prazosin

(prā'zō-sĭn)

[P(IPE)RAZ(INE) + perhaps alteration of OX(Y)- + (quinazol)in(e), one of its constituents.]

View more Health videos

Brand names: Minipress®

Chemical formula:

Drug Forms:
• Prazosin capsules (below)
• Prazosin Hydrochloride Oral capsule

Espa�ol:
• Cápsulas de prazosín
• Prazosín Clorhidrato, Cápsula oral

Prazosin capsules

What are prazosin capsules?

PRAZOSIN (Minipress®) is an antihypertensive. Prazosin lowers, but does not cure, high blood pressure. It works by relaxing the blood vessels. Prazosin is sometimes used for prostate problems. Generic prazosin capsules are available.

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

They need to know if you have any of the following conditions:
• angina
• kidney disease
• an unusual or allergic reaction to prazosin, other medicines, foods, dyes, or preservatives
• pregnant or trying to get pregnant
• breast-feeding

How should I take this medicine?

Take prazosin capsules by mouth. Follow the directions on the prescription label. Swallow the capsules with a drink of water. Taking the capsules with food can help to reduce side effects. Take your doses at regular intervals. Do not take your medicine more often than directed. Do not stop taking except on your prescriber's advice.

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

What if I miss a dose?

What drug(s) may interact with prazosin?

Do not take prazosin if you are taking the following medications:
• other alpha-blockers such as alfuzosin, doxazosin, phentolamine, phenoxybenzamine, tamsulosin, terazosin

Prazosin may also interact with the following medications:
• medicines for colds and breathing difficulties
• medicines for high blood pressure
• monoamine oxidase inhibitors (Azilect®, Eldepryl®, Emsam®, Marplan®, Nardil®, Parnate®, Zelapar™)
• sildenafil (doses of sildenafil higher than 25 mg should be taken at least 4 hours apart from taking prazosin)
• tadalafil
• vardenafil
• water pills

Tell your prescriber or health care professional about all other medicines you are taking, including nonprescription 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 prescriber or health care professional before stopping or starting any of your medicines.

What should I watch for while taking prazosin?

Check your blood pressure regularly. Ask your prescriber or health care professional what your blood pressure should be and when you should contact him or her.

You may feel drowsy or dizzy. Do not drive, use machinery, or do anything that requires mental alertness until you know how prazosin affects you. To reduce the risk of dizzy or fainting spells, do not sit or stand up quickly. Avoid alcoholic drinks; they can make you more drowsy, and can increase flushing and rapid heartbeats. Taking initial doses of prazosin at bedtime can lessen the effects of drowsiness and dizziness, but be careful if you have to get up during the night. Drowsiness and dizziness are more likely to occur after the first dose, after an increase in dose, or during hot weather or exercise. These effects can decrease once your body adjusts to this medicine.

Although extremely rare in men taking prazosin, contact you health care provider immediately if you experience prolonged and painful erection of the penis which is unrelated to sexual activity (priapism). If not brought to immediate medical attention, priapism can lead to permanent erectile dysfunction (impotence).

Your mouth may get dry. Chewing sugarless gum or sucking hard candy, and drinking plenty of water, will help.

Do not take nonprescription medicine for weight-loss without asking your prescriber or health care professional. Also, do not take cough and cold, hay fever or sinus medications without asking your prescriber or health care professional.

If you are going to have surgery, tell your prescriber or health care professional that you are taking prazosin.

What side effects may I notice from taking prazosin?

Side effects that you should report to your prescriber or health care professional as soon as possible:
Rare or uncommon:
• difficulty breathing, shortness of breath
• prolonged painful erection of the penis (priapism)
More common:
• blurred vision
• fainting spells, lightheadedness
• irregular heartbeat, palpitations or chest pain
• mental depression
• swelling of the legs and ankles
• vomiting

Side effects that usually do not require medical attention (report to your prescriber or health care professional if they continue or are bothersome):
• constipation or diarrhea
• drowsiness or dizziness
• dry mouth
• headache
• nausea
• sexual difficulties (impotence)
• stomach pain
• unusual weakness or tiredness

Where can I keep my medicine?

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

Store at room temperature between 15 and 30 degrees C (59 and 86 degrees F). Protect from light. 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 postsynaptic α-adrenergic receptor blocker that acts as a peripheral vasodilator; used as the hydrochloride salt in the treatment of congestive heart failure.

Prazosin

Systematic (IUPAC) name
2-[4-(2-furoyl)piperazin-1-yl]-6,7-dimethoxyquinazolin-4-amine
Clinical data
Trade names	Minipress
AHFS/Drugs.com	monograph
MedlinePlus	a682245
Pregnancy cat.	?
Legal status	POM (UK)
Routes	Oral
Pharmacokinetic data
Bioavailability	~60%
Protein binding	97%
Half-life	2–3 hours
Identifiers
CAS number	19216-56-9 Y
ATC code	C02CA01
PubChem	CID 4893
IUPHAR ligand	503
DrugBank	APRD00020
ChemSpider	4724 Y
UNII	XM03YJ541D Y
KEGG	D08411 Y
ChEBI	CHEBI:8364 Y
ChEMBL	CHEMBL2 Y
Chemical data
Formula	C19H21N5O4
Mol. mass	383.401 g/mol
SMILES	eMolecules & PubChem
InChI InChI=1S/C19H21N5O4/c1-26-15-10-12-13(11-16(15)27-2)21-19(22-17(12)20)24-7-5-23(6-8-24)18(25)14-4-3-9-28-14/h3-4,9-11H,5-8H2,1-2H3,(H2,20,21,22) Y Key:IENZQIKPVFGBNW-UHFFFAOYSA-N Y
N(what is this?)  (verify)

Prazosin, trade names Minipress, Vasoflex, Pressin and Hypovase, is a sympatholytic drug used to treat high blood pressure and anxiety, PTSD, and panic disorder. It is an alpha-adrenergic blocker. Specifically, prazosin is selective for the alpha-1 receptors on vascular smooth muscle. These receptors are responsible for the vasoconstrictive action of norepinephrine, which would normally raise blood pressure and cause increase in anxiety and panic. By blocking these receptors, prazosin reduces blood pressure and reduces anxiety and panic.

In addition to its alpha-blocking activity, prazosin is an antagonist of the MT₃ receptor (which is not present in humans), with selectivity for this receptor over the MT₁ and MT₂ receptors.^[1]

Contents 1 Use 2 Side effects 3 Prazosin in management of PTSD 4 Prazosin in scorpion stings 5 Chemistry 6 References

Use

Prazosin is orally active and has a minimal effect on cardiac function due to its alpha-1 receptor selectivity. However, when prazosin is initially started, heart rate and contractility go up in order to maintain the pre-treatment blood pressures because the body has reached homeostasis at its abnormally high blood pressure. The blood pressure lowering effect becomes apparent when prazosin is taken for longer periods of time. The heart rate and contractility go back down over time and blood pressure decreases.

The antihypertensive characteristics of prazosin make it a second-line choice for the treatment of high blood pressure.^[2]

Prazosin is also useful in treating urinary hesitancy associated with prostatic hyperplasia, blocking alpha-1 receptors, which control constriction of both the prostate and ureters. Although not a first line choice for either hypertension or prostatic hyperplasia, it is a choice for patients who present with both problems concomitantly.^[2]

This medication has shown to be effective in treating severe nightmares in children and people with PTSD symptoms.^[3] Veterans have also been treated successfully at the Oregon VA for sleep disturbance related to PTSD. Doses are lower for this purpose than for control of blood pressure.^[3]

Prazosin holds promise as a pharmacologic treatment for alcohol dependence after a 2009 pilot trial l was completed. A larger controlled Phase II trial "Clinical Trial of the Adrenergic Alpha-1 Antagonist Prazosin for Alcohol Dependence" is currently underway, set to be completed November 2013.

Side effects

Side effects of prazosin include orthostatic hypotension, syncope, and nasal congestion. The orthostatic hypotension and syncope are associated with the body's poor ability to control blood pressure without active alpha-adrenergic receptors. Patients on prazosin should be told not to stand up too quickly, since their poor baroreflex may cause them to faint as all their blood rushes to their feet. The nasal congestion is due to dilation of vessels in the nasal mucosa.

One phenomenon associated with prazosin is known as the "first dose response", in which the side effects of the drug, especially orthostatic hypotension and fainting, are especially pronounced in the first dose.

One very rare side effect of prazosin (and doxazosin) is priapism.^[4][5]

Another possible side effect is dreaming while awake or hallucinations of wakefulness while falling asleep on the medication (see oneirophrenia) .

Prazosin in management of PTSD

Prazosin has been reported to be useful in management of anxiety, such as PTSD. Raskin and colleagues studied the efficacy of prazosin for PTSD among ten Vietnam combat veterans in a 20-week double-blind crossover protocol with a two-week drug washout to allow for return to baseline. The CAPS and the Clinical Global Impressions-Change scale (CGI-C) were the primary outcome measures. Patients who were taking prazosin had a robust improvement in overall sleep quality (effect size, 1.6) and recurrent distressing dreams (effect size, 1.9). In each of the PTSD symptom clusters the effect size was medium to large: .7 for reexperiencing or intrusion, .6 for avoidance and numbing, and .9 for hyperarousal. The reduction in CGI-C scores (overall PTSD severity and function at endpoint) also reflected a large effect size (1.4). Prazosin appears to have promise as an effective treatment for PTSD-related sleep disturbance, including trauma-related nightmares, as well as overall Anxiety and PTSD symptoms.^[6]

Prazosin in scorpion stings

Since 1983 prazosin has revolutionized the management of severe scorpion stings.^[7]

Chemistry

Prazosin, 1-(4-amino-6,7-dimethoxy-2-quinazolinyl)-4-(2-furoyl)-piperazine, is synthesized from 2-amino-4,5-dimethoxybenzoic acid, which upon reaction with sodium cyanate undergoes heterocyclation into 2,4-dihydroxy-6,7-dimethoxyquinazoline. Substituting hydroxyl groups of this compound with chlorine atoms by reaction with thionyl chloride, or a mixture of phosphorus oxychloride with phosphorus pentachloride gives 2,4-dichloro-6,7-dimethoxyquinazoline. Upon subsequent reaction with ammonia, the chlorine atom at C4 of the pyrimidine ring is replaced with an amino group, which leads to the formation of 4-amino-2-chloro-6,7-dimethoxyquinazoline. Introducing this into a reaction with 1-(2-furoyl)piperazine gives prazosin.

• H.-J.E. Hess, U.S. Patent 3,511,836 (1970).
• H.-J.E. Hess, U.S. Patent 3,635,979 (1972).
• H.-J.E. Hess, U.S. Patent 3,663,706 (1972).
• Pfizer & Co., Inc., GB 1156973  (1970).
• E. Honkanen, A. Pippuri, P. Kairisalo, M. Koivisto, S. Tuorni, J. Heterocycl. Chem., 17, 797(1980).
• H.-J.E. Hess, U.S. Patent 3,935,213 (1976).
• Ph.D. Hammen, U.S. Patent 4,062,844 (1977).
• R.R. Crenshaw, G.M. Luke, R.A. Portike, U.S. Patent 4,138,561 (1979).
• A.K. Pippuri, E.J. Honkman, BE 861821  (1977).
• A.K. Pippuri, E.J. Honkman, BE 861822  (1977).

References

1. ^ Yu CX, Zhu CB, Xu SF, Cao XD, Wu GC (March 2000). "Selective MT(2) melatonin receptor antagonist blocks melatonin-induced antinociception in rats". Neuroscience Letters 282 (3): 161–4. PMID 10717416. http://linkinghub.elsevier.com/retrieve/pii/S0304394000008831. 
2. ^ ^{a b} Shen, Howard (2008). Illustrated Pharmacology Memory Cards: PharMnemonics. Minireview. p. 13. ISBN 1-59541-101-1. 
3. ^ ^{a b} "Drug Helps PTSD Nightmares" (Press release). Department of Veteran Affairs. March 30, 2008. http://www.research.va.gov/news/press_releases/ptsd-033007.cfm. Retrieved 2009-03-16. 
4. ^ Bhalla AK, Hoffbrand BI, Phatak PS, Reuben SR (October 1979). "Prazosin and priapism". Br Med J 2 (6197): 1039. doi:10.1136/bmj.2.6197.1039. PMC 1596841. PMID 519276. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=1596841. 
5. ^ Avisrror MU, Fernandez IA, Sánchez AS, García-Pando AC, Arias LM, del Pozo JG (January 2000). "Doxazosin and priapism". J. Urol. 163 (1): 238. doi:10.1016/S0022-5347(05)68018-4. PMID 10604360. http://linkinghub.elsevier.com/retrieve/pii/S0022-5347(05)68018-4. 
6. ^ Raskind MA, Peskind ER, Kanter ED, et al: Reduction of nightmares and other PTSD symptoms in combat veterans by prazosin: a placebo controlled study. American Journal of Psychiatry 160:371–373, 2003
7. ^ Bawaskar HS, Bawaskar PH (January 2007). "Utility of scorpion antivenin vs prazosin in the management of severe Mesobuthus tamulus (Indian red scorpion) envenoming at rural setting". J Assoc Physicians India 55: 14–21. PMID 17444339. 

v d e Sympatholytic (and closely related) antihypertensives (C02) Sympatholytics (antagonize α-adrenergic vasoconstriction) Central α2 agonist Clonidine • Guanfacine • Methyldopa # Adrenergic release inhibitors Bethanidine • Bretylium • Debrisoquine • Guanadrel • Guanazodine • Guanethidine • Guanoclor • Guanoxan • Guanazodine • Guanoxabenz • Guanoxan Imidazoline receptor agonist Moxonidine • Rilmenidine Ganglion-blocking/nicotinic antagonist Mecamylamine • Pentolinium • Trimethaphan Peripheral Indirect MAOI Pargyline Adrenergic uptake inhibitor Bietaserpine • Deserpidine • Methoserpidine • Rescinnamine • Reserpine Tyrosine hydroxylase inhibitor Metirosine Direct α1 blockers Prazosin • Indoramin • Trimazosin • Doxazosin • Urapidil Non-selective α blocker Phentolamine Other antagonists Serotonin antagonist Ketanserin Endothelin antagonist (for PH) dual (Bosentan) • selective (Ambrisentan, Sitaxentan) #WHO-EM ‡Withdrawn from market Clinical trials: †Phase III §Never to phase III M: VAS anat(a:h/u/t/a/l,v:h/u/t/a/l)/phys/devp/cell/prot noco/syva/cong/lyvd/tumr, sysi/epon, injr proc, drug(C2s+n/3/4/5/7/8/9)

v d e Adrenergics   Receptor ligands α1 Agonists: 5-FNE • 6-FNE • Amidephrine • Anisodamine • Anisodine • Cirazoline • Dipivefrine • Dopamine • Ephedrine • Epinephrine (Adrenaline) • Etilefrine • Ethylnorepinephrine • Indanidine • Levonordefrin • Metaraminol • Methoxamine • Methyldopa • Midodrine • Naphazoline • Norepinephrine (Noradrenaline) • Octopamine • Oxymetazoline • Phenylephrine • Phenylpropanolamine • Pseudoephedrine • Synephrine • Tetrahydrozoline Antagonists: Abanoquil • Adimolol • Ajmalicine • Alfuzosin • Amosulalol • Arotinolol • Atiprosin • Benoxathian • Buflomedil • Bunazosin • Carvedilol • CI-926 • Corynanthine • Dapiprazole • DL-017 • Domesticine • Doxazosin • Eugenodilol • Fenspiride • GYKI-12,743 • GYKI-16,084 • Indoramin • Ketanserin • L-765,314 • Labetalol • Mephendioxan • Metazosin • Monatepil • Moxisylyte (Thymoxamine) • Naftopidil • Nantenine • Neldazosin • Nicergoline • Niguldipine • Pelanserin • Phendioxan • Phenoxybenzamine • Phentolamine • Piperoxan • Prazosin • Quinazosin • Ritanserin • RS-97,078 • SGB-1,534 • Silodosin • SL-89.0591 • Spiperone • Talipexole • Tamsulosin • Terazosin • Tibalosin • Tiodazosin • Tipentosin • Tolazoline • Trimazosin • Upidosin • Urapidil • Zolertine * Note that many TCAs, TeCAs, antipsychotics, ergolines, and some piperazines like buspirone, trazodone, nefazodone, etoperidone, and mepiprazole all antagonize α1-adrenergic receptors as well, which contributes to their side effects such as orthostatic hypotension. α2 Agonists: (R)-3-Nitrobiphenyline • 4-NEMD • 6-FNE • Amitraz • Apraclonidine • Brimonidine • Cannabivarin • Clonidine • Detomidine • Dexmedetomidine • Dihydroergotamine • Dipivefrine • Dopamine • Ephedrine • Ergotamine • Epinephrine (Adrenaline) • Esproquin • Etilefrine • Ethylnorepinephrine • Guanabenz • Guanfacine • Guanoxabenz • Levonordefrin • Lofexidine • Medetomidine • Methyldopa • Mivazerol • Naphazoline • Norepinephrine (Noradrenaline) • Phenylpropanolamine • Piperoxan • Pseudoephedrine • Rilmenidine • Romifidine • Talipexole • Tetrahydrozoline • Tizanidine • Tolonidine • Urapidil • Xylazine • Xylometazoline Antagonists: 1-PP • Adimolol • Aptazapine • Atipamezole • BRL-44408 • Buflomedil • Cirazoline • Efaroxan • Esmirtazapine • Fenmetozole • Fluparoxan • GYKI-12,743 • GYKI-16,084 • Idazoxan • Mianserin • Mirtazapine • MK-912 • NAN-190 • Olanzapine • Phentolamine • Phenoxybenzamine • Piperoxan • Piribedil • Rauwolscine • Rotigotine • SB-269,970 • Setiptiline • Spiroxatrine • Sunepitron • Tolazoline • Yohimbine * Note that many atypical antipsychotics and azapirones like buspirone and gepirone (via metabolite 1-PP) antagonize α2-adrenergic receptors as well. β Agonists: 2-FNE • 5-FNE • Amibegron • Arbutamine • Arformoterol • Arotinolol • BAAM • Bambuterol • Befunolol • Bitolterol • Broxaterol • Buphenine • Carbuterol • Cimaterol • Clenbuterol • Denopamine • Deterenol • Dipivefrine • Dobutamine • Dopamine • Dopexamine • Ephedrine • Epinephrine (Adrenaline) • Etafedrine • Etilefrine • Ethylnorepinephrine • Fenoterol • Formoterol • Hexoprenaline • Higenamine • Indacaterol • Isoetarine • Isoprenaline (Isoproterenol) • Isoxsuprine • Labetalol • Levonordefrin • Levosalbutamol • Mabuterol • Methoxyphenamine • Methyldopa • N-Isopropyloctopamine • Norepinephrine (Noradrenaline) • Orciprenaline • Oxyfedrine • Phenylpropanolamine • Pirbuterol • Prenalterol • Ractopamine • Procaterol • Pseudoephedrine • Reproterol • Rimiterol • Ritodrine • Salbutamol (Albuterol) • Salmeterol • Solabegron • Terbutaline • Tretoquinol • Tulobuterol • Xamoterol • Zilpaterol • Zinterol Antagonists: Acebutolol • Adaprolol • Adimolol • Afurolol • Alprenolol • Alprenoxime • Amosulalol • Ancarolol • Arnolol • Arotinolol • Atenolol • Befunolol • Betaxolol • Bevantolol • Bisoprolol • Bopindolol • Bormetolol • Bornaprolol • Brefonalol • Bucindolol • Bucumolol • Bufetolol • Buftiralol • Bufuralol • Bunitrolol • Bunolol • Bupranolol • Burocrolol • Butaxamine • Butidrine • Butofilolol • Capsinolol • Carazolol • Carpindolol • Carteolol • Carvedilol • Celiprolol • Cetamolol • Cicloprolol • Cinamolol • Cloranolol • Cyanopindolol • Dalbraminol • Dexpropranolol • Diacetolol • Dichloroisoprenaline • Dihydroalprenolol • Dilevalol • Diprafenone • Draquinolol • Dropranolol • Ecastolol • Epanolol • Ericolol • Ersentilide • Esatenolol • Esmolol • Esprolol • Eugenodilol • Exaprolol • Falintolol • Flestolol • Flusoxolol • Hydroxycarteolol • Hydroxytertatolol • ICI-118,551 • Idropranolol • Indenolol • Indopanolol • Iodocyanopindolol • Iprocrolol • Isoxaprolol • Isamoltane • Labetalol • Landiolol • Levobetaxolol • Levobunolol • Levocicloprolol • Levomoprolol • Medroxalol • Mepindolol • Metalol • Metipranolol • Metoprolol • Moprolol • Nadolol • Nadoxolol • Nafetolol • Nebivolol • Neraminol • Nifenalol • Nipradilol • Oberadilol • Oxprenolol • Pacrinolol • Pafenolol • Pamatolol • Pargolol • Parodilol • Penbutolol • Penirolol • PhQA-33 • Pindolol • Pirepolol • Practolol • Primidolol • Procinolol • Pronethalol • Propafenone • Propranolol • Ridazolol • Ronactolol • Soquinolol • Sotalol • Spirendolol • SR 59230A • Sulfinalol • TA-2005 • Talinolol • Tazolol • Teoprolol • Tertatolol • Terthianolol • Tienoxolol • Tilisolol • Timolol • Tiprenolol • Tolamolol • Toliprolol • Tribendilol • Trigevolol • Xibenolol • Xipranolol   Reuptake inhibitors NET Selective norepinephrine reuptake inhibitors: Amedalin • Atomoxetine (Tomoxetine) • Ciclazindol • Daledalin • Esreboxetine • Lortalamine • Mazindol • Nisoxetine • Reboxetine • Talopram • Talsupram • Tandamine • Viloxazine; Norepinephrine-dopamine reuptake inhibitors: Amineptine • Bupropion (Amfebutamone) • Fencamine • Fencamfamine • Lefetamine • Levophacetoperane • LR-5182 • Manifaxine • Methylphenidate • Nomifensine • O-2172 • Radafaxine; Serotonin-norepinephrine reuptake inhibitors: Bicifadine • Desvenlafaxine • Duloxetine • Eclanamine • Levomilnacipran • Milnacipran • Sibutramine • Venlafaxine; Serotonin-norepinephrine-dopamine reuptake inhibitors: Brasofensine • Diclofensine • DOV-102,677 • DOV-21,947 • DOV-216,303 • JNJ-7925476 • JZ-IV-10 • Methylnaphthidate • Naphyrone • NS-2359 • PRC200-SS • SEP-225,289 • SEP-227,162 • Tesofensine; Tricyclic antidepressants: Amitriptyline • Butriptyline • Cianopramine • Clomipramine • Desipramine • Dosulepin • Doxepin • Imipramine • Lofepramine • melitracen • Nortriptyline • Protriptyline • Trimipramine; Tetracyclic antidepressants: Amoxapine • Maprotiline • Mianserin • Oxaprotiline • Setiptiline; Others: Cocaine • CP-39,332 • EXP-561 • Fezolamine • Ginkgo biloba • Indeloxazine • Nefazodone • Nefopam • Pridefrine • Tapentadol • Tedatioxetine  • Teniloxazine • Tramadol • Ziprasidone VMAT Ibogaine • Reserpine • Tetrabenazine   Releasing agents Morpholines: Fenbutrazate • Morazone • Phendimetrazine • Phenmetrazine; Oxazolines: 4-Methylaminorex • Aminorex • Clominorex • Cyclazodone • Fenozolone • Fluminorex • Pemoline • Thozalinone; Phenethylamines (also amphetamines, cathinones, phentermines, etc): 2-OH-PEA • 4-CAB • 4-FA • 4-FMA • 4-MA • 4-MMA • Alfetamine • Amfecloral • Amfepentorex • Amfepramone • Amphetamine (Dextroamphetamine, Levoamphetamine) • Amphetaminil • β-Me-PEA • BDB • Benzphetamine • BOH • Buphedrone • Butylone • Cathine • Cathinone • Clobenzorex • Clortermine • D-Deprenyl • Dimethylamphetamine • Dimethylcathinone (Dimethylpropion, metamfepramone) • DMA • DMMA • EBDB • Ephedrine • Ethcathinone • Ethylamphetamine • Ethylone • Famprofazone • Fenethylline • Fenproporex • Flephedrone • Fludorex • Furfenorex • Hordenine • IAP • IMP • L-Deprenyl (Selegiline) • Lisdexamfetamine • Lophophine • MBDB • MDA (Tenamfetamine) • MDEA • MDMA • MDMPEA • MDOH • MDPEA • Mefenorex • Mephedrone • Mephentermine • Methamphetamine (Dextromethamphetamine, Levomethamphetamine) • Methcathinone • Methedrone • Methylone • NAP • Ortetamine • Paredrine • pBA • pCA • Pentorex (Phenpentermine) • Phenethylamine • Pholedrine • Phenpromethamine • Phentermine • Phenylpropanolamine • pIA • Prenylamine • Propylamphetamine • Pseudoephedrine • Tiflorex • Tyramine • Xylopropamine • Zylofuramine; Piperazines: 2C-B-BZP • BZP • MBZP • mCPP • MDBZP • MeOPP • pFPP; Others: 2-Amino-1,2-dihydronaphthalene • 2-Aminoindane • 2-Aminotetralin • 2-Benzylpiperidine • 4-Benzylpiperidine • 5-IAI • Clofenciclan • Cyclopentamine • Cypenamine • Cyprodenate • Feprosidnine • Gilutensin • Heptaminol • Hexacyclonate • Indanorex • Isometheptene • Methylhexanamine • Octodrine • Phthalimidopropiophenone • Propylhexedrine (Levopropylhexedrine) • Tuaminoheptane   Enzyme inhibitors Anabolism PAH 3,4-Dihydroxystyrene TH 3-Iodotyrosine • Aquayamycin • Bulbocapnine • Metirosine • Oudenone AAAD Benserazide • Carbidopa • Genistein • Methyldopa DBH Bupicomide • Disulfiram • Dopastin • Fusaric acid • Nepicastat • Phenopicolinic acid • Tropolone PNMT CGS-19281A • SKF-64139 • SKF-7698 Catabolism MAO Nonselective: Benmoxin • Caroxazone • Echinopsidine • Furazolidone • Hydralazine • Indantadol • Iproclozide • Iproniazid • Isocarboxazid • Isoniazid • Linezolid • Mebanazine • Metfendrazine • Nialamide • Octamoxin • Paraxazone • Phenelzine • Pheniprazine • Phenoxypropazine • Pivalylbenzhydrazine • Procarbazine • Safrazine • Tranylcypromine; MAO-A selective: Amiflamine • Bazinaprine • Befloxatone • Befol • Brofaromine • Cimoxatone • Clorgiline • Esuprone • Harmala alkaloids (Harmine, Harmaline, Tetrahydroharmine, Harman, Norharman, etc) • Methylene Blue • Metralindole • Minaprine • Moclobemide • Pirlindole • Sercloremine • Tetrindole • Toloxatone • Tyrima; MAO-B selective: D-Deprenyl • Selegiline (L-Deprenyl) • Ladostigil • Lazabemide • Milacemide • Mofegiline • Pargyline • Rasagiline • Safinamide * Note that MAO-B inhibitors also influence norepinephrine/epinephrine levels since they inhibit the breakdown of their precursor dopamine. COMT 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: BPAP • PPAP; Release blockers: Bethanidine • Bretylium • Guanadrel • Guanazodine • Guanclofine • Guanethidine • Guanoxan; Toxins: Oxidopamine (6-Hydroxydopamine) List of adrenergic drugs

v d e Melatonergics Receptor ligands Agonists Agomelatine • LY-156,735 • Melatonin • NAS (Normelatonin) • Ramelteon • Tasimelteon Antagonists Afobazole • Luzindole • Prazosin (at MT3) Enzyme inhibitors Anabolism AANAT inhibitors   ASMT inhibitors   Catabolism   Others Precursors L-Tryptophan → 5-HTP → Serotonin → NAS (Normelatonin) Cofactors Ferrous Iron (Fe2+) • Magnesium (Mg2+) • S-Adenosyl-L-methionine • 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+)

This entry is from Wikipedia, the leading user-contributed encyclopedia. It may not have been reviewed by professional editors (see full disclaimer)