatively from those of conventional psychostimulants like [[amphetamine]] however, and the adamantane derivatives have been described contrarily as "[[adaptogen]]s" and as "actoprotectors".<ref name="MorozovIvanova2001">{{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}}</ref>


In 2004, it was discovered that [[amantadine]] and [[memantine]] bind to and act as [[agonist]]s of the [[sigma-1 receptor|σ<sub>1</sub> receptor]] (K<sub>i</sub> = 7.44 µM and 2.60 µM, respectively) and that activation of the σ<sub>1</sub> receptor is involved in the [[dopaminergic]] effects of amantadine at therapeutically relevant concentrations.<ref name="PeetersRomieu2004">{{cite journal|last1=Peeters|first1=Magali|last2=Romieu|first2=Pascal|last3=Maurice|first3=Tangui|last4=Su|first4=Tsung-Ping|last5=Maloteaux|first5=Jean-Marie|last6=Hermans|first6=Emmanuel|title=Involvement of the sigma1 receptor in the modulation of dopaminergic transmission by amantadine|journal=European Journal of Neuroscience|volume=19|issue=8|year=2004|pages=2212–2220|issn=0953-816X|doi=10.1111/j.0953-816X.2004.03297.x}}</ref> 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.<ref name="PeetersRomieu2004" />
In 2004, it was discovered that [[amantadine]] and [[memantine]] bind to and act as [[agonist]]s of the [[sigma-1 receptor|σ<sub>1</sub> receptor]] (K<sub>i</sub> = 7.44 μM and 2.60 μM, respectively) and that activation of the σ<sub>1</sub> receptor is involved in the [[dopaminergic]] effects of amantadine at therapeutically relevant concentrations.<ref name="PeetersRomieu2004">{{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 }}</ref> 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.<ref name="PeetersRomieu2004" />


==See also==
==Synthesis==
The first synthesis of adapromine was disclosed in patents by [[DuPont]] published in 1967.<ref name=US3352912>{{cite patent |country=US |number=3352912 |inventor= Prichard WW |title=Adamantanes and tricyclo[4. 3. 1. 1 3.8] undecanes |status=patent |gdate=1967-11-14 |fdate=1964-06-18 |assign1=EI Du Pont de Nemours and Co}}</ref>
:[[File:Adapromine synthesis.svg|upright=2]]
[[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 [[Redox|reduction]] using [[lithium aluminium hydride]] yields adapromine.<ref name=US3352912/><ref>{{cite journal | vauthors = Aldrich PE, Hermann EC, Meier WE, Paulshock M, Prichard WW, Snyder JA, Watts JC | title = Antiviral agents. 2. Structure-activity relationships of compounds related to 1-adamantanamine | journal = Journal of Medicinal Chemistry | volume = 14 | issue = 6 | pages = 535–543 | date = June 1971 | pmid = 5091970 | doi = 10.1021/jm00288a019 }}</ref>

== See also ==
* [[Tromantadine]]
* [[Tromantadine]]
* [[List of Russian drugs]]


==References==
== References ==
{{Reflist|2}}
{{reflist|30em}}



{{RNA antivirals}}
{{RNA antivirals}}
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[[Category:Amines]]
[[Category:Amines]]
[[Category:Anti-influenza agents]]
[[Category:Anti-influenza agents]]
[[Category:Anti-RNA virus drugs]]
[[Category:Anti–RNA virus drugs]]
[[Category:Russian drugs]]
[[Category:Russian drugs]]
[[Category:Stimulants]]
[[Category:Stimulants]]
[[Category:Drugs in the Soviet Union]]


{{drug-stub}}

Latest revision as of 02:07, 8 October 2024

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

[edit]

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

[edit]

References

[edit]
  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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