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Benzodiazepines: Difference between revisions
>Turbokees m Added Flunitrazolam to the research chemicals table with info from http://drugs.tripsit.me/flunitrazolam and personal experience |
>David Hedlund →Toxicity and harm potential: File:HarmCausedByDrugsTable.svg |
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[[File:Substituted_benzodiazepine.svg|227px|thumb|right|The core structure of benzodiazepines]] | [[File:Substituted_benzodiazepine.svg|227px|thumb|right|The core structure of benzodiazepines]] | ||
[[File:Xanax (alprazolam) 2 mg.jpg|200px|thumbnail|[[Xanax]] (alprazolam) 2 mg tri-score tablets]] | [[File:Xanax (alprazolam) 2 mg.jpg|200px|thumbnail|[[Xanax]] (alprazolam) 2 mg tri-score tablets]] | ||
'''Benzodiazepines''' (commonly referred to as '''benzos''') are a class of psychoactive substances that act as central nervous system [[depressants]]. These substances work by magnifying the efficiency and effects of the principal inhibitory [[neurotransmitter]] '''gamma-aminobutyric acid''' ([[GABA]]) by binding to and acting on its receptors.<ref>Benzodiazepine interactions with GABA receptors | '''Benzodiazepines''' (commonly referred to as '''benzos''') are a class of psychoactive substances that act as central nervous system [[depressants]]. These substances work by magnifying the efficiency and effects of the principal inhibitory [[neurotransmitter]] '''gamma-aminobutyric acid''' ([[GABA]]) by binding to and acting on its receptors.<ref name="Haefely1984">{{cite journal | vauthors=((Haefely, W.)) | journal=Neuroscience Letters | title=Benzodiazepine interactions with GABA receptors | volume=47 | issue=3 | pages=201–206 | date=29 June 1984 | issn=0304-3940 | doi=10.1016/0304-3940(84)90514-7}}</ref> | ||
The characteristic effects of benzodiazepines include [[anxiety suppression]], [[sedation]], [[muscle relaxation]], [[disinhibition]], [[sleepiness]] and [[amnesia]]. In a medical context, short-acting benzodiazepines are typically recommended for treating insomnia or acute panic attacks while long-acting ones are recommended for the treatment of anxiety disorders.<ref> | The characteristic effects of benzodiazepines include [[anxiety suppression]], [[sedation]], [[muscle relaxation]], [[disinhibition]], [[sleepiness]] and [[amnesia]]. In a medical context, short-acting benzodiazepines are typically recommended for treating insomnia or acute panic attacks while long-acting ones are recommended for the treatment of anxiety disorders.<ref>{{cite book | date= 2009 | title=Medicines used in generalized anxiety and sleep disorders | publisher=World Health Organization | url=https://www.ncbi.nlm.nih.gov/books/NBK143206/}}</ref> | ||
{{BenzoWarning}} | {{BenzoWarning}} | ||
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The first benzodiazepine, chlordiazepoxide (''Librium''), was synthesized in 1955 by Leo Sternbach while working at Hoffmann–La Roche on the development of tranquilizers. The pharmacological properties of the compounds prepared initially were disappointing, and Sternbach abandoned the project. | The first benzodiazepine, chlordiazepoxide (''Librium''), was synthesized in 1955 by Leo Sternbach while working at Hoffmann–La Roche on the development of tranquilizers. The pharmacological properties of the compounds prepared initially were disappointing, and Sternbach abandoned the project. | ||
Two years later, | Two years later, on April 1957, co-worker Earl Reeder noticed a "nicely crystalline" compound leftover from the discontinued project while spring-cleaning in the lab. This compound, later named chlordiazepoxide, had not been tested in 1955 because of Sternbach's focus on other issues. Expecting pharmacology results to be negative, and hoping to publish the chemistry-related findings, researchers submitted it for a standard battery of animal tests. | ||
However, the compound showed very strong [[sedative]], [[anticonvulsant]], and [[muscle relaxant]] effects. These impressive clinical findings led to its speedy introduction throughout the world in 1960 under the brand name ''Librium''.<ref name="pmid34039">{{cite journal | author = Sternbach LH | title = The benzodiazepine story | journal = Journal of Medicinal Chemistry | volume = 22 | issue = 1 | pages = 1–7 | year = 1979 | pmid = 34039 | doi = 10.1021/jm00187a001 | quote = During this cleanup operation, my co-worker, Earl Reeder, drew my attention to a few hundred milligrams of two products, a nicely crystalline base and its hydrochloride. Both the base, which had been prepared by treating the quinazoline N-oxide 11 with methylamine, and its hydrochloride had been made sometime in 1955. The products were not submitted for pharmacological testing at that time because of our involvement with other problems }}</ref><ref name="Miller-Gold">{{cite journal |vauthors=Miller NS, Gold MS | title = Benzodiazepines: reconsidered | journal = Adv Alcohol Subst Abuse | volume = 8 | issue = 3–4 | pages = 67–84 | year = 1990 | pmid = 1971487 | doi = 10.1300/J251v08n03_06 }}</ref> Following chlordiazepoxide, [[diazepam]] marketed by Hoffmann–La Roche under the brand name ''Valium'' in 1963, and for a while the two were the most commercially successful drugs. The introduction of benzodiazepines led to a decrease in the prescription of [[barbiturate]]s, and by the 1970s they had largely replaced the older drugs for sedative and [[hypnotic]] uses.<ref name="isbn0-19-517668-5">{{cite book |author=Shorter E |title=A Historical Dictionary of Psychiatry |publisher=Oxford University Press |year=2005 |chapter=Benzodiazepines |pages=41–2 |isbn=0-19-517668-5 }}</ref> | However, the compound showed very strong [[sedative]], [[anticonvulsant]], and [[muscle relaxant]] effects. These impressive clinical findings led to its speedy introduction throughout the world in 1960 under the brand name ''Librium''.<ref name="pmid34039">{{cite journal | author = Sternbach LH | title = The benzodiazepine story | journal = Journal of Medicinal Chemistry | volume = 22 | issue = 1 | pages = 1–7 | year = 1979 | pmid = 34039 | doi = 10.1021/jm00187a001 | quote = During this cleanup operation, my co-worker, Earl Reeder, drew my attention to a few hundred milligrams of two products, a nicely crystalline base and its hydrochloride. Both the base, which had been prepared by treating the quinazoline N-oxide 11 with methylamine, and its hydrochloride had been made sometime in 1955. The products were not submitted for pharmacological testing at that time because of our involvement with other problems }}</ref><ref name="Miller-Gold">{{cite journal |vauthors=Miller NS, Gold MS | title = Benzodiazepines: reconsidered | journal = Adv Alcohol Subst Abuse | volume = 8 | issue = 3–4 | pages = 67–84 | year = 1990 | pmid = 1971487 | doi = 10.1300/J251v08n03_06 }}</ref> Following chlordiazepoxide, [[diazepam]] marketed by Hoffmann–La Roche under the brand name ''Valium'' in 1963, and for a while the two were the most commercially successful drugs. The introduction of benzodiazepines led to a decrease in the prescription of [[barbiturate]]s, and by the 1970s they had largely replaced the older drugs for sedative and [[hypnotic]] uses.<ref name="isbn0-19-517668-5">{{cite book |author=Shorter E |title=A Historical Dictionary of Psychiatry |publisher=Oxford University Press |year=2005 |chapter=Benzodiazepines |pages=41–2 |isbn=0-19-517668-5 }}</ref> | ||
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The new group of drugs was initially greeted with optimism by the medical profession, but gradually concerns arose; in particular, the risk of dependence became evident in the 1980s. Benzodiazepines have a unique history in that they were responsible for the largest-ever class-action lawsuit against drug manufacturers in the United Kingdom, involving 14,000 patients and 1,800 law firms that alleged the manufacturers knew of the dependence potential but intentionally withheld this information from doctors. | The new group of drugs was initially greeted with optimism by the medical profession, but gradually concerns arose; in particular, the risk of dependence became evident in the 1980s. Benzodiazepines have a unique history in that they were responsible for the largest-ever class-action lawsuit against drug manufacturers in the United Kingdom, involving 14,000 patients and 1,800 law firms that alleged the manufacturers knew of the dependence potential but intentionally withheld this information from doctors. | ||
At the same time, 117 general practitioners and 50 health authorities were sued by patients to recover damages for the harmful effects of dependence and withdrawal. This led some doctors to require a signed consent form from their patients and to recommend that all patients be adequately warned of the risks of dependence and withdrawal before starting treatment with benzodiazepines.<ref>{{cite journal | author = King MB | title = Is there still a role for benzodiazepines in general practice? | journal = Br J Gen Pract | volume = 42 | issue = 358 | pages = 202–5 | year = 1992 | pmid = 1389432 | pmc = 1372025 }}</ref> The court case against the drug manufacturers never reached a verdict; legal aid had been withdrawn and there were allegations that the consultant psychiatrists, the expert witnesses, had a conflict of interest. This litigation led to changes in | At the same time, 117 general practitioners and 50 health authorities were sued by patients to recover damages for the harmful effects of dependence and withdrawal. This led some doctors to require a signed consent form from their patients and to recommend that all patients be adequately warned of the risks of dependence and withdrawal before starting treatment with benzodiazepines.<ref>{{cite journal | author = King MB | title = Is there still a role for benzodiazepines in general practice? | journal = Br J Gen Pract | volume = 42 | issue = 358 | pages = 202–5 | year = 1992 | pmid = 1389432 | pmc = 1372025 }}</ref> The court case against the drug manufacturers never reached a verdict; legal aid had been withdrawn and there were allegations that the consultant psychiatrists, the expert witnesses, had a conflict of interest. This litigation led to changes in British law, making class action lawsuits more difficult.<ref name="urlHouse of Commons">{{cite web |url=http://www.publications.parliament.uk/pa/cm199899/cmselect/cmhealth/549/99072723.htm |title=Memorandum by Dr Reg Peart |author=Peart R |date=1999-06-01 |work=Minutes of Evidence |publisher=Select Committee on Health, House of Commons, UK Parliament |accessdate=2009-05-27 }}</ref> | ||
Although antidepressants with anxiolytic properties have been introduced, and there is increasing awareness of the adverse effects of benzodiazepines, prescriptions for short-term anxiety relief have not significantly dropped.<ref name="pmid18671662">{{cite journal | author = Lader M | title = Effectiveness of benzodiazepines: do they work or not? | journal = Expert Rev Neurother | volume = 8 | issue = 8 | pages = 1189–91 | year = 2008 | pmid = 18671662 | doi = 10.1586/14737175.8.8.1189 | type = PDF }}</ref> For treatment of insomnia, benzodiazepines are now less popular than nonbenzodiazepines, which include [[zolpidem]], zaleplon and [[zopiclone|eszopiclone]].<ref>{{cite journal | author = Jufe GS | title = [New hypnotics: perspectives from sleep physiology] | journal = Vertex | volume = 18 | issue = 74 | pages = 294–9 | date = Jul–Aug 2007 | pmid = 18265473 }}</ref> Nonbenzodiazepines are molecularly distinct, but nonetheless, they work on the same benzodiazepine receptors and produce similar sedative effects.<ref name="wake">{{cite journal | author = Lemmer B | title = The sleep–wake cycle and sleeping pills | journal = Physiol Behav | volume = 90 | issue = 2–3 | pages = 285–93 | year = 2007 | pmid = 17049955 | doi = 10.1016/j.physbeh.2006.09.006 }}</ref> | Although antidepressants with anxiolytic properties have been introduced, and there is increasing awareness of the adverse effects of benzodiazepines, prescriptions for short-term anxiety relief have not significantly dropped.<ref name="pmid18671662">{{cite journal | author = Lader M | title = Effectiveness of benzodiazepines: do they work or not? | journal = Expert Rev Neurother | volume = 8 | issue = 8 | pages = 1189–91 | year = 2008 | pmid = 18671662 | doi = 10.1586/14737175.8.8.1189 | type = PDF }}</ref> For treatment of insomnia, benzodiazepines are now less popular than nonbenzodiazepines, which include [[zolpidem]], zaleplon and [[zopiclone|eszopiclone]].<ref>{{cite journal | author = Jufe GS | title = [New hypnotics: perspectives from sleep physiology] | journal = Vertex | volume = 18 | issue = 74 | pages = 294–9 | date = Jul–Aug 2007 | pmid = 18265473 }}</ref> Nonbenzodiazepines are molecularly distinct, but nonetheless, they work on the same benzodiazepine receptors and produce similar sedative effects.<ref name="wake">{{cite journal | author = Lemmer B | title = The sleep–wake cycle and sleeping pills | journal = Physiol Behav | volume = 90 | issue = 2–3 | pages = 285–93 | year = 2007 | pmid = 17049955 | doi = 10.1016/j.physbeh.2006.09.006 }}</ref> | ||
==Chemistry== | ==Chemistry== | ||
Benzodiazepines are heterocyclic compounds comprised of a benzene ring fused to a seven-member nitrogenous diazepine ring. Benzodiazepine drugs contain an additional substituted phenyl ring bonded at R<sub>5</sub>, resulting in 5-phenyl-1,4-benzodiazepines with different side groups attached to the structure to create a number of drugs with different strength, duration, and efficacy. | |||
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." | ||
=== | ==Pharmacology== | ||
Benzodiazepines produce a variety of effects by binding to the benzodiazepine receptor site and magnifying the efficiency and effects of the neurotransmitter [[GABA|gamma aminobutyric acid (GABA)]] by acting on its [[receptor]]s.<ref name="Haefely1984" /> As this site is the most prolific inhibitory receptor set within the brain, its modulation results in the [[sedating]] (or [[anxiety suppression|calming effects]]) of benzodiazepines on the nervous system. | |||
The [[anticonvulsant]] properties of benzodiazepines may be, in part or entirely, due to binding to voltage-dependent sodium channels rather than benzodiazepine receptors.<ref>{{cite journal | vauthors=((McLean, M. J.)), ((Macdonald, R. L.)) | journal=The Journal of Pharmacology and Experimental Therapeutics | title=Benzodiazepines, but not beta carbolines, limit high frequency repetitive firing of action potentials of spinal cord neurons in cell culture | volume=244 | issue=2 | pages=789–795 | date= February 1988 | issn=0022-3565}}</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>{{cite journal | vauthors=((Narimatsu, E.)), ((Niiya, T.)), ((Kawamata, M.)), ((Namiki, A.)) | journal=Masui. The Japanese Journal of Anesthesiology | title=[The mechanisms of depression by benzodiazepines, barbiturates and propofol of excitatory synaptic transmissions mediated by adenosine neuromodulation] | volume=55 | issue=6 | pages=684–691 | date= June 2006 | issn=0021-4892}}</ref> | |||
==Subjective effects== | ==Subjective effects== | ||
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*'''[[Effect::Physical euphoria]]''' | *'''[[Effect::Physical euphoria]]''' | ||
*'''[[Effect::Motor control loss]]''' | *'''[[Effect::Motor control loss]]''' | ||
*'''[[Effect::Seizure suppression]]'''<ref> | *'''[[Effect::Seizure suppression]]'''<ref>{{cite journal | vauthors=((Woolley, C. S.)), ((Schwartzkroin, P. A.)) | journal=Epilepsia | title=Hormonal Effects on the Brain | volume=39 | issue=s8 | pages=S2–S8 | date= August 1998 | url=https://onlinelibrary.wiley.com/doi/10.1111/j.1528-1157.1998.tb02601.x | issn=0013-9580 | doi=10.1111/j.1528-1157.1998.tb02601.x}}</ref> | ||
*'''[[Effect::Respiratory depression]]''' | *'''[[Effect::Respiratory depression]]''' | ||
*'''[[Effect::Dizziness]]''' | *'''[[Effect::Dizziness]]''' | ||
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{{effects/paradoxical| | {{effects/paradoxical| | ||
Paradoxical reactions to [[benzodiazepines]] such as increased seizures (in epileptics), aggression, increased anxiety, violent behavior, loss of impulse control, irritability and suicidal behavior sometimes occur (although they are rare in the general population, with an incidence rate below 1%).<ref> | Paradoxical reactions to [[benzodiazepines]] such as increased seizures (in epileptics), aggression, increased anxiety, violent behavior, loss of impulse control, irritability and suicidal behavior sometimes occur (although they are rare in the general population, with an incidence rate below 1%).<ref>{{cite journal | vauthors=((Saïas, T.)), ((Gallarda, T.)) | journal=L’Encephale | title=[Paradoxical aggressive reactions to benzodiazepine use: a review] | volume=34 | issue=4 | pages=330–336 | date= September 2008 | issn=0013-7006 | doi=10.1016/j.encep.2007.05.005}}</ref><ref>{{cite journal | vauthors=((Paton, C.)) | journal=Psychiatric Bulletin | title=Benzodiazepines and disinhibition: a review | volume=26 | issue=12 | pages=460–462 | date= December 2002 | url=https://www.cambridge.org/core/journals/psychiatric-bulletin/article/benzodiazepines-and-disinhibition-a-review/421AF197362B55EDF004700452BF3BC6 | issn=0955-6036 | doi=10.1192/pb.26.12.460}}</ref><p> | ||
These paradoxical effects occur with greater frequency in recreational abusers, individuals with mental disorders, children, and patients on high-dosage regimes.<ref>Bond | These paradoxical effects occur with greater frequency in recreational abusers, individuals with mental disorders, children, and patients on high-dosage regimes.<ref>{{cite journal | vauthors=((Bond, A. J.)) | journal=CNS Drugs | title=Drug- Induced Behavioural Disinhibition | volume=9 | issue=1 | pages=41–57 | date=1 January 1998 | url=https://doi.org/10.2165/00023210-199809010-00005 | issn=1179-1934 | doi=10.2165/00023210-199809010-00005}}</ref><ref>{{cite journal | vauthors=((Drummer, O. H.)) | journal=Forensic Science Review | title=Benzodiazepines - Effects on Human Performance and Behavior | volume=14 | issue=1–2 | pages=1–14 | date= February 2002 | issn=1042-7201}}</ref></p> | ||
}} | }} | ||
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*'''[[Effect::Anxiety suppression]]''' | *'''[[Effect::Anxiety suppression]]''' | ||
*'''[[Effect::Disinhibition]]''' | *'''[[Effect::Disinhibition]]''' | ||
*'''[[Effect::Cognitive euphoria]]''' - This effect is not consistently produced between individuals and seems to be highly dependent on personal factors. Some people do not report any euphoric effects following benzodiazepine use. When it does occur, it is typically described as mild to moderate and is commonly thought to occur at a higher rate in those with pre-existing [[anxiety]] issues. This may partly be the result of the immediateness in which the anxiety-relieving and disinhibiting effects are produced. While this effect may not be entirely consistent, many reports suggest that certain benzodiazepines are more reliable and effective at producing euphoria over others. <ref>https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3684331/ | | *'''[[Effect::Cognitive euphoria]]''' - This effect is not consistently produced between individuals and seems to be highly dependent on personal factors. Some people do not report any euphoric effects following benzodiazepine use. When it does occur, it is typically described as mild to moderate and is commonly thought to occur at a higher rate in those with pre-existing [[anxiety]] issues. This may partly be the result of the immediateness in which the anxiety-relieving and disinhibiting effects are produced. While this effect may not be entirely consistent, many reports suggest that certain benzodiazepines are more reliable and effective at producing euphoria over others. <ref>{{cite journal | vauthors=((Griffin, C. E.)), ((Kaye, A. M.)), ((Bueno, F. R.)), ((Kaye, A. D.)) | journal=The Ochsner Journal | title=Benzodiazepine Pharmacology and Central Nervous System–Mediated Effects | volume=13 | issue=2 | pages=214–223 | date= 2013 | url=https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3684331/ | issn=1524-5012}}</ref> | ||
*'''[[Effect::Memory suppression]]''' | *'''[[Effect::Memory suppression]]''' | ||
**'''[[Effect::Amnesia]]''' | **'''[[Effect::Amnesia]]''' | ||
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*'''[[Effect::Anxiety|Rebound anxiety]]''' - Rebound anxiety is a commonly observed effect with [[anxiety suppression|anxiety relieving]] substances like [[benzodiazepines]]. It typically corresponds to the total duration spent under the substance's influence along with the total amount consumed in a given period, an effect which can easily lend itself to cycles of dependence and addiction. | *'''[[Effect::Anxiety|Rebound anxiety]]''' - Rebound anxiety is a commonly observed effect with [[anxiety suppression|anxiety relieving]] substances like [[benzodiazepines]]. It typically corresponds to the total duration spent under the substance's influence along with the total amount consumed in a given period, an effect which can easily lend itself to cycles of dependence and addiction. | ||
*'''[[Effect::Dream potentiation]]'''<ref>Goyal, | *'''[[Effect::Dream potentiation]]'''<ref>{{cite journal | vauthors=((Goyal, S.)) | journal=Canadian Medical Association Journal | title=Drugs and dreams | volume=102 | issue=5 | pages=524 | date=14 March 1970 | issn=0008-4409}}</ref> or '''[[Effect::Dream suppression]]''' | ||
*'''[[Effect::Sleepiness|Residual sleepiness]]''' - While benzodiazepines can be used as an effective [[hypnotic|sleep-inducing]] aid, their effects may persist into the morning afterward, which may lead users to feeling "groggy" or "dull" for up to a few hours. | *'''[[Effect::Sleepiness|Residual sleepiness]]''' - While benzodiazepines can be used as an effective [[hypnotic|sleep-inducing]] aid, their effects may persist into the morning afterward, which may lead users to feeling "groggy" or "dull" for up to a few hours. | ||
*'''[[Effect::Thought deceleration]]''' | *'''[[Effect::Thought deceleration]]''' | ||
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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''' | |||
|- | |||
|[[Chlordiazepoxide]]|| ||NHCH<sub>3</sub>||H||O||C<sub>6</sub>H<sub>5</sub>||H||Cl||[[File:Chlordiazepoxide.svg|170px]] | |||
|- | |||
|[[Bromazepam]]||H||=O||H|| ||C<sub>5</sub>H<sub>4</sub>N||H||Br||[[File:Bromazepam.svg|170px]] | |||
|- | |||
|[[Flubromazepam]]||H||=O||H|| ||C<sub>6</sub>H<sub>4</sub>F||H||Br||[[File:Flubromazepam.svg|170px]] | |||
|- | |||
|[[Diazepam]]||CH<sub>3</sub>||=O||H|| ||C<sub>6</sub>H<sub>5</sub>||H||Cl||[[File:Diazepam.svg|170px]] | |||
|- | |||
|[[Diclazepam]]||CH<sub>3</sub>||=O||H|| ||C<sub>6</sub>H<sub>4</sub>Cl||H||Cl||[[File:Diclazepam.svg|170px]] | |||
|- | |||
|[[Lorazepam]]||H||=O||OH|| ||C<sub>6</sub>H<sub>4</sub>Cl||H||Cl||[[File:Lorazepam.svg|170px]] | |||
|- | |||
|[[Oxazepam]]||H||=O||OH|| ||C<sub>6</sub>H<sub>5</sub>||H||Cl||[[File:Oxazepam.svg|170px]] | |||
|- | |||
|[[Temazepam]]||CH<sub>3</sub>||=O||OH|| ||C<sub>6</sub>H<sub>5</sub>||H||Cl||[[File:Temazepam.svg|170px]] | |||
|- | |||
|[[Cinolazepam]]||CH<sub>2</sub>CH<sub>2</sub>≡N||=O||OH|| ||C<sub>6</sub>H<sub>4</sub>F||H||Cl||[[File:Cinolazepam.svg|170px]] | |||
|- | |||
|[[Clonazepam]]||H||=O||H|| ||C<sub>6</sub>H<sub>4</sub>Cl||H||NO<sub>2</sub>||[[File:Clonazepam.svg|170px]] | |||
|- | |||
|[[Flunitrazepam]]||CH<sub>3</sub>||=O||H|| ||C<sub>6</sub>H<sub>4</sub>F||H||NO<sub>2</sub>||[[File:Flunitrazepam.svg|170px]] | |||
|- | |||
|[[Meclonazepam]]||H||=O||CH<sub>3</sub>|| ||C<sub>6</sub>H<sub>4</sub>Cl||H||NO<sub>2</sub>||[[File:Meclonazepam.svg|170px]] | |||
|- | |||
|[[Nifoxipam]]||H||=O||OH|| ||C<sub>6</sub>H<sub>4</sub>F||H||NO<sub>2</sub>||[[File:Nifoxipam.svg|170px]] | |||
|- | |||
|[[Alprazolam]]||C(CH<sub>3</sub>)=N-||=N-||H|| ||C<sub>6</sub>H<sub>5</sub>||H||Cl||[[File:Alprazolam.svg|170px]] | |||
|- | |||
|[[Pyrazolam]]||C(CH<sub>3</sub>)=N-||=N-||H|| ||C<sub>5</sub>H<sub>4</sub>N||H||Br||[[File:Pyrazolam.svg|170px]] | |||
|- | |||
|[[Flubromazolam]]||C(CH<sub>3</sub>)=N-||=N-||H|| ||C<sub>6</sub>H<sub>4</sub>F||H||Br||[[File:Flubromazolam.svg|170px]] | |||
|- | |||
|[[Midazolam]]||C(CH<sub>3</sub>)=N-||=N-||H|| ||C<sub>6</sub>H<sub>4</sub>F||H||Cl||[[File:Midazolam.svg|170px]] | |||
|- | |||
|[[Triazolam]]||C(CH<sub>3</sub>)=N-||=N-||H|| ||C<sub>6</sub>H<sub>4</sub>Cl||H||Cl||[[File:Triazolam.svg|170px]] | |||
|- | |||
|[[Clonazolam]]||C(CH<sub>3</sub>)=N-||=N-||H|| ||C<sub>6</sub>H<sub>4</sub>Cl||H||NO<sub>2</sub>||[[File:Clonazolam.svg|170px]] | |||
|- | |||
|[[Flunitrazolam]]||C(CH<sub>3</sub>)=N-||=N-||H|| ||C<sub>6</sub>H<sub>4</sub>F||H||NO<sub>2</sub>||[[File:Flunitrazolam.svg|170px]] | |||
|- | |||
|[[Flumazenil]]||CH=N-||C(C<sub>3</sub>H<sub>5</sub>O<sub>2</sub>)-||H||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>)-||CH<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== | ||
The dosages below represent approximate equivalent dosages between various benzodiazepines in comparison to 10mg of [[diazepam]]. | The dosages below represent approximate equivalent dosages between various benzodiazepines in comparison to 10mg of [[diazepam]]. | ||
The authors of this table specifically state that their equivalents differ from those used by other authors and "are firmly based on clinical experience during switch-over to diazepam at the start of withdrawal programs but may vary between individuals."<ref> | The authors of this table specifically state that their equivalents differ from those used by other authors and "are firmly based on clinical experience during switch-over to diazepam at the start of withdrawal programs but may vary between individuals."<ref>{{Citation | title=benzo.org.uk : Benzodiazepine Equivalence Table | url=https://www.benzo.org.uk/bzequiv.htm}}</ref> | ||
<div class="flex-panel align-column" style="flex-flow: column wrap;"> | <div class="flex-panel align-column" style="flex-flow: column wrap;"> | ||
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|- | |- | ||
|'''[[Diclazepam]]'''||~120||1||a, h | |'''[[Diclazepam]]'''||~120||1||a, h | ||
|- | |||
|'''[[Flualprazolam]]'''||?||0.2||h | |||
|- | |- | ||
|'''[[Flubromazepam]]'''||106||4||h | |'''[[Flubromazepam]]'''||106||4||h | ||
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When combined with benzodiazepines, the visual hallucinations induced by [[hallucinogenic]] substances (particularly [[psychedelics]]) may significantly decrease along with any underlying [[anxiety]] that may be present.{{citation needed}} | When combined with benzodiazepines, the visual hallucinations induced by [[hallucinogenic]] substances (particularly [[psychedelics]]) may significantly decrease along with any underlying [[anxiety]] that may be present.{{citation needed}} | ||
Along with [[antipsychotics]] such as [[quetiapine]] (''Seroquel''), benzodiazepines are commonly [[administered]] in hospital settings to treat patients presenting symptoms of hallucinogen overdose or [[psychosis]].<ref>Benzodiazepines alone or in combination with antipsychotic drugs for acute psychosis | https://www.cochrane.org/CD003079/SCHIZ_benzodiazepines-alone-or-combination-antipsychotic-drugs-acute-psychosis</ref> | Along with [[antipsychotics]] such as [[quetiapine]] (''Seroquel''), benzodiazepines are commonly [[administered]] in hospital settings to treat patients presenting symptoms of hallucinogen overdose or [[psychosis]].<ref>{{Citation | title=Benzodiazepines alone or in combination with antipsychotic drugs for acute psychosis | url=https://www.cochrane.org/CD003079/SCHIZ_benzodiazepines-alone-or-combination-antipsychotic-drugs-acute-psychosis}}</ref> | ||
==Toxicity and harm potential== | ==Toxicity and harm potential== | ||
[[File:harmchart.png|thumb|right|300px|Radar plot showing relative physical harm, social harm, and dependence of benzodiazepines in comparison to other drugs.<ref>Development of a rational scale to assess the harm of drugs of potential misuse | [[File:HarmCausedByDrugsTable.svg|thumb|upright=1.35|Table from the 2010 ISCD study ranking various drugs (legal and illegal) based on statements by drug-harm experts. Benzodiazepines were found to be the 10th most dangerous drug overall.<ref name="Nutt_2010">{{cite journal | vauthors = Nutt DJ, King LA, Phillips LD | title = Drug harms in the UK: a multicriteria decision analysis | journal = Lancet | volume = 376 | issue = 9752 | pages = 1558–1565 | date = November 2010 | pmid = 21036393 | doi = 10.1016/S0140-6736(10)61462-6 | s2cid = 5667719 | citeseerx = 10.1.1.690.1283 }}</ref>]] | ||
Benzodiazepines have a [[Toxicity::low toxicity]] relative to dose, and are considered to be effectively non-lethal on their own.<ref>Benzodiazepine metabolism: an analytical perspective | [[File:harmchart.png|thumb|right|300px|Radar plot showing relative physical harm, social harm, and dependence of benzodiazepines in comparison to other drugs.<ref>{{cite journal | vauthors=((Nutt, D.)), ((King, L. A.)), ((Saulsbury, W.)), ((Blakemore, C.)) | journal=The Lancet | title=Development of a rational scale to assess the harm of drugs of potential misuse | volume=369 | issue=9566 | pages=1047–1053 | date=24 March 2007 | url=https://www.sciencedirect.com/science/article/pii/S0140673607604644 | issn=0140-6736 | doi=10.1016/S0140-6736(07)60464-4}}</ref>]] | ||
Benzodiazepines have a [[Toxicity::low toxicity]] relative to dose, and are considered to be effectively non-lethal on their own.<ref>{{cite journal | vauthors=((Mandrioli, R.)), ((Mercolini, L.)), ((Raggi, M. A.)) | journal=Current Drug Metabolism | title=Benzodiazepine metabolism: an analytical perspective | volume=9 | issue=8 | pages=827–844 | date= October 2008 | issn=1389-2002 | doi=10.2174/138920008786049258}}</ref> However, their potential [[Toxicity::potentially [[respiratory depression|lethality]] increases significantly when mixed with [[depressants]] like [[alcohol]] or [[opioids]]]]. | |||
It is strongly recommended that one use [[responsible drug use|harm reduction practices]] when using this class of substances. | It is strongly recommended that one use [[responsible drug use|harm reduction practices]] when using this class of substances. | ||
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Benzodiazepines are known to be [[Addiction potential::extremely physically and psychologically addictive]].{{citation needed}} | Benzodiazepines are known to be [[Addiction potential::extremely physically and psychologically addictive]].{{citation needed}} | ||
Tolerance will develop to the sedative-hypnotic effects [[Time to full tolerance::within a couple of days of continuous use]].<ref>Principles and Practice of Psychopharmacotherapy | | Tolerance will develop to the sedative-hypnotic effects [[Time to full tolerance::within a couple of days of continuous use]].<ref>{{cite book | vauthors=((Janicak, P. G.)), ((Marder, S. R.)), ((Pavuluri, M. N.)) | date=25 October 2010 | title=Principles and Practice of Psychopharmacotherapy | publisher=Lippincott Williams & Wilkins | isbn=9781605475653}}</ref> After cessation, the tolerance returns to baseline in [[Time to zero tolerance::7-14 days]]. Withdrawal symptoms or rebound symptoms may occur after ceasing one's usage abruptly following a few weeks or longer of steady dosing and may necessitate a gradual dose reduction.<ref>{{cite journal | vauthors=((Verster, J. C.)), ((Volkerts, E. R.)) | journal=CNS Drug Reviews | title=Clinical Pharmacology, Clinical Efficacy, and Behavioral Toxicity of Alprazolam: A Review of the Literature | volume=10 | issue=1 | pages=45–76 | date=7 June 2006 | url=https://onlinelibrary.wiley.com/doi/10.1111/j.1527-3458.2004.tb00003.x | issn=1080563X | doi=10.1111/j.1527-3458.2004.tb00003.x}}</ref><ref>{{cite book | vauthors=((Galanter, M.)), ((Kleber, H. D.)) | date= 2008 | title=The American Psychiatric Publishing Textbook of Substance Abuse Treatment | publisher=American Psychiatric Pub. | isbn=9781585622764}}</ref> | ||
===Overdose=== | ===Overdose=== | ||
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*[https://www.erowid.org/pharms/benzodiazepine/ Benzodiazepines (Erowid Vault)] | *[https://www.erowid.org/pharms/benzodiazepine/ Benzodiazepines (Erowid Vault)] | ||
*[http://www.drugs.com/drug-class/benzodiazepines.html Benzodiazepines (Drugs.com)] | *[http://www.drugs.com/drug-class/benzodiazepines.html Benzodiazepines (Drugs.com)] | ||
*[https://benzo.tripsit.me/ TripSit Benzodiazepine Converter] | |||
==Further reading== | ==Further reading== | ||
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{{reflist|2}} | {{reflist|2}} | ||
[[Category: | [[Category:Chemical class]] | ||
[[Category:Depressant]] | |||
[[Category:Benzodiazepine|*]] | |||
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