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Benzodiazepines: Difference between revisions

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Benzodiazepine drugs commonly contain an aromatic electrophilic substitution such as aromatic halogenation or nitration on R<sub>7</sub> of their rings. Benzodiazepines can be subdivided into triazolobenzodiazepines and ketone substituted benzodiazepines. Triazolobenzodiazepines contain a triazole ring bonded to the benzodiazepine structure and are distinguished by the suffix "-zolam." Ketone substituted rings contain a ketone oxygen bond at R<sub>2</sub> of their benzodiazepine structure and are distinguished by their suffix "-azepam."
Benzodiazepine drugs commonly contain an aromatic electrophilic substitution such as aromatic halogenation or nitration on R<sub>7</sub> of their rings. Benzodiazepines can be subdivided into triazolobenzodiazepines and ketone substituted benzodiazepines. Triazolobenzodiazepines contain a triazole ring bonded to the benzodiazepine structure and are distinguished by the suffix "-zolam." Ketone substituted rings contain a ketone oxygen bond at R<sub>2</sub> of their benzodiazepine structure and are distinguished by their suffix "-azepam."
===Chemical classes===
<div class="flex-panel">
    <div class="flex-column">
    <div class="panel radius">
<h3 class="panel-header">Benzodiazepines</h3>
<ul class="featured-table">
<li class="featured list-item">
*[[Clonazepam]]
*[[Diazepam]]
*[[Diclazepam]]
*[[Flubromazepam]]
*[[Lorazepam]]
*[[Nifoxipam]]
*[[Nordazepam]]
*[[Oxazepam]]
*[[Phenazepam]]
*[[Temazepam]]
</li>
</ul>
</div>
</div>
    <div class="flex-column">
    <div class="panel radius">
<h3 class="panel-header">[[Thienodiazepines]]</h3>
<ul class="featured-table">
<li class="featured list-item">
*[[Brotizolam]]
*[[Bentazepam]]
*[[Deschloroetizolam]]
*[[Etizolam]]
*[[Metizolam]]
</li>
</ul>
</div>
</div>
<div class="flex-column">
<div class="panel radius">
<h3 class="panel-header">[[Triazolobenzodiazepine]]</h3>
<ul class="featured-table">
<li class="featured list-item">
*[[Alprazolam]]
*[[Triazolam]]
*[[Estazolam]]
*[[Pyrazolam]]
*[[Flubromazolam]]
*[[Clonazolam]]
*[[Flunitrazolam]]
*[[Nitrazolam]]
</li>
</ul>
</div>
</div>
<div class="flex-column">
<div class="panel radius">
<h3 class="panel-header">[[Thienotriazolodiazepines]]</h3>
<ul class="featured-table">
<li class="featured list-item">
*[[Deschloroetizolam]]
*[[Etizolam]]
*[[Metizolam]]
*[[Brotizolam]]
</li>
</ul>
</div>
</div>
<div class="flex-column">
<div class="panel radius">
<h3 class="panel-header">[[Imidazobenzodiazepine]]</h3>
<ul class="featured-table">
<li class="featured list-item">
*[[Midazolam]]
*[[Loprazolam]]
</li>
</ul>
</div>
</div>
</div>


==Pharmacology==
==Pharmacology==
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Benzodiazepines function as weak adenosine reuptake inhibitors. It has been suggested that some of their [[anticonvulsant]], [[anxiolytic]], and [[muscle relaxant]] effects may be in part mediated by this action.<ref>[The mechanisms of depression by benzodiazepines, barbiturates and propofol of excitatory synaptic transmissions mediated by adenosine neuromodulation]. (PubMed.gov / NCBI) | https://www.ncbi.nlm.nih.gov/pubmed/16780077</ref>
Benzodiazepines function as weak adenosine reuptake inhibitors. It has been suggested that some of their [[anticonvulsant]], [[anxiolytic]], and [[muscle relaxant]] effects may be in part mediated by this action.<ref>[The mechanisms of depression by benzodiazepines, barbiturates and propofol of excitatory synaptic transmissions mediated by adenosine neuromodulation]. (PubMed.gov / NCBI) | https://www.ncbi.nlm.nih.gov/pubmed/16780077</ref>


==Subjective effects==
==Subjective effects==
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==List of substituted benzodiazepines==
====Substituted 1,4-benzodiazepines====
{| class="wikitable"
|-
! scope="col" | '''Compound'''
! scope="col" style="width: 50px;" | '''R<sub>1</sub>'''
! scope="col" style="width: 50px;" | '''R<sub>2</sub>'''
! scope="col" style="width: 50px;" | '''R<sub>3</sub>'''
! scope="col" style="width: 50px;" | '''R<sub>4</sub>'''
! scope="col" style="width: 50px;" | '''R<sub>5</sub>'''
! scope="col" style="width: 50px;" | '''R<sub>6</sub>'''
! scope="col" style="width: 50px;" | '''R<sub>7</sub>'''
! scope="col" | '''Structure'''
|-
| [[Bromazepam]] || H || =O || H<sub>2</sub> ||  || C<sub>5</sub>H<sub>4</sub>N || H || Br || [[File:Bromazepam.svg|170px]]
|-
| [[Cinolazepam]] || CH<sub>2</sub>CH<sub>2</sub>≡N || =O || HOH ||  || C<sub>6</sub>H<sub>4</sub>F || H || Cl || [[File:Cinolazepam.svg|170px]]
|-
| [[Clonazepam]] || H || =O || H<sub>2</sub> ||  || C<sub>6</sub>H<sub>4</sub>Cl || H || NO<sub>2</sub> || [[File:Clonazepam.svg|170px]]
|-
| [[Diazepam]] || CH<sub>3</sub> || =O || H<sub>2</sub> ||  || C<sub>6</sub>H<sub>5</sub> || H || Cl || [[File:Diazepam.svg|170px]]
|-
| [[Diclazepam]] || CH<sub>3</sub> || =O || H<sub>2</sub> ||  || C<sub>6</sub>H<sub>4</sub>Cl || H || Cl || [[File:Diclazepam.svg|170px]]
|-
| [[Flubromazepam]] || H || =O || H<sub>2</sub> ||  || C<sub>6</sub>H<sub>4</sub>F || H || Br || [[File:Flubromazepam.svg|170px]]
|-
| [[Flunitrazepam]] || CH<sub>3</sub> || =O || H<sub>2</sub> ||  || C<sub>6</sub>H<sub>4</sub>F || H || NO<sub>2</sub> || [[File:Flunitrazepam.svg|170px]]
|-
| [[Lorazepam]] || H || =O || HOH ||  || C<sub>6</sub>H<sub>4</sub>Cl || H || Cl || [[File:Lorazepam.svg|170px]]
|-
| [[Meclonazepam]] || H || =O || HCH<sub>3</sub> ||  || C<sub>6</sub>H<sub>4</sub>Cl || H || NO<sub>2</sub> || [[File:Meclonazepam.svg|170px]]
|-
| [[Nifoxipam]] || H || =O || HOH ||  || C<sub>6</sub>H<sub>4</sub>F || H || NO<sub>2</sub> || [[File:Nifoxipam.svg|170px]]
|-
| [[Oxazepam]] || H || =O || HOH ||  || C<sub>6</sub>H<sub>5</sub> || H || Cl || [[File:Oxazepam.svg|170px]]
|-
| [[Temazepam]] || CH<sub>3</sub> || =O || HOH ||  || C<sub>6</sub>H<sub>5</sub> || H || Cl || [[File:Temazepam.svg|170px]]
|-
| [[Alprazolam]] || C(CH<sub>3</sub>)=N- || =N- || H<sub>2</sub> ||  || C<sub>6</sub>H<sub>5</sub> || H || Cl || [[File:Alprazolam.svg|170px]]
|-
| [[Clonazolam]] || C(CH<sub>3</sub>)=N- || =N- || H<sub>2</sub> ||  || C<sub>6</sub>H<sub>4</sub>Cl || H || NO<sub>2</sub> || [[File:Clonazolam.svg|170px]]
|-
| [[Flubromazolam]] || C(CH<sub>3</sub>)=N- || =N- || H<sub>2</sub> ||  || C<sub>6</sub>H<sub>4</sub>F || H || Br || [[File:Flubromazolam.svg|170px]]
|-
| [[Flunitrazolam]] || C(CH<sub>3</sub>)=N- || =N- || H<sub>2</sub> ||  || C<sub>6</sub>H<sub>4</sub>F || H || NO<sub>2</sub> || [[File:Flunitrazolam.svg|170px]]
|-
| [[Midazolam]] || C(CH<sub>3</sub>)=N- || =N- || H<sub>2</sub> ||  || C<sub>6</sub>H<sub>4</sub>F || H || Cl || [[File:Midazolam.svg|170px]]
|-
| [[Pyrazolam]] || C(CH<sub>3</sub>)=N- || =N- || H<sub>2</sub> ||  || C<sub>5</sub>H<sub>4</sub>N || H || Br || [[File:Pyrazolam.svg|170px]]
|-
| [[Triazolam]] || C(CH<sub>3</sub>)=N- || =N- || H<sub>2</sub> ||  || C<sub>6</sub>H<sub>4</sub>Cl || H || Cl || [[File:Triazolam.svg|170px]]
|-
| [[Chlordiazepoxide]] || - || (-)NHCH<sub>3</sub> || H<sub>2</sub> || O || C<sub>6</sub>H<sub>5</sub> || H || Cl || [[File:Chlordiazepoxide.svg|170px]]
|-
| [[Flumazenil]] || CH=N- || C(C<sub>3</sub>H<sub>5</sub>O<sub>2</sub>)- || H<sub>2</sub> || CH<sub>3</sub> || =O || H || F || [[File:Flumazenil.svg|170px]]
|-
| [[Bretazenil]] || CH=N- || C(C<sub>5</sub>H<sub>9</sub>O<sub>2</sub>)- || HCH<sub>2</sub>CH<sub>2</sub>- || CH<sub>2</sub>- || =O || Br || H || [[File:Bretazenil.svg|170px]]
|-
| [[Clozapine]] || H || CH=CH- || CH=CH(Cl)- ||  || C<sub>5</sub>H<sub>11</sub>N<sub>2</sub> || H || H || [[File:Clozapine.svg|170px]]
|-
| [[Dibenzepin]] || CH<sub>3</sub> || CH=CH- || CH=CH- || C<sub>4</sub>H<sub>10</sub>N || =O || H || H || [[File:Dibenzepin.svg|170px]]
|-
|}


==Equivalent dosages==
==Equivalent dosages==
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