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Stimulants (also referred to as psychostimulants) are psychoactive drugs which induce temporary improvements in either mental or physical functions or both. Examples of these kinds of effects may include enhanced alertness, wakefulness, and locomotion, among others. Due to their effects typically having an "up" quality to them, stimulants are also occasionally referred to as "uppers". Depressants or "downers", which decrease mental and/or physical function, are in stark contrast to stimulants and are considered to be their functional opposites. Stimulants are widely used throughout the world as prescription medicines and as illicit substances of recreational use or abuse.

Effects

Stimulants produce a variety of different kinds of effects by enhancing the activity of the central and peripheral nervous systems. Common effects, which vary depending on the substance in question, may include enhanced alertness, awareness, wakefulness, endurance, productivity, and motivation, increased arousal, locomotion, heart rate, and blood pressure, and the perception of a diminished requirement for food and sleep. Many stimulants are also capable of improving mood and relieving anxiety, and some can even induce feelings of euphoria. However, many of these drugs are also capable of causing anxiety and heart failure, even the ones that may paradoxically reduce it to a degree at the same time. Stimulants exert their effects through a number of different pharmacological mechanisms, the most prominent of which include facilitation of norepinephrine (noradrenaline) and/or dopamine activity (e.g., via monoamine transporter inhibition or reversal^[1]), adenosine receptor antagonism, and nicotinic acetylcholine receptor agonism.

Medical uses

Stimulants are used both individually and clinically for therapeutic purposes in the treatment of a number of indications, including the following:

To counteract lethargy and fatigue throughout the day while at work or while doing other activities.
To reduce sleepiness and to keep the person awake when necessary, as well as to treat narcolepsy.
To decrease appetite and promote weight loss, as well as to treat obesity.
To improve concentration and focus while at work or school, especially for those with attentional disorders such as ADHD.
Occasionally, they are also used off label to treat clinical depression, more particularly, non-typical depression and treatment-resistant depression.

Types

Ampakines

Recently, there have been improvements in the area of stimulant pharmacology, producing a class of chemicals known as ampakines, or eugeroics, (good arousal). These stimulants tend to increase alertness without the peripheral (body) effects or addiction/tolerance/abuse potential of the traditional stimulants. They have minimal effect on sleep structure, and do not cause rebound hypersomnolence or "come down" effects. Ampakines such as ampalex and CX717 have been developed but are still in clinical trials and have not yet been sold commercially. Another compound with similar effects to these drugs is carphedon, which is sold as a general stimulant in Russia under the brand name Phenotropil.

Amphetamines and related substances

A chart comparing the chemical structures of different amphetamine derivatives

Amphetamines are a group of phenylethylamine stimulants such as amphetamine and methamphetamine. Like NDRIs, amphetamine increases the levels of norepinephrine and dopamine in the brain via reuptake inhibition; however, the more important mechanism by which amphetamines cause stimulation is through the direct release of these catecholamines from storage vesicles in cells. Amphetamines are known to cause elevated mood and euphoria as well as rebound depression and anxiety.^[2]

Amphetamines are often used for their therapeutic effects; physicians occasionally prescribe amphetamines to treat major depression, where subjects do not respond well to traditional SSRI medications, and numerous studies have demonstrated the effectiveness of drugs such as Adderall in controlling symptoms associated with ADD/ADHD. Due to their availability and fast-acting effects, amphetamines are prime candidates for abuse.^[3]

Catha edulis (Khat)

Khat^[4] is a flowering plant native to the Horn of Africa and the Arabian Peninsula. ^[5]

Khat contains a monoamine alkaloid called cathinone, an amphetamine-like stimulant, which is said to cause excitement, loss of appetite and euphoria. In 1980, the World Health Organization (WHO) classified it as a drug of abuse that can produce mild to moderate psychological dependence (less than tobacco or alcohol),^[6] although the WHO does not consider khat to be seriously addictive.^[5] It is a controlled substance in some countries, such as the United States, Canada and Germany, while its production, sale and consumption are legal in other nations, including Djibouti, Ethiopia, Somalia and Yemen.^[7]

Cathine

Cathinone

Bupropion

Bupropion (/bjuːˈproʊpi.ɒn/ bew-PROH-pee-on;^[8] ) is a drug marketed as Wellbutrin, Budeprion, Prexaton, Elontril, Aplenzin, or other trade names. It is one of the most frequently prescribed antidepressants in the United States. Marketed in lower-dose formulations as Zyban, Voxra, or other names, it is also widely used as a smoking cessation aid. It is taken in the form of pills, and in the United States is available only by prescription.

Medically, bupropion serves as a non-tricyclic antidepressant fundamentally different from most commonly prescribed antidepressants such as selective serotonin reuptake inhibitors (SSRIs). It is an effective antidepressant on its own, but is also popular as an add-on medication in cases of incomplete response to first-line SSRI antidepressants. In contrast to many other antidepressants, it does not cause weight gain or sexual dysfunction. The most important side effect is an increase in risk for epileptic seizures, which lead to the recommended dosage to be reduced. 300mg a day (for average body weight) has been shown to maintain the same 0.1% unprovoked seizure rate of the general population.

Bupropion affects a number of neurotransmitter systems, and its mechanisms of action are only partly understood. The primary pharmacological action of the drug is as a mild dopamine reuptake inhibitor and also a much weaker norepinephrine reuptake inhibitor as well as a nicotinic acetylcholine receptor antagonist. Chemically, bupropion belongs to the class of aminoketones and is similar in structure to stimulants such as cathinone and amfepramone, and to phenethylamines in general.

Bupropion is patented by GlaxoSmithKline. It was originally called amfebutamone, before being renamed in 2000.^[9] Its chemical name is 3-chloro-N-tert-butyl-β-ketoamphetamine. It is a substituted cathinone (β-ketoamphetamine), as well as a substituted amphetamine.

Dextroamphetamine ("Dexedrine", contained in "Adderall")

Dextromethamphetamine ("Desoxyephedrine", contained in "Desoxyn")

Ephedrine

Ephedrine is a sympathomimetic amine similar in molecular structure to the well-known drugs phenylpropanolamine and methamphetamine, as well as to the important neurotransmitter epinephrine (adrenalin). Ephedrine is commonly used as a stimulant, appetite suppressant, concentration aid, decongestant, and to treat hypotension associated with anaesthesia.

Chemically, it is an alkaloid with a phenethylamine skeleton found in various plants in the genus Ephedra (family Ephedraceae). It works mainly by increasing the activity of norepinephrine (noradrenalin) on adrenergic receptors.^[10] It is most usually marketed as the hydrochloride or sulfate salt.

The herb má huáng (麻黄, Ephedra sinica), used in traditional Chinese medicine (TCM), contains ephedrine and pseudoephedrine as its principal active constituents. The same may be true of other herbal products containing extracts from other Ephedra species.

L-Norpseudoephedrine

Levoamphetamine (contained in "Adderall")

Levoamphetamine (also levamfetamine, (R)-amphetamine or (−)-amphethamine) is a psychostimulant known to increase wakefulness and focus in association with decreased appetite and fatigue. Levoamphetamine is the levorotatory stereoisomer of the amphetamine molecule. It possesses much weaker dopaminergic activity than the dextrorotary isomer (dextroamphetamine) and acts as a selective releasing agent of norepinephrine, similarly to levomethamphetamine. The amphetamine racemate contains two stereoisomers, dextroamphetamine and levoamphetamine, both exhibiting amphetaminergic (amphetamine-like) effects.

Among the formulations for Levoamphetamine is Adderall and Benzedrine.

Levomethamphetamine (contained in Vicks Vapor Inhaler)

Lisdexamfetamine ("Vyvanse")

MDA

MDA differs from most stimulants in that its primary pharmacological effect is on the neurotransmitter serotonin rather than dopamine, epinephrine, or norepinephrine. Because of this, it is considered to be primarily an entactogen or an empathogen.

MDMA

Methylenedioxymethamphetamine (MDMA), known by its common street name "Ecstasy", typically comes in either tablet, capsule, or powder/crystal form. It had a medical application as a treatment for depression and a psychotherapy aid until 1985 when the DEA listed MDMA as a Schedule I controlled substance, prohibiting most medical studies and applications. Notably, MDMA is also unique and very popular for its entactogenic properties. The stimulant effects of MDMA include hypertension, anorexia (appetite loss), euphoria, social disinhibition, insomnia (or enhanced wakefulness), improved energy, increased arousal, and increased perspiration, among others.

MDMA differs from most stimulants in that its primary pharmacological effect is on the neurotransmitter serotonin rather than dopamine, epinephrine, or norepinephrine. Because of this, it is considered to be primarily an entactogen or an empathogen.

Mephedrone

Methamphetamines

Dextromethamphetamine and levomethamphetamine (see earlier sections) are the two enantiomers of methamphetamine, and are separate medications indicated for different uses. Unless otherwise specified "methamphetamine" refers to a racemic mixture (50%/50%) of the two.

Norephedrine

Norpseudoephedrine

Pemoline

Pentorex

Phentermine

Pseudoephedrine

Dopamine precursors

Unlike amphetamines, and other substances which are dopamine agonists, which either stimulate the release or inhibit the reuptake of dopamine or norepinephrine (which itself is synthesized from dopamine, typically with the help of the amino acid SAM-e, also available as a supplement), dopamine precursors are used by the body in the manufacturing of dopamine.

L-Dopa

L-Dopa can cross the blood-brain barrier, and can be converted by the body into dopamine.

L-Tyrosine

L-Tyrosine is the precursor that is 'closest' to being dopamine among those supplements legally available without prescription in most jurisdictions. It cannot cross the blood-brain barrier, but is converted by the body into L-Dopa, which can. Tyrosine must be taken on an empty stomach and the dosages recommended by most supplement companies may not be sufficient for a noticeable effect.

Phenylalanine

Phenylalanine is 'one step back' from L-Tyrosine--it must be converted into Tyrosine before the Tyrosine can be converted into L-Dopa, which in turn becomes dopamine.

Eugeroics

Adrafinil

Adrafinil is the prodrug of Modafinil, and is metabolized into it in about one hour, when taken on an empty stomach.

Armodafinil

Armodafinil is an enantiopure (non-racemic) version of Modafinil with similar psychoactive properties.

CRL-40,941

JZ-IV-10

JZ-IV-10 is also an SNDRI.

Modafinil

Modafinil (Provigil/Alertec/Modavigil) is an analeptic drug approved by the (FDA) for the treatment of narcolepsy, shift work sleep disorder, and excessive daytime sleepiness associated with obstructive sleep apnea.

Modafinil, like other stimulants, increases the release of monoamines but also elevates hypothalamic histamine levels, leading some researchers to consider Modafinil a "wakefulness promoting agent" rather than a classic amphetamine-like stimulant.

Modafinil has been shown to be effective in the treatment of Attention-Deficit Hyperactivity Disorder (ADHD), depression, cocaine addiction, Parkinson's Disease, schizophrenia, shift workers' sleep disorder and disease-related fatigue.

Fencamfamine

H3 antagonists

Methylhexanamine (DMAA)

NDRAs

Fenozolone

Nicotine

Nicotine is the active chemical constituent in tobacco, which is available in many forms, including cigarettes, cigars, chewing tobacco, and smoking cessation aids such as nicotine patches, nicotine gum and electronic cigarettes. Nicotine is used widely throughout the world for its stimulating, and relaxing effects.

NRIs, NDRIs, and SNDRIs

These drugs inhibit the reuptake of norepinephrine and/or dopamine, resulting in increased extracellular levels and therefore enhanced neurotransmission, ultimately producing a stimulant effect. Many of these compounds are used as ADHD medications and antidepressants. The two best-known NRIs are atomoxetine (Strattera) and reboxetine (Edronax). Many of these drugs have a considerably lower abuse potential in comparison to other stimulants like the amphetamines and cocaine. Reboxetine has been withdrawn from the market in the USA due to unproven efficacy and an unacceptable occurrence of dangerous side effects.

Atomoxetine

Cocaine

Cocaine is an SNDRI. Cocaine is made from the leaves of the coca shrub, which grows in the mountain regions of South American countries such as Bolivia, Colombia, and Peru. In Europe, North America, and in some parts of Asia, the most common form of cocaine is a white crystalline powder. Cocaine is a stimulant but is not normally prescribed therapeutically for its stimulant properties, although it sees clinical use as a local anesthetic, particularly in ophthalmology. Most cocaine use is recreational and its abuse potential is high, and so its sale and possession are strictly controlled in most jurisdictions. Other tropane derivative drugs related to cocaine are also known such as troparil and lometopane but have not been widely sold or used recreationally.^[11]

Dexmethylphenidate

Fenetylline

Fenetylline is a prodrug of both Theophyline and Amphetamine.

Methylenedioxypyrovalerone

Methylphenidate

Methylphenidate (MPH; Ritalin, Concerta, Metadate, or Methylin) is a drug approved for treatment of attention-deficit hyperactivity disorder, postural orthostatic tachycardia syndrome, and narcolepsy. It belongs to the piperidine class of compounds and increases the levels of dopamine and norepinephrine in the brain through reuptake inhibition of the monoamine transporters. It also increases the release of dopamine and norepinephrine. MPH possesses structural similarities to amphetamine, and, though it is less potent, its pharmacological effects are even more closely related to those of cocaine.^[12]^[13]^[14]

Nocaine

Norcocaine

RTI-31

Orexin

Xanthines

Caffeine

Caffeine is a stimulant compound that is found naturally in coffee, tea, and to a lesser degree, in cocoa or chocolate. It is included in many soft drinks, as well as a larger amount in energy drinks. Caffeine is the world's most widely used psychoactive drug and by far the most common stimulant. The vast majority (over 85%) of people in the United States consume caffeine on a daily basis.^{[citation needed]}A few jurisdictions restrict its sale and use. Caffeine is also included in some medications, usually for the purpose of enhancing the effect of the primary ingredient, or reducing one of its side effects (especially drowsiness). Tablets containing standardized doses of caffeine are also widely available.

Theobromine

Theophylline

Yohimbine

Yohimbine is a psychoactive drug of the tryptamine chemical class with stimulant and aphrodisiac effects. Yohimbine is sometimes used to remedy Type-2 Diabetes in animals and humans that carry the polymorphisms of the α2A-adrenergic receptor gene.^[15]

Abuse

Abuse of central nervous system stimulants is common. Addiction to some CNS stimulants can quickly lead to medical, psychiatric and psychosocial deterioration. Drug tolerance, dependence, sensitization as well as a withdrawal syndrome can occur.^[16]

Testing

The presence of stimulants in the body may be tested by a variety of procedures. Serum and urine are the common sources of testing material although saliva is sometimes used. Commonly used tests include chromatography, immunologic assay and mass spectrometry.^[17] Patients taking ADHD-prescribed, Adderall-type amphetamine compounds are commonly surprised upon being tested as "positive" for "meth", or methamphetamine (Desoxyn its licit, FDA-licensed, medicinal form) in forensically unsophisticated urinalysis, as methamphetamine is the active ingredient of the drug Desoxyn, and is chemically similar to the active ingredients of other ADHD medications.

References

^ Riddle EL, Fleckenstein AE, Hanson GR (2005). "Role of monoamine transporters in mediating psychostimulant effects". The AAPS journal. 7 (4): E847–51. doi:10.1208/aapsj070481. PMC 2750953. PMID 16594636.{{cite journal}}: CS1 maint: multiple names: authors list (link)
^ P Knapp (1952). "Amphetamine and addiction". Journal of Nervous and Mental Disorders. 115: 406–409.
^ Efforts of the National Institute on Drug Abuse to Prevent and Treat Prescription Drug Abuse, Testimony Before the Subcommittee on Criminal Justice, Drug Policy, and Human Resources Committee on Government Reform, United States House of Representatives, July 26, 2006
^ Dickens, Charles (1856). "The Orsons of East Africa". Household Words: A Weekly Journal. 14: 176. Retrieved 6 July 2013.
^ ^a ^b Khat chewing in Yemen: turning over a new leaf: Khat chewing is on the rise in Yemen, raising concerns about the health and social consequences
^ Nutt D, King LA, Blakemore C (2007). "Development of a rational scale to assess the harm of drugs of potential misuse". Lancet. 369 (9566): 1047–53. doi:10.1016/S0140-6736(07)60464-4. PMID 17382831. {{cite journal}}: Unknown parameter |month= ignored (help); line feed character in |author= at position 17 (help)CS1 maint: multiple names: authors list (link)
^ Haight-Ashbury Free Medical Clinic, Journal of psychoactive drugs, Volume 41, (Haight-Ashbury Publications: 2009), p.3.
^ entry "Bupropion (By mouth)" at "PubMed Health" (from the US government agency NIH, National Institutes of Health, retrieved March 31, 2013.
^ The INN originally assigned in 1974 by the World Health Organization was "amfebutamone". In 2000, the INN was reassigned as bupropion. See World Health Organization (2000). "International Nonproprietary Names for Pharmaceutical Substances (INN). Proposed INN: List 83" (PDF). WHO Drug Information. 14 (2). Archived from the original (PDF) on May 31, 2011. Retrieved June 22, 2009.
^ Merck Manuals > EPHEDrine Last full review/revision January 2010
^ AJ Giannini, WC Price (1986). "Contemporary drugs of abuse". American Family Physician. 33: 207–213.
^ "Ritalin & Cocaine: The Connection and the Controversy"
^ "Psychiatric nursing: contemporary practice"
^ "Why isn't methylphenidate more addictive?"^{[dead link]}
^ Rosengren, A. H.; Jokubka, R.; Tojjar, D.; Granhall, C.; Hansson, O.; Li, D.-Q.; Nagaraj, V.; Reinbothe, T. M.; Tuncel, J. (2009). "Overexpression of Alpha2A-Adrenergic Receptors Contributes to Type 2 Diabetes". Science. 327 (5962): 217–20. doi:10.1126/science.1176827. PMID 19965390.
^ Dackis CA, Gold MS (1990). "Addictiveness of central stimulants". Adv Alcohol Subst Abuse. 9 (1–2): 9–26. doi:10.1300/J251v09n01_02. PMID 1974121.
^ AJ Giannini. Drug Abuse. Los Angeles, Health Information Press, 1999, pp.203-208

External links

[1] Riddle EL, Fleckenstein AE, Hanson GR (2005). "Role of monoamine transporters in mediating psychostimulant effects". The AAPS journal. 7 (4): E847–51. doi:10.1208/aapsj070481. PMC 2750953. PMID 16594636.{{cite journal}}: CS1 maint: multiple names: authors list (link)

[2] P Knapp (1952). "Amphetamine and addiction". Journal of Nervous and Mental Disorders. 115: 406–409.

[3] Efforts of the National Institute on Drug Abuse to Prevent and Treat Prescription Drug Abuse, Testimony Before the Subcommittee on Criminal Justice, Drug Policy, and Human Resources Committee on Government Reform, United States House of Representatives, July 26, 2006

[Tooea-4] Dickens, Charles (1856). "The Orsons of East Africa". Household Words: A Weekly Journal. 14: 176. Retrieved 6 July 2013.

[Kciy-5] Khat chewing in Yemen: turning over a new leaf: Khat chewing is on the rise in Yemen, raising concerns about the health and social consequences

[King-6] Nutt D, King LA, Blakemore C (2007). "Development of a rational scale to assess the harm of drugs of potential misuse". Lancet. 369 (9566): 1047–53. doi:10.1016/S0140-6736(07)60464-4. PMID 17382831. {{cite journal}}: Unknown parameter |month= ignored (help); line feed character in |author= at position 17 (help)CS1 maint: multiple names: authors list (link)

[Hafmc-7] Haight-Ashbury Free Medical Clinic, Journal of psychoactive drugs, Volume 41, (Haight-Ashbury Publications: 2009), p.3.

[8] try "Bupropion (By mouth)" at "PubMed Health" (from the US government agency NIH, National Institutes of Health, retrieved March 31, 2013.

[9] The INN originally assigned in 1974 by the World Health Organization was "amfebutamone". In 2000, the INN was reassigned as bupropion. See World Health Organization (2000). "International Nonproprietary Names for Pharmaceutical Substances (INN). Proposed INN: List 83" (PDF). WHO Drug Information. 14 (2). Archived from the original (PDF) on May 31, 2011. Retrieved June 22, 2009.

[merck-10] Merck Manuals > EPHEDrine Last full review/revision January 2010

[11] AJ Giannini, WC Price (1986). "Contemporary drugs of abuse". American Family Physician. 33: 207–213.

[12] "Ritalin & Cocaine: The Connection and the Controversy"

[13] "Psychiatric nursing: contemporary practice"

[14] "Why isn't methylphenidate more addictive?"^{[dead link]}

[15] Rosengren, A. H.; Jokubka, R.; Tojjar, D.; Granhall, C.; Hansson, O.; Li, D.-Q.; Nagaraj, V.; Reinbothe, T. M.; Tuncel, J. (2009). "Overexpression of Alpha2A-Adrenergic Receptors Contributes to Type 2 Diabetes". Science. 327 (5962): 217–20. doi:10.1126/science.1176827. PMID 19965390.

[16] Dackis CA, Gold MS (1990). "Addictiveness of central stimulants". Adv Alcohol Subst Abuse. 9 (1–2): 9–26. doi:10.1300/J251v09n01_02. PMID 1974121.

[17] AJ Giannini. Drug Abuse. Los Angeles, Health Information Press, 1999, pp.203-208

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@@ Line 35: / Line 35: @@
 ====Catha edulis (Khat)====
 {{Main|Khat}}
+Khat<ref name="Tooea">{{cite journal|last=Dickens|first=Charles|title=The Orsons of East Africa|journal=Household Words: A Weekly Journal|volume=14|year=1856|page=176|url=http://books.google.com/books?id=EdUnAQAAIAAJ&pg=PA176#v=onepage&q&f=false|accessdate=6 July 2013}}</ref> is a [[flowering plant]] native to the [[Horn of Africa]] and the [[Arabian Peninsula]]. <ref name="Kciy">[http://goliath.ecnext.com/coms2/gi_0199-9617353/Khat-chewing-in-Yemen-turning.html Khat chewing in Yemen: turning over a new leaf: Khat chewing is on the rise in Yemen, raising concerns about the health and social consequences]</ref>
+Khat contains a [[monoamine]] [[alkaloid]] called [[cathinone]], an [[amphetamine]]-like [[stimulant]], which is said to cause excitement, [[Anorectic|loss of appetite]] and [[euphoria (emotion)|euphoria]]. In 1980, the [[World Health Organization]] (WHO) classified it as a [[drug of abuse]] that can produce mild to moderate [[Substance dependence|psychological dependence]] (less than tobacco or alcohol),<ref name="King">{{Cite journal|author=Nutt D, King LA,
+Blakemore C |title=Development of a rational scale to assess the harm of drugs of potential misuse
+|journal=Lancet |volume=369 |issue=9566 |pages=1047–53 |year=2007 |month=March |pmid=17382831
+|doi=10.1016/S0140-6736(07)60464-4}}</ref> although the WHO does not consider khat to be seriously addictive.<ref name="Kciy"/> It is a [[controlled substance]] in some countries, such as the United States, [[Canada]] and Germany, while its production, sale and consumption are legal in other nations, including [[Djibouti]], [[Ethiopia]], [[Somalia]] and [[Yemen]].<ref name="Hafmc">Haight-Ashbury Free Medical Clinic, ''Journal of psychoactive drugs'', Volume 41, (Haight-Ashbury Publications: 2009), p.3.</ref>
 ====Cathine====
 {{Main|Cathine}}
@@ Line 41: / Line 47: @@
 ====Bupropion ====
 {{Main|Bupropion}}
+Bupropion ({{IPAc-en|b|juː|ˈ|p|r|oʊ|p|i|.|ɒ|n}} {{respell|bew|PROH|pee-on}};<ref>entry "[http://www.ncbi.nlm.nih.gov/pubmedhealth/PMHT0009361/?report=details Bupropion (By mouth)]" at [http://www.ncbi.nlm.nih.gov/pubmedhealth/PMHT0009361/?report=details "PubMed Health" (from the US government agency NIH, National Institutes of Health], retrieved March 31, 2013.</ref>  ) is a drug marketed as '''Wellbutrin''', '''Budeprion''', '''Prexaton''', '''Elontril''', '''Aplenzin''', or other trade names. It is one of the most frequently prescribed [[antidepressant]]s in the United States.  Marketed in lower-dose formulations as  '''Zyban''', '''Voxra''', or other names, it is also widely used as a [[smoking cessation]] aid.  It is taken in the form of pills, and in the United States is available only by prescription.
+Medically, bupropion serves as a non-tricyclic antidepressant fundamentally different from most commonly prescribed antidepressants such as [[selective serotonin reuptake inhibitor]]s (SSRIs). It is an effective antidepressant on its own, but is also popular as an add-on medication in cases of incomplete response to first-line SSRI antidepressants. In contrast to many other antidepressants, it does not cause weight gain or sexual dysfunction.  The most important side effect is an increase in [[seizure threshold|risk for epileptic seizures]], which lead to the recommended dosage to be reduced. 300mg a day (for average body weight) has been shown to maintain the same 0.1% unprovoked seizure rate of the general population.
+Bupropion affects a number of [[neurotransmitter]] systems, and its mechanisms of action are only partly understood.  The primary pharmacological action of the drug is as a mild [[dopamine reuptake inhibitor]] and also a much weaker [[norepinephrine reuptake inhibitor]] as well as a [[nicotinic acetylcholine receptor]] [[receptor antagonist|antagonist]].  Chemically, bupropion belongs to the [[chemical classification|class]] of [[aminoketone]]s and is similar in structure to stimulants such as [[cathinone]] and [[amfepramone]], and to [[substituted phenethylamine|phenethylamine]]s in general.
+Bupropion is patented by [[GlaxoSmithKline]]. It was originally called '''amfebutamone''', before being renamed in 2000.<ref>The INN originally assigned in 1974 by the [[World Health Organization]] was "amfebutamone". In 2000, the INN was reassigned as ''bupropion''. See {{cite journal | author = [[World Health Organization]] | title = International Nonproprietary Names for Pharmaceutical Substances (INN). Proposed INN: List 83 | journal = WHO Drug Information | volume = 14 | issue = 2 | year = 2000 | url = http://82.77.46.154/gsdldata/collect/whodruginfo/index/assoc/h1463e/h1463e.pdf|format=PDF|accessdate=June 22, 2009 | archiveurl = http://web.archive.org/web/20110531073025/http://82.77.46.154/gsdldata/collect/whodruginfo/index/assoc/h1463e/h1463e.pdf | archivedate = May 31, 2011}}</ref>  Its chemical name is 3-''chloro''-''N''-''tert''-butyl-β-ketoamphetamine.  It is a [[substituted cathinone]] (β-ketoamphetamine), as well as a [[substituted amphetamine]].
 ====Dextroamphetamine ("Dexedrine", contained in "Adderall")====
 {{Main|Dextroamphetamine}}
@@ Line 47: / Line 61: @@
 ====Ephedrine====
 {{Main|Ephedrine}}
+Ephedrine is a [[sympathomimetic]] [[amine]] similar in molecular structure to the well-known drugs [[phenylpropanolamine]] and [[methamphetamine]], as well as to the important [[neurotransmitter]] [[epinephrine]] (adrenalin). Ephedrine is commonly used as a [[stimulant]], [[appetite suppressant]], concentration aid, [[decongestant]], and to treat [[hypotension]] associated with anaesthesia.
+Chemically, it is an [[alkaloid]] with a [[phenethylamine]] skeleton found in various plants in the genus ''[[Ephedra (genus)|Ephedra]]'' (family [[Ephedraceae]]). It works mainly by increasing the activity of [[norepinephrine]] (noradrenalin) on [[adrenergic receptors]].<ref name=merck>[http://www.merckmanuals.com/professional/lexicomp/ephedrine.html Merck Manuals > EPHEDrine] Last full review/revision January 2010</ref> It is most usually marketed as the ''hydrochloride'' or ''sulfate'' salt.
+The herb ''má huáng'' (麻黄, ''[[Ephedra sinica]]''), used in [[traditional Chinese medicine]] (TCM), contains ephedrine and [[pseudoephedrine]] as its principal active constituents. The same may be true of other herbal products containing extracts from other ''Ephedra'' species.
 ====L-Norpseudoephedrine====
 {{Main|L-Norpseudoephedrine}}
 ====Levoamphetamine (contained in "Adderall")====
 {{Main|Levoamphetamine}}
+Levoamphetamine (also levamfetamine, (R)-amphetamine or (&minus;)-amphethamine) is a [[psychostimulant]] known to increase [[wakefulness]] and [[Focus (cognitive process)|focus]] in association with decreased [[appetite]] and [[Fatigue (medical)|fatigue]]. Levoamphetamine is the [[left-handed|levorotatory]] [[stereoisomer]] of the [[amphetamine]] molecule. It possesses much weaker [[dopaminergic]] activity than the dextrorotary isomer ([[dextroamphetamine]]) and acts as a [[binding selectivity|selective]] [[releasing agent]] of [[norepinephrine]], similarly to [[levomethamphetamine]]. The amphetamine racemate contains two stereoisomers, dextroamphetamine and levoamphetamine, both exhibiting amphetaminergic (amphetamine-like) effects.
+Among the formulations for Levoamphetamine is [[Adderall]] and [[Benzedrine]].
 =====Levomethamphetamine (contained in Vicks Vapor Inhaler)=====
 {{Main|Levomethamphetamine}}

v t e Stimulants
Adamantanes	Adapromine Amantadine Bromantane Memantine Rimantadine
Adenosine antagonists	8-Chlorotheophylline 8-Cyclopentyltheophylline 8-Phenyltheophylline Aminophylline Caffeine CGS-15943 Dimethazan Istradefylline Paraxanthine SCH-58261 Theobromine Theophylline
Alkylamines	Cyclopentamine Cypenamine Cyprodenate Heptaminol Isometheptene Methylhexaneamine Octodrine Propylhexedrine Tuaminoheptane
Ampakines	CX-516 CX-546 CX-614 CX-691 CX-717 IDRA-21 LY-404,187 LY-503,430 Nooglutyl Org 26576 PEPA S-18986 Sunifiram Unifiram
Arylcyclohexylamines	Benocyclidine Dieticyclidine Esketamine Eticyclidine Gacyclidine Ketamine Phencyclamine Phencyclidine Rolicyclidine Tenocyclidine Tiletamine
Benzazepines	6-Br-APB SKF-77434 SKF-81297 SKF-82958
Cathinones	3-FMC 3-MMC 3,4-DMMC 4-BMC 4-CMC 4-Methylbuphedrone 4-Methylcathinone 4-MEAP 4-Methylpentedrone Amfepramone Benzedrone Buphedrone Bupropion Butylone Cathinone Dimethylcathinone Ethcathinone Ethylone Flephedrone Hexedrone Isoethcathinone Mephedrone Methcathinone Methedrone Methylenedioxycathinone Methylone Mexedrone N-Ethylbuphedrone N-Ethylhexedrone Pentedrone Pentylone Phthalimidopropiophenone
Cholinergics	A-84,543 A-366,833 ABT-202 ABT-418 AR-R17779 Altinicline Anabasine Arecoline Bradanicline Cotinine Cytisine Dianicline Epibatidine Epiboxidine GTS-21 Ispronicline Nicotine PHA-543,613 PNU-120,596 PNU-282,987 Pozanicline Rivanicline Sazetidine A SIB-1553A SSR-180,711 TC-1698 TC-1827 TC-2216 Tebanicline UB-165 Varenicline WAY-317,538
Convulsants	Anatoxin-a Bicuculline DMCM Flurothyl Gabazine Pentetrazol Picrotoxin Strychnine Thujone
Eugeroics	Adrafinil Armodafinil CRL-40,940 CRL-40,941 Fluorenol Modafinil
Oxazolines	4-Methylaminorex Aminorex Clominorex Cyclazodone Fenozolone Fluminorex Pemoline Thozalinone
Phenethylamines	1-(4-Methylphenyl)-2-aminobutane 1-Methylamino-1-(3,4-methylenedioxyphenyl)propane 2-Fluoroamphetamine 2-Fluoromethamphetamine 2-OH-PEA 2-Phenyl-3-aminobutane 2,3-MDA 3-Fluoroamphetamine 3-Fluoroethamphetamine 3-Methoxyamphetamine 3-Methylamphetamine 4-Fluoroamphetamine 4-Fluoromethamphetamine 4-MA 4-MMA 4-MTA 6-FNE AL-1095 Alfetamine a-Ethylphenethylamine Amfecloral Amfepentorex Amidephrine 2-Amino-1,2-dihydronaphthalene 2-Aminoindane 5-(2-Aminopropyl)indole 2-Aminotetralin Acridorex Amphetamine (Dextroamphetamine, Levoamphetamine) Amphetaminil Arbutamine β-Methylphenethylamine β-Phenylmethamphetamine Benfluorex Benzphetamine BDB BOH 3-Benzhydrylmorpholine BPAP Camfetamine Cathine Chlorphentermine Cilobamine Cinnamedrine Clenbuterol Clobenzorex Cloforex Clortermine Cypenamine D-Deprenyl Denopamine Dimethoxyamphetamine Dimethylamphetamine Dobutamine DOPA (Dextrodopa, Levodopa) Dopamine Dopexamine Droxidopa EBDB Ephedrine Epinephrine Epinine Etafedrine Ethylnorepinephrine Etilamfetamine Etilefrine Famprofazone Fencamfamin Fencamine Fenethylline Fenfluramine (Dexfenfluramine, Levofenfluramine) Fenproporex Feprosidnine Fludorex Formetorex Furfenorex Gepefrine Hexapradol HMMA Hordenine 4-Hydroxyamphetamine 5-Iodo-2-aminoindane Ibopamine Indanylamphetamine Iofetamine Isoetarine Isoprenaline L-Deprenyl (Selegiline) Lefetamine Lisdexamfetamine Lophophine MBDB MDA (tenamfetamine) MDBU MDEA MDMA (midomafetamine) MDMPEA MDOH MDPR MDPEA Mefenorex Mephentermine Metanephrine Metaraminol Mesocarb Methamphetamine (Dextromethamphetamine, Levomethamphetamine) Methoxamine Methoxyphenamine MMA Methoxyphenamine MMDA MMDMA MMMA Morforex N,alpha-Diethylphenylethylamine N,N-Dimethylphenethylamine Naphthylamphetamine Nisoxetine Norepinephrine Norfenefrine Norfenfluramine Normetanephrine L-Norpseudoephedrine Octopamine Orciprenaline Ortetamine Oxifentorex Oxilofrine PBA PCA PCMA PHA Pentorex Phenatine Phenpromethamine Phentermine Phenylalanine Phenylephrine Phenylpropanolamine Pholedrine PIA PMA PMEA PMMA PPAP Prenylamine Propylamphetamine Pseudoephedrine Ropinirole Salbutamol (Levosalbutamol) Sibutramine Solriamfetol Synephrine Theodrenaline Tiflorex Tranylcypromine Tyramine Tyrosine Xylopropamine Zylofuramine
Phenylmorpholines	3-Fluorophenmetrazine Fenbutrazate Fenmetramide G-130 Manifaxine Morazone Morforex Oxaflozane PD-128,907 Phendimetrazine Phenmetrazine 2-Phenyl-3,6-dimethylmorpholine Pseudophenmetrazine Radafaxine
Piperazines	2C-B-BZP 3C-PEP BZP CM156 DBL-583 GBR-12783 GBR-12935 GBR-13069 GBR-13098 GBR-13119 JJC8-088 MeOPP MBZP oMPP Vanoxerine
Piperidines	1-Benzyl-4-(2-(diphenylmethoxy)ethyl)piperidine 2-Benzylpiperidine 2-Methyl-3-phenylpiperidine 3,4-Dichloromethylphenidate 4-Benzylpiperidine 4-Fluoromethylphenidate 4-Methylmethylphenidate Desoxypipradrol Difemetorex Diphenylpyraline Ethylnaphthidate Ethylphenidate Methylnaphthidate Isopropylphenidate JZ-IV-10 Methylphenidate (Dexmethylphenidate) Nocaine Phacetoperane Pipradrol Propylphenidate Serdexmethylphenidate SCH-5472
Pyrrolidines	2-Diphenylmethylpyrrolidine 4-Cl-PVP 5-DBFPV α-PPP α-PBP α-PCYP α-PHiP α-PHP α-PHPP α-PVP α-PVT Diphenylprolinol DMPVP FPOP FPVP MDPPP MDPBP MPBP MPHP MPPP MOPVP MOPPP Indapyrophenidone MDPV Naphyrone PEP Picilorex Prolintane Pyrovalerone
Racetams	Oxiracetam Phenylpiracetam Phenylpiracetam hydrazide
Tropanes	4-fluorotropacocaine 4'-Fluorococaine Altropane (IACFT) Brasofensine CFT (WIN 35,428) β-CIT (RTI-55) Cocaethylene Cocaine Dichloropane (RTI-111) Difluoropine FE-β-CPPIT FP-β-CPPIT Ioflupane (¹²³I) Norcocaine PIT PTT RTI-31 RTI-32 RTI-51 RTI-112 RTI-113 RTI-120 RTI-121 (IPCIT) RTI-126 RTI-150 RTI-177 RTI-229 RTI-336 RTI-354 RTI-371 RTI-386 Salicylmethylecgonine Tesofensine Troparil (β-CPT, WIN 35,065-2) Tropoxane WF-23 WF-33
Tryptamines	4-HO-αMT 4-Methyl-αET 4-Methyl-αMT 5-Chloro-αMT 5-Fluoro-αMT 5-MeO-αET 5-MeO-αMT 5-MeO-DIPT 6-Fluoro-αMT 7-Methyl-αET αET αMT
Others	2-MDP 3,3-Diphenylcyclobutanamine Amfonelic acid Amineptine Amiphenazole Atipamezole Atomoxetine Bemegride Benzydamine BTQ BTS 74,398 Centanafadine Ciclazindol Clofenciclan Cropropamide Crotetamide D-161 Desipramine Diclofensine Dimethocaine Efaroxan Etamivan Fenisorex Fenpentadiol Gamfexine Gilutensin GSK1360707F GYKI-52895 Hexacyclonate Idazoxan Indanorex Indatraline JNJ-7925476 Lazabemide Leptacline Lomevactone LR-5182 Mazindol Meclofenoxate Medifoxamine Mefexamide Methamnetamine Methastyridone Methiopropamine Naphthylaminopropane Nefopam Nikethamide Nomifensine O-2172 Oxaprotiline PNU-99,194 PRC200-SS Rasagiline Rauwolscine Rubidium chloride Setazindol Tametraline Tandamine Thiopropamine Thiothinone Trazium UH-232 Yohimbine
ATC code: N06B

v t e Anxiolytics (N05B)
5-HT_1ARTooltip 5-HT1A receptor agonists	Buspirone Gepirone Tandospirone
GABA_ARTooltip GABAA receptor PAMsTooltip positive allosteric modulators	Benzodiazepines: Adinazolam Alprazolam Bromazepam Camazepam Chlordiazepoxide Clobazam Clonazepam Clorazepate Clotiazepam Cloxazolam Diazepam^# Ethyl loflazepate Etizolam Fludiazepam Halazepam Ketazolam Lorazepam^# Medazepam Nordazepam Oxazepam Pinazepam Prazepam; Others: Alpidem^‡ Barbiturates (e.g., phenobarbital) Carbamates (e.g., meprobamate) Carisoprodol Chlormezanone^‡ Ethanol (alcohol) Etifoxine
Hypnotics	Zopiclone
Gabapentinoids (α₂δ VDCC blockers)	Gabapentin Gabapentin enacarbil Phenibut Pregabalin
Antidepressants	SSRIsTooltip Selective serotonin reuptake inhibitors (e.g., escitalopram) SNRIsTooltip Serotonin-norepinephrine reuptake inhibitors (e.g., duloxetine) SARIsTooltip Serotonin antagonist and reuptake inhibitors (e.g., trazodone) TCAsTooltip Tricyclic antidepressants (e.g., clomipramine^#) TeCAsTooltip Tetracyclic antidepressants (e.g., mirtazapine) MAOIsTooltip Monoamine oxidase inhibitors (e.g., phenelzine); Others: Agomelatine Bupropion Tianeptine Vilazodone Vortioxetine
Antipsychotics	Quetiapine Flupentixol
Sympatholytics (Antiadrenergics)	Alpha-1 blockers (e.g., prazosin) Alpha-2 agonists (e.g., clonidine, dexmedetomidine, guanfacine) Beta blockers (e.g., propranolol)
Others	Benzoctamine Cycloserine Fabomotizole Hydroxyzine Lorpiprazole Mebicar Mepiprazole Nicotine Opipramol Oxaflozane^‡ Phenaglycodol Phenibut Picamilon Selank Tiagabine Tofisopam Validolum
^#WHO-EM ^‡Withdrawn from market Clinical trials: ^†Phase III ^§Never to phase III

v t e Major chemical drug groups – based upon the Anatomical Therapeutic Chemical Classification System
gastrointestinal tract / metabolism (A)	stomach acid Antacids H₂ antagonists Proton-pump inhibitors Antiemetics Laxatives Antidiarrhoeals / Antipropulsives Anti-obesity drugs Diabetes medication Vitamins Dietary minerals
blood and blood forming organs (B)	Antithrombotics Antiplatelets Anticoagulants Thrombolytics / fibrinolytics Antihemorrhagics Platelets Coagulants Antifibrinolytics
cardiovascular system (C)	cardiac therapy / antianginals Cardiac glycosides Antiarrhythmics Cardiac stimulants Antihypertensives Diuretics Vasodilators Beta blockers Calcium channel blockers renin–angiotensin system ACE inhibitors Angiotensin II receptor antagonists Renin inhibitors Antihyperlipidemics Statins Fibrates Bile acid sequestrants
skin (D)	Emollients Cicatrizants Antipruritics Antipsoriatics Medicated dressings
genitourinary system (G)	Hormonal contraception Fertility agents Selective estrogen receptor modulators Sex hormones
endocrine system (H)	Hypothalamic–pituitary hormones Corticosteroids Glucocorticoids Mineralocorticoids Sex hormones Thyroid hormones / Antithyroid agents
infections and infestations (J, P, QI)	Antimicrobials: Antibacterials (Antimycobacterials) Antifungals Antivirals Antiparasitics Antiprotozoals Anthelmintics Ectoparasiticides Intravenous immunoglobulin Vaccines
malignant disease (L01–L02)	Anticancer agents Antimetabolites Alkylating Spindle poisons Antineoplastic Topoisomerase inhibitors
immune disease (L03–L04)	Immunomodulators Immunostimulants Immunosuppressants
muscles, bones, and joints (M)	Anabolic steroids Anti-inflammatories Non-steroidal anti-inflammatory drugs Antirheumatics Corticosteroids Muscle relaxants Bisphosphonates
brain and nervous system (N)	Analgesics Anesthetics General Local Anorectics Anti-ADHD agents Antiaddictives Anticonvulsants Antidementia agents Antidepressants Antimigraine agents Antiparkinson agents Antipsychotics Anxiolytics Aphrodisiacs Depressants Entactogens Entheogens Euphoriants Hallucinogens Psychedelics Dissociatives Deliriants Hypnotics / Sedatives Mood stabilizers Motivation-enhancing drug Neuroprotectives Nootropics Neurotoxins Orexigenics Serenics Stimulants Wakefulness-promoting agents
respiratory system (R)	Decongestants Bronchodilators Cough medicines H₁ antagonists
sensory organs (S)	Ophthalmologicals Otologicals
other ATC (V)	Antidotes Contrast media Radiopharmaceuticals Dressings Senotherapeutics
Drugs Pharmacological classification systems ATC codes Medicine portal