The Info List - Prozac

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Fluoxetine, also known by trade names Prozac and Sarafem, among others, is an antidepressant of the selective serotonin reuptake inhibitor (SSRI) class.[2] It is used for the treatment of major depressive disorder, obsessive–compulsive disorder (OCD), bulimia nervosa, panic disorder and premenstrual dysphoric disorder.[2] It may decrease the risk of suicide in those over the age of 65.[2] It has also been used to treat premature ejaculation.[2] Fluoxetine
is taken by mouth.[2] Common side effects include trouble sleeping, sexual dysfunction, loss of appetite, dry mouth, rash and abnormal dreams.[2] Serious side effects include serotonin syndrome, mania, seizures, an increased risk of suicidal behavior in people under 25 years old and an increased risk of bleeding.[2] If stopped suddenly, a withdrawal syndrome may occur with anxiety, dizziness and changes in sensation.[2] It is unclear if it is safe in pregnancy.[5] If already on the medication, it may be reasonable to continue during breastfeeding.[5] Its mechanism of action is not entirely clear but believed to be related to increasing serotonin activity in the brain.[2] Fluoxetine
was discovered by Eli Lilly and Company
Eli Lilly and Company
in 1972 and entered medical use in 1986.[6] It is on the World Health Organization's List of Essential Medicines, the most effective and safe medicines needed in a health system.[7] It is available as a generic medication.[2] The wholesale cost in the developing world is between 0.01 and 0.04 USD per day as of 2014.[8] In the United States, it costs about 0.85 USD per day.[2]


1 Medical uses

1.1 Depression 1.2 Obsessive-compulsive disorder 1.3 Panic disorder 1.4 Bulimia nervosa 1.5 Premenstrual dysphoric disorder 1.6 Special

2 Adverse effects

2.1 Sexual dysfunction 2.2 Discontinuation syndrome 2.3 Suicide

3 Overdose 4 Interactions 5 Pharmacology

5.1 Pharmacodynamics 5.2 Pharmacokinetics 5.3 Measurement in body fluids

6 Usage 7 History 8 Society and culture

8.1 Airline pilots 8.2 Environmental effects

9 Research

9.1 Violence

10 See also 11 References 12 External links

Medical uses[edit]

20 mg blister pack

is frequently used to treat major depressive disorder, obsessive-compulsive disorder (OCD), post-traumatic stress disorder (PTSD), bulimia nervosa, panic disorder, premenstrual dysphoric disorder, and trichotillomania.[9][10][11][12] It has also been used for cataplexy, obesity, and alcohol dependence,[13] as well as binge eating disorder.[14] It has also been tried as a treatment for autism spectrum disorders with moderate success in adults.[15][16][17][18] Depression[edit] The effectiveness of fluoxetine and other antidepressants in the treatment of mild-to-moderate depression is controversial. A meta-analysis published by Kirsch in 2008 suggests, in those with mild or moderate symptoms, the efficacy of fluoxetine and other SSRIs is clinically insignificant.[19] A 2009 meta-analysis by Fournier which evaluated patient-level data from six trials of the SSRI
paroxetine and the non- SSRI
antidepressant imipramine has been further cited as evidence that antidepressants exhibit minimal efficacy in mild to moderate depression.[20] A 2012 meta-analysis using individual patient level-data of fluoxetine for the treatment of depression concluded statistically and clinically significant benefit was seen irrespective of baseline depression severity, and no significant effect was found on baseline severity on observed efficacy.[21] A 2009 systematic review by the National Institute of Care and Clinical Excellence (NICE) (which considered the Kirsch, but not the later meta-analyses) concluded strong evidence existed for the efficacy of SSRIs in the treatment of moderate and severe depression, with some evidence for their efficacy in the treatment of mild depression.[22] Both the NICE and the Fournier analyses concluded that greater evidence is seen for the efficacy of antidepressants in the treatment of chronic mild depression (dysthymia) than in recent-onset mild depression. NICE recommends antidepressant treatment with an SSRI
in combination with psychosocial interventions as second-line treatment for short term mild depression, and as a first line treatment for severe and moderate depression, as well as mild depression that is recurrent or long-standing. The American Psychiatric Association
American Psychiatric Association
includes antidepressant therapy among its first-line options for the treatment of depression, particularly when "a history of prior positive response to antidepressant medications, the presence of moderate to severe symptoms, significant sleep or appetite disturbances, agitation, patient preference, and anticipation of the need for maintenance therapy" exist.[23] Obsessive-compulsive disorder[edit] The efficacy of fluoxetine in the treatment of obsessive-compulsive disorder (OCD) was demonstrated in two randomized multicenter phase III clinical trials. The pooled results of these trials demonstrated that 47% of completers treated with the highest dose were "much improved" or "very much improved" after 13 weeks of treatment, compared to 11% in the placebo arm of the trial.[3] The American Academy of Child and Adolescent Psychiatry state that SSRIs, including fluoxetine, should be used as first-line therapy in children, along with cognitive behavioral therapy (CBT), for the treatment of moderate to severe OCD.[24] Panic disorder[edit] The efficacy of fluoxetine in the treatment of panic disorder was demonstrated in two 12-week randomized multicenter phase III clinical trials that enrolled patients diagnosed with panic disorder, with or without agoraphobia. In the first trial, 42% of subjects in the fluoxetine-treated arm were free of panic attacks at the end of the study, vs. 28% in the placebo arm. In the second trial, 62% of fluoxetine treated patients were free of panic attacks at the end of the study, vs. 44% in the placebo arm.[3] Bulimia nervosa[edit] A 2011 systematic review of seven trials which compared fluoxetine to a placebo in the treatment of bulimia nervosa; six of which found a statistically significant reduction in symptoms such as vomiting and binge eating.[25] However, no difference was observed between treatment arms when fluoxetine and psychotherapy were compared to psychotherapy alone. Premenstrual dysphoric disorder[edit] Fluoxetine
is used to treat premenstrual dysphoric disorder.[26][27] Special
populations[edit] In children and adolescents, fluoxetine is the antidepressant of choice due to tentative evidence favoring its efficacy and tolerability.[28][29] In pregnancy, fluoxetine is considered a category C drug. Evidence supporting an increased risk of major fetal malformations resulting from fluoxetine exposure is limited, although the Medicines and Healthcare Products Regulatory Agency
Medicines and Healthcare Products Regulatory Agency
(MHRA) of the UK has warned prescribers and patients of the potential for fluoxetine exposure in the first trimester (during organogenesis, formation of the fetal organs) to cause a slight increase in the risk of congenital cardiac malformations in the newborn.[30][31][32] Furthermore, an association between fluoxetine use during the first trimester and an increased risk of minor fetal malformations was observed in one study.[31] However, a systematic review and meta-analysis of 21 studies – published in the Journal of Obstetrics and Gynaecology Canada – concluded, "the apparent increased risk of fetal cardiac malformations associated with maternal use of fluoxetine has recently been shown also in depressed women who deferred SSRI
therapy in pregnancy, and therefore most probably reflects an ascertainment bias. Overall, women who are treated with fluoxetine during the first trimester of pregnancy do not appear to have an increased risk of major fetal malformations."[33] Per the FDA, infants exposed to SSRIs in late pregnancy may have an increased risk for persistent pulmonary hypertension of the newborn. Limited data support this risk, but the FDA
recommends physicians consider tapering SSRIs such as fluoxetine during the third trimester.[3] A 2009 review recommended against fluoxetine as a first-line SSRI
during lactation, stating, "[fluoxetine] should be viewed as a less-preferred SSRI
for breastfeeding mothers, particularly with newborn infants, and in those mothers who consumed fluoxetine during gestation."[34] Sertraline
is often the preferred SSRI
during pregnancy due to the relatively minimal fetal exposure observed and its safety profile while breastfeeding.[35] Adverse effects[edit] Side effects observed in fluoxetine-treated persons in clinical trials with an incidence >5% and at least twice as common in fluoxetine-treated persons compared to those who received a placebo pill include abnormal dreams, abnormal ejaculation, anorexia, anxiety, asthenia, diarrhea, dry mouth, dyspepsia, flu syndrome, impotence, insomnia, decreased libido, nausea, nervousness, pharyngitis, rash, sinusitis, somnolence, sweating, tremor, vasodilatation, and yawning.[36] Fluoxetine
is considered the most stimulating of the SSRIs (that is, it is most prone to causing insomnia and agitation).[37] It also appears to be the most prone of the SSRIs for producing dermatologic reactions (e.g. urticaria (hives), rash, itchiness, etc.).[31] Sexual dysfunction[edit] See also: Selective serotonin reuptake inhibitor
Selective serotonin reuptake inhibitor
§ Sexual dysfunction Sexual dysfunction, including loss of libido, anorgasmia, lack of vaginal lubrication, and erectile dysfunction, are some of the most commonly encountered adverse effects of treatment with fluoxetine and other SSRIs. While early clinical trials suggested a relatively low rate of sexual dysfunction, more recent studies in which the investigator actively inquires about sexual problems suggest that the incidence is >70%.[38] Symptoms of sexual dysfunction have been reported to persist after discontinuing SSRIs, although this is thought to be occasional.[3][39][40] Discontinuation syndrome[edit] Antidepressant
discontinuation syndrome is an adverse effect of second generation anti-depressants, including fluoxetine. The symptoms appear with rapid discontinuation of one of these drugs, and can include dizziness, disturbance of balance, headache, nausea, insomnia, and vivid dreams. Others can include sensations of tingling or numbness, ‘electric-shock’-like sensations, and irritability, with some case reports of hallucinations. They can generally be prevented by tapering off the drug over a period of four weeks, although evidence is weak for optimal tapering and there is disagreement between experts over the schedule. If a person is informed of the risk of discontinuation syndrome prior to starting the drug and again prior to beginning any tapering, discontinuation symptoms appear to be fewer and less severe, but again evidence is weak. Slower-acting drugs, like fluoxetine, may be less likely to cause discontinuation symptoms, but the evidence for this is weak as well. The mechanism by which discontinuation syndrome occurs in some people is not well understood.[41] Suicide[edit] In 2007 the FDA
required all antidepressants to carry a black box warning stating that antidepressants may increase the risk of suicide in people younger than 25.[42] This warning is based on statistical analyses conducted by two independent groups of FDA
experts that found a 2-fold increase of the suicidal ideation and behavior in children and adolescents, and 1.5-fold increase of suicidality in the 18–24 age group. The suicidality was slightly decreased for those older than 24, and statistically significantly lower in the 65 and older group.[43][44][45] This analysis was criticized by Donald Klein, who noted that suicidality, that is suicidal ideation and behavior, is not necessarily a good surrogate marker for completed suicide, and it is still possible that antidepressants may prevent actual suicide while increasing suicidality.[46] There is less data on fluoxetine than on antidepressants as a whole. For the above analysis on the antidepressant level, the FDA
had to combine the results of 295 trials of 11 antidepressants for psychiatric indications to obtain statistically significant results. Considered separately, fluoxetine use in children increased the odds of suicidality by 50%,[47] and in adults decreased the odds of suicidality by approximately 30%.[44][45] Similarly, the analysis conducted by the UK MHRA found a 50% increase of odds of suicide-related events, not reaching statistical significance, in the children and adolescents on fluoxetine as compared to the ones on placebo. According to the MHRA data, for adults fluoxetine did not change the rate of self-harm and statistically significantly decreased suicidal ideation by 50%.[48][49] Overdose[edit] See also: Serotonin
syndrome In overdose, most frequent adverse effects include:[50]

Nervous system effects

anxiety nervousness insomnia drowsiness fatigue or asthenia tremor dizziness or lightheadedness

Gastrointestinal effects

anorexia nausea diarrhea vasodilation dry mouth abnormal vision

Other effects

abnormal ejaculation rash sweating decreased libido

Interactions[edit] Contraindications include prior treatment (within the past two weeks) with MAOIs such as phenelzine and tranylcypromine, due to the potential for serotonin syndrome.[1] Its use should also be avoided in those with known hypersensitivities to fluoxetine or any of the other ingredients in the formulation used.[1] Its use in those concurrently receiving pimozide or thioridazine is also advised against.[1] In some cases, use of dextromethorphan-containing cold & cough medications with fluoxetine is advised against, due to fluoxetine increasing serotonin levels, as well as the fact that fluoxetine is a cytochrome P450 2D6 inhibitor, which causes dextromethorphan to not be metabolized at a normal rate, thus increasing the risk of serotonin syndrome and other potential side effects of dextromethorphan.[51] Patients who are taking anticoagulants or NSAIDS must be careful when taking fluoxetine or other SSRIs, as they can sometimes increase the blood-thinning effects of these medications.[52] Fluoxetine
and norfluoxetine inhibit many isozymes of the cytochrome P450 system that are involved in drug metabolism. Both are potent inhibitors of CYP2D6
(which is also the chief enzyme responsible for their metabolism) and CYP2C19, and mild to moderate inhibitors of CYP2B6
and CYP2C9.[53][54] In vivo, fluoxetine and norfluoxetine do not significantly affect the activity of CYP1A2
and CYP3A4.[53] They also inhibit the activity of P-glycoprotein, a type of membrane transport protein that plays an important role in drug transport and metabolism and hence P-glycoprotein
substrates such as loperamide may have their central effects potentiated.[55] This extensive effect on the body's pathways for drug metabolism creates the potential for interactions with many commonly used drugs.[55][56] Its use should also be avoided in those receiving other serotonergic drugs such as monoamine oxidase inhibitors, tricyclic antidepressants, methamphetamine, MDMA, triptans, buspirone, serotonin-norepinephrine reuptake inhibitors and other SSRIs due to the potential for serotonin syndrome to develop as a result.[1] There is also the potential for interaction with highly protein-bound drugs due to the potential for fluoxetine to displace said drugs from the plasma or vice versa hence increasing serum concentrations of either fluoxetine or the offending agent.[1] Pharmacology[edit]

Binding affinities
Binding affinities
(Ki in nM)[57][58] [verification needed]

Molecular Target Fluoxetine Norfluoxetine

SERT 1 19

NET 660 2700

DAT 4180 420

5-HT2A 200 300

5-HT2B 5000 5100

5-HT2C 72.6 91.2

α1 3000 3900

M1 870 1200

M2 2700 4600

M3 1000 760

M4 2900 2600

M5 2700 2200

H1 3250 10000

Entries with this color indicate a lower Ki bound.

Pharmacodynamics[edit] Fluoxetine
is a selective serotonin reuptake inhibitor (SSRI) and does not appreciably inhibit norepinephrine and dopamine reuptake at therapeutic doses. It does, however, delay the reuptake of serotonin, resulting in serotonin persisting longer when it is released. Large doses in rats have been shown to induce a significant increase in synaptic norepinephrine and dopamine.[59][60][61][62] Thus, dopamine and norepinephrine may contribute to the antidepressant action of fluoxetine in humans at supratherapeutic doses (60–80 mg) .[61][63] This effect may be mediated by 5HT2C receptors, which are inhibited by higher concentrations of fluoxetine.[64] Fluoxetine
increases the concentration of circulating allopregnanolone, a potent GABAA receptor
GABAA receptor
positive allosteric modulator, in the brain.[62][65] Norfluoxetine, a primary active metabolite of fluoxetine, produces a similar effect on allopregnanolone levels in the brains of mice.[62] Additionally, both fluoxetine and norfluoxetine are such modulators themselves, actions which may be clinically-relevant.[66] In addition, fluoxetine has been found to act as an agonist of the σ1-receptor, with a potency greater than that of citalopram but less than that of fluvoxamine. However, the significance of this property is not fully clear.[67][68] Fluoxetine
also functions as a channel blocker of anoctamin 1, a calcium-activated chloride channel.[69][70] A number of other ion channels, including nicotinic acetylcholine receptors and 5-HT3 receptors, are also known to be inhibited at similar concentrations.[66] Fluoxetine
has been shown to inhibit acid sphingomyelinase, a key regulator of ceramide levels which derives ceramide from sphingomyelin.[71][72] Pharmacokinetics[edit]

((S)-norfluoxetine) — fluoxetine's chief active metabolite.

The bioavailability of fluoxetine is relatively high (72%), and peak plasma concentrations are reached in 6–8 hours. It is highly bound to plasma proteins, mostly albumin and α1-glycoprotein.[1] Fluoxetine
is metabolized in the liver by isoenzymes of the cytochrome P450 system, including CYP2D6.[73] The role of CYP2D6
in the metabolism of fluoxetine may be clinically important, as there is great genetic variability in the function of this enzyme among people. CYP2D6
is responsible for converting fluoxetine to its only active metabolite, norfluoxetine.[74] Both drugs are also potent inhibitors of CYP2D6.[75] The extremely slow elimination of fluoxetine and its active metabolite norfluoxetine from the body distinguishes it from other antidepressants. With time, fluoxetine and norfluoxetine inhibit their own metabolism, so fluoxetine elimination half-life changes from 1 to 3 days, after a single dose, to 4 to 6 days, after long-term use.[1] Similarly, the half-life of norfluoxetine is longer (16 days) after long-term use.[73][76][77] Therefore, the concentration of the drug and its active metabolite in the blood continues to grow through the first few weeks of treatment, and their steady concentration in the blood is achieved only after four weeks.[78][79] Moreover, the brain concentration of fluoxetine and its metabolites keeps increasing through at least the first five weeks of treatment.[80] That means that the full benefits of the current dose a patient receives are not realized for at least a month since its initiation. For example, in one 6-week study, the median time to achieving consistent response was 29 days.[78] Likewise, complete excretion of the drug may take several weeks. During the first week after the treatment discontinuation, the brain concentration of fluoxetine decreases only by 50%,[80] The blood level of norfluoxetine 4 weeks after the treatment discontinuation is about 80% of the level registered by the end of the first treatment week, and 7 weeks after the discontinuation norfluoxetine is still detectable in the blood.[76] Measurement in body fluids[edit] Fluoxetine
and norfluoxetine may be quantitated in blood, plasma or serum to monitor therapy, confirm a diagnosis of poisoning in hospitalized patients or assist in a medicolegal death investigation. Blood or plasma fluoxetine concentrations are usually in a range of 50–500 μg/L in persons taking the drug for its antidepressant effects, 900–3000 μg/L in survivors of acute overdosage and 1000–7000 μg/L in victims of fatal overdosage. Norfluoxetine concentrations are approximately equal to those of the parent drug during chronic therapy, but may be substantially less following acute overdosage, since it requires at least 1–2 weeks for the metabolite to achieve equilibrium.[81][82][83] Usage[edit] In 2010, over 24.4 million prescriptions for generic fluoxetine were filled in the United States,[84] making it the third-most prescribed antidepressant after sertraline and citalopram.[84] In 2011, 6 million prescriptions for fluoxetine were filled in the United Kingdom.[85] History[edit] The work which eventually led to the discovery of fluoxetine began at Eli Lilly and Company
Eli Lilly and Company
in 1970 as a collaboration between Bryan Molloy and Robert Rathbun. It was known at that time that the antihistamine diphenhydramine shows some antidepressant-like properties. 3-Phenoxy-3-phenylpropylamine, a compound structurally similar to diphenhydramine, was taken as a starting point, and Molloy synthesized dozens of its derivatives.[86] Hoping to find a derivative inhibiting only serotonin reuptake, an Eli Lilly scientist, David T. Wong, proposed to retest the series for the in vitro reuptake of serotonin, norepinephrine and dopamine. This test, carried out by Jong-Sir Horng in May 1972,[86] showed the compound later named fluoxetine to be the most potent and selective inhibitor of serotonin reuptake of the series.[87] Wong published the first article about fluoxetine in 1974.[87] A year later, it was given the official chemical name fluoxetine and the Eli Lilly and Company
Eli Lilly and Company
gave it the trade name Prozac. In February 1977, Dista Products Company, a division of Eli Lilly & Company, filed an Investigational New Drug application to the U.S. Food and Drug Administration
U.S. Food and Drug Administration
(FDA) for fluoxetine.[88] Fluoxetine
appeared on the Belgian market in 1986.[89] In the U.S., the FDA
gave its final approval in December 1987,[90] and a month later Eli Lilly began marketing Prozac; annual sales in the U.S. reached $350 million within a year.[88] Worldwide sales eventually reached a peak of $2.6 billion a year.[91] Lilly tried several product line extension strategies, including extended release formulations and paying for clinical trials to test the efficacy and safety of fluoxetine in premenstrual dysphoric disorder and rebranding the drug in that indication as "Sarafem" after it was approved by the FDA
in 2000, following the recommendation of an advisory committee in 1999.[92][93][94] The invention of using fluoxetine to treat PMDD was made by Richard Wurtman at MIT, and the patent was licensed to his startup, Interneuron, which in turn sold it to Lilly.[95] To defend its revenue from fluoxetine, Lilly also fought a five-year, multimillion-dollar battle in court with the generic company Barr Pharmaceuticals to protect its patents on fluoxetine, and lost the cases for its line-extension patents other than those for Sarafem, opening fluoxetine to generic manufacturers starting in 2001.[96] When Lilly's patent expired in August 2001,[97] generic drug competition decreased Lily's sales of fluoxetine by 70% within two months.[92] In 2000 an investment bank had projected that annual sales of Sarafem could reach $250M/year.[98] Sales of Sarafem reached about $85M/year in 2002, and in that year Lilly sold its assets around the drug for $295M to Galen Holdings, a small Irish pharmaceutical company specializing in dermatology and women's health that had a sales force tasked to gynecologists' offices; analysts found the deal sensible since the annual sales of Sarafem made a difference to Galen, but not to Lilly.[99][100] Bringing Sarafem to market harmed Lilly's reputation in some quarters. The diagnostic category of PMDD was controversial since it was first proposed in 1987, and Lilly's role in retaining it in the appendix of the DSM-IV-TR, the discussions for which got underway in 1998, has been criticized.[98] Lilly was criticized for inventing a disease in order to make money,[98] and for not innovating but rather just seeking ways to continue making money from existing drugs.[101] It was also criticized by the FDA
and groups concerned with women's health for marketing Sarafem too aggressively when it was first launched; the campaign included a television commercial featuring a harried woman at the grocery store who asks herself if she has PMDD.[102] Society and culture[edit] Airline pilots[edit] Beginning April 5, 2010, fluoxetine became one of four antidepressant drugs that the FAA
permitted for pilots with authorization from an aviation medical examiner. The other permitted antidepressants are sertraline (Zoloft), citalopram (Celexa), and escitalopram (Lexapro).[103] These four remain the only antidepressants permitted by FAA
as of 2 December 2016.[ref][104] Environmental effects[edit] Fluoxetine
has been detected in aquatic ecosystems, especially in North America.[105] There is a growing body of research addressing the effects of fluoxetine (among other SSRIs) exposure on non-target aquatic species.[106][107][108][109] In 2003, one of the first studies addressed in detail the potential effects of fluoxetine on aquatic wildlife, this research concluded that exposure at environmental concentrations was of little risk to aquatic systems if a hazard quotient approach was applied to risk assessment.[108] However, they also stated the need for further research addressing sub-lethal consequences of fluoxetine, specifically focusing on study species sensitivity, behavioural responses, and endpoints modulated by serotonin system.[108] Since this time, a number of studies have reported fluoxetine induced impacts on a number of behavioural and physiological endpoints, inducing antipredator behaviour,[110][111][112] reproduction [113][114][114] and foraging [115][116] at or below field-detected concentrations. Although, a 2014 review on the ecotoxicology of fluoxetine concluded that at that time a consensus on the ability of environmental realistic dosages to affect the behaviour of wildlife could not be reached.[107] Research[edit] Violence[edit] Neither the American Psychiatric Association,[117] the National Institute for Health and Care Excellence (NICE),[118] nor the American College of Physicians[119] list violence among the potential side effects of treatment with serotonin selective reuptake inhibitors. Similarly, the World Health Organization and the European Psychiatric Association do not list violence among the potential side effects of SSRIs.[120][121] Serial case report studies of this type have been criticized as being subject to "confounding by indication", in which effects due to an underlying disease state are mistakenly attributed to the effects of treatment.[122] Other studies, including randomized clinical trials and observational studies, have suggested that fluoxetine and other SSRIs may reduce the propensity for violence. A randomized clinical trial performed by the US National Institutes for Mental Health found that fluoxetine reduced acts of domestic violence in alcoholics with a history of such behavior[123] A second clinical trial performed at the University of Chicago found that fluoxetine reduced aggressive behavior in patients in intermittent aggressive disorder.[124] A clinical trial found that fluoxetine reduced aggressive behavior in patients with borderline personality disorder.[125] These results are indirectly supported by studies demonstrating that other SSRIs can reduce violence and aggressive behavior.[126][127][128][129] A NBER study examining international trends in antidepressant use and crime rates in the 1990s found that increases in antidepressant drug prescriptions were associated with reductions in violent crime.[130] Despite the above cited evidence, psychiatrist David Healy and certain patient activist groups have compiled case reports of violent acts committed by individuals taking fluoxetine or other SSRIs,[131][132] and have argued that these drugs predispose susceptible individuals to commit violent acts. See also[edit]

(modified base and same termination of the molecule) it is a variant of the same structure


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External links[edit]

Wikimedia Commons has media related to Fluoxetine.

Fluoxetine, from the United States National Library of Medicine's Drug Information Portal Shorter, E (2014). "The 25th anniversary of the launch of Prozac gives pause for thought: where did we go wrong?". The British journal of psychiatry : the journal of mental science. 204: 331–2. doi:10.1192/bjp.bp.113.129916. PMID 24785765. 

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Antidepressants (N06A)

Specific reuptake inhibitors and/or receptor modulators


Citalopram Escitalopram Fluoxetine# Fluvoxamine Indalpine‡ Paroxetine Sertraline Zimelidine‡


Desvenlafaxine Duloxetine Levomilnacipran Milnacipran Tofenacin Venlafaxine


Atomoxetine Reboxetine Viloxazine


Amineptine‡ Bupropion Nomifensine‡


Mianserin Mirtazapine Setiptiline


Etoperidone Nefazodone Trazodone


Vilazodone Vortioxetine


Agomelatine Amisulpride Esketamine† Etryptamine‡ Indeloxazine flupentixol Ketamine† Medifoxamine‡ Metryptamine‡ Oxaflozane‡ Pivagabine‡ Tandospirone Teniloxazine Tianeptine

and tetracyclic antidepressants


Amineptine‡ Amitriptyline# Amitriptylinoxide Butriptyline‡ Clomipramine# Demexiptiline‡ Desipramine Dibenzepin Dimetacrine‡ Dosulepin Doxepin Imipramine Imipraminoxide‡ Iprindole‡ Lofepramine Melitracen Metapramine‡ Nitroxazepine Nortriptyline Noxiptiline Opipramol Pipofezine Propizepine‡ Protriptyline Quinupramine‡ Tianeptine Trimipramine


Amoxapine Maprotiline Mianserin Mirtazapine Setiptiline



Monoamine oxidase inhibitors


Irreversible: Benmoxin‡ Iproclozide‡ Iproniazid‡ Isocarboxazid Isoniazid# Linezolid# Mebanazine‡ Nialamide‡ Octamoxin‡ Phenelzine Pheniprazine‡ Phenoxypropazine‡ Pivhydrazine‡ Safrazine‡ Tedizolid Tranylcypromine

Reversible: Caroxazone‡

Mixed: Bifemelane


Reversible: Eprobemide Metralindole Minaprine‡ Moclobemide Pirlindole Tetrindole Toloxatone


Irreversible: Selegiline

Adjunctive therapies

Atypical antipsychotics (aripiprazole, brexpiprazole, lurasidone, olanzapine, quetiapine, risperidone) Buspirone Lithium (lithium carbonate, lithium citrate) Thyroid hormones (triiodothyronine (T3), levothyroxine (T4))


(SAMe) Hypericum perforatum
Hypericum perforatum
(St. John's Wort) Oxitriptan
(5-HTP) Rubidium chloride
Rubidium chloride
(RbCl) Tryptophan

#WHO-EM ‡Withdrawn from market Clinical trials:

†Phase III §Never to phase III

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Anxiolytics (N05B)

5-HT1AR agonists

Buspirone Gepirone† Tandospirone


Benzodiazepines: Adinazolam Alprazolam Bromazepam Camazepam Chlordiazepoxide Clobazam Clonazepam Clorazepate Clotiazepam Cloxazolam Diazepam# Ethyl loflazepate Etizolam Fludiazepam Halazepam Ketazolam Lorazepam# Medazepam Nordazepam Oxazepam Pinazepam Prazepam; Others: Alpidem‡ Barbiturates (e.g., phenobarbital) Carbamates (e.g., meprobamate) Chlormezanone‡ Ethanol (alcohol) Etifoxine Imepitoin; Herbs: Kava Skullcap Valerian

Gabapentinoids (α2δ VDCC blockers)

Gabapentin Gabapentin
enacarbil Phenibut Pregabalin


SSRIs (e.g., escitalopram) SNRIs (e.g., duloxetine) SARIs (e.g., trazodone) TCAs (e.g., clomipramine) TeCAs (e.g., mirtazapine) MAOIs (e.g., phenelzine); Others: Agomelatine Bupropion Tianeptine Vilazodone Vortioxetine

Sympatholytics (Antiadrenergics)

Alpha-1 blockers (e.g., prazosin) Alpha-2 agonists (e.g., clonidine, dexmedetomidine, guanfacine) Beta blockers (e.g., propranolol)


Benzoctamine Cannabidiol Cycloserine Fabomotizole Hydroxyzine Kanna Lavender Lorpiprazole Mebicar Mepiprazole Nicotine Opipramol Oxaflozane‡ Phenaglycodol Phenibut Picamilon Selank Tiagabine Tofisopam Validolum

#WHO-EM ‡Withdrawn from market Clinical trials:

†Phase III §Never to phase III

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OCD pharmacotherapies


SSRIs (e.g., fluoxetine, fluvoxamine, sertraline) SNRIs (e.g., venlafaxine) TCAs (e.g., clomipramine) MAOIs (e.g., phenelzine)


Antiandrogens (e.g., cyproterone acetate, leuprorelin) Antipsychotics (e.g., risperidone) Benzodiazepines (e.g., clonazepam) Lamotrigine Memantine Mirtazapine N-Acetylcysteine Ondansetron Pregabalin Psychedelics (e.g., psilocybin) Riluzole Topiramate

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Monoamine reuptake inhibitors


Piperazines: DBL-583 GBR-12783 GBR-12935 GBR-13069 GBR-13098 Nefazodone Vanoxerine

Piperidines: 4-Fluoropethidine Benocyclidine
(BTCP) Desoxypipradrol Dexmethylphenidate Difemetorex Ethylphenidate HDMP-28 Methylphenidate Pethidine
(meperidine) Phencyclidine Pipradrol Tenocyclidine

Pyrrolidines: Diphenylprolinol MDPV Naphyrone Prolintane Pyrovalerone

Tropanes: Altropane Benzatropine
(benztropine) Brasofensine CFT Cocaine Dichloropane Difluoropine Etybenzatropine
(ethybenztropine) FE-β-CPPIT FP-β-CPPIT Ioflupane (123I) RTI-55 RTI-112 RTI-113 RTI-121 RTI-126 RTI-150 RTI-177 RTI-229 RTI-336 Tesofensine Troparil Tropoxane WF-11 WF-23 WF-31 WF-33

Others: Adrafinil Amifitadine Armodafinil Amfonelic acid Amineptine Ansofaxine BTQ BTS 74,398 Bupropion Chaenomeles speciosa Ciclazindol Dasotraline Desmethylsertraline Desmethylsibutramine Diclofensine Didesmethylsibutramine Dimethocaine Diphenylpyraline Dizocilpine
(MK-801) DOV-102,677 DOV-216,303 Efavirenz Ephenidine Esketamine EXP-561 Fencamfamin Fezolamine Fluorenol GYKI-52895 Indatraline Ketamine Lefetamine Levophacetoperane Liafensine LR-5182 Manifaxine Mazindol Medifoxamine Mesocarb Metaphit MIN-117
(WF-516) Modafinil Nefopam Nomifensine NS-2359 O-2172 Oroxylin A Perafensine Pridefine Radafaxine Rimcazole Sertraline Sibutramine Solriamfetol Tametraline Tedatioxetine Tripelennamine Venlafaxine


Selective norepinephrine reuptake inhibitors: Amedalin Alseroxylon Ciclazindol Daledalin Edivoxetine Esreboxetine Lortalamine Mazindol Nisoxetine Reboxetine Talopram Talsupram Tandamine Teniloxazine Viloxazine

Norepinephrine–dopamine reuptake inhibitors: Amineptine Bupropion Fencamine Fencamfamin Hydroxybupropion Lefetamine Levophacetoperane LR-5182 Manifaxine Methylphenidate Nomifensine O-2172 Radafaxine Solriamfetol

Serotonin–norepinephrine reuptake inhibitors: Atomoxetine (tomoxetine) BTS-54505 CP-39,332 Desvenlafaxine Duloxetine Eclanamine Levomilnacipran McN-5652 Milnacipran N-Methyl-PPPA Nafenodone PPPA Tofenacin Venlafaxine WY-45233

Serotonin–norepinephrine–dopamine reuptake inhibitors: 3,3-Diphenylcyclobutanamine Amifitadine Ansofaxine Bicifadine Brasofensine Centanafadine Cocaine Dasotraline Desmethylsertraline Desmethylsibutramine Diclofensine Didesmethylsibutramine DOV-102677 DOV-216303 EXP-561 Fezolamine HDMP-28 Indatraline JNJ-7925476 JZ-IV-10 Liafensine Mazindol Naphyrone Nefazodone Nefopam NS-2359 Perafensine PRC200 Pridefine SEP-228431 SEP-228432 Sibutramine Tedatioxetine Tesofensine Tropanes (e.g., cocaine)

antidepressants: Amitriptyline Butriptyline Cianopramine Clomipramine Desipramine Dosulepin
(dothiepin) Doxepin Imipramine Lofepramine Melitracen Nortriptyline Protriptyline Trimipramine

Tetracyclic antidepressants: Amoxapine Maprotiline Mianserin Oxaprotiline Setiptiline

Others: Antihistamines (e.g., brompheniramine, chlorphenamine, pheniramine, tripelennamine) Antipsychotics (e.g., loxapine, ziprasidone) Arylcyclohexylamines (e.g., ketamine, phencyclidine) Dopexamine Ephenidine Ginkgo biloba Indeloxazine Nefazodone Opioids (e.g., desmetramadol, methadone, pethidine (meperidine), tapentadol, tramadol, levorphanol)


Selective serotonin reuptake inhibitors: Alaproclate Centpropazine Cericlamine Citalopram Dapoxetine Desmethylcitalopram Didesmethylcitalopram Escitalopram Femoxetine Fluoxetine Fluvoxamine Indalpine Ifoxetine Norfluoxetine Omiloxetine Panuramine Paroxetine PIM-35 Pirandamine RTI-353 Seproxetine Sertraline Zimelidine

Selective serotonin reuptake inhibitors
Selective serotonin reuptake inhibitors
and serotonin receptor modulators: Etoperidone Litoxetine Lubazodone LY-393558 SB-649915 TGBA01AD Trazodone Vilazodone Vortioxetine

Serotonin–norepinephrine reuptake inhibitors: Atomoxetine (tomoxetine) Bicifadine BTS-54505 CP-39332 Desvenlafaxine Duloxetine Eclanamine Levomilnacipran McN-5652 Milnacipran N-Methyl-PPPA PPPA Tofenacin Venlafaxine WY-45233

Serotonin–norepinephrine–dopamine reuptake inhibitors: 3,3-Diphenylcyclobutanamine Amifitadine Ansofaxine Bicifadine Brasofensine Centanafadine Cocaine Dasotraline Desmethylsertraline Desmethylsibutramine Diclofensine Didesmethylsibutramine DOV-102677 DOV-216303 EXP-561 Fezolamine HDMP-28 Indatraline JNJ-7925476 JZ-IV-10 Liafensine Mazindol Naphyrone Nefazodone Nefopam NS-2359 Perafensine PRC200 Pridefine SEP-228431 SEP-228432 Sibutramine Tedatioxetine Tesofensine Tropanes (e.g., cocaine)

antidepressants: Amitriptyline Cianopramine Clomipramine Cyanodothiepin Desipramine Dosulepin
(dothiepin) Doxepin Imipramine Lofepramine Nortriptyline Pipofezine Protriptyline

Others: A-80426 Amoxapine Antihistamines (e.g., brompheniramine, chlorphenamine, dimenhydrinate, diphenhydramine, mepyramine (pyrilamine), pheniramine, tripelennamine) Antipsychotics (e.g., loxapine, ziprasidone) Arylcyclohexylamines (e.g., 3-MeO-PCP, esketamine, ketamine, methoxetamine, phencyclidine) Cyclobenzaprine Delucemine Dextromethorphan Dextrorphan Efavirenz Medifoxamine Mesembrine Mifepristone MIN-117
(WF-516) N-Me-5-HT Opioids (e.g., dextropropoxyphene, methadone, pethidine (meperidine), levorphanol, tapentadol, tramadol) Roxindole


Amiodarone Amphetamines (e.g., amphetamine, methamphetamine, MDMA) APP AZIK Bietaserpine Deserpidine Deutetrabenazine Dihydrotetrabenazine Efavirenz GBR-12935 GZ-793A Ibogaine Ketanserin Lobeline Methoxytetrabenazine Reserpine Rose bengal Tetrabenazine Valbenazine Vanoxerine


DAT enhancers: Luteolin

DAT modulators: Agonist-like: SoRI-9804 SoRI-20040; Antagonist-like: SoRI-20041

See also: Receptor/signaling modulators • Monoamine releasing agents • Adrenergics • Dopaminergics • Serotonergics • Monoamine metabolism modulators • Monoamine neurotoxins

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receptor modulators



Agonists: 8-OH-DPAT Adatanserin Amphetamine Antidepressants (e.g., etoperidone, hydroxynefazodone, nefazodone, trazodone, triazoledione, vilazodone, vortioxetine) Atypical antipsychotics (e.g., aripiprazole, asenapine, brexpiprazole, cariprazine, clozapine, lurasidone, quetiapine, ziprasidone) Azapirones (e.g., buspirone, eptapirone, gepirone, perospirone, tandospirone) Bay R 1531 Befiradol BMY-14802 Cannabidiol Dimemebfe Dopamine Ebalzotan Eltoprazine Enciprazine Ergolines (e.g., bromocriptine, cabergoline, dihydroergotamine, ergotamine, lisuride, LSD, methylergometrine (methylergonovine), methysergide, pergolide) F-11461 F-12826 F-13714 F-14679 F-15063 F-15599 Flesinoxan Flibanserin Flumexadol Lesopitron LY-293284 LY-301317 mCPP MKC-242 Naluzotan NBUMP Osemozotan Oxaflozane Pardoprunox Piclozotan Rauwolscine Repinotan Roxindole RU-24969 S-14506 S-14671 S-15535 Sarizotan Serotonin
(5-HT) SSR-181507 Sunepitron Tryptamines (e.g., 5-CT, 5-MeO-DMT, 5-MT, bufotenin, DMT, indorenate, N-Me-5-HT, psilocin, psilocybin) TGBA01AD U-92016A Urapidil Vilazodone Xaliproden Yohimbine

Antagonists: Atypical antipsychotics (e.g., iloperidone, risperidone, sertindole) AV965 Beta blockers (e.g., alprenolol, carteolol, cyanopindolol, iodocyanopindolol, isamoltane, oxprenolol, penbutolol, pindobind, pindolol, propranolol, tertatolol) BMY-7378 CSP-2503 Dotarizine Ergolines (e.g., metergoline) Flopropione GR-46611 Isamoltane Lecozotan Mefway Metitepine
(methiothepin) MIN-117
(WF-516) MPPF NAN-190 Robalzotan S-15535 SB-649915 SDZ 216-525 Spiperone Spiramide Spiroxatrine UH-301 WAY-100135 WAY-100635 Xylamidine

Unknown/unsorted: Acetryptine Ergolines (e.g., ergometrine (ergonovine))


Agonists: CGS-12066A CP-93129 CP-94253 CP-122,288 CP-135807 Eltoprazine Ergolines (e.g., bromocriptine, dihydroergotamine, ergotamine, methylergometrine (methylergonovine), methysergide, pergolide) mCPP RU-24969 Serotonin
(5-HT) Triptans (e.g., avitriptan, donitriptan, eletriptan, sumatriptan, zolmitriptan) TFMPP Tryptamines (e.g., 5-BT, 5-CT, 5-MT, DMT) Vortioxetine

Antagonists: AR-A000002 Beta blockers (e.g., alprenolol, carteolol, isamoltane, oxprenolol, penbutolol, propranolol, tertatolol) Elzasonan Ergolines (e.g., metergoline) GR-127935 Isamoltane LY-393558 Metitepine
(methiothepin) SB-216641 SB-224289 SB-236057 Yohimbine

Unknown/unsorted: Ergolines (e.g., cabergoline, ergometrine (ergonovine), lisuride)


Agonists: CP-122,288 CP-135807 CP-286601 Ergolines (e.g., bromocriptine, cabergoline, dihydroergotamine, ergotamine, LSD, methysergide) GR-46611 L-694247 L-772405 mCPP PNU-109291 PNU-142633 Serotonin
(5-HT) TGBA01AD Triptans (e.g., almotriptan, avitriptan, donitriptan, eletriptan, frovatriptan, naratriptan, rizatriptan, sumatriptan, zolmitriptan) Tryptamines (e.g., 5-BT, 5-CT, 5-Et-DMT, 5-MT, 5-(nonyloxy)tryptamine, DMT)

Antagonists: Alniditan BRL-15572 Elzasonan Ergolines (e.g., metergoline) GR-127935 Ketanserin LY-310762 LY-367642 LY-393558 LY-456219 LY-456220 Metitepine
(methiothepin) Mianserin Ritanserin Yohimbine Ziprasidone

Unknown/unsorted: Acetryptine Ergolines (e.g., lisuride, lysergol, pergolide)


Agonists: BRL-54443 Ergolines (e.g., methysergide) Serotonin
(5-HT) Triptans (e.g., eletriptan) Tryptamines (e.g., tryptamine)

Antagonists: Metitepine

Unknown/unsorted: Ergolines (e.g., ergometrine (ergonovine), lysergol, methylergometrine (methylergonovine)


Agonists: BRL-54443 CP-122,288 Ergolines (e.g., bromocriptine, lysergol, methylergometrine (methylergonovine) methysergide) Lasmiditan LY-334370 Serotonin
(5-HT) Triptans (e.g., eletriptan, naratriptan, sumatriptan) Tryptamines (e.g., 5-MT)

Antagonists: Mianserin Metitepine



Agonists: 25H/NB series (e.g., 25I-NBF, 25I-NBMD, 25I-NBOH, 25I-NBOMe, 25B-NBOMe, 25C-NBOMe, 25TFM-NBOMe, 2CBCB-NBOMe, 25CN-NBOH, 2CBFly-NBOMe) 2Cs (e.g., 2C-B, 2C-E, 2C-I, 2C-T-2, 2C-T-7, 2C-T-21) 2C-B-FLY 2CB-Ind 5-Methoxytryptamines (5-MeO-DET, 5-MeO-DiPT, 5-MeO-DMT, 5-MeO-DPT, 5-MT) α-Alkyltryptamines (e.g., 5-Cl-αMT, 5-Fl-αMT, 5-MeO-αET, 5-MeO-αMT, α-Me-5-HT, αET, αMT) AL-34662 AL-37350A Bromo-DragonFLY Dimemebfe DMBMPP DOx
(e.g., DOB, DOC, DOI, DOM) Efavirenz Ergolines (e.g., 1P-LSD, ALD-52, bromocriptine, cabergoline, ergine (LSA), ergometrine (ergonovine), ergotamine, lisuride, LA-SS-Az, LSB, LSD, LSD-Pip, LSH, LSP, methylergometrine (methylergonovine), pergolide) Flumexadol Jimscaline Lorcaserin MDxx (e.g., MDA (tenamfetamine), MDMA
(midomafetamine), MDOH, MMDA) O-4310 Oxaflozane PHA-57378 PNU-22394 PNU-181731 RH-34 Phenethylamines (e.g., lophophine, mescaline) Piperazines (e.g., BZP, quipazine, TFMPP) Serotonin
(5-HT) TCB-2 TFMFly Tryptamines (e.g., 5-BT, 5-CT, bufotenin, DET, DiPT, DMT, DPT, psilocin, psilocybin, tryptamine)

Antagonists: 5-I-R91150 5-MeO-NBpBrT AC-90179 Adatanserin Altanserin Antihistamines (e.g., cyproheptadine, hydroxyzine, ketotifen, perlapine) AMDA Atypical antipsychotics (e.g., amperozide, aripiprazole, asenapine, blonanserin, brexpiprazole, carpipramine, clocapramine, clorotepine, clozapine, fluperlapine, gevotroline, iloperidone, lurasidone, melperone, mosapramine, ocaperidone, olanzapine, paliperidone, quetiapine, risperidone, sertindole, zicronapine, ziprasidone, zotepine) Cinanserin CSP-2503 Deramciclane Dotarizine Eplivanserin Ergolines (e.g., amesergide, LY-53857, LY-215840, mesulergine, metergoline, methysergide, sergolexole) Fananserin Flibanserin Glemanserin Irindalone Ketanserin KML-010 Landipirdine LY-393558 mCPP Medifoxamine Metitepine
(methiothepin) MIN-101 MIN-117
(WF-516) Naftidrofuryl Nantenine Nelotanserin Opiranserin (VVZ-149) Pelanserin Phenoxybenzamine Pimavanserin Pirenperone Pizotifen Pruvanserin Rauwolscine Ritanserin S-14671 Sarpogrelate Serotonin
antagonists and reuptake inhibitors (e.g., etoperidone, hydroxynefazodone, lubazodone, mepiprazole, nefazodone, triazoledione, trazodone) SR-46349B TGBA01AD Teniloxazine Temanogrel Tetracyclic antidepressants
Tetracyclic antidepressants
(e.g., amoxapine, aptazapine, esmirtazapine, maprotiline, mianserin, mirtazapine) Tricyclic antidepressants
Tricyclic antidepressants
(e.g., amitriptyline) Typical antipsychotics (e.g., chlorpromazine, fluphenazine, haloperidol, loxapine, perphenazine, pimozide, pipamperone, prochlorperazine, setoperone, spiperone, spiramide, thioridazine, thiothixene, trifluoperazine) Volinanserin Xylamidine Yohimbine

Unknown/unsorted: Ergolines (e.g., dihydroergotamine, nicergoline)


Agonists: 4-Methylaminorex Aminorex Amphetamines (e.g., chlorphentermine, cloforex, dexfenfluramine, fenfluramine, levofenfluramine, norfenfluramine) BW-723C86 DOx
(e.g., DOB, DOC, DOI, DOM) Ergolines (e.g., cabergoline, dihydroergocryptine, dihydroergotamine, ergotamine, methylergometrine (methylergonovine), methysergide, pergolide) Lorcaserin MDxx (e.g., MDA (tenamfetamine), MDMA
(midomafetamine), MDOH, [MMDA (drug)

Antagonists: Agomelatine Atypical antipsychotics (e.g., amisulpride, aripiprazole, asenapine, brexpiprazole, cariprazine, clozapine, N-desalkylquetiapine (norquetiapine), N-desmethylclozapine
(norclozapine), olanzapine, pipamperone, quetiapine, risperidone, ziprasidone) Cyproheptadine EGIS-7625 Ergolines (e.g., amesergide, bromocriptine, lisuride, LY-53857, LY-272015, mesulergine) Ketanserin LY-393558 mCPP Metadoxine Metitepine
(methiothepin) Pirenperone Pizotifen Propranolol PRX-08066 Rauwolscine Ritanserin RS-127445 Sarpogrelate SB-200646 SB-204741 SB-206553 SB-215505 SB-221284 SB-228357 SDZ SER-082 Tegaserod Tetracyclic antidepressants
Tetracyclic antidepressants
(e.g., amoxapine, mianserin, mirtazapine) Trazodone Typical antipsychotics (e.g., chlorpromazine) TIK-301 Yohimbine

Unknown/unsorted: Ergolines (e.g., ergometrine (ergonovine))


Agonists: 2Cs (e.g., 2C-B, 2C-E, 2C-I, 2C-T-2, 2C-T-7, 2C-T-21) 5-Methoxytryptamines (5-MeO-DET, 5-MeO-DiPT, 5-MeO-DMT, 5-MeO-DPT, 5-MT) α-Alkyltryptamines (e.g., 5-Cl-αMT, 5-Fl-αMT, 5-MeO-αET, 5-MeO-αMT, α-Me-5-HT, αET, αMT) A-372159 AL-38022A Alstonine CP-809101 Dimemebfe DOx
(e.g., DOB, DOC, DOI, DOM) Ergolines (e.g., ALD-52, cabergoline, dihydroergotamine, ergine (LSA), ergotamine, lisuride, LA-SS-Az, LSB, LSD, LSD-Pip, LSH, LSP, pergolide) Flumexadol Lorcaserin MDxx (e.g., MDA (tenamfetamine), MDMA
(midomafetamine), MDOH, MMDA) MK-212 Org 12962 Org 37684 Oxaflozane PHA-57378 Phenethylamines (e.g., lophophine, mescaline) Piperazines (e.g., aripiprazole, BZP, mCPP, quipazine, TFMPP) PNU-22394 PNU-181731 Ro60-0175 Ro60-0213 Serotonin
(5-HT) Tryptamines (e.g., 5-BT, 5-CT, bufotenin, DET, DiPT, DMT, DPT, psilocin, psilocybin, tryptamine) Vabicaserin WAY-629 WAY-161503 YM-348

Antagonists: Adatanserin Agomelatine Atypical antipsychotics (e.g., asenapine, clorotepine, clozapine, fluperlapine, iloperidone, melperone, olanzapine, paliperidone, quetiapine, risperidone, sertindole, ziprasidone, zotepine) Captodiame CEPC Cinanserin Cyproheptadine Deramciclane Desmetramadol Dotarizine Eltoprazine Ergolines (e.g., amesergide, bromocriptine, LY-53857, LY-215840, mesulergine, metergoline, methysergide, sergolexole) Etoperidone Fluoxetine FR-260010 Irindalone Ketanserin Ketotifen Latrepirdine
(dimebolin) Medifoxamine Metitepine
(methiothepin) Nefazodone Pirenperone Pizotifen Propranolol Ritanserin RS-102221 S-14671 SB-200646 SB-206553 SB-221284 SB-228357 SB-242084 SB-243213 SDZ SER-082 Tedatioxetine Tetracyclic antidepressants
Tetracyclic antidepressants
(e.g., amoxapine, aptazapine, esmirtazapine, maprotiline, mianserin, mirtazapine) TIK-301 Tramadol Trazodone Tricyclic antidepressants
Tricyclic antidepressants
(e.g., amitriptyline, nortriptyline) Typical antipsychotics (e.g., chlorpromazine, loxapine, pimozide, pipamperone, thioridazine) Xylamidine

Unknown/unsorted: Efavirenz Ergolines (e.g., ergometrine (ergonovine), methylergometrine (methylergonovine))



Agonists: Alcohols (e.g., butanol, ethanol (alcohol), trichloroethanol) m-CPBG Phenylbiguanide Piperazines (e.g., BZP, mCPP, quipazine) RS-56812 Serotonin
(5-HT) SR-57227 SR-57227A Tryptamines (e.g., 2-Me-5-HT, 5-CT, bufotenidine (5-HTQ)) Volatiles/gases (e.g., halothane, isoflurane, toluene, trichloroethane) YM-31636

Antagonists: Alosetron AS-8112 Atypical antipsychotics (e.g., clozapine, olanzapine, quetiapine) Azasetron Batanopride Bemesetron
(MDL-72222) Bupropion Cilansetron CSP-2503 Dazopride Dolasetron Galanolactone Granisetron Hydroxybupropion ICS-205930 Lerisetron Memantine Ondansetron Palonosetron Ramosetron Renzapride Ricasetron Tedatioxetine Tetracyclic antidepressants
Tetracyclic antidepressants
(e.g., amoxapine, mianserin, mirtazapine) Thujone Tropanserin Tropisetron Typical antipsychotics (e.g., loxapine) Volatiles/gases (e.g., nitrous oxide, sevoflurane, xenon) Vortioxetine Zacopride Zatosetron

Unknown/unsorted: LY-53857 Piperazines (e.g., naphthylpiperazine)


Agonists: 5-MT BIMU8 Capeserod Cinitapride Cisapride CJ-033466 Dazopride Metoclopramide Minesapride Mosapride Prucalopride PRX-03140 Renzapride RS-67333 RS-67506 Serotonin
(5-HT) Tegaserod Velusetrag Zacopride

Antagonists: GR-113808 GR-125487 L-Lysine Piboserod RS-39604 RS-67532 SB-203186 SB-204070


Agonists: Ergolines (e.g., 2-Br-LSD (BOL-148), ergotamine, LSD) Serotonin
(5-HT) Tryptamines (e.g., 5-CT) Valerenic Acid

Antagonists: Asenapine Latrepirdine
(dimebolin) Metitepine
(methiothepin) Ritanserin SB-699551

Unknown/unsorted: Ergolines (e.g., metergoline, methysergide) Piperazines (e.g., naphthylpiperazine)


Agonists: Ergolines (e.g., dihydroergocryptine, dihydroergotamine, ergotamine, lisuride, LSD, mesulergine, metergoline, methysergide) Serotonin
(5-HT) Tryptamines (e.g., 2-Me-5-HT, 5-BT, 5-CT, 5-MT, Bufotenin, E-6801, E-6837, EMD-386088, EMDT, LY-586713, N-Me-5-HT, tryptamine) WAY-181187 WAY-208466

Antagonists: ABT-354 Atypical antipsychotics (e.g., aripiprazole, asenapine, clorotepine, clozapine, fluperlapine, iloperidone, olanzapine, tiospirone) AVN-101 AVN-211 AVN-322 AVN-397 BGC20-760 BVT-5182 BVT-74316 Cerlapirdine EGIS-12233 GW-742457 Idalopirdine Ketanserin Landipirdine Latrepirdine
(dimebolin) Metitepine
(methiothepin) MS-245 PRX-07034 Ritanserin Ro 04-6790 Ro 63-0563 SB-258585 SB-271046 SB-357134 SB-399885 SB-742457 Tetracyclic antidepressants
Tetracyclic antidepressants
(e.g., amoxapine, mianserin) Tricyclic antidepressants
Tricyclic antidepressants
(e.g., amitriptyline, clomipramine, doxepin, nortriptyline) Typical antipsychotics (e.g., chlorpromazine, loxapine)

Unknown/unsorted: Ergolines (e.g., 2-Br-LSD (BOL-148), bromocriptine, lergotrile, pergolide) Piperazines (e.g., naphthylpiperazine)


Agonists: 8-OH-DPAT AS-19 Bifeprunox E-55888 Ergolines (e.g., LSD) LP-12 LP-44 RU-24969 Sarizotan Serotonin
(5-HT) Triptans (e.g., frovatriptan) Tryptamines (e.g., 5-CT, 5-MT, bufotenin, N-Me-5-HT)

Antagonists: Atypical antipsychotics (e.g., amisulpride, aripiprazole, asenapine, brexpiprazole, clorotepine, clozapine, fluperlapine, olanzapine, risperidone, sertindole, tiospirone, ziprasidone, zotepine) Butaclamol DR-4485 EGIS-12233 Ergolines (e.g., 2-Br-LSD (BOL-148), amesergide, bromocriptine, cabergoline, dihydroergotamine, ergotamine, LY-53857, LY-215840, mesulergine, metergoline, methysergide, sergolexole) JNJ-18038683 Ketanserin LY-215840 Metitepine
(methiothepin) Ritanserin SB-258719 SB-258741 SB-269970 SB-656104 SB-656104A SB-691673 SLV-313 SLV-314 Spiperone SSR-181507 Tetracyclic antidepressants
Tetracyclic antidepressants
(e.g., amoxapine, maprotiline, mianserin, mirtazapine) Tricyclic antidepressants
Tricyclic antidepressants
(e.g., amitriptyline, clomipramine, imipramine) Typical antipsychotics (e.g., acetophenazine, chlorpromazine, chlorprothixene, fluphenazine, loxapine, pimozide) Vortioxetine

Unknown/unsorted: Ergolines (e.g., lisuride, pergolide) Piperazines (e.g., naphthylpiperazine)

See also: Receptor/signaling modulators Adrenergics Dopaminergics Melatonergics Monoamine reuptake inhibitors and releasing agents Monoamine metabolism modulators Monoamine neurotoxins

v t e

Sigma receptor
Sigma receptor


Agonists: 3-PPP 4-PPBP 5-MeO-DMT Alazocine
(SKF-10047) Amantadine ANAVEX2-73 Arketamine BD-737 BD-1052 Captodiame Citalopram CGRP Cloperastine Cocaine Cutamesine
(SA-4503) Cyclazocine Dehydroepiandrosterone
(DHEA) (prasterone) Dehydroepiandrosterone
sulfate (DHEA-S) (prasterone sulfate) Dextrallorphan Dextromethorphan
(DXM) Dextrorphan
(DXO) Dimemorfan Dimethyltryptamine
(DMT) Ditolylguanidine
(DTG) Donepezil Eliprodil Escitalopram Fabomotizole
(afobazole) Fluoxetine Fluvoxamine Ifenprodil Igmesine
(JO-1784) IPAB Ketamine L-687384 MDMA
(midomafetamine) Memantine Methamphetamine Methoxetamine Methylphenidate Nepinalone Neuropeptide Y Noscapine OPC-14523 Opipramol Pentazocine Pentoxyverine
(carbetapentane) PRE-084 Pregnenolone Pregnenolone
sulfate Pridopidine Racemethorphan
(methorphan) Racemorphan
(morphanol) UMB-23 UMB-82

Antagonists: 3-PPP AC-927 BD-1008 BD-1031 BD-1047 BD-1060 BD-1063 BD-1067 BMY-14802
(BMS-181100) CM-156 Dup-734 E-5842 E-52862
(S1RA) Haloperidol LR-132 LR-172 MS-377 NE-100 NPC-16377 Panamesine
(EMD-57455) PD-144418 Pentazocine Progesterone Rimcazole
(BW-234U) Sertraline SR-31742A

Allosteric modulators: Phenytoin; Positive: Methylphenylpiracetam SOMCL-668

Unknown/unsorted: 3-Methoxydextrallorphan 3-MeO-PCP 4C-T-2 4-IBP 4-IPBS 4-MeO-PCP 5-MeO-DALT 5-MeO-DiPT Amitriptyline Azidopamil Chlorpromazine Clemastine Clomipramine Clorgiline D-Deprenyl DiPT DPT Ibogaine Imipramine KCR-12-83.1 Nemonapride Noribogaine RHL-033 RS-67,333 RTI-55 Saffron Safinamide Selegiline Spipethiane Trifluoperazine W-18 YKP10A


Agonists: 3-PPP Arketamine BD-1047 BD1063 Ditolylguanidine
(DTG) DKR-1005 DKR-1051 Haloperidol Ifenprodil Ketamine MDMA
(midomafetamine) Methamphetamine OPC-14523 Opipramol PB-28 Phencyclidine Siramesine
(Lu 28-179) UKH-1114

Antagonists: AC-927 BD-1008 BD-1067 CM-156 CT-1812 LR-172 MIN-101 Panamesine
(EMD-57455) SAS-0132

Unknown/unsorted: 3-Methoxydextrallorphan 3-MeO-PCE 4-MeO-PCP 5-MeO-DALT 5-MeO-DiPT Clemastine DiPT DPT Ibogaine Nemonapride Nepinalone Noribogaine Pentazocine RS-67,333 Safinamide TMA UMB-23 UMB-82 W-18


Agonists: Berberine Ethylketazocine Fourphit Metaphit Nalbuphine Naluzotan Tapentadol Tenocyclidine

Antagonists: AHD1 AZ66 Lamotrigine Naloxone SM-21 UMB-100 UMB-101 UMB-103 UMB-116 YZ-011 YZ-069 YZ-185

Allosteric modulators: SKF-83959

Unknown/unsorted: 18-Methoxycoronaridine BMY-13980 Butaclamol Caramiphen Carvotroline Chlorphenamine
(chlorpheniramine) Chlorpromazine Cinnarizine Cinuperone Clocapramine Dezocine EMD-59983 Hypericin
(St. John's wort) Fluphenazine Gevotroline
(WY-47384) Mepyramine
(pyrilamine) Molindone Perphenazine Pimozide Proadifen Promethazine Propranolol Quinidine Remoxipride SL 82.0715 SR-31747A Tiospirone
(BMY-13859) Venlafaxine

See also: Receptor/signaling modulators

v t e

GABAA receptor
GABAA receptor
positive modulators


Brometone Butanol Chloralodol Chlorobutanol
(cloretone) Ethanol (alcohol) (alcoholic drink) Ethchlorvynol Isobutanol Isopropanol Menthol Methanol Methylpentynol Pentanol Petrichloral Propanol tert-Butanol (2M2P) tert-Pentanol (2M2B) Tribromoethanol Trichloroethanol Triclofos Trifluoroethanol


(-)-DMBB Allobarbital Alphenal Amobarbital Aprobarbital Barbexaclone Barbital Benzobarbital Benzylbutylbarbiturate Brallobarbital Brophebarbital Butabarbital/Secbutabarbital Butalbital Buthalital Butobarbital Butallylonal Carbubarb Crotylbarbital Cyclobarbital Cyclopentobarbital Difebarbamate Enallylpropymal Ethallobarbital Eterobarb Febarbamate Heptabarb Heptobarbital Hexethal Hexobarbital Metharbital Methitural Methohexital Methylphenobarbital Narcobarbital Nealbarbital Pentobarbital Phenallymal Phenobarbital Phetharbital Primidone Probarbital Propallylonal Propylbarbital Proxibarbital Reposal Secobarbital Sigmodal Spirobarbital Talbutal Tetrabamate Tetrabarbital Thialbarbital Thiamylal Thiobarbital Thiobutabarbital Thiopental Thiotetrabarbital Valofane Vinbarbital Vinylbital


2-Oxoquazepam 3-Hydroxyphenazepam Adinazolam Alprazolam Arfendazam Avizafone Bentazepam Bretazenil Bromazepam Brotizolam Camazepam Carburazepam Chlordiazepoxide Ciclotizolam Cinazepam Cinolazepam Clazolam Climazolam Clobazam Clonazepam Clonazolam Cloniprazepam Clorazepate Clotiazepam Cloxazolam CP-1414S Cyprazepam Delorazepam Demoxepam Diazepam Diclazepam Doxefazepam Elfazepam Estazolam Ethyl carfluzepate Ethyl dirazepate Ethyl loflazepate Etizolam EVT-201 FG-8205 Fletazepam Flubromazepam Flubromazolam Fludiazepam Flunitrazepam Flunitrazolam Flurazepam Flutazolam Flutemazepam Flutoprazepam Fosazepam Gidazepam Halazepam Haloxazolam Iclazepam Imidazenil Irazepine Ketazolam Lofendazam Lopirazepam Loprazolam Lorazepam Lormetazepam Meclonazepam Medazepam Menitrazepam Metaclazepam Mexazolam Midazolam Motrazepam N-Desalkylflurazepam Nifoxipam Nimetazepam Nitrazepam Nitrazepate Nitrazolam Nordazepam Nortetrazepam Oxazepam Oxazolam Phenazepam Pinazepam Pivoxazepam Prazepam Premazepam Proflazepam Pyrazolam QH-II-66 Quazepam Reclazepam Remimazolam Rilmazafone Ripazepam Ro48-6791 Ro48-8684 SH-053-R-CH3-2′F Sulazepam Temazepam Tetrazepam Tolufazepam Triazolam Triflubazam Triflunordazepam
(Ro5-2904) Tuclazepam Uldazepam Zapizolam Zolazepam Zomebazam


Carisbamate Carisoprodol Clocental Cyclarbamate Difebarbamate Emylcamate Ethinamate Febarbamate Felbamate Hexapropymate Lorbamate Mebutamate Meprobamate Nisobamate Pentabamate Phenprobamate Procymate Styramate Tetrabamate Tybamate


6-Methylapigenin Ampelopsin
(dihydromyricetin) Apigenin Baicalein Baicalin Catechin EGC EGCG Hispidulin Linarin Luteolin Rc-OMe Skullcap constituents (e.g., baicalin) Wogonin


Etomidate Metomidate Propoxate


10-Methoxyyangonin 11-Methoxyyangonin 11-Hydroxyyangonin Desmethoxyyangonin 11-Methoxy-12-hydroxydehydrokavain 7,8-Dihydroyangonin Kavain 5-Hydroxykavain 5,6-Dihydroyangonin 7,8-Dihydrokavain 5,6,7,8-Tetrahydroyangonin 5,6-Dehydromethysticin Methysticin 7,8-Dihydromethysticin Yangonin


Acecarbromal Apronal
(apronalide) Bromisoval Carbromal Capuride Ectylurea

Neuroactive steroids

Acebrochol Allopregnanolone
(brexanolone) Alfadolone Alfaxalone 3α-Androstanediol Androstenol Androsterone Certain anabolic-androgenic steroids Cholesterol DHDOC 3α-DHP 5α-DHP 5β-DHP DHT Etiocholanolone Ganaxolone Hydroxydione Minaxolone ORG-20599 ORG-21465 P1-185 Pregnanolone
(eltanolone) Progesterone Renanolone SAGE-105 SAGE-217 SAGE-324 SAGE-516 SAGE-689 SAGE-872 Testosterone THDOC


β-Carbolines: Abecarnil Gedocarnil Harmane SL-651,498 ZK-93423

Cyclopyrrolones: Eszopiclone Pagoclone Pazinaclone Suproclone Suriclone Zopiclone

Imidazopyridines: Alpidem DS-1 Necopidem Saripidem Zolpidem

Pyrazolopyrimidines: Divaplon Fasiplon Indiplon Lorediplon Ocinaplon Panadiplon Taniplon Zaleplon

Others: Adipiplon CGS-8216 CGS-9896 CGS-13767 CGS-20625 CL-218,872 CP-615,003 CTP-354 ELB-139 GBLD-345 Imepitoin JM-1232 L-838,417 Lirequinil
(Ro41-3696) NS-2664 NS-2710 NS-11394 Pipequaline ROD-188 RWJ-51204 SB-205,384 SX-3228 TGSC01AA TP-003 TPA-023 TP-13 U-89843A U-90042 Viqualine Y-23684


Fospropofol Propofol Thymol


Glutethimide Methyprylon Piperidione Pyrithyldione


Cartazolate Etazolate ICI-190,622 Tracazolate


Afloqualone Cloroqualone Diproqualone Etaqualone Mebroqualone Mecloqualone Methaqualone Methylmethaqualone Nitromethaqualone SL-164


Acetone Acetophenone Acetylglycinamide chloral hydrate Aliflurane Benzene Butane Butylene Centalun Chloral Chloral
betaine Chloral
hydrate Chloroform Cryofluorane Desflurane Dichloralphenazone Dichloromethane Diethyl ether Enflurane Ethyl chloride Ethylene Fluroxene Gasoline Halopropane Halothane Isoflurane Kerosine Methoxyflurane Methoxypropane Nitric oxide Nitrogen Nitrous oxide Norflurane Paraldehyde Propane Propylene Roflurane Sevoflurane Synthane Teflurane Toluene Trichloroethane (methyl chloroform) Trichloroethylene Vinyl ether


3-Hydroxybutanal α-EMTBL AA-29504 Avermectins (e.g., ivermectin) Bromide compounds (e.g., lithium bromide, potassium bromide, sodium bromide) Carbamazepine Chloralose Chlormezanone Clomethiazole DEABL Dihydroergolines (e.g., dihydroergocryptine, dihydroergosine, dihydroergotamine, ergoloid (dihydroergotoxine)) DS2 Efavirenz Etazepine Etifoxine Fenamates (e.g., flufenamic acid, mefenamic acid, niflumic acid, tolfenamic acid) Fluoxetine Flupirtine Hopantenic acid Lanthanum Lavender oil Lignans (e.g., 4-O-methylhonokiol, honokiol, magnolol, obovatol) Loreclezole Menthyl isovalerate
Menthyl isovalerate
(validolum) Monastrol Niacin Nicotinamide
(niacinamide) Org 25,435 Phenytoin Propanidid Retigabine
(ezogabine) Safranal Seproxetine Stiripentol Sulfonylalkanes (e.g., sulfonmethane (sulfonal), tetronal, trional) Terpenoids (e.g., borneol) Topiramate Valerian constituents (e.g., isovaleric acid, isovaleramide, valerenic acid, valerenol)

Unsorted benzodiazepine site positive modulators: α-Pinene MRK-409 (MK-0343) TCS-1105 TCS-1205

See also: Receptor/signaling modulators • GABA receptor modulators • GABA metabolism/transport modulators

Pharmacy and pharmacology port