sumatriptan

[Alteration of SU(LFON)AM(IDE) + triptan (shortening and alteration of TRYPTAMINE).]

Brand names: Imitrex®

Chemical formula:

Drug Forms:
• Sumatriptan Succinate Oral tablet (below)
• Sumatriptan tablets
• Sumatriptan nasal spray
• Sumatriptan Nasal spray, solution
• Sumatriptan Succinate Solution for injection

Español:
• Succinato de Sumatriptán, Tableta oral
• Tabletas de sumatriptán
• Aerosol nasal de sumatriptán
• Sumatriptán, Solución para aerosol nasal
• Succinato de Sumatriptán, Solución para inyección

Sumatriptan Succinate Oral tablet

What is this medicine?

SUMATRIPTAN (soo ma TRIP tan) is used to treat migraines with or without aura. An aura is a strange feeling or visual disturbance that warns you of an attack. It is not used to prevent migraines.
 
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:
•bowel disease or colitis
•diabetes
•family history of heart disease
•fast or irregular heart beat
•heart or blood vessel disease, angina (chest pain), or previous heart attack
•high blood pressure
•high cholesterol
•history of stroke, transient ischemic attacks (TIAs or mini-strokes), or intracranial bleeding
•kidney or liver disease
•overweight
•poor circulation
•postmenopausal or surgical removal of uterus and ovaries
•Raynaud's disease
•seizure disorder
•an unusual or allergic reaction to sumatriptan, 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. This medicine is taken at the first symptoms of a migraine. It is not for everyday use. If your migraine headache returns after one dose, you can take another dose as directed. You must leave at least 2 hours between doses, and do not take more than 100 mg as a single dose. Do not take more than 200 mg total in any 24 hour period. If there is no improvement at all after the first dose, do not take a second dose without talking to your doctor or health care professional. Do not take your medicine more often than directed.

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 medicines:
•amphetamine or cocaine
•dihydroergotamine, ergotamine, ergoloid mesylates, methysergide, or ergot-type medication - do not take within 24 hours of taking sumatriptan
•feverfew
•MAOIs like Carbex, Eldepryl, Marplan, Nardil, and Parnate - do not take sumatriptan within 2 weeks of stopping MAOI therapy
•other migraine medicines like almotriptan, eletriptan, naratriptan, rizatriptan, zolmitriptan - do not take within 24 hours of taking sumatriptan
•tryptophan

This medicine may also interact with the following medications:
•lithium
•medicines for mental depression, anxiety or mood problems
•medicines for weight loss such as dexfenfluramine, dextroamphetamine, fenfluramine, or sibutramine
•St. John's wort

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?

Only take this medicine for a migraine headache. Take it if you get warning symptoms or at the start of a migraine attack. It is not for regular use to prevent migraine attacks.

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. To reduce dizzy or fainting spells, do not sit or stand up quickly, especially if you are an older patient. Alcohol can increase drowsiness, dizziness and flushing. Avoid alcoholic drinks.

Smoking cigarettes may increase the risk of heart-related side effects from using this medicine.

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
•changes in vision
•chest or throat pain, tightness
•fast, slow, or irregular heart beat
•hallucinations
•increased or decreased blood pressure
•problems with balance, talking, walking
•seizures
•severe stomach pain and cramping, bloody diarrhea
•tingling, pain, or numbness in the face, hands or feet

Side effects that usually do not require medical attention (report to your doctor or health care professional if they continue or are bothersome):
•drowsiness
•feeling warm, flushing, or redness of the face
•muscle pain or cramps
•nausea, vomiting, diarrhea or stomach upset
•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 2 and 30 degrees C (36 and 86 degrees F). 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.

Sumatriptan

Systematic (IUPAC) name
1-[3-(2-dimethylaminoethyl)-1H-indol-5-yl]- N-methyl-methanesulfonamide
Identifiers
CAS number	103628-46-2
ATC code	N02CC01
PubChem	5358
DrugBank	APRD00379
ChemSpider	5165
Chemical data
Formula	C14H21N3O2S
Mol. mass	295.402 g/mol
SMILES	eMolecules & PubChem
Pharmacokinetic data
Bioavailability	15% (oral)/ 96% (s.c)
Protein binding	14%-21%
Metabolism	MAO
Half life	2.5 hours
Excretion	60% urine; 40% feces
Therapeutic considerations
Licence data	US FDA:link
Pregnancy cat.	C
Legal status
Routes	tablet, subcutaneous injection, nasal spray
Y(what is this?)  (verify)

Sumatriptan (trade names Imitrex, Imigran, Imigran recovery) is a triptan drug including a sulfonamide group for the treatment of migraine headaches. It is marketed and manufactured by GlaxoSmithKline.

Contents 1 Approval and availability 2 Mode of action 3 Pharmacokinetics 4 Side Effects 5 Generics 6 References

Approval and availability

Sumatriptan was the first triptan available (in 1991), and, in the United States and most developed countries, is available only by medical prescription. Several dosage forms for sumatriptan have been approved, including tablets, solution for injection, and nasal inhalers.

In the United Kingdom, sumatriptan is available over the counter, under the name Imigran Recovery. It is sold in packs of two 50 mg tablets for approximately £7.99 (equivalent to about $12 US). In the U.S. the cost in 2009 is about $150. Larger pack sizes, a nasal spray preparation, and a liquid preparation for injection are also available by prescription. Patent Protection in the UK and Europe expired on 16 May 2006, under UK Patent GB2162522 (extended by supplementary protection certificate SPC/GB93/07). In the United States, Glaxo Smith Kline was able to extend their US patent considerably beyond this date through patent litigation. However, a generic injectable version of sumatriptan should be allowed to come to market in August 2008, due to the settlement of a lawsuit by a maker of the generic drug (Dr Reddy's Labs Ltd).^{[citation needed]}

On April 15, 2008, the US FDA approved a combination of sumatriptan and naproxen, an NSAID, which is marketed in the USA under the trade name Treximet.^[1]. This combination has shown a benefit over either medicine used separately.^[2]

In July 2009, the United States FDA approved Sumavel DosePro(R) (Zogenix Inc., Emeryville and San Diego, California, USA). This is a unique pre-filled, single-use delivery system for 6 mg subcutaneous sumatriptan. It has no needle, and uses gas pressure as a power source. The drug is delivered in less than 100 msec. Sumavel DosePro is about the size of a white board marker or fat felt-tipped pen, and is expected to be available for prescription in the USA in early 2010; a corresponding product application has been filed in Europe.

Mode of action

Sumatriptan is structurally similar to serotonin (5HT), and is a 5-HT (types 5-HT_1D and 5-HT_1B^[3]) agonist. The specific receptor subtypes it activates are present in the cerebral arteries. Dilation of these arteries is thought to be a major cause of headache pain, and activating these receptors causes vasoconstriction.

Pharmacokinetics

Sumatriptan is administered in several forms; tablets, subcutaneous injection, and nasal spray. Oral administration (as succinate) suffers from poor bioavailability, partly due to presystemic metabolism — some of it gets broken down in the stomach and bloodstream before it reaches the target arteries. A new rapid-release tablet formulation has the same bioavailability, but the maximum concentration is achieved on average 10–15 minutes earlier. When injected, sumatriptan is faster acting (usually within 10 minutes), but the effect lasts for a shorter time. Sumatriptan is metabolised primarily by monoamine oxidase A into an indole acetic acid analogue, part of which is further conjugated with glucuronic acid. These metabolites are excreted in the urine and bile. Even so, about 50% of all systemically available sumatriptan is excreted unchanged in the urine.

There is no simple, direct relationship between sumatriptan concentration (pharmacokinetics) per se in the blood and its anti-migraine effect (pharmacodynamics). This paradox has, to some extent been resolved by comparing the rates of absorption of the various sumatriptan formulations, rather than the absolute amounts of drug that they deliver.

Side Effects

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Large doses of sumatriptan (200 mg/day) can cause sulfhemoglobinemia, a rare condition in which the blood changes from red to greenish-black, due to the integration of sulfur into the hemoglobin molecule^[4]. If sumatriptan is discontinued, the condition reverses within a few weeks.

Serious cardiac events, including some that have been fatal, have occurred following the use of Imitrex Injection or Tablets. Events reported have included coronary artery vasospasm, transient myocardial ischemia, myocardial infarction, ventricular tachycardia, and ventricular fibrillation.

In the below table, "Common" is reported in at least 1/100 patients, "Less common" in 1/100 to 1/1000 patients and "Rare" in less than 1/1000 patients^[5].

Type	Common	Less Common	Rare
Atypical Sensations	Burning sensations and numbness Chest symptoms (not due to ischemia)	"tight feeling around the head"	Dysesthesia
Cardiovascular	Palpitations, syncope, as well as changes in blood pressure.	Arrhythmia, changes in ECG, hypertension, hypotension, pallor, pulsating sensations, and tachycardia.	Angina, atherosclerosis, bradycardia, cerebral ischemia, cerebrovascular lesion, heart block, peripheral cyanosis, thrombosis, transient myocardial ischemia, and vasodilation.
Ear, Nose, and Throat	Sinusitis, tinnitus; allergic rhinitis; upper respiratory inflammation; ear, nose, and throat hemorrhage; external otitis; hearing loss; nasal inflammation; and sensitivity to noise.	Hearing disturbances and otalgia.	Feeling of fullness in the ear(s).
Endocrine and Metabolic	Thirst.	Elevated thyrotropin stimulating hormone (TSH) levels; galactorrhea; hyperglycemia; hypoglycemia; hypothyroidism; polydipsia; weight gain; weight loss; endocrine cysts, lumps, and masses; and fluid disturbances.
Eye	Sclera, mydriasis, blindness and low vision, visual disturbances, eye edema and swelling, eye irritation and itching, accommodation disorders, external ocular muscle disorders, eye hemorrhage, eye pain, and keratitis and conjunctivitis.
Gastrointestinal	Diarrhea and gastric symptoms.	Constipation, dysphagia, and gastroesophageal reflux.	Gastrointestinal bleeding, hematemesis, melena, peptic ulcer, gastrointestinal pain, dyspeptic symptoms, dental pain, feelings of gastrointestinal pressure, gastritis, gastroenteritis, hypersalivation, abdominal distention, oral itching and irritation, salivary gland swelling, and swallowing disorders.
Hematological Disorders	Anemia
Musculoskeletal	Myalgia	Muscle cramps.	Tetany; muscle atrophy, weakness, and tiredness; arthralgia and articular rheumatitis; acquired musculoskeletal deformity; muscle stiffness, tightness, and rigidity; and musculoskeletal inflammation.
Neurological	Phonophobia and photophobia.	Confusion, depression, difficulty concentrating, disturbance of smell, dysarthria, euphoria, facial pain, heat sensitivity, incoordination, lacrimation, monoplegia, sleep disturbance, shivering, syncope, and tremor.	Aggressiveness, apathy, bradylogia, cluster headache, convulsions, decreased appetite, drug abuse, dystonic reaction, facial paralysis, hallucinations, hunger, hyperesthesia, hysteria, increased alertness, memory disturbance, neuralgia, paralysis, personality change, phobia, radiculopathy, rigidity, suicide, twitching, agitation, anxiety, depressive disorders, detachment, motor dysfunction, neurotic disorders, psychomotor disorders, taste disturbances, and raised intracranial pressure.
Respiratory	Dyspnea.	Asthma.	Hiccups, breathing disorders, cough, and bronchitis.
Skin	Sweating.	Erythema, pruritus, rash, and skin tenderness.	Dry/scaly skin, tightness of skin, wrinkling of skin, eczema, seborrheic dermatitis, and skin nodules.
Breasts	Tenderness.	Nipple discharge, swelling, cysts, lumps, masses and primary malignant breast neoplasm.
Urogenital	Dysmenorrhea, increased urination, and intermenstrual bleeding.	Abortion and hematuria, urinary frequency, bladder inflammation, micturition disorders, urethritis, urinary infections, menstruation symptoms, abnormal menstrual cycle, inflammation of fallopian tubes, and menstrual cycle symptoms.
Miscellaneous	Hypersensitivity.	Fever, fluid retention, and overdose.	Edema, hematoma, lymphadenopathy, speech disturbance, voice disturbances, contusions.

Generics

On November 6, 2008, Par Pharmaceutical announced that it would begin shipping generic versions of Imitrex Injection (sumatriptan succinate injection) 4 mg and 6 mg starter kits and 4 mg and 6 mg pre-filled syringe cartridges to the trade immediately. In addition, Par anticipates launching the 6 mg vials early in 2009. ^[6]

Mylan Laboratories Inc. has received FDA approval for its generic version of Imitrex tablets in 25, 50, and 100 milligram doses. The drug will soon be available, or is already available, in European markets since Glaxo's patent protections have expired in those jurisdictions. However, sales of the generic drug are still restricted in the U.S. since Glaxo won an extension on their patent until 2009. A generic version of the drug in tablet form became available December 2008 in the United States and is distributed by Ranbaxy.

See also Sumavel DosePro (above).

References

1. ^ GSK press release - Treximet (sumatriptan and naproxen sodium) tablets approved by FDA for acute treatment of migraine
2. ^ Brandes JL, Kudrow D, Stark SR, et al. (April 2007). "Sumatriptan-naproxen for acute treatment of migraine: a randomized trial". JAMA 297 (13): 1443–54. doi:10.1001/jama.297.13.1443. PMID 17405970. http://jama.ama-assn.org/cgi/pmidlookup?view=long&pmid=17405970. 
3. ^ Razzaque Z, Heald MA, Pickard JD, et al. (1999). "Vasoconstriction in human isolated middle meningeal arteries: determining the contribution of 5-HT1B- and 5-HT1F-receptor activation". Br J Clin Pharmacol 47 (1): 75–82. doi:10.1046/j.1365-2125.1999.00851.x. PMID 10073743. 
4. ^ BBC NEWS | Health | Patient bleeds dark green blood
5. ^ Imitrex Tablets
6. ^ "PAR PHARMACEUTICAL BEGINS SHIPMENT OF SUMATRIPTAN INJECTION". Par Pharmaceutical. 2008-11-06. http://www.parpharm.com/media/NR_20081106.jsp. Retrieved 2008-11-25. 

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 • 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: 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) 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

v • d • e Antimigraine preparations (N02C) Serotonin modulators (analgesic/abortive) Ergot alkaloids Dihydroergotamine • Ergotamine • Methysergide • Lisuride 5-HT1 agonists Triptans (Almotriptan, Eletriptan, Frovatriptan, Naratriptan, Rizatriptan, Sumatriptan, Zolmitriptan) Alniditan Other Dotarizine Corticosteroid derivatives Flumedroxone Prevention of migraines Propanolol • Verapamil Other antimigraine preparations adrenergic agonists: Clonidine other: Pizotifen • Topiramate • Amidrine • Iprazochrome • Dimetotiazine • Oxetorone • Lomerizine • Telcagepant

v • d • e Tryptamines 2-Methyl-5-HT • 4-Acetoxy-DET • 4-Acetoxy-DIPT • 4-Acetoxy-DMT • 4-HO-α-MT • 4-HO-DIPT • 5-Bromo-DMT • 5-Carboxamidotryptamine • 5-Fluoro-α-MT • 5-HO-α-MT • 5-HTP • 5-Methyl-DMT • 5-Methoxytryptamine • 5-MeO-α-ET  • 5-MeO-α-MT • 5-MeO-DALT • 5-MeO-DET • 5-MeO-DIPT • 5-MeO-DMT • 5-MeO-DPT • 5-MeO-MIPT • 5,7-Dihydroxytryptamine • α-ET • α-MT • Aeruginascin • AL-37350A • BW-723C86 • Baeocystin • Bufotenidine • Bufotenin • Desformylflustrabromine • DET • DiPT • DMT • DPT • Ethocybin • EiPT • EMDT • Ethocin • FGIN-127 • FGIN-143 • Ibogaine • Iprocin • MET • MiPT • Miprocin • Melatonin • MS-245 • NMT • Norbaeocystin • Normelatonin • PiPT • Psilocin • Psilocybin • Rizatriptan • Serotonin • Sumatriptan • Tryptamine • Tryptophan • Yohimbine • Yuremamine

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