Dexmethylphenidate

Brand names: Focalin®Focalin® XR

Chemical formula:

Drug Forms:
• Dexmethylphenidate tablets (below)
• Dexmethylphenidate extended-release capsules
• Dexmethylphenidate Hydrochloride Oral capsule, biphasic release
• Dexmethylphenidate Hydrochloride Oral tablet

Español:
• Tabletas de dexmetilfenidato
• Clorhidrato de dexmetilfenidato, Cápsula oral de liberación bifásica
• Dexmetilfenidato Clorhidrato, Tableta oral

Dexmethylphenidate tablets

What are dexmethylphenidate tablets?

DEXMETHYLPHENIDATE (Focalin®) is a stimulant. It can improve attention span, concentration, and emotional control, and reduce restless or overactive behavior. This medicine treats attention-deficit hyperactivity disorder (ADHD). Federal law prohibits the transfer of dexmethylphenidate to any person other than the person for whom it was prescribed. Do not share this medicine with anyone else. Generic dexmethylphenidate tablets are not available.

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

They need to know if you have any of these conditions:
• regularly drink beverages containing alcohol
• a history of drug abuse
• glaucoma
• heart failure or other heart disease
• heart rhythm disturbance
• history of recent heart attack
• high blood pressure
• liver disease
• mental illness, including anxiety, bipolar disorder, depression, mania or schizophrenia
• overactive thyroid
• seizures (convulsions)
• Tourette's syndrome (speech repetition or involuntary use of obscene language)
• an unusual or allergic reaction to dexmethylphenidate, methylphenidate, other medicines, foods, dyes, or preservatives
• pregnant or trying to get pregnant
• breast-feeding

How should I take this medicine?

Take dexmethylphenidate tablets by mouth. Follow the directions on the prescription label. Swallow the tablets with a drink of water. You can take this medicine with or without food. Usually the last dose of the day will be taken at least 4—6 hours before your normal bedtime, so it will not interfere with sleep. 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. This medicine is commonly prescribed for children >= 6 years old.

What drug(s) may interact with dexmethylphenidate?

• amphetamine or dextroamphetamine
• bretylium
• caffeine
• carbamazepine
• clonidine
• furazolidone
• guarana
• linezolid
• lithium
• medicines for colds, sinus, and breathing difficulties
• medicines for high blood pressure
• medicines called MAO inhibitors- examples: phenelzine (Nardil®), tranylcypromine (Parnate®), isocarboxazid (Marplan®)
• other medicines for mental depression or anxiety
• medicines for mental problems and psychotic disturbances
• medicines to decrease appetite or cause weight loss
• methylphenidate
• modafinil
• pemoline
• procarbazine
• seizure (convulsion) or epilepsy medicine
• warfarin
• water pills (diuretics)

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 dexmethylphenidate?

Visit your prescriber or health care professional for regular checks on your progress. This prescription requires that you follow special procedures with your prescriber and pharmacy; you will need to have a new written prescription from your prescriber every time you need a refill.

Dexmethylphenidate may affect your concentration, or hide signs of tiredness. Until you know how this drug affects you, do not drive, ride a bicycle, use machinery, or do anything that needs mental alertness.

Tell your prescriber or health care professional if this medicine loses its effects, or if you feel you need to take more than the prescribed amount. Do not change the dosage without advice from your prescriber or health care professional. Do not suddenly stop your medication without your prescribers approval. Ask your prescriber or health care professional for advice.

Decreased appetite is a common side effect when starting this medicine. Eating small, frequent meals or snacks can help. Talk to your prescriber if you continue to have poor eating habits. Height and weight growth of a child taking this medication will be monitored closely.

If you are going to have surgery or other medical procedures, tell your health care professional that you are taking dexmethylphenidate.

What side effects may I notice from taking dexmethylphenidate?

Side effects that you should report to your prescriber or health care professional as soon as possible:
• anxiety or severe nervousness
• bruising
• changes in mood or behavior, including seeing or hearing things that are not really there or over-focused, staring-type behavior
• chest pain, fast or irregular heartbeat (palpitations)
• fever, or hot, dry skin
• increased blood pressure
• joint pain
• skin rash, itching
• uncontrollable head, mouth, neck, arm, or leg movements

Side effects that usually do not require medical attention (report to your prescriber or health care professional if they continue or are bothersome):
Less Common or Rare:
• a sense of well being
• blurred vision
• dizziness or lightheadedness
• stomach cramps
More Common, especially in the first few weeks of treatment:
• decreased appetite or loss of appetite
• headache
• mild stomach upset
• nervousness, restlessness, or difficulty sleeping
• weight loss

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—30 degrees C (59—86 degrees F). Protect from light and moisture. Keep container tightly closed. Throw away any unused medicine after the expiration date.

Last updated: 6/8/2005 11:27:00 AM

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.

Dexmethylphenidate

Systematic (IUPAC) name
(R,R)-(+)-Methyl 2-phenyl-2-(2-piperidyl)acetate
Identifiers
CAS number	40431-64-9
ATC code	N06BA11
PubChem	4158
DrugBank	APRD00657
Chemical data
Formula	C14H19NO2
Mol. mass	233.31 g/mol
Pharmacokinetic data
Bioavailability	11 – 52%
Protein binding	30%
Metabolism	hepatic
Half life	2 – 4 hours
Excretion	renal
Therapeutic considerations
Pregnancy cat.	C
Legal status	Controlled (S8)(AU) Schedule III(CA) Class B(UK) Schedule II(US)
Routes	oral

Dexmethylphenidate (trade name Focalin, Novartis), otherwise known as d-threo-methylphenidate (D-TMP), is the dextrorotatory enantiomer of methylphenidate. It is a norepinephrine-dopamine reuptake inhibitor (NDRI) and thus a psychostimulant, which affects the CNS.

Contents 1 Mode of activity 2 Therapeutic use 3 Pharmacology 4 Efficacy 5 Concerns 5.1 Side effects 5.2 Interactions 6 Usage 7 Legal status 8 External links 9 References

Mode of activity

Methylphenidate is a catecholamine reuptake inhibitor that indirectly increases catecholaminergic neurotransmission by inhibiting the dopamine transporter (DAT) and norepinephrine transporter (NET), which are responsible for clearing catecholamines from the synapse, particularly in the striatum and meso-limbic system.^[1]

Although four stereoisomers of methylphenidate (MPH) are possible, only the threo diastereoisomers are used in modern practice. There is a high eudysmic ratio between the SS and RR enantiomers of MPH. "Dexmethylphenidate" is a preparation of the RR enantiomer of MPH.^[2][3] In theory, d-TMP can be anticipated to be twice the strength of the racemic product.^[4] However, certain authors recommend that the ratio is ~70% increase in potency upon enantiopurification of the racemate.^[5]

Compd[6]	DAT (Ki)	DA (IC50)	NET (Ki)	NE (IC50)
D-TMP	161	23	206	39
L-TMP	2250	1600	>10K	980
DL-TMP	121	20	51	788

Therapeutic use

Dexmethylphenidate is used as a treatment for ADHD, ideally in conjunction with psychological, educational, behavioral or other forms of treatment. It is proposed that stimulants help ameliorate the symptoms of ADHD by making it easier for the user to concentrate, avoid distraction, and control behavior. Dexmethylphenidate may also improve listening skills and organization of tasks, and may help prevent tic disorders. Because it is a psychostimulant, dexmethylphenidate may also help with narcolepsy and in certain cases of major depression.

Importantly, the propensity for "abuse" with d-TMP is much less than for the corresponding racemic product.^[7]

Pharmacology

Dexmethylphenidate has a 4-6 hour duration of effect (a long-acting formulation, Focalin XR, which spans 12 hours is also available and has been shown to be as effective as DL-TMP XR (Concerta, Ritalin LA), with flexible dosing and good tolerability.^[8][9]) It has also been demonstrated to reduce the symptoms of childhood ADHD,^[10] as well as ADHD in adults.^[11] d-MPH has a similar side-effect profile to MPH^[12] and can be administered without regard to food intake.^[13]

Typical daily doses of dexmethylphenidate are around 10–20mg for children and 20–40mg for adults. As with all psychostimulant compounds, certain individuals may respond to a small dose and certain individuals may require a larger than average dose, hence, dosing is usually initiated at a typical range and then titrated to suit the patient.^[14]

There is a possibility of withdrawal symptoms if dexmethylphenidate use is discontinued suddenly. As with other stimulants, withdrawal symptoms may include emotional or behavioral depression. Tapering off is recommended, under the supervision of a doctor. Addiction, which involves compulsive or harmful drug-seeking behavior, is rare but not impossible.^[15]

Efficacy

Placebo-controlled trials have shown that once-daily dexmethylphenidate XR was effective and generally well tolerated.^[16] Improvements in ADHD symptoms in children were significantly greater for dexmethylphenidate XR versus placebo. ^[16] It also showed greater efficacy than osmotic release oral system (OROS®) methylphenidate over the first half of the laboratory classroom day but assessments late in the day favoured OROS® methylphenidate. ^[16]

Concerns

The same concerns that apply to other stimulant drugs should be considered: Reports of sudden heart death in children caused Canada to stop marketing Adderall XR (another stimulant used to treat Attention-Deficit Hyperactivity Disorder) for a period in 2005, however it was returned to the market in that same year after it was demonstrated that cardiac risk is low in patients free of congenital heart defects. Heart problems have been reported, predominantly in young people taking ADD stimulants, though the FDA has not concluded that psychostimulants increase risk of cardiac problems for a person without a heart condition. Suicidal thinking has been reported in young people who are taking antidepressants at the same time they are taking an ADHD stimulant and many antidepressants carry a "black box warning" label concerning a possible increase in suicidal ideation in patients under 18 years of age.^[17]

Side effects

Insomnia, nausea, stomach pain, headache, anxiety, anorexia, and weight loss are common side effects.

Rare but much more serious side effects include uncontrolled muscle movements (e.g., stiffness, twitching, shaking), hyperthermia, tics, edema of the feet/hands, blurred vision, mental/mood/behavior changes (e.g., agitation, aggression, mood swings, depression, hallucinations, abnormal thoughts/behavior), extreme tiredness, and severe sweating, easy bleeding/bruising, shortness of breath, fainting, chest/jaw/left arm pain, sudden vision changes, signs of infection (fever, persistent sore throat), tachycardia, weakness, seizures, confusion, slurred speech, and severe headaches and in some rare cases death.^{[citation needed]}

Also, there is a potential for a severe allergic reaction, but it is extremely rare. Trouble breathing, itching, a rash, swelling, or severe dizziness are all signs/symptoms of this allergic reaction.^{[citation needed]}

Interactions

Dexmethylphenidate should not be used in combination with a monoamine oxidase inhibitor (MAOI) such as isocarboxazid (Marplan), phenelzine (Nardil), rasagiline (Azilect), selegiline (Eldepryl, Emsam), or tranylcypromine (Parnate) that has been used in the past 14 days. Serious, life-threatening side effects can occur if dexmethylphenidate is taken with an MAOI.

Usage

The Focalin XR capsules are sometimes prescribed over other extended release stimulants because the capsules can be opened and their contents mixed with applesauce or pudding to help children who cannot, or will not, swallow large capsules. This is possible due to the SODAS (Spheroidal Oral Drug Absorption System) delivery system, also used in Ritalin LA. Focalin XR come in five, ten, fifteen, and twenty milligram capsules. To determine appropriate dosage doctors first prescribe one to four 5 mg capsules. An appropriate treatment plan is then based on the patient's reaction to the initial dose. ^[18] From there, doctors usually increase dose from 5 mg to 10 mg until finding the right dosage.

Legal status

Dexmethylphenidate, due to its abuse potential is classed as a Schedule II controlled drug in the United States.^[19]

External links

• Information from the U.S. National Institute of Health

References

1. ^ Schweri, MM; Skolnick; Rafferty; Rice; Janowsky; Paul (1985). "3HThreo-(+/-)-methylphenidate binding to 3,4-dihydroxyphenylethylamine uptake sites in corpus striatum: correlation with the stimulant properties of ritalinic acid esters". Journal of neurochemistry 45 (4): 1062–70. doi:10.1111/j.1471-4159.1985.tb05524.x. PMID 4031878.  edit
2. ^ Ding, YS; Fowler; Volkow; Dewey; Wang; Logan; Gatley; Pappas (1997). "Chiral drugs: comparison of the pharmacokinetics of 11Cd-threo and L-threo-methylphenidate in the human and baboon brain". Psychopharmacology 131 (1): 71–8. doi:10.1007/s002130050267. PMID 9181638.  edit
3. ^ Ding, Y.; Gatley, S.; Thanos, P.; Shea, C.; Garza, V.; Xu, Y.; Carter, P.; King, P. et al. (2004). "Brain kinetics of methylphenidate (Ritalin) enantiomers after oral administration". Synapse (New York, N.Y.) 53 (3): 168–175. doi:10.1002/syn.20046. PMID 15236349.  edit
4. ^ Davids, E.; Zhang, K.; Tarazi, F.; Baldessarini, R. (2002). "Stereoselective effects of methylphenidate on motor hyperactivity in juvenile rats induced by neonatal 6-hydroxydopamine lesioning". Psychopharmacology 160 (1): 92–98. doi:10.1007/s00213-001-0962-5. PMID 11862378.  edit
5. ^ Markowitz, J.; Patrick, K. (2008). "Differential pharmacokinetics and pharmacodynamics of methylphenidate enantiomers: does chirality matter?". Journal of clinical psychopharmacology 28 (3 Suppl 2): S54–S61. doi:10.1097/JCP.0b013e3181733560. PMID 18480678.  edit
6. ^ Williard, R.; Middaugh, L.; Zhu, H.; Patrick, K. (2007). "Methylphenidate and its ethanol transesterification metabolite ethylphenidate: brain disposition, monoamine transporters and motor activity". Behavioural pharmacology 18 (1): 39–51. doi:10.1097/FBP.0b013e3280143226. PMID 17218796.  edit
7. ^ U.S. Patent 5,908,850
8. ^ Mcgough, J.; Pataki, C.; Suddath, R. (2005). "Dexmethylphenidate extended-release capsules for attention deficit hyperactivity disorder". Expert review of neurotherapeutics 5 (4): 437–441. doi:10.1586/14737175.5.4.437. PMID 16026226.  edit
9. ^ Silva, R.; Tilker, H.; Cecil, J.; Kowalik, S.; Khetani, V.; Faleck, H.; Patin, J. (2004). "Open-label study of dexmethylphenidate hydrochloride in children and adolescents with attention deficit hyperactivity disorder". Journal of child and adolescent psychopharmacology 14 (4): 555–563. doi:10.1089/cap.2004.14.555. PMID 15662147.  edit
10. ^ Arnold, L.E., et al. (2004). "A double-blind, placebo-controlled withdrawal trial of dexmethylphenidate hydrochloride in children with attention deficit hyperactivity disorder". J Child Adolesc Psychopharmacol. 2004 Winter;14(4):542-54.
11. ^ Spencer, T.; Adler, L.; Mcgough, J.; Muniz, R.; Jiang, H.; Pestreich, L.; Adult Adhd Research, G. (2007). "Efficacy and safety of dexmethylphenidate extended-release capsules in adults with attention-deficit/hyperactivity disorder". Biological psychiatry 61 (12): 1380–1387. doi:10.1016/j.biopsych.2006.07.032. PMID 17137560.  edit
12. ^ Keating, GM; Figgitt (2002). "Dexmethylphenidate". Drugs 62 (13): 1899–904; discussion 1905–8. doi:10.2165/00003495-200262130-00009. PMID 12215063.  edit
13. ^ Teo, S.; Scheffler, M.; Wu, A.; Stirling, D.; Thomas, S.; Stypinski, D.; Khetani, V. (2004). "A single-dose, two-way crossover, bioequivalence study of dexmethylphenidate HCl with and without food in healthy subjects". Journal of clinical pharmacology 44 (2): 173–178. doi:10.1177/0091270003261899. PMID 14747426.  edit
14. ^ Quinn, D. (2008). "Does chirality matter? Pharmacodynamics of enantiomers of methylphenidate in patients with attention-deficit/hyperactivity disorder". Journal of clinical psychopharmacology 28 (3 Suppl 2): S62–S66. doi:10.1097/JCP.0b013e3181744aa6. PMID 18480679.  edit
15. ^ "Oral Uses".
16. ^ ^{a b c} Moen M, Keam S.Dexmethylphenidate Extended Release: A Review of its Use in the Treatment of Attention-Deficit Hyperactivity Disorder. CNSDrugs 2009; 23(12):1057-1083.doi:10.2165/11201140-000000000-00000.
17. ^ Rader, R; Mccauley; Callen (2009). "Current strategies in the diagnosis and treatment of childhood attention-deficit/hyperactivity disorder". American family physician 79 (8): 657–65. PMID 19405409.  edit
18. ^ "Focalin XR for ADHD".
19. ^ "Dexmethylphenidate--Novartis/Celgene. Focalin, D-MPH, D-methylphenidate hydrochloride, D-methylphenidate, dexmethylphenidate, dexmethylphenidate hydrochloride". Drugs in R&D 3 (4): 279–82. 2002. PMID 12455205.  edit

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v • d • e Antihyperkinetics (Anti-ADHD Agents) / Psychoanaleptics: psychostimulants, agents used for ADHD and nootropics (N06B) Sympathomimetics Amphetamine • Atomoxetine • Dextroamphetamine • Dextromethamphetamine • Dexmethylphenidate • Lisdexamfetamine • Methylphenidate • Pemoline • Reboxetine α2-Adrenergic Agonists Clonidine • Guanfacine • Lofexidine Eugeroics Adrafinil • Armodafinil • Modafinil

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

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