phenelzine

[PHEN(O)- + E(THY)L + (HYDRA)ZINE.]

Brand names: Nardil®

Chemical formula:

Drug Forms:
• Phenelzine Sulfate Oral tablet (below)
• Phenelzine tablets

Español:
• Sulfato de fenelcina, Tableta oral
• Tabletas de fenelcina

Phenelzine Sulfate Oral tablet

What is this medicine?

PHENELZINE is a monoamine oxidase inhibitor (MAOI). It is used to treat depression in patients who may also have anxiety. This medicine is usually only used when other medicines have not helped.

This medicine may be used for other purposes; ask your health care provider or pharmacist if you have questions.

What should I tell my health care provider before I take this medicine?

They need to know if you have any of these conditions:
•bipolar disorder or mania
•frequently drink alcohol-containing beverages
•headaches or migraine
•heart or blood vessel disease, or irregular heart beats
•high blood pressure
•kidney disease
•liver disease
•Parkinson's disease
•pheochromocytoma
•recent head trauma
•seizures or convulsions
•schizophrenia or psychosis
•stroke or other cerebrovascular disease
•suicidal thoughts or a previous suicide attempt
•an unusual or allergic reaction to phenelzine, other medicines, foods, dyes, or preservatives
•pregnant or trying to get pregnant
•breast-feeding

How should I use this medicine?

Take this medicine by mouth with a glass of water. Follow the directions on the prescription label. Take your medicine at regular intervals. Do not take your medicine more often than directed. Do not stop taking except on your doctor's advice.

A special MedGuide will be given to you by the pharmacist with each prescription and refill. Be sure to read this information carefully each time.

Talk to your pediatrician regarding the use of this medicine in children. Special care may be needed.

Overdosage: If you think you have taken too much of this medicine contact a poison control center or emergency room at once.
NOTE: This medicine is only for you. Do not share this medicine with others.

What may interact with this medicine?

Do not take this medicine with any of the following medications:
•altretamine
•atomoxetine
•brimonidine
•buspirone
•caffeine
•carbamazepine
•certain medicines for blood pressure like clonidine, guanabenz, guanadrel, guanethidine, or reserpine
•cocaine
•cyclobenzaprine
•dextromethorphan
•diet pills or stimulants, like amphetamines or ephedra
•diphenoxylate
•doxapram
•ephedrine
•general or local anesthetics
•ginseng
•green tea
•guarana
•isoniazid
•linezolid
•MAOIs like Carbex, Eldepryl, Nardil, and Parnate
•medicines for migraine headaches
•medicines for movement abnormalities as in Parkinson's disease like entacapone, levodopa, selegiline, tolcapone
•meperidine
•other medicines for mental depression, anxiety, or mood or mental problems
•procarbazine
•SAM-e
•St. John's wort
•succinylcholine
•tramadol
•tyramine (found in cheese, red wine, beer, chocolate and other foods)
•tryptophan
•yohimbine

This medicine may also interact with the following medications:
•diuretics
•medicines for high blood pressure
•prescription pain medicines

This list may not describe all possible interactions. Give your health care provider a list of all the medicines, herbs, non-prescription drugs, or dietary supplements you use. Also tell them if you smoke, drink alcohol, or use illegal drugs. Some items may interact with your medicine.

What should I watch for while using this medicine?

Visit your doctor or health care professional for regular checks on your progress. It can take up to 3 to 6 weeks to see the full effects of this medicine. Do not suddenly stop taking your medicine. This may make your condition worse or cause withdrawal symptoms. Ask your doctor or health care professional for advice about gradually reducing your dosage. Even after you stop taking this medicine the effects can last for at least two weeks. Continue to take all precautions and avoid all food and medicine that interact with this medicine.

This medicine can interact with certain foods that contain tyramine. The combination may cause severe headaches, a rise in blood pressure, or irregular heart beat. Foods that contain significant amounts of tyramine include aged cheeses, meats and fish (especially aged, smoked, pickled, or processed such as bologna, pepperoni, salami, summer sausage), beer and ale, alcohol-free beer, wine (especially red), sherry, hard liquor, liqueurs, avocados, bananas, figs, raisins, soy sauce, miso soup, yeast/protein extracts, bean curd, fava or broad bean pods, or any over-ripe fruit. Ask your doctor or health care professional, pharmacist, or nutritionist for a complete listing of tyramine-containing foods. Also, avoid drinks containing caffeine, such as tea, coffee, chocolate, or cola.

You may get drowsy, dizzy or have blurred vision. Do not drive, use machinery, or do anything that needs mental alertness until you know how this medicine affects you. Do not stand or sit up quickly, especially if you are an older patient. This reduces the risk of dizzy or fainting spells. Alcohol may increase dizziness or drowsiness. Do not drink alcoholic beverages while taking this medicine.

Patients and their families should watch out for worsening depression or thoughts of suicide. Also watch out for sudden or severe changes in feelings such as feeling anxious, agitated, panicky, irritable, hostile, aggressive, impulsive, severely restless, overly excited and hyperactive, or not being able to sleep. If this happens, especially at the beginning of antidepressant treatment or after a change in dose, call your health care professional.

Your mouth may get dry. Chewing sugarless gum or sucking hard candy, and drinking plenty of water may help. Contact your doctor if the problem does not go away or is severe.

Do not treat yourself for coughs, colds, flu or allergies without asking your doctor or health care professional for advice. Do not take any medications for weight loss without advice either. Some ingredients in these products may increase possible side effects.

This medicine may affect blood sugar levels. If you have diabetes, check with your doctor or health care professional before you change your diet or the dose of your diabetic medicine.

Tell your health care professional that you are taking this medicine if you are scheduled to have any surgery, procedure or medical testing. You should usually stop taking this drug at least 10 days before elective surgery.

What side effects may I notice from receiving this medicine?

Side effects that you should report to your doctor or health care professional as soon as possible:
•allergic reactions like skin rash, itching or hives, swelling of the face, lips, or tongue
•breathing problems
•chest pain
•confused, excitable, restless, or nervous
•enlarged pupils, sensitivity of the eyes to light
•fast, irregular, or slow heartbeat
•feeling faint or lightheaded, falls
•fever, clammy skin, increased sweating, sore throat
•high blood pressure
•muscle or neck stiffness or spasm
•seizures
•sudden headache
•suicidal thoughts or other mood changes
•trouble passing urine or change in the amount of urine
•yellowing of the eyes or skin

Side effects that usually do not require medical attention (report to your doctor or health care professional if they continue or are bothersome):
•change in appetite or weight
•change in sex drive or performance
•constipation or diarrhea
•difficulty sleeping
•increased sensitivity to sunlight
•muscle aches or pains, trembling
•nausea or vomiting
•swelling of the feet or legs
•weak or tired

This list may not describe all possible side effects. Call your doctor for medical advice about side effects. You may report side effects to FDA at 1-800-FDA-1088.

Where should I keep my medicine?

Keep out of the reach of children.

Store at room temperature between 15 and 30 degrees C (59 and 86 degrees F). Keep container tightly closed. Throw away any unused medicine after the expiration date.

Last updated: 7/1/2002

Important Disclaimer: The drug information provided here is for educational purposes only. It is intended to supplement, not substitute for, the diagnosis, treatment and advice of a medical professional. This drug information does not cover all possible uses, precautions, side effects and interactions. It should not be construed to indicate that this or any drug is safe for you. Consult your medical professional for guidance before using any prescription or over the counter drugs.

A monoamine oxidase inhibitor, used as an antidepressant.

Phenelzine

Systematic (IUPAC) name
2-phenylethylhydrazine
Identifiers
CAS number	51-71-8
ATC code	N06AF03
PubChem	3675
DrugBank	APRD00099
Chemical data
Formula	C8H12N2
Mol. mass	136.19 g/mol
SMILES	eMolecules & PubChem
Pharmacokinetic data
Bioavailability	?
Metabolism	Liver
Half life	1.2 hours
Excretion	Urine
Therapeutic considerations
Pregnancy cat.	B3(AU) C(US)
Legal status	Uncontrolled
Routes	Oral
Y(what is this?)  (verify)

Phenelzine (Nardil) is a psychoactive drug of the hydrazine chemical class which is used as an antidepressant and anxiolytic or antipanic agent. It acts as a nonselective and irreversible monoamine oxidase inhibitor (MAOI). 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.

Contents 1 Indications 2 Adverse effects 3 Pharmacology 4 Pharmacokinetics 5 Chemistry 6 Interactions 7 See also 8 References

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]

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 inlcude 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.^[9]

Pharmacology

Phenelzine is a nonselective 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 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.^[10] 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/or its metabolites also inhibit at least two other enzymes to a lesser extent, of which are alanine transaminase (ALA-T),^[11] and γ-Aminobutyric acid transaminase (GABA-T),^[12] 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. 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 partially metabolize to phenethylamine (PEA). PEA acts as a norepinephrine and dopamine releasing agent (NDRA) 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.

Pharmacokinetics

Phenelzine 15 mg tablets.

Phenelzine is administered orally in the form of phenelzine sulfate and is rapidly absorbed from the gastrointestinal tract. Although phenelzine has a relatively short half-life (approximately 1.2 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. Acetylation is the primary routine of metabolism, and the major metabolites are phenylacetic acid and parahydroxyphenyl acetic acid, recovered as about 79% of the excreted dose of phenelzine in the urine over the course of 96 hours after single doses. The relationship between an individual patient's acetylator status and therapeutic dose is not known. Phenelzine may also interact with cytochrome P450 enzymes, inactivating these enzymes through formation of a heme adduct.

Another minor metabolite of phenelzine metabolism is phenylethylidenehydrazine (PEH), produced in a secondary reaction of phenelzine with active monoamine oxidases, which has a half-life of approximately 12 hours and is believed to be responsible for some of the anti-panic and anxiolytic effects of phenelzine.

Like many other antidepressants, phenelzine usually requires about 2–6 weeks of treatment to achieve full therapeutic effect. 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 pre-synaptic 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.

Chemistry

Phenelzine is closely related to the other hydrazine derivatives used as antidepressants such as iproclozide (Sursum), iproniazid (Marsilid), isocarboxazid (Marplan), nialamide (Niamid), and pheniprazine (Catron), all of which are also MAOIs.

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

Interactions

Main article: Monoamine oxidase inhibitor

Main article: 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. 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

• Hydrazines

References

1. ^ Parke-Davis Division of Pfizer Inc. (2003). Nardil(R) (Phenelzine sulfate tablets, USP), labeling information. Retrieved January 13, 2006, from the U.S. Food and Drug Administration's Web site: http://www.fda.gov/cder/foi/label/2003/11909slr033_nardil_lbl.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.  edit
3. ^ Vallejo, J; Gasto; Catalan; Salamero (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.  edit
4. ^ Quitkin, FM; Mcgrath; Liebowitz; Stewart; Howard (1981). "Monoamine oxidase inhibitors in bipolar endogenous depressives". Journal of clinical psychopharmacology 1 (2): 70–4. doi:10.1097/00004714-198103000-00005. PMID 7028797.  edit
5. ^ Buigues, J; Vallejo (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.  edit
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.  edit
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.  edit
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.  edit
9. ^ Gómez-Gil, E; Salmerón; Mas (1996). "Phenelzine-induced fulminant hepatic failure". Annals of internal medicine 124 (7): 692–3. PMID 8607601.  edit
10. ^ 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.  edit
11. ^ Tanay, VA; Parent; Wong; Paslawski; Martin; Baker (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.  edit
12. ^ Mckenna, KF; Mcmanus; Baker; Coutts (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.  edit
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).

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v • d • e Adrenergics Receptor Ligands α α1 Agonists: Amidephrine • Cirazoline • Dopamine • Epinephrine (Adrenaline) • Etilefrine • Isoprenaline • Levonordefrin • Metaraminol • Methoxamine • Methyldopa • Norepinephrine (Noradrenaline) • Oxymetazoline • Phenylephrine Antagonists: Alfuzosin • Arotinolol • Carvedilol • Doxazosin • Indoramin • L-765,314 • Labetalol • Moxisylyte • Nantenine • Phentolamine • Phenoxybenzamine • Prazosin • Silodosin • Tamsulosin • Terazosin • Tolazoline • Trimazosin • Urapidil α2 Agonists: (R)-3-Nitrobiphenyline • 4-NEMD • Amitraz • Apraclonidine • Brimonidine • Clonidine • Detomidine • Dexmedetomidine • Dopamine • Epinephrine (Adrenaline) • Etilefrine • Guanabenz • Guanfacine • Guanethidine • Guanoxabenz • Levonordefrin • Lofexidine • Medetomidine • Methyldopa • Norepinephrine (Noradrenaline) • Octopamine • Romifidine • Tizanidine • Tolonidine • Xylazine • Xylometazoline Antagonists: 1-PP • Atipamezole • BRL-44408 • Buspirone • Cirazoline • Efaroxan • Gepirone • Idazoxan • Ipsapirone • Mianserin • Mirtazapine • NAN-190 • Phentolamine • Phenoxybenzamine • Rauwolscine • SB-269,970 • Setiptiline • Spiroxatrine • Tandospirone • Tolazoline • Yohimbine α? Agonists: Anisodamine • Ephedrine • Ergotamine • Indanidine • Mephentermine • Midodrine • Mivazerol • Naphazoline • Phenylpropanolamine • Pseudoephedrine • Rilmenidine • Synephrine • Talipexole • Tetrahydrozoline β β1 Agonists: Denopamine • Dobutamine • Dopamine • Epinephrine (Adrenaline) • Etilefrine • Levonordefrin • Methyldopa • Norepinephrine (Noradrenaline) Antagonists: Acebutolol • Alprenolol • Amosulalol • Arotinolol • Atenolol • Bupranolol • Carvedilol • Celiprolol • Betaxolol • Bisoprolol • Dichloroisoprenaline • Esmolol • Labetalol • Metipranolol • Metoprolol • Nadolol • Nebivolol • Oxprenolol • Penbutolol • Pindolol • Practolol • Pronethalol • Propranolol • Sotalol • Tertatolol • Timolol • Tilisolol • Xamoterol β2 Agonists: Arformoterol • Bambuterol • Bitolterol • Carbuterol • Clenbuterol • Dopamine • Dopexamine • Epinephrine (Adrenaline) • Etilefrine • Fenoterol • Formoterol • Hexoprenaline • Indacaterol • Levonordefrin • Levosalbutamol • Methyldopa • Norepinephrine (Noradrenaline) • Orciprenaline • Pirbuterol • Procaterol • Reproterol • Rimiterol • Ritodrine • Salbutamol (Albuterol) • Salmeterol • Terbutaline • Tulobuterol Antagonists: Alprenolol • Amosulalol • Arotinolol • Bupranolol • Butaxamine • Carvedilol • Dichloroisoprenaline • ICI 118551 • Labetalol • Metipranolol • Nadolol • Oxprenolol • Penbutolol • Pindolol • Pronethalol • Propranolol • Sotalol • Tertatolol • Timolol • Tilisolol β3 Agonists: Amibegron • Arotinolol • Dopamine • Epinephrine (Adrenaline) • Etilefrine • Labetalol • Levonordefrin • Methyldopa • Norepinephrine (Noradrenaline) • Solabegron Antagonists: Carvedilol • SR 59230A β? Agonists: Arbutamine • BAAM • Befunolol • Broxaterol • Buphenine • Cimaterol • Ephedrine • Higenamine • Isoetarine • Isoxsuprine • Mabuterol • Methoxyphenamine • Oxyfedrine • Prenalterol • Pseudoephedrine • Ractopamine • Tretoquinol • Zilpaterol • Zinterol Reuptake Inhibitors Plasmalemmal NET Inhibitors Norepinephrine Reuptake Inhibitors: Atomoxetine (Tomoxetine) • Ciclazindol • Mazindol • Nisoxetine • Reboxetine • Tandamine • Tapentadol • Viloxazine; Norepinephrine-Dopamine Reuptake Inhibitors: Amineptine • Bupropion (Amfebutamone) • Fencamine • Fencamfamine • Lefetamine • LR-5182 • Manifaxine • Methylphenidate • Nomifensine • O-2172 • Radafaxine; Serotonin-Norepinephrine Reuptake Inhibitors: Bicifadine • Desvenlafaxine • Duloxetine • Milnacipran • Sibutramine • Tramadol • Venlafaxine; Serotonin-Norepinephrine-Dopamine Reuptake Inhibitors: Brasofensine • Diclofensine • DOV-102,677 • DOV-21,947 • DOV-216,303 • JNJ-7925476 • JZ-IV-10 • Methylnaphthidate • Naphyrone • NS-2359 • PRC200-SS • SEP-225,289 • SEP-227,162 • Tesofensine; Tricyclic Antidepressants: Amitriptyline • Butriptyline • Cianopramine • Clomipramine • Desipramine • Dosulepin • Doxepin • Imipramine • Lofepramine • Nortriptyline • Protriptyline • Trimipramine; Tetracyclic Antidepressants: Amoxapine • Maprotiline • Mianserin • Oxaprotiline; Others: Cocaine • Nefazodone • Nefopam • Ziprasidone TRPC6 Activators Adhyperforin • Hyperforin Vesicular VMAT Inhibitors Ibogaine • Reserpine • Tetrabenazine Releasing Agents Oxazolines: 4-Methylaminorex (4-MAR, 4-MAX) • Aminorex • Clominorex • Cyclazodone • Fenozolone • Fluminorex • Pemoline • Thozalinone; Phenethylamines (also Amphetamines, Cathinones, Phentermines, etc): 2-Hydroxyphenethylamine (2-OH-PEA) • 4-Methylamphetamine (4-MA) • 4-Methylmethamphetamine (4-MMA) • Alfetamine • Amphetamine (Dextroamphetamine, Levoamphetamine) • Amphetaminil • Amfepentorex • β-Methylphenethylamine (β-Me-PEA) • Benzodioxolylbutanamine (BDB) • Benzodioxolylhydroxybutanamine (BOH) • Benzphetamine • Buphedrone • Butylone • Cathine • Cathinone • Clobenzorex • Clortermine • Diethylcathinone (Diethylpropion, Amfepramone) • Dimethoxyamphetamine (DMA) • Dimethoxymethamphetamine (DMMA) • Dimethylamphetamine • Dimethylcathinone (Dimethylpropion, Metamfepramone) • Ephedrine (EPH) • Ethcathinone (Ethylpropion) • Ethylamphetamine • Ethylbenzodioxolylbutanamine (EBDB) • Ethylone • Fenethylline • Fenproporex • Flephedrone • Fludorex • Furfenorex • Hordenine • Indanorex • Indanylamphetamine (IAP) • Lisdexamfetamine • Lophophine (Homomyristicylamine) • Mefenorex • Mephedrone • Mephentermine • Methamphetamine (Desoxyephedrine, Methedrine; Dextromethamphetamine, Levomethamphetamine) • Methcathinone (Methylpropion) • Methedrone • Methoxymethylenedioxyamphetamine (MMDA) • Methoxymethylenedioxymethamphetamine (MMDMA) • Methylbenzodioxolylbutanamine (MBDB) • Methylenedioxyamphetamine (MDA; Tenamfetamine) • Methylenedioxyethylamphetamine (MDEA) • Methylenedioxyhydroxyamphetamine (MDOH) • Methylenedioxymethamphetamine (MDMA) • Methylenedioxymethylphenethylamine (MDMPEA; Homarylamine) • Methylenedioxyphenethylamine (MDPEA; Homopiperonylamine) • Methylone • Naphthylamphetamine (NAP) • Ortetamine • Oxaflozane • Parabromoamphetamine (PBA) • Parachloroamphetamine (PCA) • Parafluoroamphetamine (PFA) • Parafluoromethamphetamine (PFMA) • Parahydroxyamphetamine (PHA) • Paraiodoamphetamine (PIA) • Paramethoxyamphetamine (PMA) • Paramethoxyethylamphetamine (PMEA) • Paramethoxymethamphetamine (PMMA) • Paredrine (Norpholedrine, Oxamphetamine) • Phendimetrazine • Phenethylamine (PEA) • Phenmetrazine • Pholedrine • Phenpentermine • Phenpromethamine • Phentermine • Phenylpropanolamine (PPA) • Propylamphetamine • Pseudoephedrine (PSE) • Tiflorex (Flutiorex) • Tyramine (TRA) • Xylopropamine • Zylofuramine; Piperazines: 2,5-Dimethoxy-4-bromobenzylpiperazine (2C-B-BZP) • Benzylpiperazine (BZP) • Methoxyphenylpiperazine (MeOPP; Paraperazine) • Methylbenzylpiperazine (MBZP) • Methylenedioxybenzylpiperazine (MDBZP; Piperonylpiperazine) • Parafluorophenylpiperazine (pFPP; Fluoperazine); Others: 2-Aminoindane (2-AI) • 2-Aminotetralin (2-AT) • 2-Benzylpiperidine (2-BP) • 4-Benzylpiperidine (4-BP) • Clofenciclan • Cyclopentamine • Cypenamine • Cyprodenate • Feprosidnine • Gilutensin • Heptaminol • Hexacyclonate • Isometheptene • Methylhexanamine • Octodrine • Phthalimidopropiophenone • Propylhexedrine (PHX) • Tuaminoheptane (Tuamine) Enzyme Inhibitors Anabolism PAH Inhibitors 3,4-Dihydroxystyrene TH Inhibitors 3-Iodotyrosine • Aquayamycin • Bulbocapnine • Metirosine • Oudenone AAAD Inhibitors Benserazide • Carbidopa DBH Inhibitors Disulfiram • Nepicastat • Tropolone PNMT Inhibitors CGS-19281A • SKF-64139 • SKF-7698 Catabolism MAO Inhibitors Nonselective: Etryptamine • Furazolidone • Hydralazine • Iproclozide • Iproniazid • Isocarboxazid • Isoniazid • Linezolid • Mebanazine • Metryptamine • Nialamide • Phenelzine • Pheniprazine • Phenoxypropazine • Pivalylbenzhydrazine • Procarbazine • Safrazine • Tranylcypromine; MAO-A Selective: Befloxatone • Brofaromine • Cimoxatone • Clorgiline • Harmala Alkaloids (Harmine, Harmaline, Tetrahydroharmine, etc) • Minaprine • Moclobemide • Pirlindole • Toloxatone • Tyrima; MAO-B Selective: Lazabemide • Pargyline • Rasagiline • Selegiline * Note that MAO-B inhibitors also influence norepinephrine/epinephrine levels since they inhibit the breakdown of their precursor dopamine. COMT Inhibitors Entacapone • Tolcapone Others Precursors L-Phenylalanine → L-Tyrosine → L-DOPA (Levodopa) → Dopamine • L-DOPS (Droxidopa) Cofactors Ferrous Iron (Fe2+) • S-Adenosyl-L-Methionine • Vitamin B3 (Niacin, Nicotinamide → NADPH) • Vitamin B6 (Pyridoxine, Pyridoxamine, Pyridoxal → Pyridoxal Phosphate) • Vitamin B9 (Folic Acid → Tetrahydrofolic Acid) • Vitamin C (Ascorbic Acid) • Zinc (Zn2+) Others Activity Enhancers: Benzofuranylpropylaminopentane (BPAP) • Phenylpropylaminopentane (PPAP); Release Blockers: Bretylium • Guanethidine

v • d • e Dopaminergics Receptor Ligands Agonists Benzazepines: 6-Br-APB • Fenoldopam • SKF-38,393 • SKF-77,434 • SKF-81,297 • SKF-82,958 • SKF-83,959; Ergot-derivatives: Bromocriptine • Cabergoline • Dihydroergocryptine • Lisuride • LSD • Pergolide; Dihydrexidine-derivatives: 2-OH-NPA • A-86,929 • Dihydrexidine • Dinapsoline • Dinoxyline • Doxanthrine; Morphine-derivatives: Apomorphine • Propylnorapomorphine; Piperazines: ABT-724 • Aripiprazole • Piribedil • WAY-100,635; Others: 7-OH-DPAT • 8-OH-PBZI • A-68,930 • A-77,636 • A-412,997 • ABT-670 • Amantadine • Aplindore • CY-208,243 • Memantine • PD-128,907 • PF-219,061 • Pramipexole • Pukateine • Quinpirole • RDS-127 • Rimantadine • Ropinirole • Rotigotine • SKF-89145 • SKF-89626 Antagonists Typical Antipsychotics: Acepromazine • Azaperone • Benperidol • Bromperidol • Clopenthixol • Chlorpromazine • Chlorprothixene • Droperidol • Flupentixol • Fluphenazine • Fluspirilene • Haloperidol • Loxapine • Mesoridazine • Methotrimeprazine • Molindone • Penfluridol • Perazine • Periciazine • Perphenazine • Pimozide • Prochlorperazine • Promazine • Sulforidazine • Thioridazine • Thiothixene • Trifluoperazine • Triflupromazine • Trifluperidol • Zuclopenthixol; Atypical Antipsychotics: Amisulpride • Asenapine • Clozapine • Iloperidone • Melperone • Olanzapine • Paliperidone • Perospirone • Quetiapine • Risperidone • Sertindole • Sulpiride • Ziprasidone • Zotepine; Antiemetics: AS-8112 • Alizapride • Bromopride • Clebopride • Domperidone • Metoclopramide • Thiethylperazine; Others: Amoxapine • Blonanserin • Buspirone • Butaclamol • N-Ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline • Ecopipam • Eticlopride • Fananserin • Mosapramine • Nafadotride • Nemonapride • Nuciferine • Raclopride • Remoxipride • SB-277,011-A • SCH-23,390 • SKF-83,566 • Spiperone • Spiroxatrine • Stepholidine • Tetrahydropalmatine • Tiapride • UH-232 • Yohimbine Reuptake Inhibitors Plasmalemmal DAT Inhibitors Piperazines: DBL-583 • GBR-12,935 • Nefazodone • Vanoxerine; Piperidines: BTCP • Desoxypipradrol • Dextromethylphenidate • Ethylphenidate • Methylnaphthidate • Methylphenidate • Phencyclidine • Pipradrol; Pyrrolidines: Diphenylprolinol • Methylenedioxypyrovalerone (MDPV) • Naphyrone • Prolintane • Pyrovalerone; Tropanes: β-CPPIT • Altropane • Brasofensine • CFT • Cocaine • Dichloropane • Difluoropine • FE-β-CPPIT • FP-β-CPPIT • Ioflupane (123I) • Iometopane • RTI-112 • RTI-113 • RTI-121 • RTI-126 • RTI-150 • RTI-177 • RTI-336 • Tenocyclidine • Tesofensine • Troparil • Tropoxane • WF-11 • WF-23 • WF-31 • WF-33; Others: Amfonelic Acid • Amineptine • Benzatropine • Bromantane • BTQ • BTS-74,398 • Bupropion (Amfebutamone) • Diclofensine • Dimethocaine • Dizocilpine • DOV-102,677 • DOV-21,947 • DOV-216,303 • Etybenzatropine • Fencamine • Fencamfamine • GYKI-52,895 • Indatraline • Ketamine • Lefetamine • LR-5182 • Manifaxine • Medifoxamine • Mesocarb • Nefopam • Nomifensine • NS-2359 • O-2172 • Propylamphetamine • Radafaxine • SEP-225,289 • SEP-227,162 • Sibutramine • Tametraline • Tripelennamine TRPC6 Activators Adhyperforin • Hyperforin Vesicular VMAT Inhibitors Deserpidine • Ibogaine • Reserpine • Tetrabenazine Releasing Agents Oxazolines: 4-Methylaminorex (4-MAR, 4-MAX) • Aminorex • Clominorex • Cyclazodone • Fenozolone • Fluminorex • Pemoline • Thozalinone; Phenethylamines (also Amphetamines, Cathinones, Phentermines, etc): 2-Hydroxyphenethylamine (2-OH-PEA) • 4-Methylamphetamine (4-MA) • 4-Methylmethamphetamine (4-MMA) • Alfetamine • Amphetamine (Dextroamphetamine, Levoamphetamine) • Amphetaminil • Amfepentorex • β-Methylphenethylamine (β-Me-PEA) • Benzodioxolylbutanamine (BDB) • Benzodioxolylhydroxybutanamine (BOH) • Benzphetamine • Buphedrone • Butylone • Cathine • Cathinone • Clobenzorex • Clortermine • Diethylcathinone (Diethylpropion, Amfepramone) • Dimethoxyamphetamine (DMA) • Dimethoxymethamphetamine (DMMA) • Dimethylamphetamine • Dimethylcathinone (Dimethylpropion, Metamfepramone) • Ethcathinone (Ethylpropion) • Ethylamphetamine • Ethylbenzodioxolylbutanamine (EBDB) • Ethylone • Fenethylline • Fenproporex • Flephedrone • Fludorex • Furfenorex • Hordenine • Indanorex • Indanylamphetamine (IAP) • Lophophine (Homomyristicylamine) • Mefenorex • Mephedrone • Methamphetamine (Desoxyephedrine, Methedrine; Dextromethamphetamine, Levomethamphetamine) • Methcathinone (Methylpropion) • Methedrone • Methoxymethylenedioxyamphetamine (MMDA) • Methoxymethylenedioxymethamphetamine (MMDMA) • Methylbenzodioxolylbutanamine (MBDB) • Methylenedioxyamphetamine (MDA; Tenamfetamine) • Methylenedioxyethylamphetamine (MDEA) • Methylenedioxyhydroxyamphetamine (MDOH) • Methylenedioxymethamphetamine (MDMA) • Methylenedioxymethylphenethylamine (MDMPEA; Homarylamine) • Methylenedioxyphenethylamine (MDPEA; Homopiperonylamine) • Methylone • Naphthylamphetamine (NAP) • Ortetamine • Oxaflozane • Parabromoamphetamine (PBA) • Parachloroamphetamine (PCA) • Parafluoroamphetamine (PFA) • Parafluoromethamphetamine (PFMA) • Parahydroxyamphetamine (PHA) • Paraiodoamphetamine (PIA) • Paramethoxyamphetamine (PMA) • Paramethoxyethylamphetamine (PMEA) • Paramethoxymethamphetamine (PMMA) • Paredrine (Norpholedrine, Oxamphetamine) • Phendimetrazine • Phenethylamine (PEA) • Phenmetrazine • Pholedrine • Phenpromethamine • Propylamphetamine • Tiflorex (Flutiorex) • Tyramine (TRA) • Xylopropamine • Zylofuramine; Piperazines: 2,5-Dimethoxy-4-bromobenzylpiperazine (2C-B-BZP) • Benzylpiperazine (BZP) • Methoxyphenylpiperazine (MeOPP; Paraperazine) • Methylbenzylpiperazine (MBZP) • Methylenedioxybenzylpiperazine (MDBZP; Piperonylpiperazine); Others: 2-Aminoindane (2-AI) • 2-Aminotetralin (2-AT) • 4-Benzylpiperidine (4-BP) • Clofenciclan • Cyclopentamine • Cypenamine • Cyprodenate • Feprosidnine • Gilutensin • Heptaminol • Hexacyclonate • Isometheptene • Methylhexanamine • Octodrine • Phthalimidopropiophenone • Propylhexedrine (PHX) • Tuaminoheptane (Tuamine) Enzyme Inhibitors Anabolism PAH Inhibitors 3,4-Dihydroxystyrene TH Inhibitors 3-Iodotyrosine • Aquayamycin • Bulbocapnine • Metirosine • Oudenone AAAD / DDC Inhibitors Benserazide • Carbidopa • Methyldopa Catabolism MAO Inhibitors Nonselective: Etryptamine • Furazolidone • Hydralazine • Iproclozide • Iproniazid • Isocarboxazid • Isoniazid • Linezolid • Mebanazine • Metryptamine • Nialamide • Phenelzine • Pheniprazine • Phenoxypropazine • Pivalylbenzhydrazine • Procarbazine • Safrazine • Tranylcypromine; MAO-A Selective: Befloxatone • Brofaromine • Cimoxatone • Clorgiline • Harmala Alkaloids (Harmine, Harmaline, Tetrahydroharmine, etc) • Minaprine • Moclobemide • Pirlindole • Toloxatone • Tyrima; MAO-B Selective: Lazabemide • Pargyline • Rasagiline • Selegiline COMT Inhibitors Entacapone • Tolcapone DBH Inhibitors Disulfiram • Nepicastat • Tropolone Others Precursors L-Phenylalanine → L-Tyrosine → L-DOPA (Levodopa) Cofactors Ferrous Iron (Fe2+) • Tetrahydrobiopterin • Vitamin B3 (Niacin, Nicotinamide → NADPH) • Vitamin B6 (Pyridoxine, Pyridoxamine, Pyridoxal → Pyridoxal Phosphate) • Vitamin B9 (Folic Acid → Tetrahydrofolic Acid) • Vitamin C (Ascorbic Acid) • Zinc (Zn2+) Others Activity Enhancers: Benzofuranylpropylaminopentane (BPAP) • Phenylpropylaminopentane (PPAP)

v • d • e GABAergics Receptor Ligands GABAA Agonists: Main Site: Gaboxadol • Ibotenic Acid • Isoguvacine • Isonipecotic Acid • Muscimol (Amanita Muscaria) • Piperazine • Progabide • SL 75102 • Thiomuscimol; Positive Allosteric Modulators: Barbiturates • Benzodiazepines • Carbamates • Chlormezanone • Clomethiazole • Etazolate • Ethanol (Alcohol) • Etomidate • Kavalactones (Kava Kava) • Loreclezole • Neuroactive Steroids • Nonbenzodiazepines • Phenols • Piperidinediones • Propanidid • Quinazolinones • ROD-188 • Skullcap • Stiripentol • Thymol • Valerenic Acid (Valerian) * See here for a full list of GABAA positive allosteric modulators. Antagonists: Main Site: Bicuculline • Gabazine; Negative Allosteric Modulators: α5IA • Bilobalide • Cicutoxin • DMCM • Flumazenil • Furosemide • L-655,708 • Oenanthotoxin • Penicillin • Pentylenetetrazol • Picrotoxin • PWZ-029 • Ro15-4513 • Sarmazenil • Suritozole • Thujone (Absinthe) GABAB Agonists: Main Site: 1,4-Butanediol • Baclofen • GBL • GHB • GHV • GVL • Phenibut • Progabide; Positive Allosteric Modulators: BHF-177 • BHFF • BSPP • CGP-7930 • GS-39783 Antagonists: Main Site: Phaclofen • Saclofen • SCH-50911 GABAC Agonists: Main Site: CACA • CAMP • GABOB • N(4)-chloroacetylcytosine arabinoside Antagonists: Main Site: Bilobalide • TPMPA Reuptake Inhibitors Plasmalemmal GAT Inhibitors CI-966 • Deramciclane • EF-1502 • Gabaculine • Guvacine • Nipecotic acid • NNC 05-2090 • SKF-89976A • SNAP-5114 • Tiagabine TRPC6 Activators Adhyperforin • Hyperforin Vesicular VGAT Inhibitors ..... Enzyme Inhibitors Anabolism GAD Inhibitors Allylglycine Catabolism GABA-T Inhibitors 3-Hydrazinopropionic Acid • Aminooxyacetic Acid • Gabaculine • Isoniazid • Phenelzine • Phenylethylidenehydrazine • Valnoctamide • Valproic acid • Valpromide • Vigabatrin Others Precursors Glutamate • Glutamine Cofactors Vitamin B6 (Pyridoxine/Pyridoxamine/Pyridoxal 5-Phosphate) Others L-Theanine • Picamilon

v • d • e Serotonergics Receptor ligands 5-HT1 5-HT1A Agonists: Azapirones: Alnespirone • Binospirone • Buspirone • Eptapirone • Gepirone • Ipsapirone • Perospirone • Tandospirone • Tiospirone • Zalospirone; Lysergamides: Dihydroergotamine • Ergotamine • Methysergide • LSD; Phenethylamines: MDA • MDMA; Piperazines: Eltoprazine • Flesinoxan • Flibanserin; Tryptamines: 5-CT • 5-MeO-DMT • 5-MT • DMT • Psilocin • Psilocybin • Rauwolscine • Yohimbine; Atypical Antipsychotics: Aripiprazole • Asenapine • Clozapine • Quetiapine • Ziprasidone; Others: 8-OH-DPAT • Befiradol • F-11440 • Lesopitron • Lu AA21004 • LY-293,284 • LY-301,317 • MKC-242 • Osemozotan • Piclozotan • PRX-00023 • Repinotan • RU-24969 • S-15535 • Sarizotan • SSR-181,507 • Sunepitron • U-92016A • Urapidil • Vilazodone • Xaliproden Antagonists: Beta Blockers: Alprenolol • Cyanopindolol • Iodocyanopindolol • Oxprenolol • Pindobind • Pindolol • Propranolol; Piperazines: Nefazodone • Trazodone • WAY-100,135 • WAY-100,635; Others: AV965 • BMY-7378 • Dotarizine • GR-46611 • Isamoltane • Lecozotan • Methiothepin • MPPF • NAN-190 • Robalzotan • S-15535 • SB-649915 • SDZ 216-525 • Spiperone • Spiramide • Spiroxatrine • UH-301 • WAY-100,135 • WAY-100,635 • Xylamidine 5-HT1B Agonists: Lysergamides: Dihydroergotamine • Ergotamine • Methysergide; Piperazines: Eltoprazine • TFMPP; Triptans: Eletriptan • Sumatriptan • Zolmitriptan; Tryptamines: 5-CT • 5-MT; Others: CP-93,129 • CP-94,253 • CP-135,807 • RU-24969 Antagonists: Lysergamides: Metergoline • Methiothepin; Tryptamines: Yohimbine; Others: AR-A000002 • GR-127,935 • Isamoltane • SB-216,641 • SB-224,289 • SB-236,057 5-HT1D Agonists: Lysergamides: Dihydroergotamine • Methysergide; Triptans: Almotriptan • Eletriptan • Frovatriptan • Naratriptan • Rizatriptan • Sumatriptan • Zolmitriptan; Tryptamines: 5-CT • 5-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 • Methiothepin; Tryptamines: Rauwolscine • Yohimbine; Others: Alniditan BRL-15572 • GR-127,935 • Ketanserin • LY-310,762 • LY-367,642 • LY-456,219 • LY-456,220 • Ritanserin • Ziprasidone 5-HT1E Agonists: Lysergamides: Methysergide; Triptans: Eletriptan; Tryptamines: Tryptamine Antagonists: Methiothepin 5-HT1F Agonists: Triptans: Eletriptan • Naratriptan • Sumatriptan; Tryptamines: 5-MT; Others: LY-334,370 Antagonists: Methiothepin 5-HT2 5-HT2A Agonists: Lysergamides: ALD-52 • Ergonovine • Lisuride • LA-SS-Az • LSD • Lysergic acid 2-butyl amide • Methysergide; Phenethylamines: 25I-NBMD • 25I-NBOH • 25I-NBOMe • 2C-B • 2C-B-FLY • 2C-E • 2C-I • 2C-T-2 • 2C-T-7 • 2C-T-21 • 2CBCB-NBOMe • 2CBFly-NBOMe • Bromo-DragonFLY • DOB • DOC • DOI • DOM • MDA • MDMA • Mescaline • Myristicin • TCB-2 • TFMFly; Piperazines: BZP • Quipazine • TFMPP; Tryptamines: 5-CT • 5-MeO-α-ET • 5-MeO-α-MT • 5-MeO-DET • 5-MeO-DiPT • 5-MeO-DMT • 5-MeO-DPT • 5-MT • α-ET • α-Methyl-5-HT • α-MT • Bufotenin • DET • DiPT • DMT • DPT • Psilocin • Psilocybin; Others: AL-34662 • AL-37350A • PNU-22394 Antagonists: Atypical Antipsychotics: Amperozide • Aripiprazole • Clozapine • Iloperidone • Melperone • Olanzapine • Paliperidone • Pimozide • Quetiapine • Risperidone • Sertindole • Ziprasidone • Zotepine; Typical Antipsychotics: Loxapine • Pipamperone; Antidepressants: Amitriptyline • Amoxapine • Etoperidone • Mianserin • Mirtazapine • Nefazodone • Trazodone; Others: 5-I-R91150 • AC-90179 • Altanserin • AMDA • APD-215 • Blonanserin • Cinanserin • Cyproheptadine • Deramciclane • Dotarizine • Eplivanserin • Fananserin • Flibanserin • Ketanserin • KML-010 • Lubazodone • Methiothepin • Nantenine • Pimavanserin • Pizotifen • Ritanserin • Sarpogrelate • Setoperone • Spiperone • Spiramide • SR-46349B • Volinanserin • Xylamidine • Yohimbine 5-HT2B Agonists: Oxazolines: 4-Methylaminorex • Aminorex; Phenethylamines: Chlorphentermine • DOB • DOC • DOI • DOM • Fenfluramine • MDA • MDMA • Norfenfluramine; Tryptamines: 5-CT • 5-MT • α-Methyl-5-HT; Others: BW-723C86 • Cabergoline • mCPP • Pergolide • PNU-22394 • Ro60-0175 Antagonists: Agomelatine • Asenapine • EGIS-7625 • Ketanserin • Lisuride • LY-272,015 • Rauwolscine • Ritanserin • RS-127,445 • Sarpogrelate • SB-200,646 • SB-204,741 • SB-206,553 • SB-215,505 • SB-221,284 • SB-228,357 • SDZ SER-082 • Tegaserod • Yohimbine 5-HT2C Agonists: Phenethylamines: 2C-B • 2C-E • 2C-I • 2C-T-2 • 2C-T-7 • 2C-T-21 • DOB • DOC • DOI • DOM • MDA • MDMA • Mescaline • Myristicin; Piperazines: Aripiprazole • mCPP • TFMPP; Tryptamines: 5-CT • 5-MeO-α-ET • 5-MeO-α-MT • 5-MeO-DET • 5-MeO-DiPT • 5-MeO-DMT • 5-MeO-DPT • 5-MT • α-ET • α-Methyl-5-HT • α-MT • Bufotenin • DET • DiPT • DMT • DPT • Psilocin • Psilocybin; Others: A-372,159 • AL-38022A • CP-809,101 • Lorcaserin • MK-212 • PNU-22394 • Ro60-0175 • Vabicaserin • WAY-629 • WAY-161,503 • YM-348 Antagonists: Atypical Antipsychotics: Clozapine • Iloperidone • Melperone • Olanzapine • Paliperidone • Pimozide • Quetiapine • Risperidone • Sertindole • Ziprasidone • Zotepine; Typical Antipsychotics: Chlorpromazine • Loxapine • Pipamperone; Antidepressants: Agomelatine • Amitriptyline • Amoxapine • Etoperidone • Fluoxetine • Mianserin • Mirtazapine • Nefazodone • Nortriptyline • Trazodone; Others: Cinanserin • Cyproheptadine • Deramciclane • Dimebolin • Dotarizine • Eltoprazine • FR-260,010 • Ketanserin • Ketotifen • Methysergide • Pizotifen • Ritanserin • RS-102,221 • SB-200,646 • SB-206,553 • SB-221,284 • SB-228,357 • SB-242,084 • SB-243,213 • SDZ SER-082 • Xylamidine 5-HT3 Agonists: Piperazines: BZP • Quipazine; Tryptamines: 2-Methyl-5-HT • 5-CT; Others: Chlorophenylbiguanide • RS-56812 • SR-57,227 • SR-57,227-A • YM-31636 Antagonists: Antiemetics: AS-8112 • Alosetron • Azasetron • Batanopride • Bemesetron • Cilansetron • Dolasetron • Granisetron • Lerisetron • Ondansetron • Palonosetron • Ramosetron • Renzapride • Tropisetron • Zacopride • Zatosetron; Atypical Antipsychotics: Clozapine • Olanzapine • Quetiapine; Tetracyclic Antidepressants: Amoxapine • Mianserin • Mirtazapine; Others: ICS-205,930 • Lu AA21004 • MDL-72,222 • Memantine • Ricasetron 5-HT4 Agonists: Gastroprokinetic Agents: Cisapride • Metoclopramide • Mosapride • Prucalopride • Renzapride • Tegaserod • Zacopride; Others: 5-MT • BIMU-8 • CJ-033,466 • PRX-03140 • RS-67333 • RS-67506 • TD-5108 Antagonists: GR-113,808 • GR-125,487 • L-Lysine • Piboserod • RS-39604 • RS-67532 • SB-203,186 5-HT5 5-HT5A Agonists: Lysergamides: Ergotamine • LSD; Tryptamines: 5-CT; Others: Valerenic Acid Antagonists: Asenapine • Dimebolin • Methiothepin • Ritanserin • SB-699,551 5-HT5B* Agonists: Lysergamides: Ergotamine • LSD Antagonists: Methiothepin * Note that the 5-HT5B receptor is not functional in humans. 5-HT6 Agonists: Lysergamides: Lisuride • LSD • Metergoline; Tryptamines: 5-CT • 5-MT • E-6801 • E-6837 • EMD-386,088 • EMDT • LY-586,713 • WAY-181,187 • WAY-208,466 Antagonists: Antidepressants: Amitriptyline • Amoxapine • Clomipramine • Doxepin • Mianserin • Nortriptyline; Atypical Antipsychotics: Aripiprazole • Asenapine • Clozapine • Fluperlapine • Iloperidone • Olanzapine • Tiospirone; Typical Antipsychotics: Chlorpromazine • Loxapine; Others: BGC20-760 • BVT-5182 • BVT-74316 • Dimebolin • EGIS-12233 • GW-742,457 • Ketanserin • Methiothepin • MS-245 • PRX-07034 • Ritanserin • Ro 04-6790 • Ro 63-0563 • SB-258,585 • SB-271,046 • SB-357,134 • SB-399,885 5-HT7 Agonists: Lysergamides: LSD; Tryptamines: 5-CT • 5-MT; Others: 8-OH-DPAT • AS-19 • Bifeprunox • LP-12 • LP-44 • Sarizotan Antagonists: Antidepressants: Amitriptyline • Amoxapine • Clomipramine • Imipramine • Maprotiline • Mianserin; Atypical Antipsychotics: Amisulpride • Aripiprazole • Clozapine • Olanzapine • Risperidone • Sertindole • Tiospirone • Ziprasidone • Zotepine; Typical Antipsychotics: Chlorpromazine • Loxapine; Others: EGIS-12233 • LY-215,840 • Mesulergine • Metergoline • Methiothepin • Pimozide • Ritanserin • 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 Plasmalemmal SERT inhibitors Selective Serotonin Reuptake Inhibitors (SSRIs): Alaproclate • Citalopram • Dapoxetine • Desmethylcitalopram • Desmethylsertraline • Elzasonan • Escitalopram • Femoxetine • Fluoxetine • Fluvoxamine • Indalpine • Litoxetine • Lubazodone • Norfluoxetine • Paroxetine • RTI-353 • Sertraline • Vilazodone • Zimelidine; Serotonin-Norepinephrine Reuptake Inhibitors (SNRIs): Bicifadine • Desvenlafaxine • Duloxetine • Milnacipran • Venlafaxine; Serotonin-Norepinephrine-Dopamine Reuptake Inhibitors (SNDRIs): Brasofensine • Diclofensine • DOV-102,677 • DOV-21,947 • DOV-216,303 • NS-2359 • SEP-225,289 • SEP-227,162 • Tesofensine; Tricyclic Antidepressants (TCAs): Amitriptyline • Butriptyline • Cianopramine • Clomipramine • Desipramine • Dosulepin • Doxepin • Imipramine • Lofepramine • Nortriptyline • Protriptyline • Trimipramine; Tetracyclic Antidepressants (TeCAs): Amoxapine; Piperazines: Nefazodone • Trazodone; Antihistamines: Brompheniramine • Chlorpheniramine • Diphenhydramine • Mepyramine (Pyrilamine) • Pheniramine • Tripelennamine; Opioids: Meperidine (Pethidine) • Methadone • Propoxyphene • Tramadol; Others: Cocaine • Cyclobenzaprine (CBZ) • Dextromethorphan (DXM) • Mesembrine • Nefopam • SB-649,915 • Sibutramine • Ziprasidone TRPC6 activators Adhyperforin • Hyperforin Vesicular VMAT Inhibitors Ibogaine • Reserpine • Tetrabenazine Releasing agents Aminoindanes: Ethyltrifluoromethylaminoindane (ETAI) • Methylenedioxyaminoindane (MDAI) • Methylenedioxymethylaminoindane (MDMAI) • Methoxymethylaminoindane (MMAI) • Trifluoromethylaminoindane (TAI); Aminotetralins: 8-Hydroxydipropylaminotetralin (8-OH-DPAT); Oxazolines: 4-Methylaminorex (4-MAR, 4-MAX) • Aminorex • Clominorex • Fluminorex; Phenethylamines (also Amphetamines, Cathinones, Phentermines, etc): 4-Methylthioamphetamine (4-MTA) • 5-Aminopropyldihydrobenzofuran (5-APDB; 5-Desoxy-MDA) • Benzodioxolylbutanamine (BDB) • Benzodioxolylhydroxybutanamine (BOH) • Brephedrone • Butylone • Chlorphentermine • Diethylcathinone (Diethylpropion, Amfepramone) • Dimethoxyamphetamine (DMA) • Dimethoxymethamphetamine (DMMA) • Dimethylcathinone (Dimethylpropion, Metamfepramone) • Ethylbenzodioxolylbutanamine (EBDB) • Ethylone • Fenfluramine (Dexfenfluramine) • Flephedrone • Indanylamphetamine (IAP) • Lophophine (Homomyristicylamine) • Mephedrone • Methedrone • Methoxymethylamphetamine (MMA) • Methoxymethylenedioxyamphetamine (MMDA) • Methoxymethylenedioxymethamphetamine (MMDMA) • Methylbenzodioxolylbutanamine (MBDB) • Methylenedioxyamphetamine (MDA; Tenamfetamine) • Methylenedioxyethylamphetamine (MDEA) • Methylenedioxyhydroxyamphetamine (MDOH) • Methylenedioxymethamphetamine (MDMA) • Methylenedioxymethylphenethylamine (MDMPEA; Homarylamine) • Methylenedioxyphenethylamine (MDPEA; Homopiperonylamine) • Methylone • Naphthylamphetamine (NAP) • Norfenfluramine • Parabromoamphetamine (PBA) • Parachloroamphetamine (PCA) • Parafluoroamphetamine (PFA) • Parafluoromethamphetamine (PFMA) • Parahydroxyamphetamine (PHA) • Paraiodoamphetamine (PIA) • Paramethoxyamphetamine (PMA) • Paramethoxyethylamphetamine (PMEA) • Paramethoxymethamphetamine (PMMA); Piperazines: 2,5-Dimethoxy-4-bromobenzylpiperazine (2C-B-BZP) • Benzylpiperazine (BZP) • Metachlorophenylpiperazine (mCPP) • Methoxyphenylpiperazine (MeOPP; Paraperazine) • Methylbenzylpiperazine (MBZP) • Methylenedioxybenzylpiperazine (MDBZP; Piperonylpiperazine) • Parafluorophenylpiperazine (pFPP; Fluoperazine) • Trifluoromethylphenylpiperazine (TFMPP); Quinolines: PK-7059 • Viqualine; Tryptamines: Alphaethyltryptamine (AET; Etryptamine) • Alphamethyltryptamine (AMT; Metryptamine) Enzyme inhibitors Anabolism TPH inhibitors AGN-2979 • Fenclonine AAAD inhibitors Benserazide • Carbidopa Catabolism MAO Inhibitors Nonselective: Etryptamine • Furazolidone • Hydralazine • Iproclozide • Iproniazid • Isocarboxazid • Isoniazid • Linezolid • Mebanazine • Metryptamine • Nialamide • Phenelzine • Pheniprazine • Phenoxypropazine • Pivalylbenzhydrazine • Procarbazine • Safrazine • Tranylcypromine; MAO-A Selective: Befloxatone • Brofaromine • Cimoxatone • Clorgiline • Harmala alkaloids (Harmine, Harmaline, Tetrahydroharmine, etc) • Minaprine • Moclobemide • Pirlindole • Toloxatone • Tyrima Others Precursors L-Tryptophan → 5-HTP Cofactors Ferrous iron (Fe2+) • Magnesium (Mg2+) • Tetrahydrobiopterin • Vitamin B3 (Niacin, Nicotinamide → NADPH) • Vitamin B6 (Pyridoxine, Pyridoxamine, Pyridoxal → Pyridoxal phosphate) • Vitamin B9 (Folic Acid → Tetrahydrofolic acid) • Vitamin C (Ascorbic acid) • Zinc (Zn2+) Others Activity enhancers: Benzofuranylpropylaminopentane (BPAP) • Phenylpropylaminopentane (PPAP); Reuptake enhancers: Tianeptine

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