cyproheptadine

[CY(CLIC) + PRO(PYL) + HEPTA- + (PIPERI)DINE.]

Brand names: Periactin®

Chemical formula:

Drug Forms:
• Cyproheptadine Hydrochloride Oral tablet (below)
• Cyproheptadine Hydrochloride Oral syrup
• Cyproheptadine Hydrochloride Oral solution

Español:
• Ciproheptadina Clorhidrato, Tableta oral
• Clorhidrato de ciproheptadina, Jarabe oral
• Clorhidrato de ciproheptadina, Solución oral

Cyproheptadine Hydrochloride Oral tablet

What is this medicine?

CYPROHEPTADINE (si proe HEP ta deen) is a antihistamine. This medicine is used to treat allergy symptoms. It is can help stop runny nose, watery eyes, and itchy rash.
 
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:
• any chronic disease
• glaucoma
• prostate disease
• ulcers or other stomach problems
• an unusual or allergic reaction to cyproheptadine, 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 doses at regular intervals. Do not take your medicine more often than directed.

Talk to your pediatrician regarding the use of this medicine in children. While this drug may be prescribed for children as young as 2 years of age for selected conditions, precautions do apply.

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:
• MAOIs like Carbex, Eldepryl, Marplan, Nardil, and Parnate

This medicine may also interact with the following medications:
• alcohol
• barbiturate medicines for inducing sleep or treating seizures
• medicines for depression, anxiety or psychotic disturbances
• medicines for movement abnormalities
• medicines for sleep
• medicines for stomach problems
• some medicines for cold or allergies

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 check ups. Tell your doctor if your symptoms do not improve or if they get worse.

You may get drowsy or dizzy. 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 interfere with the effect of this medicine. Avoid alcoholic drinks.

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.

This medicine may cause dry eyes and blurred vision. If you wear contact lenses you may feel some discomfort. Lubricating drops may help. See your eye doctor if the problem does not go away or is severe.

This medicine can make you more sensitive to the sun. Keep out of the sun. If you cannot avoid being in the sun, wear protective clothing and use sunscreen. Do not use sun lamps or tanning beds/booths.

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
• agitation, nervousness, excitability, not able to sleep
• chest pain
• irregular, fast heartbeat
• pain or difficulty passing urine
• seizures
• unusual bleeding or bruising
• unusually weak or tired
• 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):
• constipation or diarrhea
• headache
• loss of appetite
• nausea, vomiting
• stomach upset
• weight gain

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 histamine and serotonin antagonist used as an antipruritic and antihistaminic. It has also been used in the treatment of pituitary-dependent hyperadrenocorticism.

Cyproheptadine

Systematic (IUPAC) name
4-(5 H-dibenzo [a,d]cyclohepten-5-ylidene)- 1 -methylpiperidine hydrochloride
Identifiers
CAS number	129-03-3
ATC code	R06AX02
PubChem	2913
DrugBank	APRD00033
ChemSpider	2810
Chemical data
Formula	C21H21N
Mol. mass	287.398 g/mol
SMILES	eMolecules & PubChem
Pharmacokinetic data
Bioavailability	?
Protein binding	96 to 99%
Metabolism	Hepatic and renal
Half life	1 to 4 hours
Excretion	Fecal and renal
Therapeutic considerations
Pregnancy cat.	B(US)
Legal status	P (UK)
Routes	Oral only
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Cyproheptadine (pronounced /ˌsaɪprɵˈhɛptədiːn/; usually as cyproheptadine hydrochloride, trade name Periactin) is an antihistaminic/anticholinergic and antiserotonergic agent. It acts as a 5-HT₂ receptor antagonist and also blocks calcium channels.^[1]

Contents 1 Uses 2 Adverse effects 3 Research 4 Veterinary use 5 References

Uses

Cyproheptadine is used to treat allergic reactions (specifically hay fever).^[2]

Cyproheptadine has shown effectiveness in the treatment of nightmares including nightmares related to post traumatic stress disorder.^[3][4]

Cyproheptadine has been used in the management of moderate to severe cases of serotonin syndrome (a complex of symptoms associated with the use of serotonergic drugs, such as selective serotonin reuptake inhibitors or stimulants),^[5][6][7] and in the disease carcinoid in which serotonin is overproduced by tumor cells.^[8][9]

Cyproheptadine can also be used as a preventative measure against migraine in children and adolescents.^{[10][11][12][13][14]}

Cyproheptadine can relieve SSRI-induced sexual dysfunction^[15][16] and drug-induced hyperhydrosis (excess sweating).^[17]

Cyproheptadine can stimulate one's appetite.

Adverse effects

While not specifically used as a sedative, cyproheptadine causes drowsiness,^[18] as is common with first-generation antihistamines.

Research has shown a suppression of growth hormone with doses of 8-12 mg per day taken for 5 days.^[19]

Other common side effects include:^[20]

• Dizziness
• Blurred vision
• Constipation
• Dry mouth, throat, or nose
• Excitability
• Nausea
• Nervousness
• Restlessness

Research

Cyproheptadine has been shown to improve quality of sleep in sleep-deprived rats...^[21]

Cyproheptadine interacts with several other medications such as MAOIs (monoamine oxidase inhibitors) and potassium salts and can cause adverse reactions. Anti-cholinergic medications such as Cyproheptadine, when used in conjunction with oral potassium salts, can cause slowing of GI transit and increases the local exposure to high potassium concentrations. High potassium concentrations may lead to GI tract ulceration or stenosis.

Veterinary use

Periactin 4 mg tablets (AU)

Cyproheptadine is used in cats as an appetite stimulant and as an adjunct in the treatment of asthma.^[22][23] Possible adverse effects include excitement and aggressive behavior.^[22]

The elimination half-life of cyproheptadine in cats is 12 hours.^[23]

References

1. ^ Lowe DA, Matthews EK, Richardson BP (November 1981). "The calcium antagonistic effects of cyproheptadine on contraction, membrane electrical events and calcium influx in the guinea-pig taenia coli". British Journal of Pharmacology 74 (3): 651–63. PMID 6271323. 
2. ^ MedlinePlus Drug Information: Cyproheptadine
3. ^ Rijnders, R. J.P.; Laman, DM; Van Diujn, H (2000). "Cyproheptadine for Posttraumatic Nightmares". American Journal of Psychiatry 157 (9): 1524-a. doi:10.1176/appi.ajp.157.9.1524-a. PMID 10964879. http://ajp.psychiatryonline.org/cgi/content/full/157/9/1524-a. 
4. ^ Gupta, S; Popli, A; Bathurst, E; Hennig, L; Droney, T; Keller, P (May 1998). "Efficacy of cyproheptadine for nightmares associated with posttraumatic stress disorder.". Comprehensive psychiatry 39 (3): 160–4. doi:10.1016/S0010-440X(98)90076-1. ISSN 0010-440X. PMID 9606583. 
5. ^ Mills KC (October 1995). "Serotonin syndrome". American Family Physician 52 (5): 1475–82. PMID 7572570. 
6. ^ Gillman PK (1999). "The serotonin syndrome and its treatment". Journal of Psychopharmacology (Oxford, England) 13 (1): 100–9. PMID 10221364. 
7. ^ Hall M, Buckley N (2003). "Serotonin syndrome". Australian Prescriber 26 (3): 62–3. http://www.australianprescriber.com/magazine/26/3/62/3. 
8. ^ Berry EM, Maunder C, Wilson M (January 1974). "Carcinoid myopathy and treatment with cyproheptadine (Periactin)". Gut 15 (1): 34–8. doi:10.1136/gut.15.1.34. PMID 4274414. PMC 1412931. http://gut.bmj.com/cgi/pmidlookup?view=long&pmid=4274414. 
9. ^ Moertel, Charles G.; Kvols, LK; Rubin, J (1991). "A study of cyproheptadine in the treatment of metastatic carcinoid tumor and the malignant carcinoid syndrome". Cancer 67 (1): 33. doi:10.1002/1097-0142(19910101)67:1<33::AID-CNCR2820670107>3.0.CO;2-E. PMID 1985720. http://www3.interscience.wiley.com/journal/112674381/abstract. 
10. ^ Wendy G Mitchell et al. (2006). "Childhood Migraine Variants". http://www.emedicine.com/neuro/TOPIC494.HTM. 
11. ^ UVA Neurogram: Treatment of Pediatric Migraine
12. ^ Netdoctor: Periactin
13. ^ Migraines in Children and Adolescents
14. ^ Klimek A (1979). "Cyproheptadine (Peritol) in the treatment of migraine and related headache". Ther Hung 27 (2): 93–4. PMID 494146. 
15. ^ Keller Ashton A, Hamer R, Rosen RC (1997). "Serotonin reuptake inhibitor-induced sexual dysfunction and its treatment: a large-scale retrospective study of 596 psychiatric outpatients". Journal of Sex & Marital Therapy 23 (3): 165–75. PMID 9292832. 
16. ^ McCormick S, Olin J, Brotman AW (September 1990). "Reversal of fluoxetine-induced anorgasmia by cyproheptadine in two patients". Journal of Clinical Psychiatry 51 (9): 383–4. PMID 2211550. 
17. ^ Ashton AK, Weinstein WL (May 2002). "Cyproheptadine for drug-induced sweating". American Journal of Psychiatry 159 (5): 874–5. doi:10.1176/appi.ajp.159.5.874-a. PMID 11986151. http://ajp.psychiatryonline.org/cgi/pmidlookup?view=long&pmid=11986151. 
18. ^ Lexi-Comp (August 2008). "Cyproheptadine". The Merck Manual Professional. http://www.merck.com/mmpe/lexicomp/cyproheptadine.html.  Retrieved on October 26, 2008.
19. ^ Rosskamp RH, Haverkamp F, von Kalckreuth G (May 1990). "The effect of cyproheptadine on plasma growth hormone (GH) and on somatostatin response to GH-releasing hormone in man". Horm. Metab. Res. 22 (5): 295–7. doi:10.1055/s-2007-1004905. PMID 1971804. 
20. ^ Cyproheptadine - Drugs.com
21. ^ Tokunaga S; Takeda Y, Shinomiya K, Hirase M, Kamei C. (February 2007). "Effects of some H1-antagonists on the sleep-wake cycle in sleep-disturbed rats." (pdf). J Pharmacol Sci. 103 (2): 201–6. doi:10.1254/jphs.FP0061173. PMID 17287588. http://www.jstage.jst.go.jp/article/jphs/103/2/201/_pdf. 
22. ^ ^{a b} Dowling PM (February 8, 2005). "Drugs Affecting Appetite". in Kahn CM, Line S, Aiello SE (eds.). The Merck Veterinary Manual (9th ed.). John Wiley & Sons. ISBN 0-911910-50-6. http://www.merckvetmanual.com/mvm/index.jsp?cfile=htm/bc/190302.htm.  Retrieved on October 26, 2008.
23. ^ ^{a b} Dowling PM (February 8, 2005). "Systemic Therapy of Airway Disease: Cyproheptadine". in Kahn CM, Line S, Aiello SE (eds.). The Merck Veterinary Manual (9th ed.). John Wiley & Sons. ISBN 0-911910-50-6. http://www.merckvetmanual.com/mvm/index.jsp?cfile=htm/bc/190907.htm.  Retrieved on October 26, 2008.

v • d • e Cholinergics Receptor Ligands mAChR Agonists: 77-LH-28-1 • AC-42 • AC-260,584 • Aceclidine • Acetylcholine • AF30 • AF150(S) • AF267B • AFDX-384 • Alvameline • AQRA-741 • Arecoline • Bethanechol • Butyrylcholine • Carbachol • CDD-0034 • CDD-0078 • CDD-0097 • CDD-0098 • CDD-0102 • Cevimeline • cis-Dioxolane • Ethoxysebacylcholine • LY-593,039 • L-689,660 • LY-2,033,298 • McNA343 • Methacholine • Milameline • Muscarine • NGX-267 • Ocvimeline • Oxotremorine • PD-151,832 • Pilocarpine • RS86 • Sabcomeline • SDZ 210-086 • Sebacylcholine • Suberylcholine • Talsaclidine • Thiopilocarpine • Vedaclidine • VU-0029767 • VU-0090157 • VU-0152099 • VU-0152100 • VU-0238429 • WAY-132,983 • Xanomeline • YM-796 Antagonists: 3-Quinuclidinyl Benzilate • 4-DAMP • Atropine • Atropine Methonitrate • Benactyzine • Benzatropine (Benztropine) • Benzydamine • BIBN 99 • Biperiden • Bornaprine • CAR-226,086 • CAR-301,060 • CAR-302,196 • CAR-302,282 • CAR-302,368 • CAR-302,537 • CAR-302,668 • CS-27349 • Cyclobenzaprine • Cyclopentolate • Darifenacin • DAU-5884 • Dimethindene • Dexetimide • DIBD • Dicyclomine (Dicycloverine) • Ditran • EA-3167 • EA-3443 • EA-3580 • EA-3834 • Elemicin • Etanautine • Etybenzatropine (Ethylbenztropine) • Flavoxate • Himbacine • HL-031,120 • Ipratropium • J-104,129 • Hyoscyamine • Mamba Toxin 3 • Mamba Toxin 7 • Mazaticol • Mebeverine • Methoctramine • Metixene • Myristicin • N-Ethyl-3-Piperidyl Benzilate • N-Methyl-3-Piperidyl Benzilate • Orphenadrine • Otenzepad • Oxybutynin • PBID • PD-102,807 • Phenglutarimide • Phenyltoloxamine • Pirenzepine • Piroheptine • Procyclidine • Profenamine • RU-47,213 • SCH-57,790 • SCH-72,788 • SCH-217,443 • Scopolamine (Hyoscine) • Solifenacin • Telenzepine • Tiotropium • Tolterodine • Trihexyphenidyl • Tripitamine • Tropatepine • Tropicamide • WIN-2299 • Zamifenacin; Others: 1st Generation Antihistamines (Brompheniramine • Chlorpheniramine, Cyclizine, Cyproheptadine, Dimenhydrinate, Diphenhydramine, Doxylamine, Hydroxyzine, Meclizine, Mepyramine/Pyrilamine, Phenindamine, Pheniramine, Tripelennamine, Triprolidine, etc) • Tricyclic Antidepressants (Amitriptyline, Doxepin, Trimipramine, etc) • Tetracyclic Antidepressants (Amoxapine, Maprotiline, etc) • Typical Antipsychotics (Chlorpromazine, Thioridazine, etc) • Atypical Antipsychotics (Clozapine, Olanzapine, Quetiapine, etc) nAChR Agonists: 5-HIAA • A-84,543 • A-366,833 • A-582,941 • A-867,744 • ABT-202 • ABT-418 • ABT-560 • ABT-894 • Acetylcholine • Altinicline • Anabasine • AR-R17779 • Butyrylcholine • Carbachol • Cotinine • Cytisine • Decamethonium • Desformylflustrabromine • Dianicline • Dimethylphenylpiperazinium • Epibatidine • Epiboxidine • Ethoxysebacylcholine • EVP-4473 • EVP-6124 • Galantamine • GTS-21 • Ispronicline • Lobeline • MEM-63,908 (RG-3487) • Nicotine • NS-1738 • PHA-543,613 • PHA-709,829 • PNU-120,596 • PNU-282,987 • Pozanicline • Rivanicline • Sazetidine A • Sebacylcholine • SIB-1508Y • SIB-1553A • SSR-180,711 • Suberylcholine • TC-1698 • TC-1734 • TC-1827 • TC-2216 • TC-5214 • TC-5619 • TC-6683 • Tebanicline • Tropisetron • UB-165 • Varenicline • XY-4083 Antagonists: 18-Methoxycoronaridine • α-Bungarotoxin • α-Conotoxin • Alcuronium • Anatruxonium • Atracurium • Bupropion (Amfebutamone) • Chandonium • Chlorisondamine • Cisatracurium • Coclaurine • Coronaridine • Dacuronium • Decamethonium • Dextromethorphan • Dextropropoxyphene • Dextrorphan • Diadonium • DHβE • Dimethyltubocurarine (Metocurine) • Dipyrandium • Dizocilpine (MK-801) • Doxacurium • Duador • Esketamine • Fazadinium • Gallamine • Hexafluronium • Hexamethonium (Benzohexonium) • Ibogaine • Ketamine • Kynurenic Acid • Levacetylmethadol • Malouetine • Mecamylamine • Memantine • Methadone • Methorphan (Racemethorphan) • Methyllycaconitine • Metocurine • Mivacurium • Morphanol (Racemorphanol) • Neramexane • Pancuronium • Pempidine • Pentamine • Pentolinium • Phencyclidine • Pipecuronium • Radafaxine • Rapacuronium • Rocuronium • Surugatoxin • Suxamethonium (Succinylcholine) • Toxiferine • Trimethaphan • Tropeinium • Tubocurarine • Vecuronium Reuptake Inhibitors Plasmalemmal CHT Inhibitors Hemicholinium-3 (Hemicholine) Vesicular VAChT Inhibitors Vesamicol Enzyme Inhibitors Anabolism ChAT Inhibitors 1-(-Benzoylethyl)pyridinium • 2-(α-Naphthoyl)ethyltrimethylammonium • 3-Chloro-4-stillbazole • 4-(1-Naphthylvinyl)pyridine • Acetylseco Hemicholinium-3 • Acryloylcholine • AF64A • B115 • BETA • CM-54,903 • N,N-Dimethylaminoethylacrylate • N,N-Dimethylaminoethylchloroacetate Catabolism AChE Inhibitors Reversible: Carbamates: Aldicarb • Bendiocarb • Bufencarb • Carbaryl • Carbendazim • Carbetamide • Carbofuran • Chlorbufam • Chloropropham • Ethienocarb • Ethiofencarb • Fenobucarb • Fenoxycarb • Formetanate • Furadan • Ladostigil • Methiocarb • Methomyl • Miotine • Oxamyl • Phenmedipham • Pinmicarb • Pirimicarb • Propamocarb • Propham • Propoxur; Stigmines: Ganstigmine • Neostigmine • Phenserine • Physostigmine • Pyridostigmine • Rivastigmine; Others: Ambenonium • Donepezil • Edrophonium • Galantamine • Huperzine A (Huperzia Serrata) • Tacrine • Zanapezil Irreversible: Organophosphates: Acephate • Azinphos-Methyl • Bensulide • Cadusafos • Chlorethoxyfos • Chlorfenvinphos • Chlorpyrifos • Chlorpyrifos-Methyl • Coumaphos • Cyclosarin (GF) • Demeton • Demeton-S-Methyl • Diazinon • Dichlorvos • Dicrotophos • Diisopropyl Fluorophosphate (Guthion) • Diisopropylphosphate • Dimethoate • Dioxathion • Disulfoton • EA-3148 • Echothiophate • Ethion • Ethoprop • Fenamiphos • Fenitrothion • Fenthion • Fosthiazate • GV • Isofluorophate • Isoxathion • Malaoxon • Malathion • Methamidophos • Methidathion • Metrifonate • Mevinphos • Monocrotophos • Naled • Novichok Agent • Omethoate • Oxydemeton-Methyl • Paraoxon • Parathion • Parathion-Methyl • Phorate • Phosalone • Phosmet • Phostebupirim • Phoxim • Pirimiphos-Methyl • Sarin (GB) • Soman (GD) • Tabun (GA) • Temefos • Terbufos • Tetrachlorvinphos • Tribufos • Trichlorfon • VE • VG • VM • VR • VX; Others: Demecarium • Onchidal (Onchidella Binneyi) BChE Inhibitors Many of the acetylcholinesterase inhibitors listed above act as butyrylcholinesterase inhibitors. Others Precursors Choline (Lecithin) • Citicoline • Dimethylethanolamine • Glycerophosphocholine • Phosphatidylcholine • Phosphatidylethanolamine • Phosphorylcholine Cofactors Acetic Acid • Acetyl-L-Carnitine • Acetyl-Coenzyme A • Vitamin B5 (Pantothenic Acid, Pantethine, Pantetheine, Panthenol) Others Acetylcholine Releasing Agents: α-Latrotoxin • β-Bungarotoxin; Acetylcholine Release Inhibitors: Botulinum Toxin (Botox); Acetylcholinesterase Reactivators: Pralidoxime

v • d • e Histaminergics Receptor Ligands H1 Agonists: 2-Pyridylethylamine • Betahistine • Histamine • HTMT • UR-AK49 Antagonists: 1st Generation: 4-Methyldiphenhydramine • Alimemazine • Antazoline • Azatadine • Bamipine • Bepotastine • Bromazine • Brompheniramine • Buclizine • Carbinoxamine • Chlorcyclizine • Chloropyramine • Chlorothen • Chlorpheniramine • Chlorphenoxamine • Cinnarizine • Clemastine • Clobenzepam • Clocinizine • Cyclizine • Cyproheptadine • Dacemazine • Deptropine • Dexbrompheniramine • Dexchlorpheniramine • Dimenhydrinate • Dimetindene • Diphenhydramine • Diphenylpyraline • Doxylamine • Embramine • Etymemazine • Histapyrrodine • Hydroxyethylpromethazine • Hydroxyzine • Iproheptine • Isopromethazine • Isothipendyl • Meclizine • Mepyramine (Pyrilamine) • Mequitazine • Methafurylene • Methapyrilene • Methdilazine • Moxastine • Niaprazine • Orphenadrine • Oxatomide • Oxomemazine • Phenindamine • Pheniramine • Phenyltoloxamine • Pimethixene • Promethazine • Pyrrobutamine • Talastine • Thenalidine • Thenyldiamine • Thiazinamium • Thonzylamine • Tolpropamine • Tripelennamine • Triprolidine; 2nd Generation: Acrivastine • Astemizole • Azelastine • Cetirizine • Clemizole • Clobenztropine • Dimebon • Ebastine • Emedastine • Epinastine • Ketotifen • Levocabastine • Loratadine • Mebhydrolin • Mizolastine • Olopatadine • Rupatadine • Setastine • Terfenadine; 3rd Generation: Desloratadine • Fexofenadine • Levocetirizine; Miscellaneous: Tricyclic Antidepressants (Amitriptyline, Doxepin, Trimipramine, etc) • Tetracyclic Antidepressants (Mianserin, Mirtazapine, etc) • Serotonin Antagonists and Reuptake Inhibitors (Trazodone, Nefazodone) • Typical Antipsychotics (Chlorpromazine, Thioridazine, etc) • Atypical Antipsychotics (Clozapine, Olanzapine, Quetiapine, etc) H2 Agonists: Amthamine • Betazole • Dimaprit • Histamine • HTMT • Impromidine • UR-AK49 Antagonists: Cimetidine • Famotidine • Lafutidine • Metiamide • Niperotidine • Nizatidine • Ranitidine • Roxatidine H3 Agonists: α-Methylhistamine • Cipralisant • Histamine • Imetit • Immepip • Immethridine • Methimepip • Proxyfan Antagonists: A-349,821 • A-423,579 • ABT-239 • Betahistine • Burimamide • Ciproxifan • Clobenpropit • Conessine • GSK-189,254 • Impentamine • Iodophenpropit • JNJ-5,207,852 • MK-0249 • NNC-38-1,049 • SCH-79,687 • Thioperamide • Tiprolisant • VUF-5,681 H4 Agonists: 4-Methylhistamine • Histamine • VUF-8,430 Antagonists: JNJ-7,777,120 • Thioperamide • VUF-6,002 Reuptake Inhibitors Plasmalemmal ..... Vesicular VMAT Inhibitors Ibogaine • Reserpine • Tetrabenazine Enzyme Inhibitors Anabolism HDC Inhibitors α-FMH • Brocresine • Catechin • Cyanidanol-3 • McN-A-1293 • ME • Meciadanol • Naringenin • Thiazol-4-yimethoxyamine • Tritoqualine • Zy-15,029 Catabolism HNMT Inhibitors Amodiaquine • BW-301U • Diphenhydramine • Harmaline • Metoprine • Quinacrine • SKF-91,488 • Tacrine DAO Inhibitors 1,4-Diamino-2-butyne • Aminoguanidine Others Precursors L-Histidine Cofactors Vitamin B6 (Pyridoxine, Pyridoxamine, Pyridoxal → Pyridoxal Phosphate)

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; Piperazines: Eltoprazine • Flesinoxan • Flibanserin; Tryptamines: 5-CT • 5-MeO-DMT • 5-MT • DMT • Psilocin • Psilocybin; 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 • Noroxaflozane • Osemozotan • Oxaflozane • Piclozotan • PRX-00023 • Rauwolscine • Repinotan • RU-24969 • S-15535 • Sarizotan • SSR-181,507 • Sunepitron • U-92016A • Urapidil • Vilazodone • Xaliproden • Yohimbine Antagonists: Beta Blockers: Alprenolol • Cyanopindolol • Iodocyanopindolol • Oxprenolol • Pindobind • Pindolol • Propranolol; Piperazines: Etoperidone • Nefazodone • Trazodone • WAY-100,135 • WAY-100,635; Others: AV965 • BMY-7378 • Dotarizine • Flopropione • GR-46611 • Isamoltane • Lecozotan • Metitepine/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: Avitriptan • Eletriptan • Sumatriptan • Zolmitriptan; Tryptamines: 5-CT • 5-MT; Others: CGS-12066A • CP-93,129 • CP-94,253 • CP-135,807 • RU-24969 Antagonists: Lysergamides: Metergoline; Others: AR-A000002 • GR-127,935 • Isamoltane • Metitepine/Methiothepin • SB-216,641 • SB-224,289 • SB-236,057 • Yohimbine 5-HT1D Agonists: Lysergamides: Dihydroergotamine • Methysergide; Triptans: Almotriptan • Avitriptan • 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; Others: Alniditan BRL-15572 • GR-127,935 • Ketanserin • LY-310,762 • LY-367,642 • LY-456,219 • LY-456,220 • Metitepine/Methiothepin • Ritanserin • Yohimbine • Ziprasidone 5-HT1E Agonists: Lysergamides: Methysergide; Triptans: Eletriptan; Tryptamines: Tryptamine Antagonists: Metitepine/Methiothepin 5-HT1F Agonists: Triptans: Eletriptan • Naratriptan • Sumatriptan; Tryptamines: 5-MT; Others: LY-334,370 Antagonists: Metitepine/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• Medifoxamine • Noroxaflozane • Oxaflozane • 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 • Metitepine/Methiothepin • Nantenine • Pimavanserin • Pizotifen • Rauwolscine • 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 • Metitepine/Methiothepin • 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• Medifoxamine • MK-212 • Noroxaflozane • ORG-37,684 • Oxaflozane • 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 • Metitepine/Methiothepin • 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 • Metitepine/Methiothepin • Ritanserin • SB-699,551 5-HT5B* Agonists: Lysergamides: Ergotamine • LSD Antagonists: Metitepine/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 • Metitepine/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 • Metitepine/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; 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: 5-Iodoaminoindane (5-IAI) • Ethyltrifluoromethylaminoindane (ETAI) • Methylenedioxyaminoindane (MDAI) • Methylenedioxymethylaminoindane (MDMAI) • Methoxymethylaminoindane (MMAI) • Trifluoromethylaminoindane (TAI); Aminotetralins: 6-Chloroaminotetralin (6-CAT) • 8-Hydroxydipropylaminotetralin (8-OH-DPAT) • Methylenedioxyaminotetralin (MDAT); Oxazolines: 4-Methylaminorex (4-MAR, 4-MAX) • Aminorex • Clominorex • Fluminorex; Phenethylamines (also Amphetamines, Cathinones, Phentermines, etc): 4-Methylthioamphetamine (4-MTA) • Benzodioxolylbutanamine (BDB) • Benzodioxolylhydroxybutanamine (BOH) • Brephedrone • Butylone • Chlorphentermine • Diethylcathinone (Diethylpropion, Amfepramone) • Dimethoxyamphetamine (DMA) • Dimethoxymethamphetamine (DMMA) • Dimethylcathinone (Dimethylpropion, Metamfepramone) • Ethylbenzodioxolylbutanamine (EBDB) • Ethylone • Fenfluramine (Dexfenfluramine) • Flephedrone • 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 • 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: α-Ethyltryptamine (αET; Etryptamine) • α-Methyltryptamine (αMT; Metryptamine); Others: 5-Aminopropyldihydrobenzofuran (5-APDB; 5-Desoxy-MDA) • Indanylaminopropane (IAP) • Naphthylaminopropane (NAP) • Tramadol Enzyme inhibitors Anabolism TPH inhibitors AGN-2979 • Fenclonine AAAD inhibitors Benserazide • Carbidopa Catabolism MAO Inhibitors Nonselective: Benmoxin • Furazolidone • Hydralazine • Iproclozide • Iproniazid • Isocarboxazid • Isoniazid • Linezolid • Mebanazine • Metfendrazine • Nialamide • Octamoxin • Phenelzine • Pheniprazine • Phenoxypropazine • Pivalylbenzhydrazine • Procarbazine • Safrazine • Tranylcypromine; MAO-A Selective: Befloxatone • Brofaromine • Cimoxatone • Clorgiline • Harmala alkaloids (Harmine, Harmaline, Tetrahydroharmine, Harman, Norharman, etc) • Metralindole • 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

v • d • e Tricyclics Antidepressants Amineptine • Amitriptyline • Amitriptylinoxide • Amoxapine • Azepindole • Butriptyline • Cianopramine • Clomipramine • Cyanodothiepin • Demexiptiline • Desipramine • Dibenzepine • Dimetacrine • Dosulepin/Dothiepin • Doxepin • Fluotracen • Hepzidine • Homopipramol • Imipramine • Imipraminoxide • Intriptyline • Iprindole • Ketipramine • Litracen • Lofepramine • Lortalamine • Losindole • Loxapine • Maprotiline • Mariptiline • Melitracen • Metapramine • Mezepine • Mianserin • Mirtazapine • Naranol • Nitroxazepine • Nortriptyline • Noxiptiline • Octriptyline • Opipramol • Oxaprotiline • Propizepine • Protriptyline • Quinupramine • Setiptiline/Teciptiline • Tianeptine • Tienopramine • Trimipramine Antihistamines Alimemazine • Azatadine • Clobenzepam • Cyproheptadine • Dacemazine • Deptropine • Desloratadine • Dimebolin • Epinastine • Etymemazine • Hydroxyethylpromethazine • Isopromethazine • Isothipendyl • Ketotifen • Loratadine • Mebhydrolin • Mequitazine • Methdilazine • Olopatadine • Oxomemazine • Phenindamine • Pimethixene • Promethazine • Rupatadine • Thiazinamium Antipsychotics Amoxapine • Asenapine • Carpipramine • Chlorpromazine • Chlorprothixene • Clocapramine • Clomacran • Clotiapine • Clozapine • Flupentixol • Fluphenazine • Homopipramol • Levomepromazine/Methotrimeprazine • Loxapine • Maroxepin • Mesoridazine • Metitepine/Methiothepin • Mosapramine • Naranol • Olanzapine • Perazine • Perphenazine • Periciazine • Prochlorperazine • Promazine • Quetiapine • Sulforidazine • Thioridazine • Thiothixene • Trifluoperazine • Triflupromazine • Zotepine • Zuclopenthixol Others Carvedilol • Cyclobenzaprine • Pizotifen

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