Dextroamphetamine

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Psychological: Low – moderate<ref name="Stahl's Essential Psychopharmacology" />Dextroamphetamine B3By mouth, transdermal, intravenous, insufflation, rectalDexedrine, othersStimulantN06 | _legal_data=<ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref><ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref>S8<ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref>A3/Template:NbspSchedule G (CDSA I)<ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref>Rx-onlyAnlage III<ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref>Rx-onlyClass BP II<ref name="Dexedrine FDA label">{{#invoke:citation/CS1|citation |CitationClass=web }}</ref><ref name="Xelstrym FDA label">{{#invoke:citation/CS1|citation |CitationClass=web }}</ref>Schedule IISE: Förteckning II

| _other_data=(2S)-1-Phenylpropan-2-amine

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Dextroamphetamine (INN: dexamfetamine) is a potent central nervous system (CNS) stimulant and enantiomer<ref name="Enantiomer" group="note" /> of amphetamine that is used in the treatment of attention deficit hyperactivity disorder (ADHD) and narcolepsy.<ref name="Dexedrine FDA label" /><ref name="Amph Uses" /> It is also used illicitly to enhance cognitive and athletic performance, and recreationally as an aphrodisiac and euphoriant. Dextroamphetamine is generally regarded as the prototypical stimulant.

The amphetamine molecule exists as two enantiomers,<ref group="note" name="Enantiomer">Enantiomers are molecules that are mirror images of one another; they are structurally identical, but of the opposite orientation.<ref name="Enantiomers">Template:GoldBookRef</ref></ref> levoamphetamine and dextroamphetamine. Dextroamphetamine is the dextrorotatory, or 'right-handed', enantiomer and exhibits more pronounced effects on the central nervous system than levoamphetamine. Pharmaceutical dextroamphetamine sulfate is available as both a brand name and generic drug in a variety of dosage forms. Dextroamphetamine is sometimes prescribed as the inactive prodrug lisdexamfetamine.

Side effects of dextroamphetamine at therapeutic doses include elevated mood, decreased appetite, dry mouth, excessive grinding of the teeth, headache, increased heart rate, increased wakefulness or insomnia, anxiety, and irritability, among others.<ref name="AHFS2019" /> At excessively high doses, psychosis (i.e., hallucinations, delusions), addiction, and rapid muscle breakdown may occur. However, for individuals with pre-existing psychotic disorders, there may be a risk of psychosis even at therapeutic doses.<ref name="Adderall XR FDA label" />

Dextroamphetamine, like other amphetamines, elicits its stimulating effects via several distinct actions: it inhibits or reverses the transporter proteins for the monoamine neurotransmitters (namely the serotonin, norepinephrine and dopamine transporters) either via trace amine-associated receptor 1 (TAAR1) or in a TAAR1 independent fashion when there are high cytosolic concentrations of the monoamine neurotransmitters<ref name=Miller/> and it releases these neurotransmitters from synaptic vesicles via vesicular monoamine transporter 2 (VMAT2).<ref name="E Weihe" /> It also shares many chemical and pharmacological properties with human trace amines, particularly phenethylamine and Template:Nowrap, the latter being an isomer of amphetamine produced within the human body. It is available as a generic medication.<ref name=AHFS2019>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref> In 2022, mixed amphetamine salts (Adderall) was the 14th most commonly prescribed medication in the United States, with more than 34Template:Nbspmillion prescriptions.<ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref><ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref> Template:TOC limit

Uses

Medical

File:Dexedrine doj2.jpeg

Dexedrine Spansule 5, 10 and 15 mg capsules, a sustained-release dosage form of dextroamphetamine

Dextroamphetamine is used to treat attention deficit hyperactivity disorder (ADHD) and narcolepsy,<ref name="Dexedrine FDA label" /> and is sometimes prescribed Template:Nowrap for depression and obesity.<ref name="Amph Uses" />

ADHD

{{#lsth:Amphetamine|ADHD}}

Narcolepsy

{{#lsth:Amphetamine|Narcolepsy}}

Recreational

Dextroamphetamine is also used recreationally as a euphoriant and aphrodisiac, and, like other amphetamines, is used as a club drug for its energetic and euphoric high. Dextroamphetamine is considered to have a high potential for misuse in a recreational manner since individuals typically report feeling euphoric, more alert, and more energetic after taking the drug.<ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref><ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref><ref name="NIDA ADHD stimulants" /> Dextroamphetamine's dopaminergic (rewarding) properties affect the mesocorticolimbic circuit; a group of neural structures responsible for incentive salience (i.e., "wanting"; desire or craving for a reward and motivation), positive reinforcement and positively-valenced emotions, particularly ones involving pleasure.<ref name=Schultz>Template:Cite journal</ref> Large recreational doses of dextroamphetamine may produce symptoms of dextroamphetamine overdose.<ref name="NIDA ADHD stimulants" /> Recreational users sometimes open dexedrine capsules and crush the contents in order to insufflate (snort) it or subsequently dissolve it in water and inject it.<ref name="NIDA ADHD stimulants">{{#invoke:citation/CS1|citation |CitationClass=web }}</ref> Immediate-release formulations have higher potential for abuse via insufflation (snorting) or intravenous injection due to a more favorable pharmacokinetic profile and easy crushability (especially tablets).<ref name="CADDRA_2018">Template:Cite book</ref><ref name="Bright2008">Template:Cite journal</ref>

The reason for using crushed spansules for insufflation and injection methods is evidently due to the instant-release forms of the drug seen in tablet preparations often containing a sizable amount of inactive binders and fillers alongside the active d-amphetamine, such as dextrose.<ref name="Contextual conditioning">Template:Cite journal</ref> Injection into the bloodstream can be dangerous because insoluble fillers within the tablets can block small blood vessels.<ref name="NIDA ADHD stimulants" /> Chronic overuse of dextroamphetamine can lead to severe drug dependence, resulting in withdrawal symptoms when drug use stops.<ref name="NIDA ADHD stimulants" />

Interactions

Many types of substances are known to interact with amphetamine, resulting in altered drug action or metabolism of amphetamine, the interacting substance, or both.<ref name="FDA Pharmacokinetics" /><ref name="Adderall FDA label" /><ref name="Adderall XR FDA label" /> Inhibitors of the enzymes that metabolize amphetamine (e.g., CYP2D6 and FMO3) will prolong its elimination half-life, meaning that its effects will last longer.<ref name="FMO" /><ref name="Adderall FDA label">{{#invoke:citation/CS1|citation |CitationClass=web }}</ref><ref name="Adderall XR FDA label">{{#invoke:citation/CS1|citation |CitationClass=web }}</ref> Amphetamine also interacts with Template:Abbr, particularly monoamine oxidase A inhibitors, since both MAOIs and amphetamine increase plasma catecholamines (i.e., norepinephrine and dopamine);<ref name="Adderall FDA label" /><ref name="Adderall XR FDA label" /> therefore, concurrent use of both is dangerous.<ref name="Adderall FDA label" /><ref name="Adderall XR FDA label" /> Amphetamine modulates the activity of most psychoactive drugs. In particular, amphetamine may decrease the effects of sedatives and depressants and increase the effects of stimulants and antidepressants.<ref name="Adderall FDA label" /><ref name="Adderall XR FDA label" /> Amphetamine may also decrease the effects of antihypertensives and antipsychotics due to its effects on blood pressure and dopamine respectively.<ref name="Adderall FDA label" /><ref name="Adderall XR FDA label" /> Zinc supplementation may reduce the minimum effective dose of amphetamine when it is used for the treatment of ADHD.<ref group="note">The human dopamine transporter contains a high affinity extracellular zinc binding site which, upon zinc binding, inhibits dopamine reuptake and amplifies amphetamine-induced dopamine efflux in vitro.<ref name="Zinc binding sites + ADHD review">Template:Cite journal</ref><ref name="Review - cites 2002 amph-zinc primary study">Template:Cite journal</ref><ref name="Primary 2002 amph-zinc study">Template:Cite journal</ref> The human serotonin transporter and norepinephrine transporter do not contain zinc binding sites.<ref name="Primary 2002 amph-zinc study" /></ref><ref name="Zinc and PEA">Template:Cite journal</ref> Norepinephrine reuptake inhibitors (NRIs) like atomoxetine prevent norepinephrine release induced by amphetamines and have been found to reduce the stimulant, euphoriant, and sympathomimetic effects of dextroamphetamine in humans.<ref name="TreuerGauMéndez2013">Template:Cite journal</ref><ref name="HealSmithFindling2012">Template:Cite book</ref><ref name="SofuogluPolingHill2009">Template:Cite journal</ref>

Pharmacology

Pharmacodynamics

{{#invoke:Hatnote|hatnote}}

Template:Nowrap

Compound	Template:Abbrlink	Template:Abbrlink	Template:Abbrlink	Ref
Phenethylamine	10.9	39.5	>10,000	<ref name="ReithBLoughHong2015">Template:Cite journal</ref><ref name="Forsyth2012" /><ref name="Blough2008" />
Dextroamphetamine	6.6–7.2	5.8–24.8	698–1,765	<ref name="RothmanBaumannDersch2001">Template:Cite journal</ref><ref name="BaumannPartillaLehner2013">Template:Cite journal</ref>
Levoamphetamine	9.5	27.7	Template:Abbr	<ref name="Forsyth2012">Template:Cite journal</ref><ref name="Blough2008">Template:Cite book</ref>
Dextromethamphetamine	12.3–13.8	8.5–24.5	736–1,292	<ref name="RothmanBaumannDersch2001" /><ref name="BaumannAyestasPartilla2012">Template:Cite journal</ref>
Levomethamphetamine	28.5	416	4,640	<ref name="RothmanBaumannDersch2001" />
Notes: The smaller the value, the more strongly the drug releases the neurotransmitter. See also Monoamine releasing agent § Activity profiles for a larger table with more compounds. Refs: <ref name="RothmanBaumann2003">Template:Cite journal</ref><ref name="RothmanBaumann2006">Template:Cite journal</ref>

Template:Amphetamine pharmacodynamics Amphetamine and its enantiomers have been identified as potent full agonists of trace amine-associated receptor 1 (TAAR1), a GPCR, discovered in 2001, that is important for regulation of monoaminergic systems in the brain.<ref name="pmid11723224">Template:Cite journal</ref><ref name="TAAR1 stereoselective" /> Activation of TAAR1 increases cAMP production via adenylyl cyclase activation and inhibits the function of the dopamine transporter, norepinephrine transporter, and serotonin transporter, as well as inducing the release of these monoamine neurotransmitters (effluxion).<ref name="Miller">Template:Cite journal</ref><ref name="pmid11723224" /><ref name="pmid11459929">Template:Cite journal</ref> Amphetamine enantiomers are also substrates for a specific neuronal synaptic vesicle uptake transporter called VMAT2.<ref name="E Weihe" /> When amphetamine is taken up by VMAT2, the vesicle releases (effluxes) dopamine, norepinephrine, and serotonin, among other monoamines, into the cytosol in exchange.<ref name="E Weihe">Template:Cite journal</ref>

Dextroamphetamine (the dextrorotary enantiomer) and levoamphetamine (the levorotary enantiomer) have identical pharmacodynamics, but their binding affinities to their biomolecular targets vary.<ref name="TAAR1 stereoselective" /><ref name="WestfallDP">Template:Cite book</ref> Dextroamphetamine is a more potent agonist of TAAR1 than levoamphetamine.<ref name="TAAR1 stereoselective" /> Consequently, dextroamphetamine produces roughly three to four times more central nervous system (CNS) stimulation than levoamphetamine;<ref name="TAAR1 stereoselective">Template:Cite journal</ref><ref name="WestfallDP" /> however, levoamphetamine has slightly greater cardiovascular and peripheral effects.<ref name="WestfallDP" />

History, society, and culture

{{#invoke:Labelled list hatnote|labelledList|Main article|Main articles|Main page|Main pages}} Racemic amphetamine was first synthesized under the chemical name "phenylisopropylamine" in Berlin, 1887 by the Romanian chemist Lazăr Edeleanu. It was not widely marketed until 1932, when the pharmaceutical company Smith, Kline & French (now known as GlaxoSmithKline) introduced it in the form of the Benzedrine inhaler for use as a bronchodilator. Notably, the amphetamine contained in the Benzedrine inhaler was the liquid free-base,<ref group="note">Free-base form amphetamine is a volatile oil, hence the efficacy of the inhalers.</ref> not a chloride or sulfate salt.

Three years later, in 1935, the medical community became aware of the stimulant properties of amphetamine, specifically the dextroamphetamine isomer, and in 1937 Smith, Kline, and French introduced tablets under the brand name Dexedrine.<ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref> In the United States, Dexedrine was approved to treat narcolepsy and attention deficit hyperactivity disorder (ADHD).<ref name="Dexedrine FDA label" /> In Canada indications once included epilepsy and parkinsonism.<ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref> Dextroamphetamine was marketed in various other forms in the following decades, primarily by Smith, Kline, and French, such as several combination medications including a mixture of dextroamphetamine and amobarbital (a barbiturate) sold under the brand name Dexamyl and, in the 1950s, an extended release capsule (the "Spansule").<ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref> Preparations containing dextroamphetamine were also used in World War II as a treatment against fatigue.<ref name="Amph Uses">Template:Cite journal</ref>

It quickly became apparent that dextroamphetamine and other amphetamines had a high potential for misuse, although they were not heavily controlled until 1970, when the Comprehensive Drug Abuse Prevention and Control Act was passed by the United States Congress. Dextroamphetamine, along with other sympathomimetics, was eventually classified as Schedule II, the most restrictive category possible for a drug with a government-sanctioned, recognized medical use.<ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref> Internationally, it has been available under the names AmfeDyn (Italy), Curban (US), Obetrol (Switzerland), Simpamina (Italy), Dexedrine/GSK (US & Canada), Dexedrine/UCB (United Kingdom), Dextropa (Portugal), and Stild (Spain).<ref name="pharaman">Template:Cite book</ref> It became popular on the mod scene in England in the early 1960s, and carried through to the Northern Soul scene in the north of England to the end of the 1970s.

In October 2010, GlaxoSmithKline sold the rights for Dexedrine Spansule to Amedra Pharmaceuticals (a subsidiary of CorePharma).<ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref>

The U.S. Air Force uses dextroamphetamine as one of its "go pills", given to pilots on long missions to help them remain focused and alert. Conversely, "no-go pills" are used after the mission is completed, to combat the effects of the mission and "go-pills".<ref name="Bonné_2003">{{#invoke:citation/CS1|citation |CitationClass=web }}</ref><ref name=airforcegopills>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref><ref>Template:Cite journal</ref> The Tarnak Farm incident was linked by media reports to the use of this drug on long term fatigued pilots. The military did not accept this explanation, citing the lack of similar incidents. Newer stimulant medications or awakeness promoting agents with different side effect profiles, such as modafinil, are being investigated and sometimes issued for this reason.<ref name=airforcegopills />

Formulations

citation

CitationClass=web }}</ref> Dexedrine listed here represents the extended release "Spansule" capsule which was approved in 1976.<ref>{{#invoke:citation/CS1|citation	CitationClass=web }}</ref><ref>{{#invoke:citation/CS1|citation	CitationClass=web }}</ref> Amphetamine sulfate tablets, now sold as Evekeo (brand), were originally sold as Benzedrine (brand) sulfate in 1935<ref>Template:Cite journal</ref><ref name="Amph Uses" /> and discontinued sometime after 1982.<ref name="Amph Uses" /><ref>{{#invoke:citation/CS1|citation	CitationClass=web }}</ref></ref>	Brand name	United States Adopted Name	(D:L) ratio	Dosage form	Marketing start date	Sources
Adderall	Mixed amphetamine salts	3:1 (salts)	tablet	1996	<ref name="Amph Uses" /><ref name="NDCD" />
Adderall XR	Mixed amphetamine salts	3:1 (salts)	capsule	2001	citation	CitationClass=web }}</ref>
Mydayis	Mixed amphetamine salts	3:1 (salts)	capsule	2017	citation	CitationClass=web }}</ref>
Adzenys XR-ODT	amphetamine	3:1 (base)	ODT	2016	citation	CitationClass=web }}</ref><ref name="FDA Adzenys approval date">{{#invoke:citation/CS1|citation	CitationClass=web }}</ref>
Dyanavel XR	amphetamine	3.2:1 (base)	suspension	2015	citation	CitationClass=web }}</ref>
Evekeo	amphetamine sulfate	1:1 (salts)	tablet	2012	citation	CitationClass=web }}</ref>
Dexedrine	dextroamphetamine sulfate	1:0 (salts)	capsule	1976	<ref name="Amph Uses" /><ref name="NDCD" />
Zenzedi	dextroamphetamine sulfate	1:0 (salts)	tablet	2013	<ref name="NDCD" />
Vyvanse	lisdexamfetamine dimesylate	1:0 (prodrug)	capsule	2007	<ref name="Amph Uses" /><ref name=USVyvanselabel />
			tablet
Xelstrym	dextroamphetamine	1:0 (base)	patch	2022	<ref name="Xelstrym FDA label" />

Transdermal Dextroamphetamine Patches

Dextroamphetamine is available as a transdermal patch containing dextroamphetamine base under the brand name Xelstrym.<ref name="Xelstrym FDA label" />

Dextroamphetamine sulfate

In the United States, immediate release (IR) formulations of dextroamphetamine sulfate are available generically as 5 mg and 10 mg tablets, marketed by Barr (Teva Pharmaceutical Industries), Mallinckrodt Pharmaceuticals, Wilshire Pharmaceuticals, Aurobindo Pharmaceutical USA and CorePharma. Previous IR tablets sold under the brand names Dexedrine and Dextrostat have been discontinued but in 2015, IR tablets became available by the brand name Zenzedi, offered as 2.5 mg, 5 mg, 7.5 mg, 10 mg, 15 mg, 20 mg and 30 mg tablets.<ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref> Dextroamphetamine sulfate is also available as a controlled-release (CR) capsule preparation in strengths of 5 mg, 10 mg, and 15 mg under the brand name Dexedrine Spansule, with generic versions marketed by Barr and Mallinckrodt. A bubblegum flavored oral solution is available under the brand name ProCentra, manufactured by FSC Pediatrics, which is designed to be an easier method of administration in children who have difficulty swallowing tablets, each 5 mL contains 5 mg dextroamphetamine.<ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref> The conversion rate between dextroamphetamine sulfate to amphetamine free base is .728.<ref>Template:Cite patent</ref>

In Australia, dexamfetamine is available in bottles of 100 instant release 5 mg tablets as a generic drug<ref>Template:Cite journal</ref> or slow release dextroamphetamine preparations may be compounded by individual chemists.<ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref> In the United Kingdom, it is available in 5 mg instant release sulfate tablets under the generic name dexamfetamine sulfate as well as 10 mg and 20 mg strength tablets under the brand name Amfexa. It is also available in generic dexamfetamine sulfate 5 mg/ml oral sugar-free syrup.<ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref> The brand name Dexedrine was available in the United Kingdom prior to UCB Pharma disinvesting the product to another pharmaceutical company (Auden Mckenzie).<ref>Template:Cite journal</ref>

Lisdexamfetamine

{{#invoke:Labelled list hatnote|labelledList|Main article|Main articles|Main page|Main pages}} Dextroamphetamine is the active metabolite of the prodrug lisdexamfetamine (L-lysine-dextroamphetamine), available by the brand name Vyvanse (Elvanse in the European market) (Venvanse in the Brazil market) (lisdexamfetamine dimesylate). Dextroamphetamine is liberated from lisdexamfetamine enzymatically following contact with red blood cells. The conversion is rate-limited by the enzyme, which prevents high blood concentrations of dextroamphetamine and reduces lisdexamfetamine's drug liking and abuse potential at clinical doses.<ref>Template:Cite journal</ref><ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref> Vyvanse is marketed as once-a-day dosing as it provides a slow release of dextroamphetamine into the body. Vyvanse is available as capsules, and chewable tablets, and in seven strengths; 10 mg, 20 mg, 30 mg, 40 mg, 50 mg, 60 mg, and 70 mg. The conversion rate between lisdexamfetamine dimesylate (Vyvanse) to dextroamphetamine base is 29.5%.<ref>Template:Cite journal</ref><ref>Template:Cite journal</ref><ref>Template:Cite journal</ref>

Adderall

{{#invoke:Labelled list hatnote|labelledList|Main article|Main articles|Main page|Main pages}}

File:Amph salts.jpg

Adderall 20 mg tablets, some broken in half, with a lengthwise-folded US dollar bill along the bottom

Another pharmaceutical that contains dextroamphetamine is commonly known by the brand name Adderall.<ref name="Adderall FDA label" /><ref name="Adderall XR FDA label" /> It is available as immediate release (IR) tablets and extended release (XR) capsules.<ref name="Adderall FDA label" /><ref name="Adderall XR FDA label" /> Adderall contains equal amounts of four amphetamine salts:<ref name="Adderall FDA label" /><ref name="Adderall XR FDA label" />

• One-quarter racemic (d,l-)amphetamine aspartate monohydrate
• One-quarter dextroamphetamine saccharate
• One-quarter dextroamphetamine sulfate
• One-quarter racemic (d,l-)amphetamine sulfate

Adderall has a total amphetamine base equivalence of 63%.<ref name="Adderall FDA label" /><ref name="Adderall XR FDA label" /> While the enantiomer ratio by dextroamphetamine salts to levoamphetamine salts is 3:1, the amphetamine base content is 75.9% dextroamphetamine, 24.1% levoamphetamine. <ref group="note">Calculated by dextroamphetamine base percent / total amphetamine base percent = 47.49/62.57 = 75.90% from table: Amphetamine base in marketed amphetamine medications. The remainder is levoamphetamine.</ref>

Research

Schizophrenia

Dextroamphetamine reduces the negative symptoms of schizophrenia, and has been shown to enhance the effects of auditory discrimination training in schizophrenic patients.<ref>Template:Cite journal</ref><ref>Template:Cite journal</ref><ref>Template:Cite journal</ref>

Notes

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