hidden pixel

Phenelzine Information

Phenelzine (Nardil) is a non-selective and irreversible monoamine oxidase inhibitor (MAOI) of the hydrazine class which is used as an antidepressant and anxiolytic. Along with tranylcypromine and isocarboxazid, phenelzine is one of the few non-selective MAOIs still in widespread clinical use.

Phenelzine and the other MAOIs are typically considered to be significantly more effective against clinical depression in comparison to more mainstream antidepressants like the selective serotonin reuptake inhibitors (SSRIs), but are usually reserved only as a last resort due to their prominent side effects and potentially hazardous food and drug interactions. Notably, phenelzine has demonstrated superior efficacy in treating anxiety disorders compared to related agents, likely due to its unique actions on GABA.

Contents

Indications

Phenelzine is used primarily in the treatment of major depressive disorder (MDD). Patients with depressive symptomology characterized as "atypical", "nonendogenous", and/or "neurotic", have been reported to respond particularly well to phenelzine.[1] The medication has also been found to be useful in patients who do not respond favorably to first and second-line treatments for depression, or are said to be "treatment-resistant".[2] In addition to being a recognized treatment for major depressive disorder, phenelzine has been found in studies to be effective in treating dysthymia,[3] bipolar depression (BD),[4] panic disorder (PD),[5] social anxiety disorder (SAD),[6] bulimia,[7] and post-traumatic stress disorder (PTSD).[8]

Pharmacology

Pharmacodynamics

Phenelzine is a non-selective and irreversible inhibitor of the enzyme monoamine oxidase (MAO). It inhibits both of the respective isoforms of MAO, MAO-A and MAO-B, and does so almost equally, with slight preference for the former. By inhibiting MAO, phenelzine prevents the breakdown of the monoamine neurotransmitters serotonin, melatonin, norepinephrine, epinephrine, and dopamine, as well as the trace amine neuromodulators such as phenethylamine, tyramine, octopamine, and tryptamine. This leads to an increase in the extracellular concentrations of these neurochemicals and therefore an alteration in neurochemistry and subsequently neurotransmission. It is this action that is thought to be the primary mediator in phenelzine's therapeutic benefits.

Notably, although phenelzine inhibits the breakdown of norepinephrine and epinephrine (which in concept should lead to increased levels of these two respective neurotransmitters), it actually typically significantly decreases their overall activity with time via a complex interaction with octopamine. This is the cause of the side effect of orthostatic hypotension commonly seen with phenelzine and the other MAOIs. Importantly, it has been demonstrated that the antidepressant effects of serotonin are actually mediated through norepinephrine.[9] As a result, this depletion of norepinephrine and epinephrine may significantly inhibit the full therapeutic potential of phenelzine and the other MAOIs. For this reason, augmenting with an adrenergic agent such as a norepinephrine reuptake inhibitor (NRI) or releasing agent (NRA) in conjunction may be desirable, though strict professional supervision is advised to minimize the risk of a potentially dangerous drug interaction such as hypertensive crisis.

Phenelzine and its metabolites also inhibit at least two other enzymes to a lesser extent, of which are alanine transaminase (ALA-T),[10] and γ-Aminobutyric acid transaminase (GABA-T),[11] the latter of which is not caused by phenelzine itself, but by a phenelzine metabolite phenylethylidenehydrazine (PEH). By inhibiting ALA-T and GABA-T, phenelzine causes an increase in the alanine and GABA levels in the brain and body. GABA is the major inhibitory neurotransmitter in the mammalian central nervous system, and is very important for the normal suppression of anxiety and stress, as well as keeping depression at bay. It is thought that phenelzine's action in increasing GABA concentrations may significantly contribute to its antidepressant, and especially, anxiolytic/antipanic properties, the latter of which have typically been considered superior to those of other antidepressants. As for ALA-T inhibition, though the consequences of disabling this enzyme are currently not well understood, there is some evidence to suggest that it is this action of the hydrazines (including phenelzine) which may be responsible for the occasional incidence of hepatitis and liver failure.

Phenelzine has also been shown to metabolize to phenethylamine (PEA).[12] PEA acts as a releasing agent of norepinephrine and dopamine, and produces effects very similar to those of amphetamine, though with markedly different pharmacokinetics such as a far shorter duration of action. Phenelzine's enhancement of PEA levels may contribute further to its overall antidepressant effects to some degree. In addition, phenethylamine is a substrate for MAO-B, and treatment with MAOIs that inhibit MAO-B such as phenelzine have been shown to consistently and significantly elevate its concentrations.

Like many other antidepressants, phenelzine usually requires several weeks of treatment to achieve full therapeutic effects. The reason for this delay has not fully been elucidated, but it is believed to be due to many factors, including achieving steady-state levels of MAO inhibition and the resulting adaptations in mean neurotransmitter levels, as well as the possibility of necessary desensitization of autoreceptors which normally inhibit the release of neurotransmitters like serotonin and dopamine. Typically, a therapeutic response to MAOIs is believed to be associated with an inhibition of at least 80-85% of monoamine oxidase activity.

Pharmacokinetics

Phenelzine 15 mg tablets.

Phenelzine is administered orally in the form of phenelzine sulfate and is rapidly absorbed from the gastrointestinal tract. Time to peak plasma concentration is 43 minutes and half-life is 11.6 hours. Unlike most other drugs, phenelzine irreversibly disables MAO, and as a result, it does not necessarily need to be present in the blood at all times for its effects to be sustained. Because of this, upon phenelzine treatment being ceased, its effects typically do not actually wear off until the body replenishes its enzyme stores, a process which can take as long as 2–3 weeks.

Phenelzine is metabolized primarily in the liver and its metabolites are excreted in the urine. Oxidation is the primary routine of metabolism, and the major metabolites are phenylacetic acid and parahydroxyphenylacetic acid, recovered as about 73% of the excreted dose of phenelzine in the urine over the course of 96 hours after single doses. Acetylation to N2-acetylphenelzine is a minor pathway. Phenelzine may also interact with cytochrome P450 enzymes, inactivating these enzymes through formation of a heme adduct. Two other minor metabolites of phenelzine, as mentioned above, include phenylethylidenehydrazine and phenethylamine.

Chemistry

Phenelzine is made relatively easily through the reaction of 2-phenylethylbromide with hydrazine.[13][14][15]

Adverse effects

Common side effects of phenelzine may include dizziness, blurry vision, dry mouth, headache, lethargy, sedation, somnolence, insomnia, anorexia, weight gain or loss, nausea and vomiting, diarrhea, constipation, urinary retention, mydriasis, muscle tremors, hyperthermia, sweating, hypertension or hypotension, orthostatic hypotension, paresthesia, hepatitis, and sexual dysfunction (consisting of loss of libido and anorgasmia). Rare side effects usually only seen in susceptible individuals may include hypomania or mania, psychosis, and acute liver failure, the latter of which is usually only seen in people with pre-existing liver damage, old age, alcohol consumption, or viral infection.[16]

Interactions

See also: Monoamine oxidase inhibitor#Dangers See also: Foods containing tyramine

The MAOIs are infamous for their problematic food restrictions and drug interactions. Hypertensive crisis may result from the overconsumption of tyramine-containing foods. As a result, patients on phenelzine and other MAOIs must avoid excess quantities of certain foods that contain tyramine such as aged cheeses and cured meats, among others. Serotonin syndrome may result from an interaction with certain drugs which increase serotonin activity such as selective serotonin reuptake inhibitors and pethidine (known as mepiridine in the US). Several deaths have been reported due to drug interaction-related serotonin syndrome such as the case of Libby Zion.

Phenelzine has also been linked to vitamin B6 deficiency. It reacts with vitamin B6 via an unknown enzyme to form a biologically inert metabolite. Both phenelzine and vitamin B6 are rendered inactive upon this reaction occurring. For this reason, it is recommended to supplement with vitamin B6 while taking phenelzine. High doses of vitamin B6 may significantly lower phenelzine levels and subsequently inhibit its therapeutic benefits, however, and thus, excess quantities of vitamin B6 should be avoided. It may be advisable to dose them separately during opposite intervals of the day (e.g., take one, then take the other 12 hours later) to avoid interaction as much as possible.

See also

References

  1. ^ Parke-Davis Division of Pfizer Inc. (2007). Nardil(R) (Phenelzine sulfate tablets, USP), labeling information. Retrieved December 14, 2009 from the U.S. Food and Drug Administration's Web site: http://www.accessdata.fda.gov/drugsatfda_docs/label/2007/011909s038lbl.pdf
  2. ^ Fiedorowicz, JG; Swartz (2004). "The role of monoamine oxidase inhibitors in current psychiatric practice". Journal of psychiatric practice 10 (4): 239–48. doi:10.1097/00131746-200407000-00005. PMID 15552546.
  3. ^ Vallejo, J; Gasto, C; Catalan, R; Salamero, M (1987). "Double-blind study of imipramine versus phenelzine in Melancholias and Dysthymic Disorders". The British journal of psychiatry : the journal of mental science 151: 639–42. doi:10.1192/bjp.151.5.639. PMID 3446308.
  4. ^ Quitkin, FM; Mcgrath, P; Liebowitz, MR; Stewart, J; Howard, A (1981). "Monoamine oxidase inhibitors in bipolar endogenous depressives". Journal of clinical psychopharmacology 1 (2): 70–4. doi:10.1097/00004714-198103000-00005. PMID 7028797.
  5. ^ Buigues, J; Vallejo, J (1987). "Therapeutic response to phenelzine in patients with panic disorder and agoraphobia with panic attacks". The Journal of clinical psychiatry 48 (2): 55–9. PMID 3542985.
  6. ^ Blanco, C.; Schneier, F.; Schmidt, A.; Blanco-Jerez, C.; Marshall, R.; Sánchez-Lacay, A.; Liebowitz, M. (2003). "Pharmacological treatment of social anxiety disorder: a meta-analysis". Depression and anxiety 18 (1): 29–40. doi:10.1002/da.10096. PMID 12900950.
  7. ^ Walsh, BT; Gladis; Roose; Stewart; Stetner; Glassman (1988). "Phenelzine vs placebo in 50 patients with bulimia". Archives of general psychiatry 45 (5): 471–5. PMID 3282482.
  8. ^ Frank, JB; Kosten; Giller El; Dan (1988). "A randomized clinical trial of phenelzine and imipramine for posttraumatic stress disorder". The American journal of psychiatry 145 (10): 1289–91. PMID 3048121.
  9. ^ Cryan, J.; O'Leary, O.; Jin, S.; Friedland, J.; Ouyang, M.; Hirsch, B.; Page, M.; Dalvi, A. et al. (2004). "Norepinephrine-deficient mice lack responses to antidepressant drugs, including selective serotonin reuptake inhibitors". Proceedings of the National Academy of Sciences of the United States of America 101 (21): 8186–8191. doi:10.1073/pnas.0401080101. PMID 15148402.
  10. ^ Tanay, VA; Parent, MB; Wong, JT; Paslawski, T; Martin, IL; Baker, GB (2001). "Effects of the antidepressant/antipanic drug phenelzine on alanine and alanine transaminase in rat brain". Cellular and molecular neurobiology 21 (4): 325–39. doi:10.1023/A:1012697904299. PMID 11775064.
  11. ^ Mckenna, KF; Mcmanus, DJ; Baker, GB; Coutts, RT (1994). "Chronic administration of the antidepressant phenelzine and its N-acetyl analogue: effects on GABAergic function". Journal of neural transmission. Supplementum 41: 115–22. PMID 7931216.
  12. ^ Dyck LE, Durden DA, Boulton AA (June 1985). "Formation of beta-phenylethylamine from the antidepressant, beta-phenylethylhydrazine". Biochemical Pharmacology 34 (11): 1925–9. doi:10.1016/0006-2952(85)90310-7. PMID 4004908. http://linkinghub.elsevier.com/retrieve/pii/0006-2952(85)90310-7.
  13. ^ J.H. Biel, U.S. Patent 3,000,903 (1961).
  14. ^ J.H. Biel, A.E. Drukker, et al. J. Am. Chem. Soc., 81, 2805 (1959).
  15. ^ T.S. Gardner, E. Wenis, U.S. Patent 2,908,688 (1959).
  16. ^ Gómez-Gil, E; Salmerón; Mas (1996). "Phenelzine-induced fulminant hepatic failure". Annals of internal medicine 124 (7): 692–3. PMID 8607601.
· · Antidepressants (N06A)
Specific reuptake inhibitors (RIs), enhancers (REs), and releasing agents (RAs)
Selective serotonin reuptake inhibitors (SSRIs) AlaproclateCitalopramEscitalopramFemoxetineFluoxetineFluvoxamineIndalpineIfoxetineLitoxetineLubazodonePanuramineParoxetinePirandamineSeproxetineSertralineVilazodoneZimelidine
Serotonin-norepinephrine reuptake inhibitors (SNRIs) BicifadineClovoxamineDesvenlafaxineDuloxetineLevomilnacipranEclanamineMilnacipranSibutramineVenlafaxine
Serotonin-norepinephrine-dopamine reuptake inhibitors (SNDRIs) BrasofensineBTS-74,398CocaineDiclofensineDOV-21,947DOV-102,677DOV-216,303EXP-561FezolamineJNJ-7,925,476NS-2359PRC200-SSPridefrineSEP-225,289SEP-227,162Tesofensine
Norepinephrine reuptake inhibitors (NRIs) AmedalinAtomoxetine/TomoxetineBinedalineCiclazindolDaledalinEsreboxetineLortalamineMazindolNisoxetineReboxetineTalopramTalsupramTandamineViloxazine
Dopamine reuptake inhibitors (DRIs) MedifoxamineVanoxerine
Norepinephrine-dopamine reuptake inhibitors (NDRIs) AmineptineBupropion/AmfebutamoneCilobamineManifaxineMethylphenidateNomifensineRadafaxineTametraline
Norepinephrine-dopamine releasing agents (NDRAs) AmphetamineBefuralineLisdexamfetamine • Methamphetamine • PhenethylaminePiberalineTranylcypromine
Serotonin-norepinephrine-dopamine releasing agents (SNDRAs) 4-Methyl-αMTαET/EtryptamineαMT/Metryptamine
Selective serotonin reuptake enhancers (SSREs) Tianeptine
Others IndeloxazineTramadolViqualine
Receptor antagonists and/or reuptake inhibitors
Serotonin antagonists and reuptake inhibitors (SARIs) EtoperidoneNefazodoneTrazodone
Noradrenergic and specific serotonergic antidepressants (NaSSAs) AptazapineEsmirtazapineMianserinMirtazapineSetiptiline/Teciptiline
Norepinephrine-dopamine disinhibitors (NDDIs) Agomelatine
Serotonin modulators and stimulators (SMSs) Lu AA21004
Tricyclic and tetracyclic antidepressants (TCAs/TeCAs)
Tricyclics: AmezepineAmineptineAmitriptylineAmitriptylinoxideAzepindoleButriptylineCianopramineClomipramineCotriptyline • Cyanodothiepin • DemexiptilineDepramine/BalipramineDesipramineDibenzepineDimetacrineDosulepin/DothiepinDoxepinEnprazepineFluotracenHepzidineHomopipramolImipramineImipraminoxideIntriptylineIprindoleKetipramineLitracenLofepramineLosindoleMariptilineMelitracenMetapramineMezepineNaranolNitroxazepineNortriptylineNoxiptilineOctriptylineOpipramolPipofezinePropizepineProtriptylineQuinupramineTampramineTianeptineTienopramineTrimipramine; Tetracyclics: 7-OH-AmoxapineAmoxapineAptazapineAzipramineCiclazindolCiclopramineEsmirtazapineLoxapineMaprotilineMazindolMianserinMirtazapineOxaprotilineSetiptiline/Teciptiline
Monoamine oxidase inhibitors (MAOIs)
Nonselective: Irreversible: BenmoxinEchinopsidineIproclozideIproniazidIsocarboxazidMebanazineMetfendrazineNialamideOctamoxinPhenelzinePheniprazinePhenoxypropazinePivalylbenzhydrazineSafrazineTranylcypromine; Reversible: CaroxazoneParaxazone; MAOA-Selective: Irreversible: Clorgyline; Reversible: Amiflamine • Bazinaprine • Befloxatone • Befol • BrofaromineCimoxatone • Esuperone • Harmala Alkaloids (Harmine, Harmaline, Tetrahydroharmine, Harman, Norharman, etc) • Methylene BlueMetralindoleMinaprineMoclobemidePirlindole • Sercloremine • Tetrindole • ToloxatoneTyrima; MAOB-Selective: Irreversible: Ladostigil • Mofegiline • PargylineRasagilineSelegiline; Reversible: Lazabemide • Milacemide
Azapirones and other 5-HT1A receptor agonists
AlnespironeAripiprazoleBefiradolBuspironeEptapironeFlesinoxanFlibanserinGepironeIpsapironeOxaflozaneTandospironeVilazodoneZalospirone
Dietary supplements (vitamins, minerals, amino acids, etc)
Ascorbic acid (Vitamin C) • Fish oilFolic acid (Vitamin B9) • L-5-HTP (Oxitriptan) • L-DOPA (Levodopa) • L-MethionineL-PhenylalanineL-TryptophanL-TyrosineLithiumMagnesiumMelatoninNiacin/Niacinamide (Vitamin B3) • Omega-3 fatty acidsPyridoxine (Vitamin B6) • RubidiumSAMeZinc
Research compounds and miscellaneous agents
5-HT4R agonists RS-67,333SL65.0155
5-HT7R antagonists Amisulpride
α2δ-VDCC blockers GabapentinPregabalin
β3-Adrenoceptor agonists AmibegronSolabegron
σ1R agonists AfobazoleDextromethorphanFluvoxamineIgmesineOpipramolPRE-084
CB1R agonists NabiloneTetrahydrocannabinol/Dronabinol
COMT inhibitors EntacaponeTolcapone
CRF1R antagonists AntalarminCP-154,526PexacerfontPivagabine
D2/D3 AR antagonists AmisulprideSulpiride
D2/D3/D4 R agonists PiribedilPramipexoleRopiniroleRotigotineRoxindole
DOR agonists BU-48BuprenorphineBW373U86DPI-287HeroinKratomSNC-80
Enkephalinase inhibitors D-PhenylalanineRB-101
FAAH inhibitors Acetaminophen/ParacetamolAM-404URB-597
KOR antagonists 5-GNTIBuprenorphineJDTicNorbinaltorphimine
MOR agonists BuprenorphineCodeineDextropropoxypheneDihydrocodeineFentanylHeroinHydrocodoneHydromorphoneKratomMethadoneMorphineOpiumOxycodoneOxymorphonePethidine/MeperidineTapentadolTramadol
MT1/MT2R agonists AgomelatineMelatoninRamelteonTasimelteon
NK1R antagonists AprepitantCasopitantFosaprepitantL-733,060MaropitantVestipitant
NMDAR antagonists DextromethorphanKetamineMagnesiumMemantineZinc
PDE4 inhibitors Mesembrine (Kanna) • Rolipram
TRPC6 activators Adhyperforin (St. John's Wort) • Hyperforin (St. John's Wort)

: PSO/PSI

(, , , , , , ), /,

, drug(/////)

· · Anxiolytics (N05B)
GABAA PAMs
Benzodiazepine AdinazolamAlprazolamBretazenilBromazepamCamazepamChlordiazepoxideClobazamClonazepamClorazepateClotiazepamCloxazolamDiazepamEthyl LoflazepateEtizolamFludiazepamHalazepamImidazenilKetazolamLorazepamMedazepamNordazepamOxazepamPinazepamPrazepam
Carbamates EmylcamateMebutamateMeprobamate (Carisoprodol, Tybamate) • PhenprobamateProcymate
Nonbenzodiazepines AbecarnilAdipiplonAlpidemCGS-9896CGS-20625DivaplonELB-139FasiplonGBLD-345GedocarnilL-838,417NS-2664NS-2710OcinaplonPagoclonePanadiplonPipequalineRWJ-51204SB-205,384SL-651,498TaniplonTP-003TP-13TPA-023Y-23684ZK-93423
Pyrazolopyridines CartazolateEtazolateICI-190,622Tracazolate
Others ChlormezanoneEthanol (Alcohol) • EtifoxineKavalactones (Kava Kava) • SkullcapValerenic Acid (Valerian)
α2δ VDCC Blockers GabapentinPregabalin
5-HT1A Agonists Azapirones: BuspironeGepironeTandospirone; Others: FlesinoxanOxaflozane
H1 Antagonists Diphenylmethanes: CaptodiameHydroxyzine; Others: BrompheniramineChlorpheniraminePheniramine
CRH1 Antagonists AntalarminCP-154,526PexacerfontPivagabine
NK2 Antagonists GR-159,897Saredutant
MCH1 antagonists ATC-0175SNAP-94847
mGluR2/3 Agonists Eglumegad
mGluR5 NAMs Fenobam
TSPO agonists DAA-1097DAA-1106EmapunilFGIN-127FGIN-143
σ1 agonists AfobazoleOpipramol
Others BenzoctamineCarbetocinDemoxytocinMephenoxaloneMepiprazoleOxanamideOxytocinPromoxolaneTofisopamTrimetozineWAY-267,464
#WHO-EM. Withdrawn from market. Clinical trials: Phase III. §Never to phase III

: PSO/PSI

(, , , , , , ), /,

, drug(/////)

· · Adrenergics
Receptor ligands
α1 Agonists: 5-FNE • 6-FNEAmidephrineAnisodamineAnisodineCirazolineDipivefrineDopamineEphedrineEpinephrine (Adrenaline) • EtilefrineEthylnorepinephrineIndanidineLevonordefrinMetaraminolMethoxamineMethyldopaMidodrineNaphazolineNorepinephrine (Noradrenaline) • OctopamineOxymetazolinePhenylephrinePhenylpropanolaminePseudoephedrineSynephrineTetrahydrozoline Antagonists: AbanoquilAdimololAjmalicineAlfuzosinAmosulalolArotinololAtiprosin • Benoxathian • BuflomedilBunazosinCarvedilol • CI-926 • CorynanthineDapiprazole • DL-017 • Domesticine • Doxazosin • Eugenodilol • Fenspiride • GYKI-12,743 • GYKI-16,084 • IndoraminKetanserinL-765,314Labetalol • Mephendioxan • Metazosin • MonatepilMoxisylyte (Thymoxamine) • NaftopidilNantenine • Neldazosin • NicergolineNiguldipine • Pelanserin • Phendioxan • PhenoxybenzaminePhentolaminePiperoxanPrazosin • Quinazosin • Ritanserin • RS-97,078 • SGB-1,534 • Silodosin • SL-89.0591 • SpiperoneTalipexoleTamsulosinTerazosin • Tibalosin • Tiodazosin • Tipentosin • TolazolineTrimazosin • Upidosin • Urapidil • Zolertine * Note that many TCAs, TeCAs, antipsychotics, ergolines, and some piperazines like buspirone, trazodone, nefazodone, etoperidone, and mepiprazole all antagonize α1-adrenergic receptors as well, which contributes to their side effects such as orthostatic hypotension.
α2 Agonists: (R)-3-Nitrobiphenyline4-NEMD6-FNEAmitrazApraclonidineBrimonidineClonidineDetomidineDexmedetomidineDihydroergotamineDipivefrineDopamineEphedrineErgotamineEpinephrine (Adrenaline) • Esproquin • EtilefrineEthylnorepinephrineGuanabenzGuanfacineGuanoxabenzLevonordefrinLofexidineMedetomidineMethyldopaMivazerolNaphazolineNorepinephrine (Noradrenaline) • PhenylpropanolaminePiperoxanPseudoephedrineRilmenidineRomifidineTalipexoleTetrahydrozolineTizanidineTolonidineUrapidilXylazineXylometazoline Antagonists: 1-PPAdimololAptazapineAtipamezoleBRL-44408BuflomedilCirazolineEfaroxanEsmirtazapineFenmetozoleFluparoxan • GYKI-12,743 • GYKI-16,084 • IdazoxanMianserinMirtazapine • MK-912 • NAN-190OlanzapinePhentolaminePhenoxybenzaminePiperoxanPiribedilRauwolscineRotigotineSB-269,970SetiptilineSpiroxatrineSunepitronTolazolineYohimbine * Note that many atypical antipsychotics and azapirones like buspirone and gepirone (via metabolite 1-PP) antagonize α2-adrenergic receptors as well.
β Agonists: 2-FNE • 5-FNE • AmibegronArbutamineArformoterolArotinololBAAMBambuterolBefunololBitolterolBroxaterolBuphenineCarbuterolCimaterolClenbuterolDenopamine • Deterenol • DipivefrineDobutamineDopamineDopexamineEphedrineEpinephrine (Adrenaline) • EtafedrineEtilefrineEthylnorepinephrineFenoterolFormoterolHexoprenalineHigenamineIndacaterolIsoetarineIsoprenaline (Isoproterenol) • IsoxsuprineLabetalolLevonordefrinLevosalbutamolMabuterolMethoxyphenamineMethyldopaN-Isopropyloctopamine • Norepinephrine (Noradrenaline) • OrciprenalineOxyfedrinePhenylpropanolaminePirbuterolPrenalterolRactopamineProcaterolPseudoephedrineReproterolRimiterolRitodrineSalbutamol (Albuterol) • SalmeterolSolabegronTerbutalineTretoquinolTulobuterolXamoterolZilpaterolZinterol Antagonists: AcebutololAdaprololAdimololAfurololAlprenololAlprenoximeAmosulalolAncarololArnololArotinololAtenololBefunololBetaxololBevantololBisoprololBopindolol • Bormetolol • Bornaprolol • Brefonalol • Bucindolol • Bucumolol • Bufetolol • Buftiralol • Bufuralol • Bunitrolol • Bunolol • Bupranolol • Burocrolol • Butaxamine • Butidrine • Butofilolol • Capsinolol • Carazolol • Carpindolol • CarteololCarvedilolCeliprolol • Cetamolol • Cicloprolol • Cinamolol • CloranololCyanopindolol • Dalbraminol • Dexpropranolol • DiacetololDichloroisoprenalineDihydroalprenolol • Dilevalol • Diprafenone • Draquinolol • Dropranolol • Ecastolol • Epanolol • Ericolol • Ersentilide • Esatenolol • Esmolol • Esprolol • Eugenodilol • Exaprolol • Falintolol • Flestolol • Flusoxolol • Hydroxycarteolol • Hydroxytertatolol • ICI-118,551 • Idropranolol • Indenolol • Indopanolol • Iodocyanopindolol • Iprocrolol • Isoxaprolol • IsamoltaneLabetalolLandiololLevobetaxololLevobunolol • Levocicloprolol • Levomoprolol • MedroxalolMepindolol • Metalol • MetipranololMetoprolol • Moprolol • Nadolol • Nadoxolol • Nafetolol • Nebivolol • Neraminol • Nifenalol • Nipradilol • Oberadilol • Oxprenolol • Pacrinolol • Pafenolol • Pamatolol • Pargolol • Parodilol • Penbutolol • Penirolol • PhQA-33 • Pindolol • Pirepolol • Practolol • Primidolol • Procinolol • PronethalolPropafenonePropranolol • Ridazolol • Ronactolol • Soquinolol • Sotalol • Spirendolol • SR 59230A • Sulfinalol • TA-2005 • TalinololTazolol • Teoprolol • Tertatolol • Terthianolol • Tienoxolol • TilisololTimolol • Tiprenolol • Tolamolol • Toliprolol • Tribendilol • Trigevolol • XibenololXipranolol
Reuptake inhibitors
NET Selective norepinephrine reuptake inhibitors: AmedalinAtomoxetine (Tomoxetine) • CiclazindolDaledalinEsreboxetineLortalamineMazindolNisoxetineReboxetineTalopramTalsupramTandamineViloxazine; Norepinephrine-dopamine reuptake inhibitors: AmineptineBupropion (Amfebutamone) • FencamineFencamfamineLefetamineLevophacetoperaneLR-5182ManifaxineMethylphenidateNomifensineO-2172Radafaxine; Serotonin-norepinephrine reuptake inhibitors: BicifadineDesvenlafaxineDuloxetineEclanamineLevomilnacipranMilnacipranSibutramineVenlafaxine; Serotonin-norepinephrine-dopamine reuptake inhibitors: BrasofensineDiclofensineDOV-102,677DOV-21,947DOV-216,303JNJ-7925476JZ-IV-10MethylnaphthidateNaphyroneNS-2359PRC200-SSSEP-225,289SEP-227,162Tesofensine; Tricyclic antidepressants: AmitriptylineButriptylineCianopramineClomipramineDesipramineDosulepinDoxepinImipramineLofepramineNortriptylineProtriptylineTrimipramine; Tetracyclic antidepressants: AmoxapineMaprotilineMianserinOxaprotilineSetiptiline; Others: CocaineCP-39,332EXP-561FezolamineNefazodoneNefopamPridefrineTapentadolTramadolZiprasidone
VMAT IbogaineReserpineTetrabenazine
Releasing agents
Morpholines: FenbutrazateMorazonePhendimetrazinePhenmetrazine; Oxazolines: 4-MethylaminorexAminorexClominorexCyclazodoneFenozoloneFluminorexPemolineThozalinone; Phenethylamines (also amphetamines, cathinones, phentermines, etc): 2-OH-PEA4-CAB4-FA4-FMA4-MA4-MMAAlfetamineAmfecloralAmfepentorexAmfepramoneAmphetamine (Dextroamphetamine, Levoamphetamine) • Amphetaminilβ-Me-PEABDBBenzphetamineBOHBuphedroneButyloneCathineCathinoneClobenzorexClortermineD-DeprenylDimethylamphetamineDimethylcathinone (Dimethylpropion, metamfepramone) • DMADMMAEBDBEphedrineEthcathinoneEthylamphetamineEthyloneFamprofazoneFenethyllineFenproporexFlephedroneFludorexFurfenorexHordenineIAPIMPL-Deprenyl (Selegiline) • LisdexamfetamineLophophineMBDBMDA (Tenamfetamine) • MDEAMDMAMDMPEAMDOHMDPEAMefenorexMephedroneMephentermine • Methamphetamine (Dextromethamphetamine, Levomethamphetamine) • MethcathinoneMethedroneMethyloneNAPOrtetamineParedrinepBApCAPentorex (Phenpentermine) • PhenethylaminePholedrinePhenpromethaminePhenterminePhenylpropanolaminepIAPrenylaminePropylamphetaminePseudoephedrineTiflorexTyramineXylopropamineZylofuramine; Piperazines: 2C-B-BZPBZPMBZPmCPPMDBZPMeOPPpFPP; Others: 2-Amino-1,2-dihydronaphthalene2-Aminoindane2-Aminotetralin2-Benzylpiperidine4-Benzylpiperidine5-IAIClofenciclanCyclopentamineCypenamineCyprodenateFeprosidnineGilutensinHeptaminolHexacyclonateIndanorexIsomethepteneMethylhexanamineOctodrinePhthalimidopropiophenonePropylhexedrine (Levopropylhexedrine) • Tuaminoheptane
Enzyme inhibitors
Anabolism
PAH 3,4-Dihydroxystyrene
TH 3-IodotyrosineAquayamycinBulbocapnineMetirosineOudenone
AAAD BenserazideCarbidopaGenisteinMethyldopa
DBH Bupicomide • Disulfiram • Dopastin • Fusaric acidNepicastat • Phenopicolinic acid • Tropolone
PNMT CGS-19281A • SKF-64139 • SKF-7698
Catabolism
MAO Nonselective: BenmoxinCaroxazoneEchinopsidineFurazolidoneHydralazineIndantadolIproclozideIproniazidIsocarboxazidIsoniazidLinezolidMebanazineMetfendrazineNialamideOctamoxinParaxazonePhenelzinePheniprazinePhenoxypropazinePivalylbenzhydrazineProcarbazineSafrazineTranylcypromine; MAO-A selective: Amiflamine • Bazinaprine • Befloxatone • Befol • BrofaromineCimoxatoneClorgiline • Esuprone • Harmala alkaloids (Harmine, Harmaline, Tetrahydroharmine, Harman, Norharman, etc) • Methylene BlueMetralindoleMinaprineMoclobemidePirlindole • Sercloremine • Tetrindole • ToloxatoneTyrima; MAO-B selective: D-DeprenylSelegiline (L-Deprenyl) • LadostigilLazabemide • Milacemide • Mofegiline • PargylineRasagiline * Note that MAO-B inhibitors also influence norepinephrine/epinephrine levels since they inhibit the breakdown of their precursor dopamine.
COMT EntacaponeTolcapone
Others
Precursors L-PhenylalanineL-TyrosineL-DOPA (Levodopa) → DopamineL-DOPS (Droxidopa)
Cofactors Ferrous Iron (Fe2+) • S-Adenosyl-L-MethionineVitamin B3 (Niacin, NicotinamideNADPH) • Vitamin B6 (Pyridoxine, Pyridoxamine, PyridoxalPyridoxal Phosphate) • Vitamin B9 (Folic acidTetrahydrofolic acid) • Vitamin C (Ascorbic acid) • Zinc (Zn2+)
Others Activity enhancers: BPAPPPAP; Release blockers: BethanidineBretyliumGuanadrelGuanazodine • Guanclofine • GuanethidineGuanoxan; Toxins: Oxidopamine (6-Hydroxydopamine)
· · Dopaminergics
Receptor ligands
Agonists Adamantanes: AmantadineMemantineRimantadine; Aminotetralins: 7-OH-DPAT8-OH-PBZIRotigotineUH-232; Benzazepines: 6-Br-APBFenoldopamSKF-38,393SKF-77,434SKF-81,297SKF-82,958SKF-83,959; Ergolines: BromocriptineCabergolineDihydroergocryptineLisurideLSDPergolide; Dihydrexidine derivatives: 2-OH-NPAA-86,929CiladopaDihydrexidineDinapsolineDinoxylineDoxanthrine; Others: A-68,930A-77,636A-412,997ABT-670ABT-724AplindoreApomorphineAripiprazoleBifeprunoxBP-897CY-208,243DizocilpineEtilevodopaFlibanserinKetamineMelevodopaModafinilPardoprunoxPhencyclidinePD-128,907PD-168,077PF-219,061PiribedilPramipexolePropylnorapomorphinePukateineQuinagolideQuineloraneQuinpiroleRDS-127Ro10-5824RopiniroleRotigotineRoxindoleSalvinorin ASKF-89,145SumaniroleTergurideUmespironeWAY-100,635
Antagonists Typical antipsychotics: AcepromazineAzaperoneBenperidolBromperidolClopenthixolChlorpromazineChlorprothixeneDroperidolFlupentixolFluphenazineFluspirileneHaloperidolLoxapineMesoridazineMethotrimeprazineNemonapridePenfluridolPerazinePericiazinePerphenazinePimozideProchlorperazinePromazineSulforidazineSulpirideSultoprideThioridazineThiothixeneTrifluoperazineTriflupromazineTrifluperidolZuclopenthixol; Atypical antipsychotics: AmisulprideAsenapineBlonanserinCarpipramineClocapramineClozapineGevotrolineIloperidoneLurasidoneMelperoneMolindoneMosapramine • Ocaperidone • OlanzapinePaliperidonePerospironePiquindoneQuetiapineRemoxiprideRisperidoneSertindoleTiospironeZiprasidoneZotepine; Antiemetics: AS-8112AlizaprideBromoprideCleboprideDomperidoneMetoclopramideThiethylperazine; Others: AmoxapineBuspironeButaclamolEcopipamEEDQEticloprideFananserinL-745,870NafadotrideNuciferinePNU-99,194RacloprideSarizotanSB-277,011-ASCH-23,390 • SKF-83,566 • SKF-83,959SonepiprazoleSpiperoneSpiroxatrineStepholidineTetrahydropalmatineTiaprideUH-232Yohimbine
Reuptake inhibitors
Plasmalemmal
DAT inhibitors Piperazines: DBL-583GBR-12,935NefazodoneVanoxerine; Piperidines: BTCPDesoxypipradrolDextromethylphenidateDifemetorexEthylphenidateMethylnaphthidateMethylphenidatePhencyclidinePipradrol; Pyrrolidines: DiphenylprolinolMethylenedioxypyrovalerone (MDPV) • NaphyroneProlintanePyrovalerone; Tropanes: β-CPPITAltropaneBrasofensineCFTCocaineDichloropaneDifluoropineFE-β-CPPITFP-β-CPPITIoflupane (123I)IometopaneRTI-112RTI-113RTI-121RTI-126RTI-150RTI-177RTI-229RTI-336TenocyclidineTesofensineTroparilTropoxaneWF-11WF-23WF-31WF-33; Others: AdrafinilArmodafinilAmfonelic acidAmineptineBenzatropine (Benztropine) • BromantaneBTQBTS-74,398Bupropion (Amfebutamone) • CiclazindolDiclofensineDimethocaineDiphenylpyralineDizocilpineDOV-102,677DOV-21,947DOV-216,303Etybenzatropine (Ethylbenztropine) • EXP-561FencamineFencamfamineFezolamineGYKI-52,895IndatralineKetamineLefetamineLevophacetoperaneLR-5182ManifaxineMazindolMedifoxamineMesocarbModafinilNefopamNomifensineNS-2359O-2172PridefrinePropylamphetamineRadafaxineSEP-225,289SEP-227,162SertralineSibutramineTametralineTripelennamine
Vesicular
VMAT inhibitors DeserpidineIbogaineReserpineTetrabenazine
Releasing agents
Morpholines: FenbutrazateMorazonePhendimetrazinePhenmetrazine; Oxazolines: 4-Methylaminorex (4-MAR, 4-MAX) • AminorexClominorexCyclazodoneFenozoloneFluminorexPemolineThozalinone; Phenethylamines (also amphetamines, cathinones, phentermines, etc): 2-Hydroxyphenethylamine (2-OH-PEA) • 4-CAB4-Methylamphetamine (4-MA) • 4-Methylmethamphetamine (4-MMA) • AlfetamineAmfecloralAmfepentorexAmfepramoneAmphetamine (Dextroamphetamine, Levoamphetamine) • Amphetaminilβ-Methylphenethylamine (β-Me-PEA) • Benzodioxolylbutanamine (BDB) • Benzodioxolylhydroxybutanamine (BOH) • BenzphetamineBuphedroneButyloneCathineCathinoneClobenzorexClortermineD-DeprenylDimethoxyamphetamine (DMA) • Dimethoxymethamphetamine (DMMA) • DimethylamphetamineDimethylcathinone (Dimethylpropion, metamfepramone) • Ethcathinone (Ethylpropion) • EthylamphetamineEthylbenzodioxolylbutanamine (EBDB) • EthyloneFamprofazoneFenethyllineFenproporexFlephedroneFludorexFurfenorexHordenineLophophine (Homomyristicylamine) • MefenorexMephedrone • Methamphetamine (Desoxyephedrine, Methedrine; Dextromethamphetamine, Levomethamphetamine) • Methcathinone (Methylpropion) • MethedroneMethoxymethylenedioxyamphetamine (MMDA) • Methoxymethylenedioxymethamphetamine (MMDMA) • Methylbenzodioxolylbutanamine (MBDB) • Methylenedioxyamphetamine (MDA, tenamfetamine) • Methylenedioxyethylamphetamine (MDEA) • Methylenedioxyhydroxyamphetamine (MDOH) • Methylenedioxymethamphetamine (MDMA) • Methylenedioxymethylphenethylamine (MDMPEA, homarylamine) • Methylenedioxyphenethylamine (MDPEA, homopiperonylamine) • MethyloneOrtetamineParabromoamphetamine (PBA) • Parachloroamphetamine (PCA) • Parafluoroamphetamine (PFA) • Parafluoromethamphetamine (PFMA) • Parahydroxyamphetamine (PHA) • Paraiodoamphetamine (PIA) • Paredrine (Norpholedrine, Oxamphetamine) • Phenethylamine (PEA) • PholedrinePhenpromethaminePrenylaminePropylamphetamineTiflorex (Flutiorex) • Tyramine (TRA) • XylopropamineZylofuramine; Piperazines: 2,5-Dimethoxy-4-bromobenzylpiperazine (2C-B-BZP) • Benzylpiperazine (BZP) • Methoxyphenylpiperazine (MeOPP, paraperazine) • Methylbenzylpiperazine (MBZP) • Methylenedioxybenzylpiperazine (MDBZP, piperonylpiperazine); Others: 2-Amino-1,2-dihydronaphthalene (2-ADN) • 2-Aminoindane (2-AI) • 2-Aminotetralin (2-AT) • 4-Benzylpiperidine (4-BP) • 5-IAIClofenciclanCyclopentamineCypenamineCyprodenateFeprosidnineGilutensinHeptaminolHexacyclonateIndanylaminopropane (IAP) • IndanorexIsomethepteneMethylhexanamineNaphthylaminopropane (NAP) • OctodrinePhthalimidopropiophenonePropylhexedrine (Levopropylhexedrine) • Tuaminoheptane (Tuamine)
Enzyme inhibitors
Anabolism
PAH inhibitors 3,4-Dihydroxystyrene
TH inhibitors 3-IodotyrosineAquayamycinBulbocapnineMetirosineOudenone
AAAD / DDC inhibitors BenserazideCarbidopaGenisteinMethyldopa
Catabolism
MAO inhibitors Nonselective: BenmoxinCaroxazoneEchinopsidineFurazolidoneHydralazineIndantadolIproclozideIproniazidIsocarboxazidIsoniazidLinezolidMebanazineMetfendrazineNialamideOctamoxinParaxazonePhenelzinePheniprazinePhenoxypropazinePivalylbenzhydrazineProcarbazineSafrazineTranylcypromine; MAO-A selective: Amiflamine • Bazinaprine • Befloxatone • Befol • BrofaromineCimoxatoneClorgiline • Esuprone • Harmala alkaloids (Harmine, Harmaline, Tetrahydroharmine, Harman, Norharman, etc) • Methylene BlueMetralindoleMinaprineMoclobemidePirlindole • Sercloremine • Tetrindole • ToloxatoneTyrima; MAO-B selective: D-DeprenylL-Deprenyl (Selegiline) • LadostigilLazabemide • Milacemide • Mofegiline • PargylineRasagiline
COMT inhibitors EntacaponeTolcapone
DBH inhibitors Bupicomide • Disulfiram • Dopastin • Fusaric acidNepicastat • Phenopicolinic acid • Tropolone
Others
Precursors L-PhenylalanineL-TyrosineL-DOPA (Levodopa)
Cofactors Ferrous Iron (Fe2+) • TetrahydrobiopterinVitamin B3 (Niacin, NicotinamideNADPH) • Vitamin B6 (Pyridoxine, Pyridoxamine, PyridoxalPyridoxal Phosphate) • Vitamin B9 (Folic acidTetrahydrofolic acid) • Vitamin C (Ascorbic acid) • Zinc (Zn2+)
Others Activity Enhancers: Benzofuranylpropylaminopentane (BPAP) • Phenylpropylaminopentane (PPAP); Toxins: Oxidopamine (6-Hydroxydopamine)
· · GABAergics
Receptor ligands
GABAA

Agonists: Main site: BamaluzoleGaboxadolIbotenic acidIsoguvacineIsonipecotic acidMuscimol (Amanita Muscaria) • Progabide • SL 75102 • Thiomuscimol • Tolgabide; Positive allosteric modulators: BarbituratesBenzodiazepinesCarbamatesChlormezanoneClomethiazoleEthanol (Alcohol) • EtomidateKavalactones (Kava kava) • LoreclezoleNeuroactive steroidsNonbenzodiazepinesPhenolsPiperidinedionesPropanididPyrazolopyridinesQuinazolinonesROD-188SkullcapStiripentolThymolValerenic acid (Valerian) * See for a full list of GABAA positive allosteric modulators.

Antagonists: Main site: BicucullineGabazinePitrazepin; Negative allosteric modulators: α5IABilobalideCicutoxinCyclothiazideDMCMFlumazenilFlurothylFurosemideL-655,708OenanthotoxinPenicillinPentylenetetrazolPicrotoxinPWZ-029Ro15-4513SarmazenilSuritozoleThujone (Absinthe) • Thiocolchicoside
GABAB Agonists: Main site: 1,4-ButanediolBaclofenGBLGHBGHVGVLPhenibutProgabideSKF-97,541Tolgabide; Positive allosteric modulators: BHF-177BHFFBSPPCGP-7930GS-39783 Antagonists: Main site: CGP-35348PhaclofenSaclofenSCH-50911
GABAC Agonists: Main site: CACACAMPGABOBN(4)-chloroacetylcytosine arabinosideProgabideTolgabide Antagonists: Main site: BilobalideTPMPA
Reuptake inhibitors
Plasmalemmal
GAT inhibitors CI-966 • Deramciclane • EF-1502 • Gabaculine • Guvacine • Nipecotic acid • NNC 05-2090 • SKF-89976A • SNAP-5114 • Tiagabine
Enzyme inhibitors
Anabolism
GAD inhibitors Allylglycine
Catabolism
GABA-T inhibitors 3-Hydrazinopropionic acid • Aminooxyacetic acid • GabaculineIsoniazidPhenelzinePhenylethylidenehydrazineSodium valproateValnoctamideValproate pivoxilValproate semisodium (Divalproex sodium) • Valproic acidValpromideVigabatrin
Others
Precursors GlutamateGlutamine
Cofactors Vitamin B6 (pyridoxine, pyridoxamine, pyridoxal phosphate)
Others GabapentinL-TheaninePicamilonPregabalin
· · Serotonergics
5-HT1 receptor ligands
5-HT1A Agonists: Azapirones: AlnespironeBinospironeBuspironeEnilospironeEptapironeGepironeIpsapironePerospironeRevospironeTandospironeTiospironeUmespironeZalospirone; Antidepressants: EtoperidoneNefazodoneTrazodone; Antipsychotics: AripiprazoleAsenapineClozapineQuetiapineZiprasidone; Ergolines: DihydroergotamineErgotamineLisurideMethysergideLSD; Tryptamines: 5-CT5-MeO-DMT5-MTBufoteninDMTPsilocinPsilocybin; Others: 8-OH-DPATAdatanserinBefiradolBMY-14802CannabidiolDimemebfeEbalzotanEltoprazine • F-11,461 • F-12,826 • F-13,714 • F-14,679 • F-15,063 • F-15,599FlesinoxanFlibanserinLesopitronLu AA21004LY-293,284 • LY-301,317 • MKC-242 • NBUMPOsemozotanOxaflozanePardoprunoxPiclozotanRauwolscineRepinotanRoxindoleRU-24,969 • S 14,506 • S-14,671S-15,535Sarizotan • SSR-181,507 • SunepitronU-92016AUrapidilVilazodoneXaliprodenYohimbine Antagonists: Antipsychotics: IloperidoneRisperidoneSertindole; Beta blockers: AlprenololCyanopindololIodocyanopindololOxprenolol • Pindobind • PindololPropranololTertatolol; Others: AV965 • BMY-7378CSP-2503DotarizineFlopropione • GR-46611 • IsamoltaneLecozotanMetitepine/MethiothepinMPPFNAN-190PRX-00023RobalzotanS-15535SB-649915 • SDZ 216-525 • SpiperoneSpiramideSpiroxatrineUH-301WAY-100,135WAY-100,635Xylamidine
5-HT1B Agonists: Lysergamides: DihydroergotamineErgotamineMethysergide; Piperazines: EltoprazineTFMPP; Triptans: AvitriptanEletriptanSumatriptanZolmitriptan; Tryptamines: 5-CT5-MT; Others: CGS-12066ACP-93,129CP-94,253 • CP-135,807 • RU-24969 Antagonists: Lysergamides: Metergoline; Others: AR-A000002ElzasonanGR-127,935IsamoltaneMetitepine/MethiothepinSB-216,641 • SB-224,289 • SB-236,057 • Yohimbine
5-HT1D Agonists: Lysergamides: DihydroergotamineMethysergide; Triptans: AlmotriptanAvitriptanEletriptanFrovatriptanNaratriptanRizatriptanSumatriptanZolmitriptan; Tryptamines: 5-CT5-MT; Others: CP-135,807 • CP-286,601 • GR-46611 • L-694,247 • L-772,405 • PNU-109,291 • PNU-142,633 Antagonists: Lysergamides: Metergoline; Others: AlniditanBRL-15572ElzasonanGR-127,935Ketanserin • LY-310,762 • LY-367,642 • LY-456,219 • LY-456,220 • Metitepine/MethiothepinRitanserinYohimbineZiprasidone
5-HT1E Agonists: Lysergamides: Methysergide; Triptans: Eletriptan; Tryptamines: BRL-54443Tryptamine Antagonists: Metitepine/Methiothepin
5-HT1F Agonists: Triptans: EletriptanNaratriptanSumatriptan; Tryptamines: 5-MT; Others: BRL-54443LasmiditanLY-334,370 Antagonists: Metitepine/Methiothepin
5-HT2 receptor ligands
5-HT2A Agonists: Lysergamides: ALD-52ErgonovineLisurideLA-SS-AzLSDLSD-PipLysergic acid 2-butyl amideMethysergide; Phenethylamines: 25I-NBF25I-NBMD25I-NBOH25I-NBOMe2C-B2C-B-FLY2CB-Ind2C-C-NBOMe2C-E2C-I2C-TFM-NBOMe2C-T-22C-T-72C-T-212CBCB-NBOMe2CBFly-NBOMeBromo-DragonFLYDOBDOCDOIDOMMDAMDMAMescalineTCB-2TFMFly; Piperazines: BZPQuipazineTFMPP; Tryptamines: 5-CT5-MeO-α-ET5-MeO-α-MT5-MeO-DET5-MeO-DiPT5-MeO-DMT5-MeO-DPT5-MTα-ETα-Methyl-5-HTα-MTBufoteninDETDiPTDMTDPTPsilocinPsilocybin; Others: AL-34662AL-37350ADimemebfeMedifoxamineOxaflozanePNU-22394RH-34 Antagonists: Atypical antipsychotics: AmperozideAripiprazoleCarpipramineClocapramineClozapineGevotrolineIloperidoneMelperoneMosapramineOlanzapinePaliperidonePimozideQuetiapineRisperidoneSertindoleZiprasidoneZotepine; Typical antipsychotics: LoxapinePipamperone; Antidepressants: AmitriptylineAmoxapineAptazapineEtoperidoneMianserinMirtazapineNefazodoneTrazodone; Others: 5-I-R91150 • AC-90179 • AdatanserinAltanserinAMDA • APD-215 • BlonanserinCinanserinCSP-2503CyproheptadineDeramciclaneDotarizineEplivanserinEsmirtazapineFananserinFlibanserinKetanserinKML-010LubazodoneMepiprazoleMetitepine/MethiothepinNanteninePimavanserinPizotifenPruvanserinRauwolscineRitanserinS-14,671SarpogrelateSetoperoneSpiperoneSpiramide • SR-46349B • VolinanserinXylamidineYohimbine
5-HT2B Agonists: Oxazolines: 4-MethylaminorexAminorex; Phenethylamines: ChlorphentermineCloforexDOBDOCDOIDOMFenfluramineMDAMDMANorfenfluramine; Tryptamines: 5-CT5-MTα-Methyl-5-HT; Others: BW-723C86CabergolinemCPPPergolidePNU-22394Ro60-0175 Antagonists: AgomelatineAsenapine • EGIS-7625 • KetanserinLisurideLY-272,015Metitepine/MethiothepinPRX-08066RauwolscineRitanserinRS-127,445Sarpogrelate • SB-200,646 • SB-204,741 • SB-206,553 • SB-215,505 • SB-221,284 • SB-228,357 • SDZ SER-082TegaserodYohimbine
5-HT2C Agonists: Phenethylamines: 2C-B2C-E2C-I2C-T-22C-T-72C-T-21DOBDOCDOIDOMMDAMDMAMescaline; Piperazines: AripiprazolemCPPTFMPP; Tryptamines: 5-CT5-MeO-α-ET5-MeO-α-MT5-MeO-DET5-MeO-DiPT5-MeO-DMT5-MeO-DPT5-MTα-ETα-Methyl-5-HTα-MTBufoteninDETDiPTDMTDPTPsilocinPsilocybin; Others: A-372,159AL-38022ACP-809,101DimemebfeLorcaserinMedifoxamine • MK-212 • ORG-37,684OxaflozanePNU-22394Ro60-0175Vabicaserin • WAY-629 • WAY-161,503 • YM-348 Antagonists: Atypical antipsychotics: ClozapineIloperidoneMelperoneOlanzapinePaliperidonePimozideQuetiapineRisperidoneSertindoleZiprasidoneZotepine; Typical antipsychotics: ChlorpromazineLoxapinePipamperone; Antidepressants: AgomelatineAmitriptylineAmoxapineAptazapineEtoperidoneFluoxetineMianserinMirtazapineNefazodoneNortriptylineTrazodone; Others: AdatanserinCinanserinCyproheptadineDeramciclaneDotarizineEltoprazineEsmirtazapine • FR-260,010 • KetanserinKetotifenLatrepirdineLu AA24530Metitepine/MethiothepinMethysergidePizotifenRitanserinRS-102,221S-14,671 • SB-200,646 • SB-206,553 • SB-221,284 • SB-228,357 • SB-242,084 • SB-243,213 • SDZ SER-082Xylamidine
5-HT3, 5-HT4, 5-HT5, 5-HT6, 5-HT7 ligands
5-HT3 Agonists: Piperazines: BZPQuipazine; Tryptamines: 2-Methyl-5-HT5-CT; Others: ChlorophenylbiguanideButanolEthanolHalothaneIsofluraneRS-56812 • SR-57,227 • SR-57,227-A • Toluene • Trichloroethane • TrichloroethanolTrichloroethylene • YM-31636 Antagonists: Antiemetics: AS-8112AlosetronAzasetronBatanoprideBemesetronCilansetronDazoprideDolasetronGranisetronLerisetronOndansetronPalonosetronRamosetronRenzaprideTropisetronZacoprideZatosetron; Atypical antipsychotics: ClozapineOlanzapineQuetiapine; Tetracyclic antidepressants: AmoxapineMianserinMirtazapine; Others: CSP-2503 • ICS-205,930 • Lu AA21004Lu AA24530 • MDL-72,222 • MemantineNitrous OxideRicasetronSevofluraneThujoneXenon
5-HT4 Agonists: Gastroprokinetic Agents: CinitaprideCisaprideDazoprideMetoclopramideMosapridePrucaloprideRenzaprideTegaserodZacopride; Others: 5-MTBIMU-8 • CJ-033,466 • PRX-03140 • RS-67333 • RS-67506 • SL65.0155 • TD-5108 Antagonists: GR-113,808 • GR-125,487 • L-LysinePiboserod • RS-39604 • RS-67532 • SB-203,186
5-HT5A Agonists: Lysergamides: ErgotamineLSD; Tryptamines: 5-CT; Others: Valerenic Acid Antagonists: AsenapineLatrepirdineMetitepine/MethiothepinRitanserinSB-699,551 * Note that the 5-HT5B receptor is not functional in humans.
5-HT6 Agonists: Lysergamides: DihydroergotamineErgotamineLisurideLSDMesulergineMetergolineMethysergide; Tryptamines: 2-Methyl-5-HT5-BT5-CT5-MTBufotenin • E-6801 • E-6837 • EMD-386,088EMDT • LY-586,713 • N-Methyl-5-HT • Tryptamine; Others: WAY-181,187WAY-208,466 Antagonists: Antidepressants: AmitriptylineAmoxapineClomipramineDoxepinMianserinNortriptyline; Atypical antipsychotics: AripiprazoleAsenapineClozapine • Fluperlapine • IloperidoneOlanzapineTiospirone; Typical antipsychotics: ChlorpromazineLoxapine; Others: BGC20-760 • BVT-5182 • BVT-74316 • EGIS-12233 • GW-742,457 • KetanserinLatrepirdineLu AE58054Metitepine/MethiothepinMS-245PRX-07034RitanserinRo 04-6790 • Ro 63-0563 • SB-258,585SB-271,046SB-357,134SB-399,885SB-742,457
5-HT7 Agonists: Lysergamides: LSD; Tryptamines: 5-CT5-MTBufotenin; Others: 8-OH-DPATAS-19Bifeprunox • LP-12 • LP-44 • RU-24,969Sarizotan Antagonists: Lysergamides: 2-Bromo-LSD • BromocriptineDihydroergotamineErgotamineMesulergineMetergolineMethysergide; Antidepressants: AmitriptylineAmoxapineClomipramineImipramineMaprotilineMianserin; Atypical antipsychotics: AmisulprideAripiprazoleClozapineOlanzapineRisperidoneSertindoleTiospironeZiprasidoneZotepine; Typical antipsychotics: ChlorpromazineLoxapine; Others: ButaclamolEGIS-12233Ketanserin • LY-215,840 • Metitepine/MethiothepinPimozideRitanserin • SB-258,719 • SB-258,741 • SB-269,970 • SB-656,104 • SB-656,104-A • SB-691,673 • SLV-313 • SLV-314 • Spiperone • SSR-181,507
Reuptake inhibitors
SERT Selective serotonin reuptake inhibitors (SSRIs): AlaproclateCitalopramDapoxetineDesmethylcitalopramDesmethylsertralineEscitalopramFemoxetineFluoxetineFluvoxamineIndalpineIfoxetineLitoxetineLu AA21004LubazodonePanuramineParoxetinePirandamineRTI-353SeproxetineSertralineVilazodoneZimelidine; Serotonin-norepinephrine reuptake inhibitors (SNRIs): BicifadineDesvenlafaxineDuloxetineEclanamineLevomilnacipranMilnacipranSibutramineVenlafaxine; Serotonin-norepinephrine-dopamine reuptake inhibitors (SNDRIs): BrasofensineDiclofensineDOV-102,677DOV-21,947DOV-216,303NS-2359SEP-225,289SEP-227,162Tesofensine; Tricyclic antidepressants (TCAs): AmitriptylineButriptylineCianopramineClomipramineDesipramineDosulepinDoxepinImipramineLofepramineNortriptylinePipofezineProtriptylineTrimipramine; Tetracyclic antidepressants (TeCAs): Amoxapine; Piperazines: NefazodoneTrazodone; Antihistamines: BrompheniramineChlorpheniramineDiphenhydramineMepyramine/PyrilaminePheniramineTripelennamine; Opioids: Meperidine (Pethidine) • MethadonePropoxyphene; Others: CocaineCP-39,332CyclobenzaprineDextromethorphanDextrorphanEXP-561FezolamineMesembrineNefopamPIM-35PridefrineRoxindoleSB-649,915Ziprasidone
VMAT IbogaineReserpineTetrabenazine
Releasing agents
Aminoindanes: 5-IAIETAIMDAIMDMAIMMAITAI; Aminotetralins: 6-CAT8-OH-DPATMDATMDMAT; Oxazolines: 4-MethylaminorexAminorexClominorexFluminorex; Phenethylamines (also Amphetamines, Cathinones, Phentermines, etc): 2-Methyl-MDA4-CAB4-FA4-FMA4-HA4-MTA5-APDB5-Methyl-MDA6-APDB6-Methyl-MDAAmiflamineBDBBOHBrephedroneButyloneChlorphentermineCloforexDiethylcathinoneDimethylcathinoneDMADMMAEBDBEDMAEthyloneEtolorexFenfluramine (Dexfenfluramine) • FlephedroneIAPIMPLophophineMBDBMDAMDEAMDHMAMDMAMDMPEAMDOHMDPEAMephedroneMethedroneMethyloneMMAMMDAMMDMANAPNorfenfluraminepBApCApIAPMAPMEAPMMATAP; Piperazines: 2C-B-BZPBZPMBZPmCPPMDBZPMeOPPMepiprazolepFPPTFMPP; Tryptamines: 4-Methyl-αET4-Methyl-αMT5-CT5-MeO-αET5-MeO-αMT5-MTαETαMTDMTTryptamine (itself); Others: IndeloxazineTramadolViqualine
Enzyme inhibitors
Anabolism
TPH AGN-2979Fenclonine
AAAD BenserazideCarbidopaGenisteinMethyldopa
Catabolism
MAO Nonselective: BenmoxinCaroxazoneEchinopsidineFurazolidoneHydralazineIndantadolIproclozideIproniazidIsocarboxazidIsoniazidLinezolidMebanazineMetfendrazineNialamideOctamoxinParaxazonePhenelzinePheniprazinePhenoxypropazinePivalylbenzhydrazineProcarbazineSafrazineTranylcypromine; MAO-A Selective: Amiflamine • Bazinaprine • Befloxatone • Befol • BrofaromineCimoxatoneClorgiline • Esuprone • Harmala alkaloids (Harmine, Harmaline, Tetrahydroharmine, Harman, Norharman, etc) • Methylene BlueMetralindoleMinaprineMoclobemidePirlindole • Sercloremine • Tetrindole • ToloxatoneTyrima
Others
Precursors L-Tryptophan5-HTP
Cofactors Ferrous iron (Fe2+) • Magnesium (Mg2+) • TetrahydrobiopterinVitamin B3 (Niacin, NicotinamideNADPH) • Vitamin B6 (Pyridoxine, Pyridoxamine, PyridoxalPyridoxal phosphate) • Vitamin B9 (Folic AcidTetrahydrofolic acid) • Vitamin C (Ascorbic acid) • Zinc (Zn2+)
Others Activity enhancers: BPAPPPAP; Reuptake enhancers: Tianeptine
· · Hydrazines
4-PTSCAcylhydrazineADHAdjudinAgaritineBenmoxinCadralazine • Carbazide • Carbazone • CarbidopaCarbohydrazideDaminozideDihydralazineDNPHEndralazineGyromitrinHBTHydralazineHydrazideHydrazineHydrazone • IDH • IproclozideIproniazidIsocarboxazidIsoniazidMebanazineMetfendrazineMMHNialamideOctamoxinPEHPhenelzinePheniprazinePhenoxypropazinePhenylhydrazinePimagedinePivalylbenzhydrazineProcarbazineSafrazine • SDH • SemicarbazideSemicarbazoneSDMHTetrafluorohydrazineThiosemicarbazideThiosemicarbazoneUDMH

Categories: Monoamine oxidase inhibitors | Phenethylamines | Hydrazines

 

The above information uses material from Wikipedia and is licensed under the GNU Free Documentation License.
Some facts may not have been fully verified for accuracy. [Disclaimers]
This page was last archived by our server on Mon Jun 13 18:15:28 2011.
Displaying this page or its contents does not use any Wikimedia Foundation's resources.
The owners of this site proudly support the Wikimedia Foundation.