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Drug class of psycotropic drugs
Buspirone , the prototypical azapirone anxiolytic, which contains azaspirodecanedione and pyrimidinylpiperazine bound via a butyl chain.
Azapirones are a class of drugs used as anxiolytics , antidepressants , and antipsychotics .[1] [2] [3] [4] They are commonly used as add-ons to other antidepressants , such as selective serotonin reuptake inhibitors (SSRIs).[5] [6] [7] [8] [9] [10]
List of azapirones [ edit ]
The azapirones include the following agents:[11]
Antipsychotics
others
Medical uses [ edit ]
Azapirones have shown benefit in general anxiety[14] and augmenting SSRIs in social anxiety[15] and depression.[16] Evidence is not clear for panic disorder [17] and functional gastrointestinal disorders .[18]
Tandospirone has also been used to augment antipsychotics in Japan as it improves cognitive and negative symptoms of schizophrenia .[19] Buspirone is being investigated for this purpose as well.[20] [21]
Side effects [ edit ]
Side effects of azapirones may include dizziness , headaches , restlessness , nausea , and diarrhea .[4] [22]
Azapirones have more tolerable adverse effects than many other available anxiolytics, such as benzodiazepines or SSRIs. Unlike benzodiazepines, azapirones lack abuse potential and are not addictive , do not cause cognitive/memory impairment or sedation , and do not appear to induce appreciable tolerance or physical dependence . However, azapirones are considered less effective with slow onset in controlling symptoms.[23]
Chemistry [ edit ]
Buspirone was originally classified as an azaspirodecanedione , shortened to azapirone or azaspirone due to the fact that its chemical structure contained this moiety , and other drugs with similar structures were labeled as such as well. However, despite all being called azapirones, not all of them actually contain the azapirodecanedione component, and most in fact do not or contain a variation of it. Additionally, many azapirones are also pyrimidinylpiperazines , though again this does not apply to them all.
Drugs classed as azapirones can be identified by their -spirone or -pirone suffix.[24]
Pharmacology [ edit ]
Pharmacodynamics [ edit ]
On a pharmacological level, azapirones varyingly possess activity at the following receptors :[25] [26] [27] [28] [29] [30] [31] [32]
Actions at D 4 , 5-HT2C , 5-HT7 , and sigma receptors have also been shown for some azapirones.[33] [34] [35] [36]
While some of the listed properties such as 5-HT2A and D2 blockade may be useful in certain indications such as in the treatment of schizophrenia (as with perospirone and tiospirone), all of them except 5-HT1A agonism are generally undesirable in anxiolytics and only contribute to side effects . As a result, further development has commenced to bring more selective of anxiolytic agents to the market. An example of this initiative is gepirone, which was recently approved after completing clinical trials in the United States for the treatment of major depression and generalized anxiety disorder . Another example is tandospirone which has been licensed in Japan for the treatment of anxiety and as an augmentation to antidepressants for depression.
5-HT1A receptor partial agonists have demonstrated efficacy against depression in rodent studies and human clinical trials.[37] [38] [39] [40] Unfortunately, however, their efficacy is limited and they are only relatively mild antidepressants. Instead of being used as monotherapy treatments, they are more commonly employed as augmentations to serotonergic antidepressants like the SSRIs.[6] [7] [8] [9] [10] It has been proposed that high intrinsic activity at 5-HT1A postsynaptic receptors is necessary for maximal therapeutic benefits to come to prominence, and as a result, investigation has commenced in azapirones which act as 5-HT1A receptor full agonists such as alnespirone and eptapirone.[41] [42] [43] [44] Indeed, in preclinical studies , eptapirone produces robust antidepressant effects which surpass those of even high doses of imipramine and paroxetine .[41] [42] [43] [44]
Comparison of binding profiles [ edit ]
Affinities of Azapirones for Neurotransmitter Binding Sites (K i , nM)[25]
Gepirone
Ipsapirone
Tandospirone
20 ± 3
70 ± 10
7.9 ± 2
27 ± 5
> 100,000
> 100,000
> 100,000
> 100,000
> 100,000
> 100,000
33,000 ± 8,000
> 100,000
1,300 ± 400
3,000 ± 50
6,400 ± 4,000
1,300 ± 200
1,100 ± 200
5,000 ± 700
5,000 ± 1,000
2,600 ± 60
SERT Tooltip Serotonin transporter
–
–
–
> 100,000
33,000 ± 1,000
> 100,000
15,000 ± 2,000
41,000 ± 10,000
240 ± 50
2,200 ± 200
1,900 ± 200
1,700 ± 300
1,000 ± 400
2,300 ± 300
40 ± 7
1,600 ± 80
6,000 ± 700
1,600 ± 200
1,900 ± 500
1,900 ± 400
8,800 ± 1,000
> 100,000
> 100,000
> 100,000
mACh Tooltip Muscarinic acetylcholine receptor
38,000 ± 5,000
> 100,000
49,000 ± 5,000
> 100,000
> 100,000
> 100,000
> 100,000
> 100,000
Pharmacokinetics [ edit ]
Azapirones are poorly but nonetheless appreciably absorbed and have a rapid onset of action , but have only very short half-lives ranging from 1–3 hours. As a result, they must be administered 2–3 times a day. The only exception to this rule is umespirone, which has a very long duration with a single dose lasting as long as 23 hours.[45] Unfortunately, umespirone has not been commercialized. Although never commercially produced, Bristol-Myers Squibb applied for a patent on October 28, 1993, and received the patent on July 11, 1995, for an extended release formulation of buspirone.[46] An extended release formulation of gepirone is currently under development and if approved, should help to improve this issue.
Metabolism of azapirones occurs in the liver and they are excreted in urine and feces . A common metabolite of several azapirones including buspirone , gepirone , ipsapirone , revospirone , and tandospirone is 1-(2-pyrimidinyl)piperazine (1-PP).[47] [48] [49] 1-PP possesses 5-HT1A partial agonist and α2 -adrenergic antagonist actions and likely contributes overall mostly to side effects.[47] [48] [50]
References [ edit ]
^ Cadieux RJ (May 1996). "Azapirones: an alternative to benzodiazepines for anxiety". American Family Physician . 53 (7 ): 2349–53. PMID 8638511 .
^ Chessick CA, Allen MH, Thase M, Batista Miralha da Cunha AB, Kapczinski FF, de Lima MS, dos Santos Souza JJ, et al. (2006). Chessick CA (ed.). "Azapirones for generalized anxiety disorder" . Cochrane Database of Systematic Reviews . 3 (3 ): CD006115. doi :10.1002/14651858.CD006115 . PMC 8915394 . PMID 16856115 .
^ a b Feighner JP, Boyer WF (1989). "Serotonin-1A anxiolytics: an overview". Psychopathology . 22 Suppl 1 (1 ): 21–6. doi :10.1159/000284623 . PMID 2567039 .
^ Masdrakis VG, Turic D, Baldwin DS (2013). "Pharmacological treatment of social anxiety disorder". Anxiety Disorders . Modern Trends in Pharmacopsychiatry. Vol. 29. pp. 144–53. doi :10.1159/000351960 . ISBN 978-3-318-02463-0 . PMID 25225024 .
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^ a b Bouwer C, Stein DJ (April 1997). "Buspirone is an effective augmenting agent of serotonin selective re-uptake inhibitors in severe treatment-refractory depression". South African Medical Journal . 87 (4 Suppl): 534–7, 540. PMID 9180827 .
^ a b Dimitriou EC, Dimitriou CE (December 1998). "Buspirone augmentation of antidepressant therapy". Journal of Clinical Psychopharmacology . 18 (6 ): 465–9. doi :10.1097/00004714-199812000-00009 . PMID 9864079 .
^ a b Appelberg BG, Syvälahti EK, Koskinen TE, Mehtonen OP, Muhonen TT, Naukkarinen HH (June 2001). "Patients with severe depression may benefit from buspirone augmentation of selective serotonin reuptake inhibitors: results from a placebo-controlled, randomized, double-blind, placebo wash-in study". The Journal of Clinical Psychiatry . 62 (6 ): 448–52. doi :10.4088/JCP.v62n0608 . PMID 11465522 .
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^ CID 10319570 from PubChem
^ CID 9845181 from PubChem
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^ Masdrakis VG, Turic D, Baldwin DS (September 20, 2013). "Pharmacological treatment of social anxiety disorder". Anxiety Disorders . Modern Trends in Pharmacopsychiatry. Vol. 29. pp. 144–53. doi :10.1159/000351960 . ISBN 978-3-318-02463-0 . PMID 25225024 .
^ Stahl SM, Lee-Zimmerman C (May 1, 2013). "Serotonergic drugs for depression and beyond". Curr Drug Targets . 14 (5 ): 578–85. doi :10.2174/1389450111314050007 . PMID 23531115 .
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^ Grover M, Camilleri M (February 2013). "Effects on gastrointestinal functions and symptoms of serotonergic psychoactive agents used in functional gastrointestinal diseases" . J Gastroenterol . 48 (2 ): 177–81. doi :10.1007/s00535-012-0726-5 . PMC 3698430 . PMID 23254779 .
^ Sumiyoshi T, Matsui M, Nohara S, et al. (October 2001). "Enhancement of cognitive performance in schizophrenia by addition of tandospirone to neuroleptic treatment". The American Journal of Psychiatry . 158 (10 ): 1722–5. doi :10.1176/appi.ajp.158.10.1722 . PMID 11579010 .
^ Sumiyoshi T, Park S, Jayathilake K, Roy A, Ertugrul A, Meltzer HY (September 2007). "Effect of buspirone, a serotonin1A partial agonist, on cognitive function in schizophrenia: a randomized, double-blind, placebo-controlled study". Schizophrenia Research . 95 (1–3): 158–68. doi :10.1016/j.schres.2007.06.008 . PMID 17628435 . S2CID 36027848 .
^ Piskulić D, Olver JS, Maruff P, Norman TR (August 2009). "Treatment of cognitive dysfunction in chronic schizophrenia by augmentation of atypical antipsychotics with buspirone, a partial 5-HT(1A) receptor agonist" . Human Psychopharmacology . 24 (6 ): 437–46. doi :10.1002/hup.1046 . PMID 19637398 . S2CID 21289248 .
^ Newton RE, Marunycz JD, Alderdice MT, Napoliello MJ (March 1986). "Review of the side-effect profile of buspirone". The American Journal of Medicine . 80 (3B): 17–21. doi :10.1016/0002-9343(86 )90327-X . PMID 2870641 .
^ Davidson JR, Feltner DE, Dugar A (2010). "Management of Generalized Anxiety Disorder in Primary Care: Identifying the Challenges and Unmet Needs" . Prim Care Companion J Clin Psychiatry . 12 (2 ). doi :10.4088/PCC.09r00772blu . PMC 2911006 . PMID 20694114 .
^ "The use of stems in the selection of International Nonproprietary Names (INN) for pharmaceutical substances" (PDF) . 2004. Archived from the original (PDF) on July 22, 2011. Retrieved April 1, 2010 .
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^ Barnes NM, Costall B, Domeney AM, et al. (September 1991). "The effects of umespirone as a potential anxiolytic and antipsychotic agent". Pharmacology Biochemistry and Behavior . 40 (1 ): 89–96. doi :10.1016/0091-3057(91 )90326-W . PMID 1685786 . S2CID 9762359 .
^ Ahlenius S, Wijkström A (November 1992). "Mixed agonist-antagonist properties of umespirone at neostriatal dopamine receptors in relation to its behavioral effects in the rat". European Journal of Pharmacology . 222 (1 ): 69–74. doi :10.1016/0014-2999(92 )90464-F . PMID 1361441 .
^ Sumiyoshi T, Suzuki K, Sakamoto H, et al. (February 1995). "Atypicality of several antipsychotics on the basis of in vivo dopamine-D2 and serotonin-5HT2 receptor occupancy". Neuropsychopharmacology . 12 (1 ): 57–64. doi :10.1016/0893-133X(94 )00064-7 . PMID 7766287 .
^ Weiner DM, Burstein ES, Nash N, et al. (October 2001). "5-hydroxytryptamine2A receptor inverse agonists as antipsychotics" . The Journal of Pharmacology and Experimental Therapeutics . 299 (1 ): 268–76. PMID 11561089 .
^ Hirose A, Kato T, Ohno Y, et al. (July 1990). "Pharmacological actions of SM-9018, a new neuroleptic drug with both potent 5-hydroxytryptamine2 and dopamine2 antagonistic actions" . Japanese Journal of Pharmacology . 53 (3 ): 321–9. doi :10.1254/jjp.53.321 . PMID 1975278 .
^ Kato T, Hirose A, Ohno Y, Shimizu H, Tanaka H, Nakamura M (December 1990). "Binding profile of SM-9018, a novel antipsychotic candidate" . Japanese Journal of Pharmacology . 54 (4 ): 478–81. doi :10.1254/jjp.54.478 . PMID 1982326 .
^ Odagaki Y, Toyoshima R (2007). "5-HT1A receptor agonist properties of antipsychotics determined by [35S]GTPgammaS binding in rat hippocampal membranes". Clinical and Experimental Pharmacology & Physiology . 34 (5–6): 462–6. doi :10.1111/j.1440-1681.2007.04595.x . PMID 17439416 . S2CID 22450517 .
^ Roth BL , Tandra S, Burgess LH, Sibley DR, Meltzer HY (August 1995). "D4 dopamine receptor binding affinity does not distinguish between typical and atypical antipsychotic drugs". Psychopharmacology . 120 (3 ): 365–8. doi :10.1007/BF02311185 . PMID 8524985 . S2CID 13549491 .
^ Herrick-Davis K, Grinde E, Teitler M (October 2000). "Inverse agonist activity of atypical antipsychotic drugs at human 5-hydroxytryptamine2C receptors" . The Journal of Pharmacology and Experimental Therapeutics . 295 (1 ): 226–32. PMID 10991983 .
^ Rauly-Lestienne I, Boutet-Robinet E, Ailhaud MC, Newman-Tancredi A, Cussac D (October 2007). "Differential profile of typical, atypical and third generation antipsychotics at human 5-HT7a receptors coupled to adenylyl cyclase: detection of agonist and inverse agonist properties". Naunyn-Schmiedeberg's Archives of Pharmacology . 376 (1–2): 93–105. doi :10.1007/s00210-007-0182-6 . PMID 17786406 . S2CID 29337002 .
^ Itzhak Y, Ruhland M, Krähling H (February 1990). "Binding of umespirone to the sigma receptor: evidence for multiple affinity states" . Neuropharmacology . 29 (2 ): 181–4. doi :10.1016/0028-3908(90 )90058-Y . PMID 1970425 . S2CID 54326248 .
^ Kennett GA, Dourish CT, Curzon G (February 1987). "Antidepressant-like action of 5-HT1A agonists and conventional antidepressants in an animal model of depression". European Journal of Pharmacology . 134 (3 ): 265–74. doi :10.1016/0014-2999(87 )90357-8 . PMID 2883013 .
^ Blier P, Ward NM (February 2003). "Is there a role for 5-HT1A agonists in the treatment of depression?". Biological Psychiatry . 53 (3 ): 193–203. doi :10.1016/S0006-3223(02 )01643-8 . PMID 12559651 . S2CID 23792607 .
^ Robinson DS, Rickels K, Feighner J, et al. (June 1990). "Clinical effects of the 5-HT1A partial agonists in depression: a composite analysis of buspirone in the treatment of depression". Journal of Clinical Psychopharmacology . 10 (3 Suppl): 67S–76S. doi :10.1097/00004714-199006001-00013 . PMID 2198303 . S2CID 7849957 .
^ Bielski RJ, Cunningham L, Horrigan JP, Londborg PD, Smith WT, Weiss K (April 2008). "Gepirone extended-release in the treatment of adult outpatients with major depressive disorder: a double-blind, randomized, placebo-controlled, parallel-group study". The Journal of Clinical Psychiatry . 69 (4 ): 571–7. doi :10.4088/jcp.v69n0408 . PMID 18373383 . S2CID 39524249 .
^ a b Koek W, Patoiseau JF, Assié MB, et al. (October 1998). "F 11440, a potent, selective, high efficacy 5-HT1A receptor agonist with marked anxiolytic and antidepressant potential" . The Journal of Pharmacology and Experimental Therapeutics . 287 (1 ): 266–83. PMID 9765347 .
^ a b Koek W, Vacher B, Cosi C, et al. (May 2001). "5-HT1A receptor activation and antidepressant-like effects: F 13714 has high efficacy and marked antidepressant potential". European Journal of Pharmacology . 420 (2–3): 103–12. doi :10.1016/S0014-2999(01 )01011-1 . PMID 11408031 .
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^ a b Maurel JL, Autin JM, Funes P, Newman-Tancredi A, Colpaert F, Vacher B (October 2007). "High-efficacy 5-HT1A agonists for antidepressant treatment: a renewed opportunity". Journal of Medicinal Chemistry . 50 (20 ): 5024–33. doi :10.1021/jm070714l . PMID 17803293 .
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^ US patent 5431922 , Nicklasson AGM, "Method for administration of buspirone", issued 1995-07-11, assigned to Bristol-Myers Squibb Company url=https://patents.google.com/patent/US5431922
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^ a b Blier P, Curet O, Chaput Y, de Montigny C (July 1991). "Tandospirone and its metabolite, 1-(2-pyrimidinyl)-piperazine--II. Effects of acute administration of 1-PP and long-term administration of tandospirone on noradrenergic neurotransmission". Neuropharmacology . 30 (7 ): 691–701. doi :10.1016/0028-3908(91 )90176-C . PMID 1681447 . S2CID 44297577 .
^ Löscher W, Witte U, Fredow G, Traber J, Glaser T (September 1990). "The behavioural responses to 8-OH-DPAT, ipsapirone and the novel 5-HT1A receptor agonist Bay Vq 7813 in the pig". Naunyn-Schmiedeberg's Archives of Pharmacology . 342 (3 ): 271–7. doi :10.1007/bf00169437 . PMID 2149168 . S2CID 24769939 .
^ Zuideveld KP, Rusiç-Pavletiç J, Maas HJ, Peletier LA, Van der Graaf PH, Danhof M (December 2002). "Pharmacokinetic-pharmacodynamic modeling of buspirone and its metabolite 1-(2-pyrimidinyl)-piperazine in rats". The Journal of Pharmacology and Experimental Therapeutics . 303 (3 ): 1130–7. doi :10.1124/jpet.102.036798 . PMID 12438536 . S2CID 14139919 .
Gepirone
Tandospirone
GABAA R Tooltip GABAA receptor PAMs Tooltip positive allosteric modulators
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 )
Carisoprodol
Chlormezanone ‡
Ethanol (alcohol)
Etifoxine
Gabapentin enacarbil
Phenibut
Pregabalin
SNRIs Tooltip Serotonin-norepinephrine reuptake inhibitors (e.g., duloxetine )
SARIs Tooltip Serotonin antagonist and reuptake inhibitors (e.g., trazodone )
TCAs Tooltip Tricyclic antidepressants (e.g., clomipramine # )
TeCAs Tooltip Tetracyclic antidepressants (e.g., mirtazapine )
MAOIs Tooltip Monoamine oxidase inhibitors (e.g., phenelzine ); Others: Agomelatine
Bupropion
Tianeptine
Vilazodone
Vortioxetine
Flupentixol
Alpha-2 agonists (e.g., clonidine , dexmedetomidine , guanfacine )
Beta blockers (e.g., propranolol )
Cycloserine
Fabomotizole
Hydroxyzine
Lorpiprazole
Mebicar
Mepiprazole
Nicotine
Opipramol
Oxaflozane ‡
Phenaglycodol
Phenibut
Picamilon
Selank
Tiagabine
Tofisopam
Validolum
Indalpine ‡
Paroxetine
Sertraline
Zimelidine ‡
SNRIs Tooltip Serotonin–norepinephrine reuptake inhibitors
Duloxetine
Levomilnacipran
Milnacipran
Tofenacin
Venlafaxine
NRIs Tooltip Norepinephrine reuptake inhibitors
Reboxetine
Viloxazine
NDRIs Tooltip Norepinephrine–dopamine reuptake inhibitors
Bupropion
Nomifensine ‡
NaSSAs Tooltip Noradrenergic and specific serotonergic antidepressants
Mirtazapine
Setiptiline
SARIs Tooltip Serotonin antagonist and reuptake inhibitors
Nefazodone
Trazodone
SMS Tooltip Serotonin modulator and stimulators
Vortioxetine
Amisulpride
Dextromethorphan/bupropion
Esketamine
Etryptamine ‡
Gepirone
Indeloxazine
Flupentixol
Ketamine §
Medifoxamine ‡
Metryptamine ‡
Oxaflozane ‡
Pivagabine ‡
Tandospirone
Teniloxazine
Tianeptine
Butriptyline ‡
Clomipramine #
Demexiptiline ‡
Desipramine
Dibenzepin
Dimetacrine ‡
Dosulepin
Doxepin
Imipramine
Imipraminoxide ‡
Iprindole ‡
Lofepramine
Melitracen
Metapramine ‡
Nitroxazepine
Nortriptyline
Noxiptiline
Opipramol
Pipofezine
Propizepine ‡
Protriptyline
Quinupramine ‡
Tianeptine
Trimipramine
TeCAs Tooltip Tetracyclic antidepressants
Mianserin
Mirtazapine
Setiptiline
Isoniazid #
Linezolid #
Mebanazine ‡
Nialamide ‡
Octamoxin ‡
Phenelzine
Pheniprazine ‡
Phenoxypropazine ‡
Pivhydrazine ‡
Safrazine ‡
Tedizolid
Tranylcypromine
MAOA Tooltip Monoamine oxidase A -selective
Metralindole
Minaprine ‡
Moclobemide
Pirlindole
Tetrindole
Toloxatone
MAOB Tooltip Monoamine oxidase B -selective
Lithium (lithium carbonate , lithium citrate )
Thyroid hormones (triiodothyronine (T 3 ), levothyroxine (T 4 ))
Hypericum perforatum (St. John's Wort)
Oxitriptan (5-HTP )
Rubidium chloride (RbCl)
Tryptophan
Bromperidol
Droperidol
Haloperidol #
Moperone
Pipamperone
Spiperone
Timiperone
Trifluperidol
Levosulpiride
Nemonapride
Remoxipride ‡
Sulpiride
Sultopride
Tiapride
Veralipride ‡
Lurasidone
Paliperidone
Perospirone
Risperidone #
Ziprasidone
Reserpine
Tetrabenazine
Cirazoline
Corbadrine
Deoxyepinephrine (epinine, N -methyldopamine)
Desglymidodrine
Dexisometheptene
Dipivefrine
Dopamine
Droxidopa (L -DOPS)
Epinephrine
Etilefrine
Etilevodopa
Ethylnorepinephrine
Ibopamine
Indanidine
Isometheptene
L -DOPA (levodopa)
L -Phenylalanine
L -Tyrosine
Melevodopa
Metaraminol
Methoxamine
Methyldopa
Midodrine
Naphazoline
Norepinephrine
Octopamine
Oxymetazoline
Phenylephrine
Phenylpropanolamine
Synephrine
Tetryzoline
Tiamenidine
XP21279
Xylometazoline
Ajmalicine
Alfuzosin
Anisodamine
Anisodine
Atiprosin
Atypical antipsychotics (e.g., brexpiprazole , clozapine , olanzapine , quetiapine , risperidone )
Benoxathian
Beta blockers (e.g., adimolol , amosulalol , arotinolol , carvedilol , eugenodilol , labetalol )
Buflomedil
Bunazosin
Corynanthine
Dapiprazole
Domesticine
Doxazosin
Ergolines (e.g., acetergamine , ergotamine , dihydroergotamine , lisuride , nicergoline , terguride )
Etoperidone
Fenspiride
Hydroxyzine
Indoramin
Ketanserin
L-765,314
mCPP
Mepiprazole
Metazosin
Monatepil
Moxisylyte
Naftopidil
Nantenine
Neldazosin
Niaprazine
Niguldipine
Pardoprunox
Pelanserin
Perlapine
Phendioxan
Phenoxybenzamine
Phentolamine
Phenylpiperazine antidepressants (e.g., hydroxynefazodone , nefazodone , trazodone , triazoledione )
Piperoxan
Prazosin
Quinazosin
Quinidine
Silodosin
Spegatrine
Spiperone
Talipexole
Tamsulosin
Terazosin
Tiodazosin
Tolazoline
Tetracyclic antidepressants (e.g., amoxapine , maprotiline , mianserin )
Tricyclic antidepressants (e.g., amitriptyline , clomipramine , doxepin , imipramine , trimipramine )
Trimazosin
Typical antipsychotics (e.g., chlorpromazine , fluphenazine , loxapine , thioridazine )
Urapidil
WB-4101
Zolertine
Amitraz
Apraclonidine
Brimonidine
Clonidine
Corbadrine
Deoxyepinephrine (epinine, N -methyldopamine)
Detomidine
Dexmedetomidine
Dihydroergotamine
Dipivefrine
Dopamine
Droxidopa (L -DOPS)
Etilevodopa
Ergotamine
Epinephrine
Etilefrine
Ethylnorepinephrine
Guanabenz
Guanfacine
Guanoxabenz
L -DOPA (levodopa)
L -Phenylalanine
L -Tyrosine
Ibopamine
Lofexidine
Medetomidine
Melevodopa
Methyldopa
Mivazerol
Moxonidine
Naphazoline
Norepinephrine
Oxymetazoline
Phenylpropanolamine
Piperoxan
PS75
Rezatomidine
Rilmenidine
Romifidine
Talipexole
Tasipimidine
Tetryzoline
Tiamenidine
Tizanidine
Tolonidine
Urapidil
Vatinoxan
XP21279
Xylazine
Xylometazoline
Adimolol
Amesergide
Aptazapine
Atipamezole
Atypical antipsychotics (e.g., asenapine , brexpiprazole , clozapine , lurasidone , olanzapine , paliperidone , quetiapine , risperidone , zotepine )
Azapirones (e.g., buspirone , gepirone , ipsapirone , tandospirone )
BRL-44408
Buflomedil
Cirazoline
Efaroxan
Esmirtazapine
Fenmetozole
Fluparoxan
Idazoxan
Ketanserin
Lisuride
mCPP
Mianserin
Mirtazapine
NAN-190
Pardoprunox
Phentolamine
Phenoxybenzamine
Piperoxan
Piribedil
Rauwolscine
Rotigotine
Setiptiline
Spegatrine
Spiroxatrine
Sunepitron
Terguride
Tolazoline
Typical antipsychotics (e.g., chlorpromazine , fluphenazine , loxapine , thioridazine )
Yohimbine
Arbutamine
Arformoterol
Arotinolol
BAAM
Bambuterol
Befunolol
Bitolterol
Broxaterol
Buphenine
Carbuterol
Carmoterol
Cimaterol
Clenbuterol
Colterol
Corbadrine
Denopamine
Deoxyepinephrine (epinine, N -methyldopamine)
Dipivefrine
Dobutamine
Dopamine
Dopexamine
Droxidopa (L -DOPS)
Epinephrine
Etafedrine
Etilefrine
Etilevodopa
Ethylnorepinephrine
Eugenodilol
Fenoterol
Formoterol
Hexoprenaline
Higenamine
Ibopamine
Indacaterol
Isoetarine
Isoprenaline
Isoxsuprine
L -DOPA (levodopa)
L -Phenylalanine
L -Tyrosine
Levosalbutamol
Lubabegron
Mabuterol
Melevodopa
Methoxyphenamine
Methyldopa
Mirabegron
Norepinephrine
Orciprenaline
Oxyfedrine
PF-610355
Phenylpropanolamine
Pirbuterol
Prenalterol
Ractopamine
Procaterol
Reproterol
Rimiterol
Ritodrine
Salbutamol
Salmeterol
Solabegron
Terbutaline
Tretoquinol
Tulobuterol
Vibegron
Vilanterol
Xamoterol
XP21279
Zilpaterol
Zinterol
Adaprolol
Adimolol
Afurolol
Alprenolol
Alprenoxime
Amosulalol
Ancarolol
Arnolol
Arotinolol
Atenolol
Befunolol
Betaxolol
Bevantolol
Bisoprolol
Bopindolol
Bornaprolol
Brefonalol
Bucindolol
Bucumolol
Bufetolol
Bufuralol
Bunitrolol
Bunolol
Bupranolol
Butaxamine
Butidrine
Butofilolol
Capsinolol
Carazolol
Carpindolol
Carteolol
Carvedilol
Celiprolol
Cetamolol
Cicloprolol
Cinamolol
Cloranolol
Cyanopindolol
Dalbraminol
Dexpropranolol
Diacetolol
Dichloroisoprenaline
Dihydroalprenolol
Dilevalol
Diprafenone
Draquinolol
Ecastolol
Epanolol
Ericolol
Ersentilide
Esatenolol
Esprolol
Eugenodilol
Exaprolol
Falintolol
Flestolol
Flusoxolol
Hydroxycarteolol
Hydroxytertatolol
ICI-118,551
Idropranolol
Indenolol
Indopanolol
Iodocyanopindolol
Iprocrolol
Isoxaprolol
Isamoltane
Labetalol
Landiolol
Levobetaxolol
Levobunolol
Levomoprolol
Medroxalol
Mepindolol
Metipranolol
Metoprolol
Moprolol
Nadolol
Nadoxolol
Nebivolol
Nifenalol
Nipradilol
Oxprenolol
Pacrinolol
Pafenolol
Pamatolol
Pargolol
Penbutolol
Pindolol
Practolol
Primidolol
Procinolol
Pronethalol
Propafenone
Propranolol
Ridazolol
Ronactolol
Soquinolol
Sotalol
Spirendolol
SR 59230A
Sulfinalol
Talinolol
Tazolol
Tertatolol
Tienoxolol
Tilisolol
Timolol
Tiprenolol
Tolamolol
Toliprolol
Xibenolol
Xipranolol
Serotonergics
Monoamine reuptake inhibitors
Monoamine releasing agents
Monoamine metabolism modulators
Monoamine neurotoxins
SKF-77,434
SKF-81,297
SKF-82,958
SKF-83,959
Trepipam
Zelandopam
Tetrahydroisoquinolines : DETQ
DPTQ
Mevidalen
Chlorpromazine
Chlorprothixene
Flupentixol (flupenthixol) (+melitracen )
Fluphenazine
Loxapine
Perphenazine (+amitriptyline )
Pifluthixol
Thioridazine
Thiothixene
Trifluoperazine (+tranylcypromine )
Zuclopenthixol
Acetophenazine
Azaperone
Benperidol
Bromperidol
Butaclamol
Butaperazine
Chloracizine
Chlorproethazine
Chlorpromazine
Chlorprothixene
Ciclindole
Clopenthixol
Clothixamide
Clopimozide
Droperidol
Fluacizine
Fluanisone
Flucindole
Fluotracen
Flupentixol (flupenthixol) (+melitracen )
Fluphenazine
Fluprothixene
Fluspirilene
Haloperidol
Homopipramol
Lenperone
Levomepromazine (methotrimeprazine)
Levosulpiride
Loxapine
Mesoridazine
Moperone
Naranol
Nemonapride
Penfluridol
Perathiepin
Perazine
Pericyazine (periciazine)
Perphenazine (+amitriptyline )
Piflutixol (pifluthixol)
Pimozide
Pipamperone
Preclamol
Prochlorperazine
Promazine
Prothipendyl
Spiperone (spiroperidol)
Sulforidazine
Sulpiride
Sultopride
Teflutixol
Thiopropazate
Thioproperazine
Thioridazine
Thiothixene
Timiperone
Trifluoperazine (+tranylcypromine )
Triflupromazine
Trifluperidol
Zetidoline
Zuclopenthixol
Serotonergics
Monoamine reuptake inhibitors
Monoamine releasing agents
Monoamine metabolism modulators
Monoamine neurotoxins
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-11,461
F-12826
F-13714
F-14679
F-15063
F-15,599
Flesinoxan
Flibanserin
Flumexadol
Hypidone
Lesopitron
LY-293284
LY-301317
mCPP
MKC-242
Naluzotan
NBUMP
Osemozotan
Oxaflozane
Pardoprunox
Piclozotan
Rauwolscine
Repinotan
Roxindole
RU-24,969
S-14,506
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-92,016-A
Urapidil
Vilazodone
Xaliproden
Yohimbine
Beta blockers (e.g., alprenolol , carteolol , cyanopindolol , iodocyanopindolol , isamoltane , oxprenolol , penbutolol , pindobind , pindolol , propranolol , tertatolol )
BMY-7,378
CSP-2503
Dotarizine
Ergolines (e.g., metergoline )
FCE-24379
Flopropione
GR-46611
Isamoltane
Lecozotan
Mefway
Metitepine (methiothepin)
MIN-117 (WF-516)
MPPF
NAN-190
Robalzotan
S-15535
SB-649,915
SDZ 216-525
Spiperone
Spiramide
Spiroxatrine
UH-301
WAY-100135
WAY-100635
Xylamidine
Ergolines (e.g., ergometrine (ergonovine) )
CP-122,288
CP-135807
Eltoprazine
Ergolines (e.g., bromocriptine , dihydroergotamine , ergotamine , methylergometrine (methylergonovine) , methysergide , pergolide )
mCPP
RU-24,969
Serotonin (5-HT)
Triptans (e.g., avitriptan , donitriptan , eletriptan , sumatriptan , zolmitriptan )
TFMPP
Tryptamines (e.g., 5-BT , 5-CT , 5-MT , DMT )
Vortioxetine
Elzasonan
Ergolines (e.g., metergoline )
GR-127935
Isamoltane
LY-393558
Metitepine (methiothepin)
SB-216641
SB-224289
SB-236057
Yohimbine
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 )
Elzasonan
Ergolines (e.g., metergoline )
GR-127935
Ketanserin
LY-310762
LY-367642
LY-393558
LY-456219
LY-456220
Metitepine (methiothepin)
Mianserin
Ritanserin
Yohimbine
Ziprasidone
Tryptamines (e.g., tryptamine )
LY-334370
Serotonin (5-HT)
Triptans (e.g., eletriptan , naratriptan , sumatriptan )
Tryptamines (e.g., 5-MT )
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
IHCH-7113
Jimscaline
Lorcaserin
MDxx (e.g., MDA (tenamfetamine) , MDMA (midomafetamine) , MDOH , MMDA )
O-4310
Oxaflozane
PHA-57378
PNU-22394
PNU-181731
RH-34
SCHEMBL5334361
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 )
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 )
Chlorprothixene
Cinanserin
CSP-2503
Deramciclane
Dotarizine
Eplivanserin
Ergolines (e.g., amesergide , LY-53857 , LY-215,840 , mesulergine , metergoline , methysergide , sergolexole )
Fananserin
Flibanserin
Glemanserin
Irindalone
Ketanserin
KML-010
Landipirdine
LY-393558
mCPP
Medifoxamine
Metitepine (methiothepin)
MIN-117 (WF-516)
Naftidrofuryl
Nantenine
Nelotanserin
Opiranserin (VVZ-149)
Pelanserin
Phenoxybenzamine
Pimavanserin
Pirenperone
Pizotifen
Pruvanserin
Rauwolscine
Ritanserin
Roluperidone
S-14671
Sarpogrelate
Serotonin antagonists and reuptake inhibitors (e.g., etoperidone , hydroxynefazodone , lubazodone , mepiprazole , nefazodone , triazoledione , trazodone )
SR-46349B
TGBA01AD
Teniloxazine
Temanogrel
Tetracyclic antidepressants (e.g., amoxapine , aptazapine , esmirtazapine , maprotiline , mianserin , mirtazapine )
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
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 )
Piperazines (e.g., TFMPP )
PNU-22394
Ro60-0175
Serotonin (5-HT)
Tryptamines (e.g., 5-BT , 5-CT , 5-MT , α-Me-5-HT , bufotenin , DET , DiPT , DMT , DPT , psilocin , psilocybin , tryptamine )
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 (e.g., amoxapine , mianserin , mirtazapine )
Trazodone
Typical antipsychotics (e.g., chlorpromazine )
TIK-301
Yohimbine
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
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-215,840 , 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 (e.g., amoxapine , aptazapine , esmirtazapine , maprotiline , mianserin , mirtazapine )
TIK-301
Tramadol
Trazodone
Tricyclic antidepressants (e.g., amitriptyline , nortriptyline )
Typical antipsychotics (e.g., chlorpromazine , loxapine , pimozide , pipamperone , thioridazine )
Xylamidine
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
Arazasetron
AS-8112
Atypical antipsychotics (e.g., clozapine , olanzapine , quetiapine )
Azasetron
Batanopride
Bemesetron (MDL-72222)
Bupropion
Cilansetron
CSP-2503
Dazopride
Dolasetron
Galanolactone
Granisetron
Hydroxybupropion
Lerisetron
Memantine
Ondansetron
Palonosetron
Ramosetron
Renzapride
Ricasetron
Tedatioxetine
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
Cisapride
CJ-033466
Dazopride
Metoclopramide
Minesapride
Mosapride
Prucalopride
PRX-03140
Renzapride
RS-67,333
RS-67,506
Serotonin (5-HT)
Tegaserod
Usmarapride
Velusetrag
Zacopride
L-Lysine
Piboserod
RS-39604
RS-67532
SB-203186
SB-204070
Metitepine (methiothepin)
Ritanserin
SB-699551
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 , ST-1936 , tryptamine )
WAY-181187
WAY-208466
AVN-101
AVN-211
AVN-322
AVN-397
BGC20-760
BVT-5182
BVT-74316
Cerlapirdine
EGIS-12,233
GW-742457
Idalopirdine
Ketanserin
Landipirdine
Latrepirdine (dimebolin)
Masupirdine
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 (e.g., amoxapine , mianserin )
Tricyclic antidepressants (e.g., amitriptyline , clomipramine , doxepin , nortriptyline )
Typical antipsychotics (e.g., chlorpromazine , loxapine )
Ergolines (e.g., LSD )
LP-12
LP-44
LP-211
RU-24,969
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-12,233
Ergolines (e.g., 2-Br-LSD (BOL-148) , amesergide , bromocriptine , cabergoline , dihydroergotamine , ergotamine , LY-53857 , LY-215,840 , mesulergine , metergoline , methysergide , sergolexole )
JNJ-18038683
Ketanserin
LY-215,840
Metitepine (methiothepin)
Ritanserin
SB-258719
SB-258741
SB-269970
SB-656104
SB-656104A
SB-691673
SLV-313
SLV-314
Spiperone
SSR-181507
Tetracyclic antidepressants (e.g., amoxapine , maprotiline , mianserin , mirtazapine )
Tricyclic antidepressants (e.g., amitriptyline , clomipramine , imipramine )
Typical antipsychotics (e.g., acetophenazine , chlorpromazine , chlorprothixene , fluphenazine , loxapine , pimozide )
Vortioxetine
Dopaminergics
Melatonergics
Monoamine reuptake inhibitors and releasing agents
Monoamine metabolism modulators
Monoamine neurotoxins
4-PPBP
5-MeO-DMT
Alazocine (SKF-10047)
Amantadine
Arketamine
BD-737
BD-1052
Blarcamesine
Captodiame
Citalopram
CGRP Tooltip Calcitonin gene-related peptide
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
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
Ethylketazocine
Fourphit
Metaphit
Naluzotan
Tapentadol
Tenocyclidine
Simple piperazines(no additional rings)
Diethylcarbamazine
HEPPS
Midafotel
Piperazine
PIPES
3,4-CFP
Acaprazine
Antrafenine
Aripiprazole
Batoprazine
Bifeprunox
BRL-15,572
Ciprofloxacin
CSP-2503
Dapiprazole
DCPP
DMPP
Diphenylpiperazine
Dropropizine
EGIS-12,233
Elopiprazole
Eltoprazine
Enpiprazole
Ensaculin
Etoperidone
Flesinoxan
Fluanisone
Flibanserin
Fluprazine
Itraconazole
Ketoconazole
Levodropropizine
Lorpiprazole
mCPP
Mefway
MeOPP
Mepiprazole
Naftopidil
Naluzotan
Naphthylpiperazine
Nefazodone
Niaprazine
Oxypertine
Pardoprunox
pCPP
pFPP
Posaconazole
S-14,506
S-14,671
S-15,535
SB-258,585
SB-271,046
SB-357,134
SB-399,885
Sonepiprazole
TFMPP
Tolpiprazole
Trazodone
Urapidil
Vesnarinone
Vilazodone
Vortioxetine
WAY-100,135
WAY-100,635
3-Methylbenzylpiperazine
Befuraline
Bifeprunox
Buclizine
BZP
Chlorbenzoxamine
DBZP
Fipexide
Imatinib
MBZP
MDBZP
Meclozine
Methoxypiperamide
NSI-189
Piberaline
Piribedil
RN-1747
Sunifiram
Trimetazidine
Vesnarinone
Almitrine
Amperozide
BRL-15,572
Buclizine
BW373U86
Cetirizine
Chlorbenzoxamine
Chlorcyclizine
Cinnarizine
Clocinizine
Cyclizine
DBL-583
Diphenpipenol
Diphenylmethylpiperazine
Dotarizine
DPI-221
DPI-287
DPI-3290
GBR-12,783
GBR-12,935
GBR-13,069
GBR-13,098
GBR-13,119
Hydroxyzine
Lidoflazine
Manidipine
Meclozine
MT-45
Oxatomide
SNC-80
Vanoxerine
Dasatinib
Eptapirone
Gepirone
Ipsapirone
Piribedil
Prazitone
Pyrimidinylpiperazine
Revospirone
Tandospirone
Tirilazad
Trimazosin
Umespirone
Zalospirone
Azaperone
Delavirdine
Mirtazapine
ORG-12962
Pyridinylpiperazine
Perospirone
Revospirone
Tiospirone
Ziprasidone
Clopenthixol
Clorotepine
Clozapine
Cyanothepin
Doclothepin
Docloxythepin
Flupentixol
Fluphenazine
Isofloxythepin
Loxapine
Meperathiepin
Metitepine
Octomethothepin
Olanzapine
Opipramol
Oxyclothepin
Oxyprothepin
Peradithiepin
Perathiepin
Perazine
Perphenazine
Pirenzepine
Prochlorperazine
Thiethylperazine
Thiothixene
Trifluoperazine
Trifluthepin
Zuclopenthixol
AP-238
Azimilide
Bucinnazine
Cinepazet
Cinepazic acid
Cinepazide
CPD-1
Cyclohexylpiperazine
EGIS-7625
Hexocyclium
Indinavir
JNJ-7777120
Lodenafil
MK-212
Mirodenafil
PB-28
Quipazine
Ranolazine
SA-4503
Sildenafil
Tadalafil
Vardenafil
VUF-6002
WY-46824
Zipeprol
R e t r i e v e d f r o m " https://en.wikipedia.org/w/index.php?title=Azapirone&oldid=1227938740 "
C a t e g o r y :
● A z a p i r o n e s
H i d d e n c a t e g o r i e s :
● C S 1 : l o n g v o l u m e v a l u e
● P u b C h e m I D ( C I D ) n o t i n W i k i d a t a
● A r t i c l e s w i t h s h o r t d e s c r i p t i o n
● S h o r t d e s c r i p t i o n m a t c h e s W i k i d a t a
● U s e m d y d a t e s f r o m M a y 2 0 2 3
● T h i s p a g e w a s l a s t e d i t e d o n 8 J u n e 2 0 2 4 , a t 1 6 : 1 7 ( U T C ) .
● T e x t i s a v a i l a b l e u n d e r t h e C r e a t i v e C o m m o n s A t t r i b u t i o n - S h a r e A l i k e L i c e n s e 4 . 0 ;
a d d i t i o n a l t e r m s m a y a p p l y . B y u s i n g t h i s s i t e , y o u a g r e e t o t h e T e r m s o f U s e a n d P r i v a c y P o l i c y . W i k i p e d i a ® i s a r e g i s t e r e d t r a d e m a r k o f t h e W i k i m e d i a F o u n d a t i o n , I n c . , a n o n - p r o f i t o r g a n i z a t i o n .
● P r i v a c y p o l i c y
● A b o u t W i k i p e d i a
● D i s c l a i m e r s
● C o n t a c t W i k i p e d i a
● C o d e o f C o n d u c t
● D e v e l o p e r s
● S t a t i s t i c s
● C o o k i e s t a t e m e n t
● M o b i l e v i e w