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'''Adamantanes''' | '''Adamantanes''' are a chemical class of organic compounds that are based on the adamantane structure. Members of this class have various pharmacological actions which includes [[dopaminergic]] [[stimulation]] and [[NMDA receptor antagonists|NMDA receptor antagonism]]. [[Memantine]] and [[bromantane]] are two prominent members of this class. | ||
==History== | ==History== | ||
In the 1960s, the adamantane derivative amantadine was developed as an antiviral drug for the treatment of influenza. Other adamantane antivirals subsequently followed, such as rimantadine and adapromine.<ref> | In the 1960s, the adamantane derivative amantadine was developed as an antiviral drug for the treatment of influenza. Other adamantane antivirals subsequently followed, such as rimantadine and adapromine.<ref>{{cite book | vauthors=((Mandell, L.)), ((Woodhead, M.)), ((Ewig, S.)), ((Torres, A.)) | date=27 October 2006 | title=Respiratory Infections | publisher=CRC Press | isbn=9780340816943}}</ref> It was serendipitously discovered in 1969 that amantadine possesses central [[dopaminergic]] [[stimulant|psychostimulant]]-like properties,<ref>{{cite book | vauthors=((Brandt, T.)), ((Caplan, L. R.)), ((Dichgans, J.)), ((Diener, H.-C.)), ((Kennard, C.)) | date=3 January 2003 | title=Neurological Disorders: Course and Treatment | publisher=Gulf Professional Publishing | isbn=9780121258313}}</ref> and subsequent investigation revealed that rimantadine and adapromine also possess such properties.<ref name="Adamantane Pharmacology">{{cite journal | vauthors=((Spasov, A. A.)), ((Khamidova, T. V.)), ((Bugaeva, L. I.)), ((Morozov, I. S.)) | journal=Pharmaceutical Chemistry Journal | title=Adamantane derivatives: Pharmacological and toxicological properties (review) | volume=34 | issue=1 | pages=1–7 | date=1 January 2000 | url=https://doi.org/10.1007/BF02524549 | issn=1573-9031 | doi=10.1007/BF02524549}}</ref> | ||
Adamantane was identified as a key structural subunit in several synthetic cannabinoid designer drugs, namely AB-001 and [[SDB-001]].<ref>The synthesis and pharmacological evaluation of adamantane-derived indoles: cannabimimetic drugs of abuse | Amantadine was then developed and introduced for the treatment of Parkinson's disease due to its ability to increase [[dopamine]] levels in the brain. It has also notably since been used to help alleviate fatigue in multiple sclerosis. With the knowledge of the dopaminergic psychostimulant effects of the adamantane derivatives, in the 1980s was developed [[bromantane]] as "a drug having psychoactivating and adaptogen properties under complicated conditions".<ref>{{cite journal | vauthors=((Oliynyk, S.)), ((Oh, S.)) | journal=Biomolecules & Therapeutics | title=The Pharmacology of Actoprotectors: Practical Application for Improvement of Mental and Physical Performance | volume=20 | issue=5 | pages=446–456 | date= September 2012 | url=https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3762282/ | issn=1976-9148 | doi=10.4062/biomolther.2012.20.5.446}}</ref> | ||
Adamantane was identified as a key structural subunit in several [[synthetic cannabinoid]] [[designer drugs]], namely [[wikipedia:AB-001|AB-001]] and [[SDB-001]].<ref>{{cite journal | vauthors=((Banister, S. D.)), ((Wilkinson, S. M.)), ((Longworth, M.)), ((Stuart, J.)), ((Apetz, N.)), ((English, K.)), ((Brooker, L.)), ((Goebel, C.)), ((Hibbs, D. E.)), ((Glass, M.)), ((Connor, M.)), ((McGregor, I. S.)), ((Kassiou, M.)) | journal=ACS chemical neuroscience | title=The synthesis and pharmacological evaluation of adamantane-derived indoles: cannabimimetic drugs of abuse | volume=4 | issue=7 | pages=1081–1092 | date=17 July 2013 | issn=1948-7193 | doi=10.1021/cn400035r}}</ref> | |||
==Chemistry== | ==Chemistry== | ||
{{chemistry}} | |||
Adamantane molecules consists of three connected ''cyclohexane rings'' arranged in the "armchair" configuration. | Adamantane molecules consists of three connected ''cyclohexane rings'' arranged in the "armchair" configuration. | ||
==Pharmacology== | ==Pharmacology== | ||
The psychotropic activity spectrum of many adamantane-containing compounds is determined by the nature of their amine substituents, their positions in the polycyctic nucleus, and the basicity of the amino groups. Many have been demonstrated to possesses central dopaminergic psychostimulant-like properties. Some adamantanes produce blocking of the open channels of NMDA and | The psychotropic activity spectrum of many adamantane-containing compounds is determined by the nature of their amine substituents, their positions in the polycyctic nucleus, and the basicity of the amino groups. Many have been demonstrated to possesses central dopaminergic psychostimulant-like properties. Some adamantanes produce blocking of the open channels of NMDA and n-cholinergic receptors. It was found that some the derivatives of adamantane markedly increases the production of [[acetylcholine]] in the frontal cortex and hippocampus.<ref name="Adamantane Pharmacology"/> | ||
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 central [[dopaminergic]] effects of amantadine at therapeutically relevant concentrations. These findings may also extend to the other adamantanes such as adapromine, rimantadine, and [[bromantane]], and might potentially explain the psychostimulant-like effects of this family of compounds | 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 central [[dopaminergic]] effects of [[wikipedia:amantadine|amantadine]] at therapeutically relevant concentrations. These findings may also extend to the other adamantanes such as [[wikipedia:Adapromine|adapromine]], [[wikipedia:Rimantadine|rimantadine]], and [[bromantane]], and might potentially explain the [[stimulant|psychostimulant]]-like effects of this family of compounds.<ref>{{cite journal | vauthors=((Peeters, M.)), ((Romieu, P.)), ((Maurice, T.)), ((Su, T.-P.)), ((Maloteaux, J.-M.)), ((Hermans, E.)) | journal=The European Journal of Neuroscience | title=Involvement of the sigma 1 receptor in the modulation of dopaminergic transmission by amantadine | volume=19 | issue=8 | pages=2212–2220 | date= April 2004 | issn=0953-816X | doi=10.1111/j.0953-816X.2004.03297.x}}</ref> | ||
==Examples== | ==Examples== | ||
* [[ | |||
* [[Bromantane]] | ====NMDA receptor antagonists==== | ||
* [[ | *[[Amantadine]] | ||
* [[STS-135]] | *[[Memantine]] | ||
*[[Nitromemantine]] | |||
====Stimulants==== | |||
*[[Bromantane]] | |||
====Depressants==== | |||
*[[N-Adamantylamphetamine]] | |||
====Synthetic cannabinoids==== | |||
*[[5F-AKB48]] | |||
*[[Adamantyl-THPINACA]] | |||
*[[APICA]] | |||
*[[APINACA]] | |||
*[[STS-135]] | |||
==See also== | ==See also== | ||
| Line 36: | Line 53: | ||
==References== | ==References== | ||
<references/> | <references/> | ||
[[Category: | [[Category:Chemical class]] | ||
[[Category: | [[Category:Adamantane|*]] | ||
Latest revision as of 20:28, 4 August 2022
 |
This article is a stub. As such, it may contain incomplete or wrong information. You can help by expanding it. |
Adamantanes are a chemical class of organic compounds that are based on the adamantane structure. Members of this class have various pharmacological actions which includes dopaminergic stimulation and NMDA receptor antagonism. Memantine and bromantane are two prominent members of this class.
History
In the 1960s, the adamantane derivative amantadine was developed as an antiviral drug for the treatment of influenza. Other adamantane antivirals subsequently followed, such as rimantadine and adapromine.[1] It was serendipitously discovered in 1969 that amantadine possesses central dopaminergic psychostimulant-like properties,[2] and subsequent investigation revealed that rimantadine and adapromine also possess such properties.[3]
Amantadine was then developed and introduced for the treatment of Parkinson's disease due to its ability to increase dopamine levels in the brain. It has also notably since been used to help alleviate fatigue in multiple sclerosis. With the knowledge of the dopaminergic psychostimulant effects of the adamantane derivatives, in the 1980s was developed bromantane as "a drug having psychoactivating and adaptogen properties under complicated conditions".[4]
Adamantane was identified as a key structural subunit in several synthetic cannabinoid designer drugs, namely AB-001 and SDB-001.[5]
Chemistry
 |
This chemistry section is incomplete. You can help by adding to it. |
Adamantane molecules consists of three connected cyclohexane rings arranged in the "armchair" configuration.
Pharmacology
The psychotropic activity spectrum of many adamantane-containing compounds is determined by the nature of their amine substituents, their positions in the polycyctic nucleus, and the basicity of the amino groups. Many have been demonstrated to possesses central dopaminergic psychostimulant-like properties. Some adamantanes produce blocking of the open channels of NMDA and n-cholinergic receptors. It was found that some the derivatives of adamantane markedly increases the production of acetylcholine in the frontal cortex and hippocampus.[3]
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 central dopaminergic effects of amantadine at therapeutically relevant concentrations. These findings may also extend to the other adamantanes such as adapromine, rimantadine, and bromantane, and might potentially explain the psychostimulant-like effects of this family of compounds.[6]
Examples
NMDA receptor antagonists
Stimulants
Depressants
Synthetic cannabinoids
See also
External links
References
- ↑ Mandell, L., Woodhead, M., Ewig, S., Torres, A. (27 October 2006). Respiratory Infections. CRC Press. ISBN 9780340816943.
- ↑ Brandt, T., Caplan, L. R., Dichgans, J., Diener, H.-C., Kennard, C. (3 January 2003). Neurological Disorders: Course and Treatment. Gulf Professional Publishing. ISBN 9780121258313.
- ↑ 3.0 3.1 Spasov, A. A., Khamidova, T. V., Bugaeva, L. I., Morozov, I. S. (1 January 2000). "Adamantane derivatives: Pharmacological and toxicological properties (review)". Pharmaceutical Chemistry Journal. 34 (1): 1–7. doi:10.1007/BF02524549. ISSN 1573-9031.
- ↑ Oliynyk, S., Oh, S. (September 2012). "The Pharmacology of Actoprotectors: Practical Application for Improvement of Mental and Physical Performance". Biomolecules & Therapeutics. 20 (5): 446–456. doi:10.4062/biomolther.2012.20.5.446. ISSN 1976-9148.
- ↑ Banister, S. D., Wilkinson, S. M., Longworth, M., Stuart, J., Apetz, N., English, K., Brooker, L., Goebel, C., Hibbs, D. E., Glass, M., Connor, M., McGregor, I. S., Kassiou, M. (17 July 2013). "The synthesis and pharmacological evaluation of adamantane-derived indoles: cannabimimetic drugs of abuse". ACS chemical neuroscience. 4 (7): 1081–1092. doi:10.1021/cn400035r. ISSN 1948-7193.
- ↑ Peeters, M., Romieu, P., Maurice, T., Su, T.-P., Maloteaux, J.-M., 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. ISSN 0953-816X.