thioridazine

[THIO- + (PIPE)RID(INE) + AZINE.]

Brand names: Mellaril®Mellaril-S®

Chemical formula:

Drug Forms:
• Thioridazine oral concentrate or suspension (below)
• Thioridazine Hydrochloride Oral solution
• Thioridazine Hydrochloride Oral tablet
• Thioridazine Oral suspension

Español:
• Concentrado o suspensión oral de tioridazina
• Clorhidrato de tioridazina, Solución oral
• Clorhidrato de tioridazina, Tableta oral
• Tioridazina, Suspensión oral

Thioridazine oral concentrate or suspension

What is thioridazine oral concentrate or suspension?

THIORIDAZINE (Mellaril®, Mellaril-S®) helps to treat disordered thoughts and some other emotional, nervous, and mental problems. It also treats behavioral problems in children. Generic thioridazine oral concentrate is available, but not generic oral suspension.

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

They need to know if you have any of these conditions:
• blood disorders or disease
• difficulty passing urine
• glaucoma
• head injury
• heart or liver disease
• low blood level of calcium
• Parkinson's disease
• prostate trouble
• Reye's syndrome
• seizures (convulsions)
• stomach problems or peptic ulcer
• an unusual or allergic reaction to thioridazine, other medicines foods, dyes, or preservatives
• pregnant or trying to get pregnant
• breast-feeding

How should I take this medicine?

Take thioridazine oral concentrate or suspension by mouth. Follow the directions on the prescription label. Shake well before using. Use a specially marked spoon or dropper to measure your medicine. Ask your pharmacist if you do not have one; household spoons are not always accurate. Mix the oral concentrate with half a glass (4 fluid ounces) of distilled water, acidified tap water, orange or grapefruit juice. Do not mix with any drink containing caffeine (coffee, cola), tannins (tea), or pectinates (apple juice). Take your doses at regular intervals. Do not take your medicine more often than directed.

Contact your pediatrician or health care professional regarding the use of this medicine in children. Special care may be needed.

Elderly patients over age 65 years may have a stronger reaction to this medicine and need smaller doses.

What drug(s) may interact with thioridazine?

• alcohol
• antacids
• some antibiotics
• antidiarrheal medications
• atropine
• bromocriptine
• cimetidine
• cisapride
• dextroamphetamine or amphetamine
• doxercalciferol
• dronabinol or marijuana
• haloperidol or droperidol
• levodopa
• lithium
• medicines for an over-active thyroid gland
• medicines for colds and flu
• medicines for hay fever and other allergies
• medicines for mental depression
• medicines for movement abnormalities as in Parkinson's disease
• medicines to prevent or treat malaria
• medications for treating seizures (convulsions)
• medicines for pain or for use as muscle relaxants, including tramadol
• medicines to treat urine or bladder incontinence
• metoclopramide
• pimozide
• probucol
• some medications for high blood pressure or heart problems
• some weight loss medications

Tell your prescriber or health care professional about all other medicines you are taking, including non-prescription medicines, nutritional supplements, or herbal products. Also tell your prescriber or health care professional if you are a frequent user of drinks with caffeine or alcohol, if you smoke, or if you use illegal drugs. These may affect the way your medicine works. Check with your health care professional before stopping or starting any of your medicines.

What should I watch for while taking thioridazine?

Visit your prescriber or health care professional for regular checks on your progress. Do not stop taking thioridazine suddenly; this can cause nausea, vomiting, and dizziness. Ask your prescriber or health care professional for advice if you are to stop taking this medicine.

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 thioridazine 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 can increase possible dizziness or drowsiness. Avoid alcoholic drinks.

Do not spill any thioridazine solution on the skin, it can cause skin irritation or dermatitis.

Thioridazine can reduce the response of your body to heat or cold. Try not to get overheated. Avoid temperature extremes, such as saunas, hot tubs, or very hot or cold baths or showers. Dress warmly in cold weather.

Thioridazine can make your skin more sensitive to sun or ultraviolet light. Keep out of the sun, or wear protective clothing outdoors and use a sunscreen (at least SPF 15). Do not use sun lamps or sun tanning beds or booths. Wear sunglasses to protect your eyes.

Thioridazine may make your mouth dry, chewing sugarless gum or sucking hard candy and drinking plenty of water will help.

Do not treat yourself for coughs, colds, sore throat, indigestion, diarrhea, or allergies. Ask your prescriber or health care professional for advice.

If you are going to have surgery or will need a procedure that uses contrast agents, tell your prescriber or health care professional that you are taking this medicine.

What side effects may I notice from taking thioridazine?

Side effects that you should report to your prescriber or health care professional as soon as possible:
• blurred vision
• breast enlargement in men or women
• breast milk in women who are not breast-feeding
• chest pain, fast or irregular heartbeat
• confusion, restlessness
• dark yellow or brown urine
• difficulty breathing or swallowing
• dizziness or fainting spells
• drooling, shaking, movement difficulty (shuffling walk) or rigidity
• fever, chills, sore throat
• hot, dry skin, unable to sweat
• involuntary or uncontrollable movements of the eyes, mouth, head, arms, and legs
• menstrual changes
• puffing cheeks, smacking lips, or worm-like movements of the tongue
• seizures (convulsions)
• slurred speech
• stomach area pain
• sweating
• unusual weakness or tiredness
• unusual bleeding or bruising
• yellowing of skin or eyes

Side effects that usually do not require medical attention (report to your prescriber or health care professional if they continue or are bothersome):
• constipation
• difficulty passing urine
• difficulty sleeping, agitation or restlessness
• drowsiness
• dry mouth
• headache
• increased sensitivity to the sun or ultraviolet light
• sexual difficulties (impotence in men; increased sexual desire in women)
• skin rash, or itching
• stuffy nose
• weight gain

Where can I keep my medicine?

Keep out of the reach of children in a container that small children cannot open.

Store the oral concentrate at room temperature below 30 degrees C (86 degrees F); do not freeze. protect from light. Dilute immediately before use, and do not store diluted solution.
Store the oral suspension at room temperature below 25 degrees C (77 degrees F); do not freeze. Protect from light. 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 phenothiazine tranquilizer used in the treatment of stereotypic and aggressive behavior in dogs.

Thioridazine

Systematic (IUPAC) name
10-{2-[(RS)-1-Methylpiperidin-2-yl]ethyl}- 2-methylsulfanyl-phenothiazine
Identifiers
CAS number	50-52-2
ATC code	N05AC02
PubChem	5452
DrugBank	APRD00596
Chemical data
Formula	C21H26N2S2
Mol. mass	370.577
Pharmacokinetic data
Bioavailability	incomplete
Metabolism	hepatic
Half life	7–13 hours (up to 20 hours)
Excretion	feces
Therapeutic considerations
Pregnancy cat.	Only if clearly needed
Legal status	RX-only-medication, non-narcotic
Routes	oral (tablets, concentration, sometimes syrup)
Y(what is this?)  (verify)

Thioridazine is a piperidine antipsychotic drug belonging to the phenothiazine drug group and was previously widely used in the treatment of schizophrenia and psychosis. It is available from various companies under the names Mellaril, Novoridazine, and Thioril. Due to concerns about cardiotoxicity and retinopathy at high doses this drug is not commonly prescribed, reserved for patients who have failed to respond to, or have contraindications for, more widely used antipsychotics. A serious side effect is the potentially fatal neuroleptic malignant syndrome. It exerts its actions through a central adrenergic-blocking, a dopamine-blocking and minor anticholinergic activity.

In older references, it is sometimes described as atypical,^[1] but more recently it is usually described as typical,^[2] with the term "atypical" usually reserved for agents showing D4 selectivity or serotonin antagonism.

Contents 1 Indications 2 Metabolism 3 Side effects 4 Discontinuation 5 History 6 References 7 External links

Indications

Previous additional indications were agitated depression, tension and anxiety linked to alcohol withdrawal and dysphoria of epileptic patients. It was even indicated in Europe for the treatment of psychosis in children and adolescents as Melleretten (10 mg to 60 mg daily).

It was also given off-label for the treatment of insomnia and for alleviation of opiate withdrawal.^{[citation needed]}

Thioridazine is known to kill multidrug-resistant mycobacterium tuberculosis and MRSA at clinical concentrations.^{[3][citation needed]}

Metabolism

Thioridazine is a racemic compound with two enantiomers, both of which are metabolized, according to Eap et al., by CYP2D6 into (S)- and (R)-thioridazine 2-sulfoxide, better known as mesoridazine,^[4] and into (S)- and (R)-thioridazine-5-sulfoxide.^[5] Mesoridazine is in turn metabolized into sulforidazine.^[6] Thioridazine is an inhibitor of CYP1A2 and CYP3A2^[7]

Side effects

For further information see: Phenothiazine

The most commonly complained about side effect is akathisia which is the main reason for low patient compliance

Tardive dyskinesia characterized by involuntary movements of the lips, mouth, and tongue can be long lasting or irreversible, tremor of the mouth and lips without tongue involvement constitutes Rabbit syndrome. Neuroleptic malignant syndrome is potentially fatal.

Central nervous system side-effects occur. These are mainly drowsiness, dizziness, fatigue, and vertigo. Early and late extrapyramidal side-effects are seen only infrequently (less than 1% altogether). There is no clear dose-effect relationship, as with higher doses anticholinergic effects of thioridazine become more prominent.

Thioridazine causes also an unusual high incidence of impotence and anorgasmia due to a strong alpha-blocking activity. Painful ejaculation or no ejaculation at all is also sometimes seen.^{[citation needed]}

Autonomous side-effects (dry mouth, urination-difficulties, obstipation, induction of glaucoma, postural hypotension, and sinus tachycardia) occur obviously less often than with most other mildly potent antipsychotics.

Thioridazine is no longer recommended as first-line treatment due its side-effect of prolonging the QT interval on the EKG. Thioridazine-5-sulfoxide is responsible for the ventricular tachycardia, torsades de pointes according to Heath, Svensson and Martensson.^[8]

Also, the serious and sometimes fatal blood damage agranulocytosis is seen more frequently (approximately 1/500 to 1/1,000 patients) with thioridazine than with other typical phenothiazines (1/2,000 to 1/10,000 patients).

Thioridazine if given over a prolonged time and in high doses can be stored in the ocula and the retina of the eyes and in the heart muscle. Clinical consequences (disturbed or blurred vision) are rare although chromatopsia has been reported. ^{[9][citation needed]}

Discontinuation

It is advisable to withdraw thioridazine gradually and not abruptly to avoid unpleasant withdrawal symptoms (agitation, insomnia, anxiety). Another neuroleptic may be introduced to the therapeutic regime step by step (overlapping), if needed. If sudden withdrawal of thioridazine is necessary, withdrawal symptoms can also be alleviated with the benzodiazepines lorazepam (Ativan) 1 mg—2 mg, alprazolam (Xanax) 0,5 mg prn or clonazepam (Klonopin, Rivotril) 0,5 mg to 2 mg prn (as needed)or Diazepam (Valium)5 - 10mg prn for up to 2 weeks (not longer to avoid addiction).^{[citation needed]}

History

The manufacturer Novartis/Sandoz/Wander of the brands of thioridazine, Mellaril in the USA and Canada and Melleril in Europe, discontinued the drug worldwide in June 2005.

The usual dosage was 50 mg per day for mild cases to 600–800 mg per day for severely disturbed patients.

Thioridazine may still be available from other manufacturers as a generic drug with the precaution that it is used only in psychotic patients refractory to other forms of drug treatment. ECG-monitoring and frequent white blood cell counts are required before initiating therapy and in close intervals afterwards.

A multi-year UK study by the Alzheimer's Research Trust suggested that this and other neuroleptic anti-psychotic drugs commonly given to Alzheimer's patients with mild behavioural problems often make their condition worse.^{[citation needed][10]} The study concluded that

“

For most patients with AD, withdrawal of neuroleptics had no overall detrimental effect on functional and cognitive status and by some measures improved functional and cognitive status. Neuroleptics may have some value in the maintenance treatment of more severe neuropsychiatric symptoms, but this possibility must be weighed against the unwanted effects of therapy. The current study helps to inform a clinical management strategy for current practice, but the considerable risks of maintenance therapy highlight the urgency of further work to find, develop, and implement safer and more effective treatment approaches for neuropsychiatric symptoms in people with AD.

”

^[11]

This section requires expansion.

References

1. ^ Robertson A, MacDonald C (July 1984). "Atypical neuroleptics clozapine and thioridazine enhance amphetamine-induced stereotypy". Pharmacol. Biochem. Behav. 21 (1): 97–101. doi:10.1016/0091-3057(84)90137-0. PMID 6540455. 
2. ^ Ichikawa J, Dai J, O'Laughlin IA, Fowler WL, Meltzer HY (March 2002). "Atypical, but not typical, antipsychotic drugs increase cortical acetylcholine release without an effect in the nucleus accumbens or striatum". Neuropsychopharmacology 26 (3): 325–39. doi:10.1016/S0893-133X(01)00312-8. PMID 11850147. 
3. ^ Amaral L, Viveiros M, Molnar J. "Antimicrobial activity of phenothiazines."
4. ^ PubChem Substance Summary: Mesoridazine National Center for Biotechnology Information.
5. ^ Eap CB, Guentert TW, Schaublin-Loidl M, Stabl M, Koeb L, Powell K, Baumann P. "Plasma levels of the enantiomers of thioridazine, thioridazine 2-sulfoxide, thioridazine 2-sulfone, and thioridazine 5-sulfoxide in poor and extensive metabolizers of dextromethorphan and mephenytoin." Clinical Pharmacology & Therapy. 1996 Mar;59(3):322–31. PMID 8653995
6. ^ PubChem Substance Summary: Sulforidazine National Center for Biotechnology Information.
7. ^ Daniel WA, Syrek M, Rylko Z, Kot M. "Effects of phenothiazine neuroleptics on the rate of caffeine demethylation and hydroxylation in the rat liver." Polish Journal of Pharmacology. 2001 Nov-Dec;53(6):615–21. PMID 11985335 Fulltext (PDF)
8. ^ Heath A, Svensson C, Martensson E. "Thioridazine toxicity--an experimental cardiovascular study of thioridazine and its major metabolites in overdose." Veterinary and Human Toxicology. 1985 Apr;27(2):100–5. PMID 3992882
9. ^ AJ Giannini, PJ Mahar. An unusual ocular complication of thioridazine. International Journal of Psychiatry in Medicine. 10:217-219, 1980.
10. ^ "Medication 'worsens Alzheimer's'". BBC News. 1 April 2008. http://news.bbc.co.uk/1/hi/health/7319393.stm. Retrieved 2008-04-01. "Neuroleptics provided no benefit for patients with mild behavioural problems, but were associated with a marked deterioration in verbal skills." 
11. ^ Ballard C, Lana MM, Theodoulou M, Douglas S, McShane R, et al. (2008). "A Randomised, Blinded, Placebo-Controlled Trial in Dementia Patients Continuing or Stopping Neuroleptics (The DART-AD Trial)". PLOS Medicine 5 (4, e76): e76. doi:10.1371/journal.pmed.0050076. 

External links

• PubChem Substance Summary: Thioridazine National Center for Biotechnology Information,.
• Antipsychotic Mellaril Removed from Market Schizophrenia Daily News Blog.

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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 Histaminergics Receptor Ligands H1 Agonists: 2-Pyridylethylamine • Betahistine • Histamine • HTMT • UR-AK49 Antagonists: 1st Generation: Alimemazine • Azatadine • Bamipine • Bepotastine • Bromazine • Brompheniramine • Buclizine • Carbinoxamine • Chlorcyclizine • Chloropyramine • Chlorothen • Chlorpheniramine • Chlorphenoxamine • Cinnarizine • Clemastine • Clobenzepam • Clocinizine • Cyclizine • Cyproheptadine • Dacemazine • Deptropine • Dexbrompheniramine • Dexchlorpheniramine • Dimetindene • Diphenhydramine • Diphenylpyraline • Doxylamine • Embramine • Etymemazine • Histapyrrodine • Hydroxyethylpromethazine • Hydroxyzine • Iproheptine • Isopromethazine • Isothipendyl • Meclizine • Mepyramine • Mequitazine • Methafurylene • Methapyrilene • Methdilazine • Moxastine • Niaprazine • Orphenadrine • Oxatomide • Oxomemazine • p-Methyldiphenhydramine • Pheniramine • Phenyltoloxamine • Promethazine • Pyrilamine • Pyrrobutamine • Setastine • Talastine • Thenalidine • Thenyldiamine • Thiazinamium • Thonzylamine • Tolpropamine • Tripelennamine • Triprolidine; 2nd Generation: Acrivastine • Antazoline • Astemizole • Azatadine • Azelastine • Bamipine • Cetirizine • Clemizole • Clobenztropine • Deptropine • Dimebon • Ebastine • Emedastine • Epinastine • Ketotifen • Levocabastine • Loratadine • Mebhydrolin • Mizolastine • Olopatadine • Phenindamine • Pimethixene • Pyrrobutamine • Rupatadine • Terfenadine • Thenalidine • Tritoqualine; 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)

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