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Encyclopedia > Bupropion
Bupropion
Systematic (IUPAC) name
(±)-1-(3-chlorophenyl)-2-[(1,1-dimethylethyl)amino]-
1-propanone
Identifiers
CAS number 34841-39-9
ATC code N07BA02
PubChem 444
DrugBank APRD00621
Chemical data
Formula C13H18ClNO 
Mol. mass 239.74 g/mol
Pharmacokinetic data
Bioavailability 5 to 20% in animals; no studies in humans
Metabolism Hepatic
Half life 20 hours
Excretion Renal (87%), fecal (10%)
Therapeutic considerations
Pregnancy cat.

B(US) The formula was drawn in bkchem and GIMP. This image has been released into the public domain by the copyright holder, its copyright has expired, or it is ineligible for copyright. ... Image File history File links No higher resolution available. ... IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. ... The Anatomical Therapeutic Chemical Classification System is used for the classification of drugs. ... A section of the Anatomical Therapeutic Chemical Classification System. ... PubChem is a database of chemical molecules. ... The DrugBank database available at the University of Alberta is a unique bioinformatics and cheminformatics resource that combines detailed drug (i. ... This article or section does not cite any references or sources. ... General Name, Symbol, Number carbon, C, 6 Chemical series nonmetals Group, Period, Block 14, 2, p Appearance black (graphite) colorless (diamond) Standard atomic weight 12. ... General Name, Symbol, Number hydrogen, H, 1 Chemical series nonmetals Group, Period, Block 1, 1, s Appearance colorless Atomic mass 1. ... General Name, Symbol, Number chlorine, Cl, 17 Chemical series halogens Group, Period, Block 17, 3, p Appearance yellowish green Standard atomic weight 35. ... General Name, Symbol, Number nitrogen, N, 7 Chemical series nonmetals Group, Period, Block 15, 2, p Appearance colorless gas Standard atomic weight 14. ... General Name, Symbol, Number oxygen, O, 8 Chemical series nonmetals, chalcogens Group, Period, Block 16, 2, p Appearance colorless (gas) very pale blue (liquid) Standard atomic weight 15. ... The molecular mass (abbreviated Mr) of a substance, formerly also called molecular weight and abbreviated as MW, is the mass of one molecule of that substance, relative to the unified atomic mass unit u (equal to 1/12 the mass of one atom of carbon-12). ... In pharmacology, bioavailability is used to describe the fraction of an administered dose of unchanged drug that reaches the systemic circulation, one of the principal pharmacokinetic properties of drugs. ... Drug metabolism is the metabolism of drugs, their biochemical modification or degradation, usually through specialized enzymatic systems. ... The liver is an organ present in vertebrates and some other animals. ... It has been suggested that Effective half-life be merged into this article or section. ... Excretion is the process of eliminating waste products of metabolism and other materials that are of no use. ... The kidneys are organs that filter wastes (such as urea) from the blood and excrete them, along with water, as urine. ... The pregnancy category of a pharmaceutical agent is an assessment of the risk of fetal injury due to the pharmaceutical, if it is used as directed by the mother during pregnancy. ... Motto: (Out Of Many, One) (traditional) In God We Trust (1956 to date) Anthem: The Star-Spangled Banner Capital Washington D.C. Largest city New York City None at federal level (English de facto) Government Federal constitutional republic  - President George Walker Bush (R)  - Vice President Dick Cheney (R) Independence from...

Legal status

POM(UK) ℞-only(US) The regulation of therapeutic goods, that is drugs and therapeutic devices, varies by jurisdiction. ... A prescription drug is a licensed medicine that is regulated by legislation to require a prescription before it can be obtained. ... A prescription drug is a licensed medicine that is regulated by legislation to require a prescription before it can be obtained. ... Motto: (Out Of Many, One) (traditional) In God We Trust (1956 to date) Anthem: The Star-Spangled Banner Capital Washington D.C. Largest city New York City None at federal level (English de facto) Government Federal constitutional republic  - President George Walker Bush (R)  - Vice President Dick Cheney (R) Independence from...

Routes Oral

Bupropion (INN; also amfebutamone,[1] brand names Wellbutrin, Zyban, Budeprion and Buproban) is an atypical antidepressant, which acts as a norepinephrine reuptake inhibitor and dopamine reuptake inhibitor,[2] and a nicotinic antagonist.[3][4] Bupropion belongs to the chemical class of aminoketones and is similar in structure to stimulant cathinone, anorectic diethylpropion and to phenethylamines in general. Bupropion is primarily used as an antidepressant and as a smoking cessation aid. In 2006 it was the fourth most prescribed antidepressant on the U.S. retail market with 21,141,000 prescriptions.[5] In pharmacology and toxicology, a route of administration is the path by which a drug, fluid, poison or other substance is brought into contact with the body 1. ... An International Nonproprietary Name (INN) is the official non-proprietary or generic name given to a pharmaceutical substance, as designated by the World Health Organization. ... A recent form of antidepressant medication - Prozac Serotonin-norepinephrine reuptake inhibitor, Venlafaxine An antidepressant, in the most common usage, is a psychiatric medication taken to alleviate clinical depression or dysthymia (milder depression). ... Norepinephrine reuptake inhibitors (NRIs) are compounds that increase amounts of the neurotransmitter norepinephrine in the brain by inhibiting its reuptake at synapses. ... This does not cite any references or sources. ... Antagonists In medicine and biology, a receptor antagonist is a ligand that inhibits the function of an agonist and inverse agonist for a specific receptor. ... Stimulants are drugs that temporarily increase alertness and wakefulness. ... Cathinone (β-ketoamphetamine) is a monoamine alkaloid found in the shrub Catha edulis (Khat). ... Anorectics, anorexigenics or appetite suppressants are drugs that reduce the desire to eat (anorectic, from the Greek an- = not and oreg- = extend, reach). (Anorectic is also a term for an anorexic person, a person suffering from Anorexia nervosa. ... Diethylpropion (Tenuate®) is a sympathomimetic stimulant drug marketed as an appetite suppressant. ... Phenethylamine, or β-Phenylethylamine, is an alkaloid and monoamine. ... A recent form of antidepressant medication - Prozac Serotonin-norepinephrine reuptake inhibitor, Venlafaxine An antidepressant, in the most common usage, is a psychiatric medication taken to alleviate clinical depression or dysthymia (milder depression). ... A No Smoking sign Smoking cessation (commonly known as quitting, or kicking the habit) is the effort to stop smoking tobacco products. ...

Contents

History

Bupropion was first synthesized by Burroughs Research in 1966, and patented by Burroughs-Wellcome (later Glaxo-Wellcome, and, as of 2000, GlaxoSmithKline) in 1974. It was approved by the Food and Drug Administration (FDA) as an antidepressant in 1984 and marketed under the name Wellbutrin. However, a significant incidence of seizures at the originally recommended dosage (400–600 mg) caused in 1986 the removal of the drug from the market. It was shown that the risk of seizures increases from 0.1% at 100–300 mg/day to 0.3–0.4% at 450 mg/day to 2% at 600 mg/day. Reflecting this experience, bupropion was re-introduced to the market in 1989 with the maximum dose of 450 mg/day. GlaxoSmithKline plc (LSE: GSK NYSE: GSK) is a British based pharmaceutical, biologicals, and healthcare company. ... hi “FDA” redirects here. ... This article is about the medical condition. ...

Wellbutrin XL
Wellbutrin XL

In 1996 the FDA approved sustained-release (SR) and in 2003 extended release (XL) formulations of Wellbutrin that release bupropion at a slower rate. Wellbutrin SR is taken twice a day and Wellbutrin XL once a day, as compared to three times a day for the immediate release bupropion. Wellbutrin SR and XL are now available in generic form. In 1997, bupropion was approved by the FDA for use as a smoking cessation aid under the name Zyban. In late 2006, Wellbutrin XL was approved for use by the FDA as treatment for seasonal affective disorder. Image File history File linksMetadata Download high-resolution version (1071x1298, 174 KB) The antidepressant Wellbutrin XL (bupropion HCl, 300mg): bottle and tablets. ... Image File history File linksMetadata Download high-resolution version (1071x1298, 174 KB) The antidepressant Wellbutrin XL (bupropion HCl, 300mg): bottle and tablets. ... Year 1996 (MCMXCVI) was a leap year starting on Monday (link will display full 1996 Gregorian calendar). ... Sustained-release (SR), extended-release (ER, XR, or XL), time-release or timed-release, controlled-release (CR), or continuous-release (CR or Contin) pills are tablets or capsules formulated to dissolve slowly and release a drug over time. ... Year 2003 (MMIII) was a common year starting on Wednesday of the Gregorian calendar. ... A generic drug (pl. ... Year 1997 (MCMXCVII) was a common year starting on Wednesday (link will display full 1997 Gregorian calendar). ... Year 2006 (MMVI) was a common year starting on Sunday (link displays full 2006 calendar) of the Gregorian calendar. ... Seasonal affective disorder, or SAD, also known as winter depression or winter blues is an affective, or mood, disorder. ...


In the UK, bupropion was approved in 2000 as a smoking cessation aid, and has not been approved for the treatment of depression.[6]


Indications

Depression

Multiple placebo-controlled studies have confirmed efficacy of bupropion for depression.[7] Equivalent antidepressant potency of bupropion and sertraline (Zoloft), fluoxetine (Prozac), paroxetine (Paxil)[8] and escitalopram (Lexapro)[9] was demonstrated in comparative clinical studies. A significantly higher remission rate for bupropion than for venlafaxine (Effexor) treatment was observed in a recent study.[10] Unlike most other antidepressants, with the exception of mirtazapine (Remeron) and maprotiline (Ludiomil), bupropion does not cause sexual dysfunction and its rate of sexual side-effects is not different from placebo.[11][12] Bupropion treatment is not associated with weight gain; on the contrary, in every study comparing bupropion with placebo or other antidepressants the bupropion group ended up with lower average weight.[13] Bupropion is more effective than SSRIs at improving the symptoms of hypersomnia and fatigue in depressed patients.[14] Zoloft bottles, with blue and green tablets Sertraline hydrochloride (also sold under brand names Zoloft, Lustral, Apo-Sertral, Asentra, Gladem, Serlift, Stimuloton, Xydep, Serlain, Concorz) is an antidepressant of the selective serotonin reuptake inhibitor (SSRI) class. ... Fluoxetine pills. ... Paroxetine or paroxetine hydrochloride is a selective serotonin reuptake inhibitor (SSRI) antidepressant. ... Lexapro pills Escitalopram (Lexapro, Cipralex, Sipralexa and Seroplex)[1] is an antidepressant of the selective serotonin reuptake inhibitor (SSRI) class. ... Venlafaxine hydrochloride is a prescription antidepressant used in the treatment of clinical depression, anxiety disorders, and (controversially) bipolar disorder. ... Mirtazapine is an antidepressant introduced by Organon International in 1996 used for the treatment of mild to severe depression. ... To meet Wikipedias quality standards, this article may require cleanup. ... Hypersomnia, also known as excessive daytime sleepiness (EDS), is excessive amount of sleepiness. ... “Fatigue (physical)” redirects here. ...


According to several surveys, adding bupropion to an SSRI (augmentation) is the preferred strategy among clinicians when the patient does not respond to the SSRI (treatment resistant depression). Although no placebo-controlled studies of bupropion augmentation have been conducted, multiple open-label trials and case reports generally support this strategy.[15] For example, combination of bupropion and citalopram (Celexa) was observed to be more effective than switch to a single antidepressant. Addition of bupropion to an SSRI (primarily fluoxetine or sertraline) resulted in a significant improvement (70–80% of the patients responded) in patients who had an incomplete response to the corresponding first line antidepressant.[16][17] Bupropion improved "energy" ratings, which originally decreased under the influence of the SSRI; improvements in mood and motivation, and some improvement of cognitive and sexual functions were also noted. Interestingly, sleep quality and anxiety in most cases stayed unchanged.[17]


Smoking cessation

Bupropion reduces the severity of nicotine cravings and addiction/withdrawal symptoms. Urge to smoke was a problem for 27% of subjects receiving bupropion vs 56% receiving placebo at the end of a 7-week treatment. 21% of the bupropion group reported mood swings vs 32% of the placebo group in the same study.[18] Bupropion treatment course lasts for seven to twelve weeks, with the patient halting the use of tobacco around ten days into the course. The efficacy of bupropion is similar to that of nicotine replacement therapy. Bupropion approximately doubles the chance of quitting smoking successfully after 3 months. 1 year after the treatment the odds of sustaining smoking cessation are still 1.5 higher in the bupropion group than in the placebo group.[19] Combination of bupropion and nicotine appears not to further increase the cessation rate. In a direct comparison, recently approved varenicline (Chantix) showed superior efficacy. After 1 year the rate of continuous abstinency was 10% for placebo, 15% for bupropion, and 23% for varenicline.[20] Bupropion slows down the weight gain occurring in the first weeks after quitting smoking (after 7 weeks, the placebo group had an average 2.7 kg increase in weight vs 1.5 kg for the bupropion group). However, with time this effect becomes negligible (after 26 weeks, both placebo and bupropion group recorded 4.8 kg weight gain).[18] Nicotine is an alkaloid found in the nightshade family of plants (Solanaceae), predominantly in tobacco, and in lower quantities in tomato, potato, eggplant (aubergine), and green pepper. ... Withdrawal, also known as withdrawal syndrome, refers to the characteristic signs and symptoms that appear when a drug that causes physical dependence is regularly used for a long time and then suddenly discontinued or decreased in dosage. ... “Placebo effect” redirects here. ... Varenicline (trade name Chantix in the USA and Champix in Europe and Canada, manufactured by Pfizer, usually in the form of varenicline tartrate) is a prescription medication used to treat smoking addiction. ...


Sexual dysfunction

Although it is not an FDA-approved indication, a large body of evidence exists in favor of bupropion's use for sexual dysfunction. According to a survey, bupropion is the drug of choice among psychiatrists for the treatment of serotonin reuptake inhibitor (SSRI) induced sexual dysfunction. In that survey, 36 percent of the responding psychiatrists said they preferred switching their patients with sexual dysfunction to bupropion; however, 43 percent said they favored the addition of bupropion to the current medication (augmentation).[21] There are studies demonstrating efficacy of both approaches, with improvement of desire and orgasm components of the sexual function being the most often noted. For the augmentation approach, indications exist that the addition of at least 200 mg/day of bupropion to the SSRI medication is necessary to achieve a statistically significant improvement. The addition of 150 mg/day of bupropion to the SSRI regimen of the patients with sexual dysfunction did not produce a statistically significant difference from that of placebo.[22][23][24][25][26][27] Selective serotonin reuptake inhibitors (SSRIs) are a class of antidepressants. ... In music and music theory augmentation is the lengthening or widening of rhythms, melodies, intervals, chords. ...


Several studies have indicated that bupropion also relieves sexual dysfunction among non-depressed patients. After a 12-weeks course in a mixed male/female double-blind study, 63% of subjects on bupropion rated their condition as improved or much improved vs. only 3% of subjects on placebo.[28] Two studies, one of which was placebo-controlled, demonstrated efficacy of bupropion for women with hypoactive sexual desire[29][30] resulting in significant improvement of arousal, orgasm and overall satisfaction. Bupropion also showed promise as a treatment for sexual dysfunction caused by chemotherapy for breast cancer[31] and for orgasmic dysfunction.[32] As with the treatment of SSRI-induced sexual disorder, a higher dose of bupropion (300 mg) may be necessary, since a randomized study, which employed a lower dose (150 mg), failed to find any significant difference between bupropion, sexual therapy or combined treatment.[33] Interestingly, bupropion does not affect any measures of sexual functioning in healthy males.[34]


Obesity

A recent review/meta-analysis of anti-obesity medications pooled the results of three double-blind placebo controlled trials of bupropion. This meta-analysis confirmed efficacy of bupropion (400 mg/day) for obesity. Over 6-12 months period, weight loss in the bupropion group (4.4 kg) was significantly greater than in the placebo group (1.7 kg). The same review found the differences in weight loss between bupropion and other established weight loss medications, such as sibutramine, orlistat and diethylpropion, to be statistically insignificant.[35] A meta-analysis is a statistical practice of combining the results of a number of studies. ... Sibutramine (Meridia® in the USA, Reductil® in Europe), usually as sibutramide hydrochloride monohydrate, is an orally administered agent for the treatment of obesity. ... Orlistat (marketed under the trade name Xenical by Roche; or over-the-counter as alli by GlaxoSmithKline, pronounced , like the English word ally)—also known as tetrahydrolipstatin—is a drug designed to treat obesity. ... Diethylpropion (Tenuate®) is a sympathomimetic stimulant drug marketed as an appetite suppressant. ...


Other indications

Bupropion is also effective for adult attention-deficit hyperactivity disorder[36] and for prevention of seasonal affective disorder[37] and was approved by the FDA for the latter indication.[38] Attention-Deficit/Hyperactivity Disorder (ADHD) (sometimes referred to as ADD for those without hyperactivity) is thought to be a neurological disorder, always present from childhood, which manifests itself with symptoms such as hyperactivity, forgetfulness, poor impulse control, and distractibility. ... Seasonal affective disorder, or SAD, also known as winter depression or winter blues is an affective, or mood, disorder. ...


Mode of action

Bupropion is a dopamine and norepinephrine reuptake inhibitor. It is about twice as potent an inhibitor of dopamine uptake than norepinephrine uptake. As bupropion is rapidly converted in the body into several metabolites with differing activity, its action cannot be understood without understanding its metabolism. Occupancy of dopamine transporter (DAT) by bupropion and its metabolites in human brain measured by positron emission tomography was 6–22% according to an independent study[39] and 12–35% according to GSK researchers.[40] Based on the analogy with serotonin reuptake inhibitors, higher than 50% inhibition of DAT would be needed for the dopamine reuptake mechanism to be a major mechanism of bupropion action. Bupropion does not inhibit MAO (i.e. is not a MAOI) and serotonin reuptake. However, it has been shown to indirectly enhance firing of serotonergic neurons (via activation of downstream norepinephrine flow). Bupropion has also been shown to act as a noncompetitive α3β4 nicotinic antagonist.[41] The degree of inhibition of α3β4-receptors correlates well with the decrease of self-administration of morphine and metamphetamine in rats,[42] and may be relevant to the effect of bupropion on nicotine addiction. Dopamine is a phenethylamine naturally produced by the human body. ... Norepinephrine (INN)(abbr. ... The dopamine transporter or DAT is a monoamine transporter that is specific for clearing the neurotransmitter dopamine out of the synaptic cleft and into a glial cell or the presynaptic neuron. ... Image of a typical positron emission tomography (PET) facility Positron emission tomography (PET) is a nuclear medicine medical imaging technique which produces a three-dimensional image or map of functional processes in the body. ... Monoamine oxidase Monoamine oxidases (singular abbreviation MAO) (EC 1. ... Monoamine oxidase inhibitors (MAOIs) are a class of antidepressant drugs prescribed for the treatment of depression. ... Serotonin (pronounced ) (5-hydroxytryptamine, or 5-HT) is a monoamine neurotransmitter synthesized in serotonergic neurons in the central nervous system (CNS) and enterochromaffin cells in the gastrointestinal tract of animals including humans. ...


Pharmacokinetics

Important metabolites of bupropion

Bupropion is metabolized in the liver. It has several active metabolites: R,R-hydroxybupropion, S,S-hydroxybupropion, threo-hydrobupropion and erythro-hydrobupropion. These active metabolites are further metabolized to inactive metabolites and eliminated through excretion into the urine. Pharmacological data on bupropion and its metabolites combined from several sources are presented in the Table below. In addition, bupropion is known to inhibit weakly α1 adrenaline receptor (with 14% potency of its dopamine uptake inhibition) and histamine H1 receptor (with 9% potency of dopamine uptake inhibition).[43] Image File history File links This is a lossless scalable vector image. ... Image File history File links This is a lossless scalable vector image. ... The liver is an organ present in vertebrates and some other animals. ...


Table. Pharmacology of bupropion and its metabolites.[44][45][46][43][47]

Exposure (concentration over time; bupropion exposure = 100%) and half-life
Bupropion R,R-
Hydroxy
bupropion		 S,S-
Hydroxy
bupropion		 Threo-
hydro
bupropion		 Erythro-
hydro
bupropion
Exposure 100% 800% 160% 310% 90%
Half-life 10 h (IR)
17 h (SR)		 21 h 25 h 26 h 26 h
Inhibition potency (potency of DA uptake inhibition by bupropion = 100%)
DA uptake 100% 0% (rat) 70% (rat) 4% (rat) No data
NE uptake 27% 0% (rat) 106% (rat) 16% (rat) No data
Ser uptake 2% 0% (rat) 4%(rat) 3% (rat) No data
α3β4 nicotinic 53% 15% 10% 7% (rat) No data
α4β2 nicotinic 8% 3% 29% No data No data
α1* nicotinic 12% 13% 13% No data No data

Thus, the biological activity of bupropion can be attributed to a great degree to its active metabolites, in particular to S,S-hydroxybupropion. GSK developed this metabolite as a separate drug radafaxine,[48] but discontinued development in 2006 due to "poor test results". There are very few or no other articles that link to this one. ...


Bupropion is metabolized to hydroxybupropion by a cytochrome P450 enzyme CYP2B6. Alcohol causes increase of CYP2B6 in the liver, and persons with a history of alcohol use metabolize bupropion faster. The mechanism of formation of erythro-hydrobupropion and threo-hydrobupropion has not been studied but probably it is mediated by one of the carbonyl reductase enzymes. The metabolism of bupropion is highly variable: the effective dose of bupropion received by different individuals, who ingested the same amount of the drug, may differ as much as 5.5 times (and half-life time from 3 to 16 hours), and of hydroxybupropion as much as 7.5 times (and half-life time from 12 to 38 h)[49][50] Cytochrome P450 Oxidase (CYP2E1) Cytochrome P450 oxidase (commonly abbreviated CYP) is a generic term for a large number of related, but distinct, oxidative enzymes (EC 1. ...


Significant interspecies differences in metabolism of bupropion exist, with guinea pigs' metabolism of the drug being closest to the human metabolism.[51] Particular caution is needed when extrapolating the results of the experiments on rats to humans since hydroxybupropion, the main metabolite of bupropion in humans, is absent in rats.[52] Binomial name Cavia porcellus (Linnaeus, 1758) Guinea pigs (also called cavies) are rodents belonging to the family Caviidae and the genus Cavia, originally indigenous to the Andes. ...


Contraindications and warnings

Bupropion is contraindicated at

Caution should be exercised when treating patients with This article is about the medical term, epileptic seizure, as distinct from a non-epileptic seizure. ... Alprazolam 2mg tablets The benzodiazepines (pronounced , or benzos for short) are a class of psychoactive drugs considered as minor tranquilizers with varying hypnotic, sedative, anxiolytic, anticonvulsant, muscle relaxant and amnesic properties, which are brought on by slowing down the central nervous system. ... For the symphonic black metal band, see Anorexia Nervosa (band) For other uses, see Anorexia Anorexia nervosa is a psychiatric diagnosis that describes an eating disorder characterized by low body weight and body image distortion with an obsessive fear of gaining weight. ... Bulimia nervosa, more commonly known as bulimia, is a psychological condition in which the subject engages in recurrent binge eating followed by intentionally doing one or more of the following in order to compensate for the intake of the food and prevent weight gain: vomiting inappropriate use of laxatives, enemas... Monoamine oxidase inhibitors (MAOIs) are a class of antidepressant drugs prescribed for the treatment of depression. ...

  • Liver damage (e.g. cirrhosis) as the drug levels may be higher than in other patients
  • Severe kidney disease as in such patients the levels of hydroxybupropion and threo-hydrobupropion are 2-3 times higher than in normal subjects
  • Severe hypertension as bupropion is known to cause hypertension
  • Pediatric patients, adolescents and young adults (see below)[53]

Cirrhosis of the liver is a consequence of chronic liver disease characterized by replacement of liver tissue by fibrotic scar tissue as well as regenerative nodules, leading to progressive loss of liver function. ... See the article on the kidney for the anatomy and function of healthy kidneys and a list of diseases involving the kidney. ... This article does not cite any references or sources. ...

Suicide risk

The FDA requires all antidepressants, including bupropion, to carry a black box warning that states "Antidepressants increased the risk of suicidal thinking and behavior (suicidality) in short-term studies in children and adolescents with Major Depressive Disorder (MDD) and other psychiatric disorders... The average risk of such events in patients receiving antidepressants was 4%, twice the placebo risk of 2%." Further generic warnings in the prescribing information say "It is unknown whether the suicidality risk in pediatric patients extends to longer-term use, i.e., beyond several months. It is also unknown whether the suicidality risk extends to adults... Adults with MDD or co-morbid depression in the setting of other psychiatric illness being treated with antidepressants should be observed similarly for clinical worsening and suicidality, especially during the initial few months of a course of drug therapy, or at times of dose changes, either increases or decreases."[53]


FDA analysts also found that the risk of suicidal thoughts and behavior strongly depends on age of a person. In addition to increasing this risk in children and adolescents, antidepressants may increase it as much as 1.5 times in young (age 18–24) adults (data close to statistical significance). However, they decrease the suicidal thoughts and behavior for persons aged 31 to 64 years by 23% (statistically significant). Most importantly, considering the high risk of suicide among older people, antidepressants decrease suicidal thoughts and behavior 2.5-fold for persons 65 or more years old.[54]


The suicidal ideation/behavior in clinical trials is rare. For the above analysis, the FDA had to combine the results of 295 recent trials of 11 different antidepressants for psychiatric indications in order to obtain statistically significant results. Considered separately, bupropion and 9 other antidepressants were not statistically different from placebo. Only fluoxetine caused a significant decrease in suicidal ideation/behavior.[54]


The suicidal behavior is even less likely when bupropion is prescribed for quitting smoking. According to Cochrane Database review there have been 4 suicides per 1,000,000 prescriptions and 1 case of suicidal behavior/ideation per 10,000 prescriptions of bupropion for smoking cessation in the UK. The review concludes that "Although some suicides and deaths while taking bupropion have been reported, thus far there is insufficient evidence to suggest they were caused by bupropion."[55]


Abuse liability

According to the US government classification of psychiatric medications, bupropion is non-abusable[56] or has low abuse potential[57]. However, in animal studies bupropion maintained intravenous self-administration by squirrel monkeys[58] and rats[59], which may indicate abuse potential. On the other hand, important differences of bupropion metabolism in rats and humans make any extrapolation of rats' results to humans invalid (see Pharmacokinetics). An intravenous drip in a hospital Intravenous therapy or IV therapy is the administration of liquid substances directly into a vein. ...


Two studies on drug abusers indicated that subjective effects of bupropion are markedly different from those of amphetamine.[60][61] Healthy volunteers trained to discriminate amphetamine and placebo, recognized bupropion (400 mg) as amphetamine in 20% of cases as compared to 10% for placebo and 75% for methylphenidate (Ritalin) (20 mg). They also reported feeling alert, vigorous, elated and energetic, reflecting general stimulating properties of bupropion. However, in contrast to amphetamine and methylphenidate, there was no feeling of "liking the drug" and desire to take it again.[62] A comparison of bupropion SR (150 mg) and caffeine (178 mg) indicated that caffeine may have higher abuse liability since caffeine resulted in greater frequency of reports of pleasant feelings and "high" than bupropion.[63] Amphetamine or Amfetamine (Alpha-Methyl-PHenEThylAMINE), also known as, beta-phenyl-isopropylamine, and benzedrine, is a prescription stimulant commonly used to treat Attention-deficit hyperactivity disorder (ADHD) in adults and children. ... Vitamin R redirects here. ... Caffeine is a xanthine alkaloid compound that acts as a stimulant in humans. ...


There have been only three reports of bupropion abuse in the literature. All three cases were teenagers crushing and insufflating (snorting) bupropion, one of them ending up with seizures.[64] An article on abuse of medications in prisons mostly concerned with the recreational use of quetiapine (Seroquel) mentions bupropion as one of the psychotropic medications commonly abused by inmates. Other such medications are gabapentin (Neurontin), tricyclic antidepressants and trihexyphenidyl.[65] Insufflation (Latin insufflatio blowing on or into) is the practice of inhaling substances into a body cavity. ... Quetiapine (pronounced kwe-TYE-a-peen or ), marketed by AstraZeneca, with the brand name Seroquel, belongs to a series of neuroleptics known as atypical antipsychotics, which have, over the last two decades, become increasingly popular alternatives to typical antipsychotics, such as haloperidol (Haldol). ... Gabapentin (brand name: Neurontin®) was initially synthesized to mimic the structure of GABA for the treatment of epilepsy. ... Chemical structure of the tricyclic antidepressant amitriptyline Tricyclic antidepressants are a class of antidepressant drugs first used in the 1950s. ... // Introduction Trihexyphenidyl is an antiparkinson agent of the antimuscarinic class of agents and is chemically a tertiary amine. ...


Side effects

For Bupropion SR (300 mg/day) common side effects with the greatest difference from placebo are dry mouth (17% vs 7% for placebo), nausea (13% vs 8% for placebo), insomnia (11% vs 6% for placebo), tremor (6% vs 1% for placebo), excessive sweating (6% vs 2% for placebo) and tinnitus (6% vs 2% for placebo). The two side effects which most often resulted in interruption of the treatment in the same trial were rash (2.4%) and nausea (0.8%). (The development of mild to moderate skin rashes is associated with sensitivity to dye components within the pill coating. This can often be alleviated by simply prescribing a different color pill.) [53] Adverse effect, in medicine, is an abnormal, harmful, undesired and/or unintended side-effect, although not necessarily unexpected, which is obtained as the result of a therapy or other medical intervention, such as drug/chemotherapy, physical therapy, surgery, medical procedure, use of a medical device, etc. ... Xerostomia is the medical term for a dry mouth due to a lack of saliva. ... For the Beck song, see Nausea (song). ... This article is about the sleeping disorder. ... For the film see Tremors (film). ... Sweating (also called perspiration or sometimes transpiration) is the production and evaporation of a fluid, consisting primarily of water as well as a smaller amount of sodium chloride (the main constituent of table salt), that is excreted by the sweat glands in the skin of mammals. ... Tinnitus (IPA pronunciation: or ,[1] from the Latin word for ringing[2]) is the perception of sound in the human ear in the absence of corresponding external sound(s). ... A rash is a change in skin which affects its color, appearance or texture. ...


Seizure is the most controversial side effect of bupropion, which caused its temporary withdrawal (see History). The risk of seizure is highly dose-dependent: 0.1% at 100–300 mg of bupropion, 0.4% at 300–450 mg, and 2% at 600 mg. For comparison, the incidence of first unprovoked seizure in general population is 0.07-0.09%; the risk of seizure for other antidepressants is as follows: imipramine 0.1-0.6% depending on dosage, amitriptiline 0-0.06% depending on dosage, clomipramine 0.5%, maprotiline 0.4%, fluoxetine and fluvoxamine 0.2%.[66] Experiments on mice indicate that increased susceptibility to seizure is a general side effect of antidepressants inhibiting norepinephrine transporter, such as imipramine, desipramine and reboxetine, given chronically.[67] On the other hand, depression was reported to increase occurrence of seizures 2-7 fold as compared to the general population. In this light, the above statistics could indicate that low to moderate doses of antidepressants, including bupropion, may actually have an anti-convulsive action.[68] Nevertheless, patients using bupropion should still be screened for pre-disposing factors that could contribute to and/or indicate a low seizure threshold. A prescriber may also review all other medications/substances the patient is using and make dosing decisions based on the results. This article is about the medical term, epileptic seizure, as distinct from a non-epileptic seizure. ... Bupropion (INN; also amfebutamone,[1] brand names Wellbutrin, Zyban, Budeprion and Buproban) is an atypical antidepressant, which acts as a dopamine reuptake inhibitor,[2] and a nicotinic antagonist. ... This article does not cite any references or sources. ... Amitriptyline (or Amitryptyline) hydrochloride (sold as Elavil®, Tryptanol®, Endep®, Elatrol®, Tryptizol®, Trepiline®, Laroxyl®) is a tricyclic antidepressant drug. ... Clomipramine (brand-name Anafranil®) is a tricyclic antidepressant. ... To meet Wikipedias quality standards, this article may require cleanup. ... Fluoxetine pills. ... Fluvoxamine (brand name as Luvox®, Faverin®, Fevarin® and Dumyrox®) is an antidepressant which functions pharmacologically as a selective serotonin reuptake inhibitor. ... This article does not cite any references or sources. ... Desipramine is a tricyclic antidepressant (TCA) that inhibits the reuptake of norepinephrine. ... Reboxetine is an antidepressant drug used in the treatment of clinical depression, panic disorder and ADD/ADHD. Its mesilate ( methanesulfonate) salt is sold under tradenames including Edronax®, Norebox®, Prolift®, Solvex® or Vestra®. Reboxetine has two chiral centers, but it only exists as two enantiomers, (R,R)-(-)- and (S,S)-(+)-reboxetine. ...


Three cases of liver toxicity of bupropion have been reported in the literature[69]. This is extremely rare considering the widespread use of the drug.


The prescribing information notes that hypertension, sometimes severe, was observed in some patients, both with and without pre-existing hypertension, treated with bupropion. At the same time, the frequency of this side effect was under 1% and not significantly higher than for placebo.[53] In a group of cardiac patients with depression, high doses of bupropion (400-500 mg/day) caused a rise of supine blood pressure but no effect on pulse rate.[70] No statistically significant changes in blood pressure or heart rate occurred in patients both with and without heart conditions at a lower dose (300 mg/day) .[71] In a study of bupropion for ADHD, a rise of systolic blood pressure by 6 mm Hg and heartbeat rate by 7 bits per minute (both statistically significant) was observed.[72] A study of smokers hospitalized for heart disease found a 1.5-fold increase (close to being statistically significant) in the subsequent cardiovascular events in bupropion group as compared to the placebo group but no difference in blood pressure.[73] Although cardiovascular side effects of bupropion appear to be mild, it can not be recommended for patients with heart disease since the safety comparison with SSRI antidepressants (such as sertraline and fluoxetine which may have a preventative effect after a myocardial infarction[74]) is not in its favor. This article does not cite any references or sources. ... Supine as an adjective generally refers to any upward-facing position. ... DISCLAIMER Please remember that Wikipedia is offered for informational use only. ... Systolic is the adjective form of systole, typically referring to the contraction activity of the heart. ... Zoloft bottles, with blue and green tablets Sertraline hydrochloride (also sold under brand names Zoloft, Lustral, Apo-Sertral, Asentra, Gladem, Serlift, Stimuloton, Xydep, Serlain, Concorz) is an antidepressant of the selective serotonin reuptake inhibitor (SSRI) class. ... Fluoxetine pills. ... Acute myocardial infarction (AMI or MI), more commonly known as a heart attack, is a disease state that occurs when the blood supply to a part of the heart is interrupted. ...


A single case of clitoral priapism (clitorism) has been reported in the literature.[75] Fresco of Priapus, House of the Vettii, Pompeii. ... Clitorism (klitor-Izm), from the Greek kleitoris + ismos, is the female counterpart of priapism. ...


In the UK, more than 7,600 reports of suspected adverse reactions were collected in the first two years after bupropion's approval by MHRA as a part of the Yellow Card Scheme which monitored side effects. Approximately 540,000 people were treated by bupropion for smoking cessation during that period. 60 reports of "suspected (emphasis by MHRA) adverse reactions to Zyban which had a fatal outcome" were received. The agency concluded that "in the majority of cases the individual’s underlying condition may provide an alternative explanation."[76] This is consistent with a large (9300 patients) safety study, which indicated that mortality of smokers taking bupropion is not higher than natural mortality of smokers of the same age.[77] The logo of the MHRA. The Medicines and Healthcare products Regulatory Agency (MHRA) is the UK government agency which is responsible for ensuring that medicines and medical devices work and are acceptably safe. ...


Interactions

As bupropion is metabolized to hydroxybupropion by CYP2B6, drug interactions with CYP2B6 inhibitors (paroxetine, sertraline, fluoxetine metabolite norfluoxetine, diazepam, clopidogrel, orphenadrine and others) are possible. The expected result is the increase of bupropion and decrease of hydroxybupropion blood concentration. The reverse effect (decrease of bupropion and increase of hydroxybupropion) can be expected with CYP2B6 inducers (carbamazepine, clotrimazole, rifampicin, ritonavir, St John's Wort and others).[78] CYP2B6 is a member of the Cytochrome P450 group of enzymes. ... Carbamazepine (sold under the brand-names Biston, Calepsin, Carbatrol, Epitol, Equetro, Finlepsin, Sirtal, Stazepine, Tegretol, Telesmin, Timonil, sometimes abbreviated CBZ) is an anticonvulsant and mood stabilizing drug, used primarily in the treatment of epilepsy and bipolar disorder. ... Clotrimazole is a potent, specific inhibitor of p450 enzymes. ... Rifampicin (INN) (IPA: ) or rifampin (USAN) is a bacteriocidal antibiotic drug of the rifamycin group. ... Ritonavir is a drug from the protease inhibitor class used to treat AIDS. It is manufactured as Norvir® by Abbott Laboratories. ... Binomial name Hypericum perforatum L. St Johns wort (IPA pronunciation: , rhyming with hurt, or ) used alone refers to the species Hypericum perforatum, also known as Klamath weed or Goat weed, but, with qualifiers, is used to refer to any species of the genus Hypericum. ...


Hydroxybupropion (but not bupropion) inhibits CYP2D6 and is a substrate of that enzyme. Significant increase of the concentration of some drugs metabolized by CYP2D6 (venlafaxine, desipramine and dextromethorphan, but not fluoxetine or paroxetine) when taken with bupropion has been observed.[78][79] Cytochrome P450 2D6 (CYP2D6), a member of the cytochrome P450 mixed-function oxidase system, is one of the most important enzymes involved in the metabolism of xenobiotics in the body. ...


Bupropion lowers the seizure threshold; therefore, extreme care should be taken when prescribing bupropion with other medications lowering the seizure threshold (antipsychotics, theophylline, steroids, some tricyclic antidepressants (see: Side effects).[53] Combination with nicotine replacement therapies can elevate blood pressure; at the same time, it is not more effective than nicotine patch or bupropion alone (see:Indications--Smoking cessation), so it should not be recommended. Nicotine replacement therapy (NRT) is the use of various forms of nicotine delivery methods intended to replace nicotine obtained from smoking or other tobacco usage. ...


The prescribing information recommends to minimize the use of alcohol, since in rare cases bupropion reduced alcohol tolerance, and also because the excessive use of alcohol may lower the seizure threshold.[53] A small study conducted by GSK indicated that bupropion (100 mg) may counteract the subjective effects of small doses of alcohol (16-32 mL, slightly less than 1-2 US standard drinks). The volunteers reported feeling more sober and clear headed, and less sedated. Bupropion also partially neutralized the detrimental effect of alcohol on auditory vigilance. In addition, the combination of bupropion (100 mg) and 2 drinks of alcohol increased the heart rate by 6 beats/min (statistically significant).[80]


Dosage

  • Depression: the target dosage is 300 mg daily, starting with 150 mg in the first few days. If indicated and directed by physician, the dosage may be increased to a maximum of 450 mg daily.
  • Tobacco withdrawal: 150 mg initially, may be increased to 300 mg if indicated and directed by physician. In patients also receiving insulin, sympathomimetic anorectical drugs, or antimalaria agents, the daily dose of bupropion should not exceed 150 mg.
  • Due to high variability of bupropion's pharmacokinetics (see Pharmacokinetics) the recommended starting dose of 150 mg in some patients may be equivalent to 450-500 mg for an average patient. Based on this, some researchers advocated monitoring of the blood level of bupropion and hydroxybupropion.[81] As this is impossible in a routine clinical practice, a lower starting dose of 75 mg should be considered. This dose can be increased gradually based on individual tolerability up to the maximum dose of 450 mg. According to GSK, a 150-mg Bupropion SR tablet can be divided in two and still retain its sustain-release characteristics.[82]

Malaria is a vector-borne infectious disease that is widespread in tropical and subtropical regions, including parts of the Americas, Asia, and Africa. ...

Dose forms

Brand and generic pills are available in three forms: immediate release, sustained release (SR), and extended release (XL, ER). Sustained-release (SR), extended-release (ER, XR, or XL), time-release or timed-release, controlled-release (CR), or continuous-release (CR or Contin) pills are tablets or capsules formulated to dissolve slowly and release a drug over time. ... Sustained-release (SR), extended-release (ER, XR, or XL), time-release or timed-release, controlled-release (CR), or continuous-release (CR or Contin) tablets are pills formulated to dissolve slowly and release a drug over time. ...


Availability in the UK

Zyban is available via prescription, only if you are able to get a letter from a smoking cessation clinic to your GP confirming that you are a heavy smoker on whom nicotine replacement therapies have been tried and are useless.

Brand Name Dosage Color
Wellbutrin 75 mg yellow-gold
Wellbutrin 100 mg red
Wellbutrin SR 100 mg blue
Wellbutrin SR 150 mg purple
Wellbutrin SR 200 mg pink
Wellbutrin XL 150 mg white
Wellbutrin XL 300 mg white
Zyban SR 150 mg purple
Budeprion SR 100 mg light yellow
Budeprion XL 300 mg light yellow
Zylexx SR 75 mg white


Overdosage

GlaxoSmithKline has reported that overdoses of up to 30 g or more of Wellbutrin (bupropion) had resulted in seizure in about one third of all cases. Hallucinations, loss of consciousness, sinus tachycardia, and ECG changes such as conduction disturbances or arrhythmias were reported as other serious reactions of overdoses of bupropion alone. Multiple overdoses including bupropion had resulted in fever, rhabdomyolysis, stupor, hypotension, coma, muscle rigidity, and respiratory failure.[53] A hallucination is a sensory perception experienced in the absence of an external stimulus, as distinct from an illusion, which is a misperception of an external stimulus. ... Sinus tachycardia is a rhythm with elevated rate of impulses originating from the SA node, defined as a rate greater than 100 beats/min in an average adult. ... “QRS” redirects here. ... Cardiac arrhythmia is any of a group of conditions in which the electrical activity of the heart is irregular or is faster or slower than normal. ... Rhabdomyolysis is the breakdown of skeletal muscle due to injury, either mechanical, physical or chemical. ... This article is being considered for deletion in accordance with Wikipedias deletion policy. ... In physiology and medicine, hypotension refers to an abnormally low blood pressure. ... In medicine, a coma (from the Greek koma, meaning deep sleep) is a profound state of unconsciousness. ... Hypertonia is a condition marked by an abnormal increase in the tightness of muscle tone and a reduced ability of a muscle to stretch (i. ... Respiratory failure is a medical term for inadequate gas exchange by the respiratory system. ...


Additional information

Trade names

Korea (Korean: 한국 in South Korea or 조선 in North Korea, see below) is a geographic area, civilization, and former state situated on the Korean Peninsula in East Asia. ...

May cause false-positive for amphetamine

Two cases of false-positive urine amphetamine tests in persons taking bupropion have been reported. It is likely that bupropion metabolites erythro-hydrobupropion and threo-hydrobupropion, which have phenethylamine structure resembling amphetamine, were responsible for this reaction. More specific tests conducted afterwards were negative.[83][84]


Bipolar disorder

Recently, addition of bupropion to a mood-stabilizer in patients with bipolar depressions was shown to have the same effectiveness as placebo.[85]


References

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A digital object identifier (or DOI) is a standard for persistently identifying a piece of intellectual property on a digital network and associating it with related data, the metadata, in a structured extensible way. ... Year 2007 (MMVII) is the current year, a common year starting on Monday of the Gregorian calendar and the AD/CE era. ... is the 83rd day of the year (84th in leap years) in the Gregorian calendar. ... A digital object identifier (or DOI) is a standard for persistently identifying a piece of intellectual property on a digital network and associating it with related data, the metadata, in a structured extensible way. ... GlaxoSmithKline plc (LSE: GSK NYSE: GSK) is a British based pharmaceutical, biologicals, and healthcare company. ... Year 2007 (MMVII) is the current year, a common year starting on Monday of the Gregorian calendar and the AD/CE era. ... is the 133rd day of the year (134th in leap years) in the Gregorian calendar. ... 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Year 2007 (MMVII) is the current year, a common year starting on Monday of the Gregorian calendar and the AD/CE era. ... is the 147th day of the year (148th in leap years) in the Gregorian calendar. ... A digital object identifier (or DOI) is a standard for persistently identifying a piece of intellectual property on a digital network and associating it with related data, the metadata, in a structured extensible way. ... The logo of the MHRA. The Medicines and Healthcare products Regulatory Agency (MHRA) is the UK government agency which is responsible for ensuring that medicines and medical devices work and are acceptably safe. ... Year 2006 (MMVI) was a common year starting on Sunday (link displays full 2006 calendar) of the Gregorian calendar. ... is the 280th day of the year (281st in leap years) in the Gregorian calendar. ... 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External links

v • d • e
Stimulants
Ampakines Adrafinil • Armodafinil • Carphedon • Modafinil
Phenethylamines

4-Fluoroamphetamine • 4-MTA • α-PPP • Adderal • Amphetamine (Dexamphetamine) • Benzphetamine • Bupropion • Cathinone • Chlorphentermine • Clortermine •  • Diethylpropion • Dimethoxyamphetamine • Ephedrine • Epinephrine • Ethylamphetamine • Fenethylline • Fenfluramine • Levomethamphetamine • Lisdexamfetamine • MDMA • MDPV • Methamphetamine • Methcathinone • Methylone • Methylphenidate (Dexmethylphenidate) • Octopamine • Phendimetrazine • Phenmetrazine • Phentermine • Phenylephrine • Phenylpropanolamine • PMA • PMEA • PMMA • Propylamphetamine • Pseudoephedrine • Synephrine • Xylopropamine The Open Directory Project (ODP), also known as dmoz (from , its original domain name), is a multilingual open content directory of World Wide Web links owned by Netscape that is constructed and maintained by a community of volunteer editors. ... Stimulants are drugs that temporarily increase alertness and wakefulness. ... Ampakines are a new class of modified benzamide compounds known to enhance attention span and alertness. ... Adrafinil chemical structure Adrafinil is a mild central nervous system stimulant drug used to relieve excessive sleepiness and inattention in elderly patients. ... Armodafinil (Nuvigil®) is a drug produced by the pharmaceutical company Cephalon, currently in the process of receiving FDA approval. ... Carphedon was developed in Russia and is claimed to increase physical stamina along with improved tolerance to cold, its also used for amnesia treatment. ... Modafinil is a eugeroic drug generally prescribed to treat narcolepsy, made by the pharmaceutical company Cephalon Inc. ... Phenethylamine is an alkaloid and monoamine. ... 4-FMP, also known by its full chemical name 4-fluoroamphetamine, or 4-Fluoro-alpha-Methyl-Phenethylamine, is a central nervous system stimulant. ... 4MT structure 4-methylthioamphetamine is a drug known as 4MT, 4-MTA, Flatliners, 1-(4-methylthiophenyl)-2-aminopropane. ... Alpha-pyrrolidinopropiophenone (α-PPP) is a stimulant drug. ... Adderall 25 mg XR Capsules Adderall is a pharmaceutical stimulant amphetamine used to treat attention-deficit disorder/attention-deficit hyperactivity disorder and narcolepsy. ... Amphetamine or Amfetamine (Alpha-Methyl-PHenEThylAMINE), also known as, beta-phenyl-isopropylamine, and benzedrine, is a prescription stimulant commonly used to treat Attention-deficit hyperactivity disorder (ADHD) in adults and children. ... Dextroamphetamine (also known as dextroamphetamine sulfate, dexamphetamine, dexedrine, Dexampex, Ferndex, Oxydess II, Robese, Spancap #1, and, informally, Dex), a stereoisomer of amphetamine, is an indirect-acting stimulant that releases norepinephrine from nerve terminals, thus promoting nerve impulse transmission. ... USA by Pharmacia. ... Cathinone (β-ketoamphetamine) is a monoamine alkaloid found in the shrub Catha edulis (Khat). ... Chlorphentermine (Apsedon, Desopimon, Lucofen) is a stimulant drug which was used as an appetite suppressant. ... Clortermine is a stimulant drug which was used as an appetite suppressant. ... Diethylpropion (Tenuate®) is a sympathomimetic stimulant drug marketed as an appetite suppressant. ... DMA, or dimethoxyamphetamine, is a series of lesser-known psychedelic drugs similar in structure to Amphetamine and to TMA (Trimethoxyamphetamine). ... Ephedrine (EPH) is a sympathomimetic amine similar in structure to the synthetic derivatives amphetamine and methamphetamine. ... Adrenaline redirects here. ... N-ethylamphetamine (Etilamfetamine, Apetinil) is a stimulant drug derived from amphetamine which was invented in the early 1900s. ... Fenethylline (Captagon) is a synthetic stimulant drug. ... Fenfluramine is a drug that was part of the Fen-Phen anti-obesity (the other drug being phentermine). ... Levomethamphetamine (other names: l-desoxyephedrine, l-methamphetamine, levmetamfetamine ) is the l- stereoisomer of methamphetamine, a sympathomimetic vasoconstrictor which is the active ingredient used in some over-the-counter nasal decongestants. ... Lisdexamfetamine (L-lysine-d-amphetamine) is a prodrug of the psychostimulant d-amphetamine coupled with the essential amino acid L-lysine. ... ecstasy and religious ecstasy MDMA, most commonly known today by the street name ecstasy, is a synthetic entactogen of the phenethylamine family whose primary effect is to stimulate the brain to rapidly secrete large amounts of serotonin, causing a general sense of openness, empathy, energy, euphoria, and well-being. ... This page may meet Wikipedia’s criteria for speedy deletion. ... Methamphetamine (methylamphetamine or desoxyephedrine), popularly shortened to meth, is a psychostimulant and sympathomimetic drug. ... This article or section is not written in the formal tone expected of an encyclopedia article. ... Methylone is a designer drug that is an analog of MDMA (Ecstasy). ... Vitamin R redirects here. ... Dexmethylphenidate (commercially known as Focalin) is a pharmaceutical drug used to treat Attention Deficit Hyperactivity Disorder. ... Octopamine (4-(2-amino-1-hydroxy-ethyl)phenol) is a biogenic amine which is closely related to noradrenaline. ... Phendimetrazine (Bontril®) is a weight loss medication. ... Phenmetrazine is an amphetamine-like drug. ... Phentermine is an appetite suppressant of the amphetamine and phenethylamine class. ... Phenylephrine or neosynephrine is an α-adrenergic receptor agonist used primarily as a decongestant, as an agent to dilate the pupil and, rarely, to increase blood pressure. ... Phenylpropanolamine (PPA) is a drug of the phenethylamine family used as a decongestant and also as an appetite suppressant. ... 8 pills of PMA recovered by the DEA PMA structure PMA 3D structure PMA (paramethoxyamphetamine, or p-methoxyamphetamine) is a synthetic phenethylamine drug, psychostimulant and hallucinogen. ... Para-methoxy-ethylamphetamine or PMEA is a stimulant drug related to PMA and ethylamphetamine. ... Para-methoxy-methamphetamine or PMMA is a stimulant drug related to PMA and methamphetamine. ... N-propylamphetamine is a stimulant drug derived from amphetamine which was invented in the 1970s. ... Pseudoephedrine (commonly abbreviated as PSE) is a sympathomimetic amine commonly used as a decongestant. ... Synephrine Synephrine is a dietary supplement aimed at encouraging fat loss. ... 3,4-dimethylamphetamine (Xylopropamine, α,3,4-trimethylphenethylamine) is a stimulant drug derived from amphetamine which was invented in the 1950s. ...

Piperazines BZP • MeOPP • MBZP
Xanthines Caffeine • Aminophylline • Paraxanthine • Theobromine • Theophylline
Others

4-Methyl-aminorex • Aminorex • Arecoline • Bemegride • CFT • Clenbuterol • Cocaethylene • Cocaine • Cotinine • Cyclopentamine • Desoxypipradrol • Diphenyl prolinol • Fencamfamine • Indatraline • Leptacline • Mazindol • Mesocarb • Naphthylisopropylamine • Nicotine • Nikethamide • Nocaine • Nomifensine • Pemoline • Pentetrazol • Pipradrol • Propylhexedrine • Pyrovalerone • Sibutramine • Strychnine • Troparil • Vanoxerine • Yohimbine Basic piperazine structure Piperazine is a six-sided organic ring compound containing two opposing nitrogen atoms (see image). ... Benzylpiperazine (BZP) is a recreational drug with euphoric, stimulant properties. ... 4-methoxyphenylpiperazine (Paraperazine, MeOPP, 4-MeOPP) is a piperazine derivative with stimulant effects which has been sold as an ingredient in Party pills, initially in New Zealand and subsequently in other countries around the world. ... MBZP (1-methyl-4-benzylpiperazine) is a stimulant drug which is a derivative of benzylpiperazine. ... Xanthine (IPA: ), (3,7-dihydro-purine-2,6-dione), is a purine base found in most body tissues and fluids and in other organisms. ... Caffeine is a xanthine alkaloid compound that acts as a stimulant in humans. ... Aminophylline is a drug combination that contains theophylline and ethylenediamine in 2:1 ratio. ... Paraxanthine, or 1,7-dimethylxanthine, is a dimethylxanthine compound structurally related to caffeine. ... Theobromine, also known as xantheose,[1] is a bitter alkaloid of the cacao plant. ... Theophylline is a methylxanthine drug used in therapy for respiratory diseases such as COPD or asthma under a variety of brand names. ... 4-Methyl-aminorex is a stimulant drug of the 2-Amino-5-Aryloxazoline class. ... Aminorex is an anorectic stimulant drug of the 2-Amino-5-Aryloxazoline class. ... Arecoline is a natural organic compound which is an alkaloid found in betel nuts from the betel palm (Areca catechu) [1]. It is an oily liquid that is soluble in water, alcohols, and ether. ... Bemegride is a CNS stimulant and antidote for barbiturate poisoning. ... (-)-2-β-Carbomethoxy-3-β-(4-fluorophenyl)tropane (β-CFT, WIN 35,428) is a stimulant drug used in scientific research. ... Clenbuterol is a drug prescribed to sufferers of breathing disorders as a decongestant and bronchodilator. ... Cocaethylene is the chemical that is formed when cocaine and alcohol mix inside the body. ... Cocaine is a crystalline tropane alkaloid that is obtained from the leaves of the coca plant. ... Cotinine is a metabolite of nicotine. ... Cyclopentamine is a stimulant drug structurally related to methamphetamine, wherein the aromatic phenyl ring is replaced with a cyclopentane ring. ... Desoxypipradrol, also known as 2-(diphenylmethyl)piperidine or 2-DPMP, is a long-acting stimulant drug. ... Diphenyl prolinol, or (R,S)(+,-)-diphenyl-2-pyrrolidinyl-methanol, is a mild dopamine and norepinephrine reuptake inhibitor. ... Fencamfamine (Glucoenergan, Reactivan) is a stimulant which was developed in the 1960s as an appetite supressant, but was later withdrawn for this application due to problems with dependence and abuse. ... Illicit cocaine use is a major medical, public health problem, and economic problem, with approximately 2 million chronic users in the US alone. ... Mazindol is a central nervous system simulant. ... Mesocarb (Sidnocarb, Sydnocarb) is a stimulant drug which was developed in the USSR in the 1970s. ... Naphthylisopropylamine (PAL-287) is a stimulant drug developed for the treatment of amphetamine and cocaine addiction. ... Nicotine is an alkaloid found in the nightshade family of plants (Solanaceae), predominantly in tobacco, and in lower quantities in tomato, potato, eggplant (aubergine), and green pepper. ... Nikethamide is a stimulant which mainly affects the respiratory cycle. ... The Nocaine family includes a diverse assortment of piperidine based cocaine mimics. ... Nomifensine is a dopamine reuptake inhibitor that increases the amount of synaptic dopamine available to receptors by blocking dopamines re-uptake transporter. ... Pemoline is a medication for Attention-deficit hyperactivity disorder (ADHD). ... Metrazol is the commercial trademark of pentetrazol, pentamethylenetetrazol, or pentylenetetrazol (PTZ), a drug used as a circulatory and respiratory stimulant (another commercial name is Cardiazol). ... Pipradrol (Meretran) is a mild CNS stimulant which is no longer widely used in most countries due to concerns about its abuse potential, although this is less of a problem than with other stimulants that still are in current use such as methylphenidate. ... Propylhexedrine, also known as hexahydrodesoxyephedrine or dimethylcyclohexaneethanamine, is a sympathomimetic with varied medicinal uses, is an adrenergic compound used mainly to provide temporary symptomatic relief of nasal congestion due to colds, allergies and allergic rhinitis. ... Pyrovalerone (Centroton, Thymergix) is a stimulant drug developed in the late 1960s and used in France and some other European countries. ... Sibutramine (Meridia® in the USA, Reductil® in Europe), usually as sibutramide hydrochloride monohydrate, is an orally administered agent for the treatment of obesity. ... Strychnine (pronounced (British, U.S.), or (U.S.)) is a very toxic (LD50 = 10 mg approx. ... (-)-2β-Carbomethoxy-3β-phenyltropane (Troparil, β-CPT, WIN-35065-2) is a stimulant drug used in scientific research. ... Vanoxerine, also known as GBR-12909, is a piperazine derivative which is a potent and selective dopamine reuptake inhibitor. ... Yohimbine, also known under the outdated names quebrachin, aphrodin, corynine, yohimvetol and hydroergotocin, is the principal alkaloid of the bark of the West-African tree Pausinystalia yohimbe Pierre (formerly Corynanthe yohimbe), family Rubiaceae (Madder family). ...

See also Sympathomimetic amines
v • d • e
Phenethylamines
2C-B • 2C-C • 2C-D • 2C-E • 2C-I • 2C-N • 2C-T-2 • 2C-T-21 • 2C-T-4 • 2C-T-7 • 2C-T-8 • 3C-E • 4-FMP • Bupropion • Cathine • Cathinone • Clenbuterol • DESOXY • Dextroamphetamine • Methamphetamine • Diethylcathinone • Dimethylcathinone • DOC • DOB • DOI • DOM • bk-MBDB • Dopamine • Br-DFLY • Ephedrine • Epinephrine • Escaline • Fenfluramine • Levalbuterol • Levmetamfetamine • MBDB • MDA • MDMA • MDMC • MDEA • MDPV • Mescaline • Methcathinone • Methylphenidate • Norepinephrine • Phentermine • Salbutamol • Tyramine • Venlafaxine
v • d • e
Psychoanaleptics: antidepressants (N06A)
Monoamine oxidase inhibitors (MAOI) Harmaline • Iproniazid • Isocarboxazid • Nialamide • Pargyline • Phenelzine • Selegiline • Toloxatone • Tranylcypromine • Rasagiline
RIMAs: Brofaromine • Moclobemide
Dopamine reuptake inhibitor (DRI) Vanoxerine • Phenmetrazine
Norepinephrine-dopamine reuptake inhibitors (NDRI) Bupropion
Norepinephrine reuptake inhibitor (NRI) Atomoxetine • Maprotiline • Reboxetine • Viloxazine
Serotonin-norepinephrine reuptake inhibitor (SNRI) Desvenlafaxine • Duloxetine • Milnacipran • Nefazodone • Venlafaxine
Selective serotonin reuptake inhibitor (SSRI) Alaproclate • Citalopram • Dapoxetine • Escitalopram • Etoperidone • Fluoxetine • Fluvoxamine • Paroxetine • Sertraline • Zimelidine
Serotonin-noradrenaline-dopamine reuptake inhibitor (SNDRI) Brasofensine • Tesofensine • Nomifensine
Selective serotonin reuptake enhancer (SSRE) Tianeptine
Noradrenergic and specific serotonergic antidepressant (NaSSA) Mirtazapine
Tricyclic antidepressants (TCA) Amineptine • Amitriptyline • Amoxapine • Butriptyline • Clomipramine • Desipramine • Dibenzepin • Dothiepin • Doxepin • Imipramine • Iprindole • Lofepramine • Melitracen • Nortriptyline • Opipramol • Protriptyline • Trimipramine
Tetracyclic antidepressants Maprotiline • Mianserin • Mirtazapine• Nefazodone • Trazodone
v • d • e
Drugs used in addictive disorders (N07B)
Nicotine dependence Nicotine - Bupropion - Varenicline
Alcohol dependence Disulfiram - Calcium carbimide - Acamprosate - Naltrexone
Opioid dependence Buprenorphine - Methadone - Levacetylmethadol - Lofexidine - Naltrexone

  Results from FactBites:
 
Bupropion - Encyclopedia, History, Geography and Biography (1942 words)
Bupropion is both a dopamine reuptake inhibitor and a norepinephrine reuptake inhibitor.
Bupropion was first synthesized by Burroughs Research in 1966, and patented by Burroughs-Wellcome (later Glaxo-Wellcome, and, as of 2000, GlaxoSmithKline) in 1974.
Bupropion has also been shown to act as an competitive α3β4 nicotinic antagonist, the α3β4-antagonism has been shown to interrupt addiction in studies of other drugs such as ibogaine.
BUPROPION (3117 words)
Bupropion is a pharmacologically unique antidepressant, with structural similarities to amphetamines and diethylpropion.
Bupropion was voluntarily withdrawn from marketing due to the potential for seizures in 1986, and re-introduced in July, 1989.
Bupropion is an antidepressant and is approved as an aid in smoking cessation (Sigg, 1999) and in the treatment of bulimia (Ayers and Tobias, 2001).
  More results at FactBites »


 

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