dextroamphetamine

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Dextroamphetamine is used to treat attention deficit hyperactivity disorder (ADHD) and narcolepsy, and is sometimes prescribed {{nowrap|off-label}} for depression and obesity.

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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.{{cite web|url=http://www.drugabuse.gov/drugs-abuse/commonly-abused-drugs/commonly-abused-prescription-drugs-chart |title=Commonly Abused Prescription Drugs Chart |publisher=National Institute on Drug Abuse|access-date=7 May 2012}}{{cite web |url=http://www.drugabuse.gov/publications/infofacts/stimulant-adhd-medications-methylphenidate-amphetamines |title=Stimulant ADHD Medications – Methylphenidate and Amphetamines |publisher=National Institute on Drug Abuse |access-date=7 May 2012 |archive-date=2 May 2012 |archive-url=https://web.archive.org/web/20120502072325/http://www.drugabuse.gov/publications/infofacts/stimulant-adhd-medications-methylphenidate-amphetamines |url-status=dead }} 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.{{cite journal | vauthors = Schultz W | year = 2015 | title = Neuronal reward and decision signals: from theories to data | journal = Physiological Reviews | volume = 95 | issue = 3 | pages = 853–951 | pmid = 26109341 | pmc = 4491543 | doi=10.1152/physrev.00023.2014 | quote = Rewards in operant conditioning are positive reinforcers. ... Operant behavior gives a good definition for rewards. Anything that makes an individual come back for more is a positive reinforcer and therefore a reward. Although it provides a good definition, positive reinforcement is only one of several reward functions. ... Rewards are attractive. They are motivating and make us exert an effort. ... Rewards induce approach behavior, also called appetitive or preparatory behavior, sexual behavior, and consummatory behavior. ... Thus any stimulus, object, event, activity, or situation that has the potential to make us approach and consume it is by definition a reward. ... Rewarding stimuli, objects, events, situations, and activities consist of several major components. First, rewards have basic sensory components (visual, auditory, somatosensory, gustatory, and olfactory) ... Second, rewards are salient and thus elicit attention, which are manifested as orienting responses. The salience of rewards derives from three principal factors, namely, their physical intensity and impact (physical salience), their novelty and surprise (novelty/surprise salience), and their general motivational impact shared with punishers (motivational salience). A separate form not included in this scheme, incentive salience, primarily addresses dopamine function in addiction and refers only to approach behavior (as opposed to learning) ... Third, rewards have a value component that determines the positively motivating effects of rewards and is not contained in, nor explained by, the sensory and attentional components. This component reflects behavioral preferences and thus is subjective and only partially determined by physical parameters. Only this component constitutes what we understand as a reward. It mediates the specific behavioral reinforcing, approach generating, and emotional effects of rewards that are crucial for the organism's survival and reproduction, whereas all other components are only supportive of these functions. ... Rewards can also be intrinsic to behavior. They contrast with extrinsic rewards that provide motivation for behavior and constitute the essence of operant behavior in laboratory tests. Intrinsic rewards are activities that are pleasurable on their own and are undertaken for their own sake, without being the means for getting extrinsic rewards. ... Intrinsic rewards are genuine rewards in their own right, as they induce learning, approach, and pleasure, like perfectioning, playing, and enjoying the piano. Although they can serve to condition higher order rewards, they are not conditioned, higher order rewards, as attaining their reward properties does not require pairing with an unconditioned reward. ... These emotions are also called liking (for pleasure) and wanting (for desire) in addiction research and strongly support the learning and approach generating functions of reward.}} Large recreational doses of dextroamphetamine may produce symptoms of dextroamphetamine overdose. 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.{{cite web|title=National Institute on Drug Abuse. 2009. Stimulant ADHD Medications – Methylphenidate and Amphetamines|url=https://nida.nih.gov/publications/research-reports/misuse-prescription-drugs/overview|publisher=National Institute on Drug Abuse|access-date=27 February 2013}} 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).{{cite book |title=Canadian ADHD Practice Guidelines |date=2018 |publisher=Canadian ADHD Resource Alliance |page=67 |edition=Fourth |url=https://www.caddra.ca/wp-content/uploads/CADDRA-Guidelines-4th-Edition_-Feb2018.pdf |access-date=2 May 2023 |archive-date=2 May 2023 |archive-url=https://web.archive.org/web/20230502204112/https://www.caddra.ca/wp-content/uploads/CADDRA-Guidelines-4th-Edition_-Feb2018.pdf |url-status=dead }}{{cite journal | vauthors = Bright GM | title = Abuse of medications employed for the treatment of ADHD: results from a large-scale community survey | journal = Medscape Journal of Medicine | volume = 10 | issue = 5 | pages = 111 | date = May 2008 | pmid = 18596945 | pmc = 2438483 }}

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.{{cite journal | vauthors = Childs E, de Wit H | title = Contextual conditioning enhances the psychostimulant and incentive properties of d-amphetamine in humans | journal = Addiction Biology | date = November 2013 | volume = 18 | issue = 6 | pages = 985–992 | pmid = 22129527 | pmc = 4242554 | doi = 10.1111/j.1369-1600.2011.00416.x }} Injection into the bloodstream can be dangerous because insoluble fillers within the tablets can block small blood vessels. Chronic overuse of dextroamphetamine can lead to severe drug dependence, resulting in withdrawal symptoms when drug use stops.

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Many types of substances are known to interact with amphetamine, resulting in altered drug action or metabolism of amphetamine, the interacting substance, or both. 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.{{cite web | title=Adderall- dextroamphetamine saccharate, amphetamine aspartate, dextroamphetamine sulfate, and amphetamine sulfate tablet | website=DailyMed | date=27 February 2022 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=f22635fe-821d-4cde-aa12-419f8b53db81 | access-date=28 March 2022}}{{cite web | title=Adderall XR- dextroamphetamine sulfate, dextroamphetamine saccharate, amphetamine sulfate and amphetamine aspartate capsule, extended release | website=DailyMed | date=3 March 2022 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=aff45863-ffe1-4d4f-8acf-c7081512a6c0 | access-date=28 March 2022}} Amphetamine also interacts with {{abbr|MAOIs|monoamine oxidase inhibitors}}, particularly monoamine oxidase A inhibitors, since both MAOIs and amphetamine increase plasma catecholamines (i.e., norepinephrine and dopamine); therefore, concurrent use of both is dangerous. 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. Amphetamine may also decrease the effects of antihypertensives and antipsychotics due to its effects on blood pressure and dopamine respectively. Zinc supplementation may reduce the minimum effective dose of amphetamine when it is used for the treatment of ADHD.{{#tag:ref|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.{{cite journal | vauthors = Krause J | title = SPECT and PET of the dopamine transporter in attention-deficit/hyperactivity disorder | journal = Expert Rev. Neurother. | volume = 8 | issue = 4 | pages = 611–625 | date = April 2008 | pmid = 18416663 | doi = 10.1586/14737175.8.4.611 | s2cid = 24589993 | quote = Zinc binds at ... extracellular sites of the DAT [103], serving as a DAT inhibitor. In this context, controlled double-blind studies in children are of interest, which showed positive effects of zinc [supplementation] on symptoms of ADHD [105,106]. It should be stated that at this time [supplementation] with zinc is not integrated in any ADHD treatment algorithm.}}{{cite journal | vauthors = Sulzer D | title = How addictive drugs disrupt presynaptic dopamine neurotransmission | journal = Neuron | volume = 69 | issue = 4 | pages = 628–649 | date = February 2011 | pmid = 21338876 | pmc = 3065181 | doi = 10.1016/j.neuron.2011.02.010 | quote = They did not confirm the predicted straightforward relationship between uptake and release, but rather that some compounds including AMPH were better releasers than substrates for uptake. Zinc, moreover, stimulates efflux of intracellular [3H]DA despite its concomitant inhibition of uptake (Scholze et al., 2002).}}{{cite journal | vauthors = Scholze P, Nørregaard L, Singer EA, Freissmuth M, Gether U, Sitte HH | title = The role of zinc ions in reverse transport mediated by monoamine transporters | journal = J. Biol. Chem. | volume = 277 | issue = 24 | pages = 21505–21513 | date = June 2002 | pmid = 11940571 | doi = 10.1074/jbc.M112265200| doi-access = free}} The human serotonin transporter and norepinephrine transporter do not contain zinc binding sites.|group="note"}}{{cite journal |vauthors=Scassellati C, Bonvicini C, Faraone SV, Gennarelli M | title = Biomarkers and attention-deficit/hyperactivity disorder: a systematic review and meta-analyses | journal = J. Am. Acad. Child Adolesc. Psychiatry | volume = 51 | issue = 10 | pages = 1003–1019.e20 | date = October 2012 | pmid = 23021477 | doi = 10.1016/j.jaac.2012.08.015}} 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.{{cite journal | vauthors = Treuer T, Gau SS, Méndez L, Montgomery W, Monk JA, Altin M, Wu S, Lin CC, Dueñas HJ | title = A systematic review of combination therapy with stimulants and atomoxetine for attention-deficit/hyperactivity disorder, including patient characteristics, treatment strategies, effectiveness, and tolerability | journal = J Child Adolesc Psychopharmacol | volume = 23 | issue = 3 | pages = 179–193 | date = April 2013 | pmid = 23560600 | pmc = 3696926 | doi = 10.1089/cap.2012.0093 | url = }}{{cite book | vauthors = Heal DJ, Smith SL, Findling RL | title = Behavioral Neuroscience of Attention Deficit Hyperactivity Disorder and Its Treatment | chapter = ADHD: current and future therapeutics | series = Current Topics in Behavioral Neurosciences | volume = 9 | issue = | pages = 361–390 | date = 2012 | pmid = 21487953 | doi = 10.1007/7854_2011_125 | isbn = 978-3-642-24611-1 | chapter-url = | quote = Adjunctive therapy with DL-methylphenidate in atomoxetine partial responders has been successful (Wilens et al. 2009), but this also increases the rates of insomnia, irritability and loss of appetite (Hammerness et al. 2009). This combination therapy has not included amphetamine because blockade of NET by atomoxetine prevents entry of amphetamine into presynaptic noradrenergic terminals (Sofuoglu et al. 2009). }}{{cite journal | vauthors = Sofuoglu M, Poling J, Hill K, Kosten T | title = Atomoxetine attenuates dextroamphetamine effects in humans | journal = Am J Drug Alcohol Abuse | volume = 35 | issue = 6 | pages = 412–416 | date = 2009 | pmid = 20014909 | pmc = 2796580 | doi = 10.3109/00952990903383961 | url = }}

{{hatnote|Main section: {{section link|Amphetamine|Pharmacodynamics}}}}

{{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.{{cite journal | vauthors = Bunzow JR, Sonders MS, Arttamangkul S, Harrison LM, Zhang G, Quigley DI, Darland T, Suchland KL, Pasumamula S, Kennedy JL, Olson SB, Magenis RE, Amara SG, Grandy DK | title = Amphetamine, 3,4-methylenedioxymethamphetamine, lysergic acid diethylamide, and metabolites of the catecholamine neurotransmitters are agonists of a rat trace amine receptor | journal = Molecular Pharmacology | volume = 60 | issue = 6 | pages = 1181–1188 | date = December 2001 | pmid = 11723224 | doi = 10.1124/mol.60.6.1181 | s2cid = 14140873 }} 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).{{cite journal | vauthors = Miller GM | title = The emerging role of trace amine-associated receptor 1 in the functional regulation of monoamine transporters and dopaminergic activity | journal = Journal of Neurochemistry | volume = 116 | issue = 2 | pages = 164–176 | date = January 2011 | pmid = 21073468 | pmc = 3005101 | doi = 10.1111/j.1471-4159.2010.07109.x }}{{cite journal | vauthors = Borowsky B, Adham N, Jones KA, Raddatz R, Artymyshyn R, Ogozalek KL, Durkin MM, Lakhlani PP, Bonini JA, Pathirana S, Boyle N, Pu X, Kouranova E, Lichtblau H, Ochoa FY, Branchek TA, Gerald C | title = Trace amines: identification of a family of mammalian G protein-coupled receptors | journal = Proceedings of the National Academy of Sciences of the United States of America | volume = 98 | issue = 16 | pages = 8966–8971 | date = July 2001 | pmid = 11459929 | pmc = 55357 | doi = 10.1073/pnas.151105198 | doi-access = free | bibcode = 2001PNAS...98.8966B }} Amphetamine enantiomers are also substrates for a specific neuronal synaptic vesicle uptake transporter called VMAT2. When amphetamine is taken up by VMAT2, the vesicle releases (effluxes) dopamine, norepinephrine, and serotonin, among other monoamines, into the cytosol in exchange.{{cite journal | vauthors = Eiden LE, Weihe E | title = VMAT2: a dynamic regulator of brain monoaminergic neuronal function interacting with drugs of abuse | journal = Annals of the New York Academy of Sciences | volume = 1216 | issue = 1 | pages = 86–98 | date = January 2011 | pmid = 21272013 | pmc = 4183197 | doi = 10.1111/j.1749-6632.2010.05906.x | bibcode = 2011NYASA1216...86E }}

Dextroamphetamine (the dextrorotary enantiomer) and levoamphetamine (the levorotary enantiomer) have identical pharmacodynamics, but their binding affinities to their biomolecular targets vary.{{cite book |veditors=Brunton LL, Chabner BA, Knollmann BC | title = Goodman & Gilman's Pharmacological Basis of Therapeutics | year = 2010 | publisher = McGraw-Hill | location = New York | isbn = 978-0-07-162442-8 |vauthors=Westfall DP, Westfall TC | section = Miscellaneous Sympathomimetic Agonists | section-url = http://www.accessmedicine.com/content.aspx?aID=16661601 | edition = 12th }} Dextroamphetamine is a more potent agonist of TAAR1 than levoamphetamine. Consequently, dextroamphetamine produces roughly three to four times more central nervous system (CNS) stimulation than levoamphetamine;{{cite journal |vauthors=Lewin AH, Miller GM, Gilmour B | title = Trace amine-associated receptor 1 is a stereoselective binding site for compounds in the amphetamine class | journal = Bioorg. Med. Chem. | volume = 19 | issue = 23 | pages = 7044–7048 | date = December 2011 | pmid = 22037049 | pmc = 3236098 | doi = 10.1016/j.bmc.2011.10.007 }} however, levoamphetamine has slightly greater cardiovascular and peripheral effects.

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{{Main|History and culture of amphetamines}}

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,Free-base form amphetamine is a volatile oil, hence the efficacy of the inhalers. 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.{{cite web|title=Dexedrine|url=http://www.medic8.com/medicines/Dexedrine.html|website=Medic8|access-date=27 November 2013|url-status=dead|archive-url=https://web.archive.org/web/20091219120223/http://www.medic8.com/medicines/Dexedrine.html|archive-date=19 December 2009}} In the United States, Dexedrine was approved to treat narcolepsy and attention deficit hyperactivity disorder (ADHD). In Canada indications once included epilepsy and parkinsonism.{{cite web| url =http://www.mentalhealth.com/drug/p30-d04.html| title =Dextroamphetamine [monograph]| website =Internet Mental Health| archive-url =https://web.archive.org/web/20060427084347/http://www.mentalhealth.com/drug/p30-d04.html| access-date =6 September 2015| archive-date=27 April 2006}} 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").{{cite web|url=http://www.weitzlux.com/Dexedrine/information_403484.html |title=Information on Dexedrine: A Quick Review {{pipe}} Weitz & Luxenberg |publisher=Weitzlux.com |date=31 August 2013 |access-date=5 January 2017}} Preparations containing dextroamphetamine were also used in World War II as a treatment against fatigue.{{cite journal |vauthors=Heal DJ, Smith SL, Gosden J, Nutt DJ | title = Amphetamine, past and present—a pharmacological and clinical perspective | journal = Journal of Psychopharmacology | volume = 27 | issue = 6 | pages = 479–96 | date = June 2013 | pmid = 23539642 | doi = 10.1177/0269881113482532 | pmc = 3666194 }}

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.{{cite web | vauthors = King DG | date = 4 January 2017 | url = http://www.denton.handwritingexperts.com/articles/prescriptionforgery1.html | title = Prescription Forgery | work = Handwriting Services International | archive-url = https://web.archive.org/web/20080705185842/http://www.denton.handwritingexperts.com/articles/prescriptionforgery1.html | archive-date = 5 July 2008 }} 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).{{cite book | url = http://www.knovel.com/web/portal/browse/display?_EXT_KNOVEL_DISPLAY_bookid=598 | title = Pharmaceutical Manufacturing Encyclopedia | date = January 1988 | edition = 2nd | veditors = Sittig M | volume = 1 | publisher = Noyes Publications | isbn = 978-0-8155-1144-1}} 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).{{cite web|title=Dexedrine FAQs|url=http://www.dexedrine.net/faq.asp|url-status=dead|archive-url=https://web.archive.org/web/20110617013326/http://www.dexedrine.net/faq.asp|archive-date=17 June 2011}}

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".{{cite web | vauthors = Bonné J |url=https://www.nbcnews.com/id/wbna3071789 |title='Go pills': A war on drugs? |work=NBC News |date=9 January 2003 |access-date=5 January 2017}}{{cite web | vauthors = Woodring JC |url=https://www.af.mil/News/story/id/123007615/ |title=Air Force scientists battle aviator fatigue |access-date=5 January 2017 |url-status= live |archive-url=https://web.archive.org/web/20121014113247/http://www.af.mil/news/story.asp?id=123007615 |archive-date=14 October 2012 }}{{cite journal |vauthors=Emonson DL, Vanderbeek RD | title = The use of amphetamines in U.S. Air Force tactical operations during Desert Shield and Storm | journal = Aviation, Space, and Environmental Medicine | volume = 66 | issue = 3 | pages = 260–3 | year = 1995 | pmid = 7661838 }} 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.

Dextroamphetamine is available as a transdermal patch containing dextroamphetamine base under the brand name Xelstrym.

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.{{cite web|url=http://zenzedi.com/ |title=Zenzedi (dextroamphetamine sulfate, USP) |publisher=Zenzedi.com |access-date=5 January 2017}} 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.{{cite web | url = http://www.fsclabs.com/ProCentra.html | title = ProCentra (dextroamphetamine sulfate 5 mg/5 mL Oral Solution) | work = FSC Laboratories | archive-url = https://web.archive.org/web/20101005052859/http://www.fsclabs.com/ProCentra.html | archive-date = 5 October 2010 }} The conversion rate between dextroamphetamine sulfate to amphetamine free base is .728.{{cite patent | inventor = Mickle T, Krishnan S, Bishop B, Lauderback C, Moncrief JS, Oberlender R, Piccariello T, Paul BJ, Verbicky CD | gdate = 2010 | title = Abuse-resistant amphetamine prodrugs | country = US | number = 7655630 | assign1 = Takeda Pharmaceutical Co Ltd }}

In Australia, dexamfetamine is available in bottles of 100 instant release 5 mg tablets as a generic drug{{cite journal|doi=10.18773/austprescr.1995.064 |title=Stimulant treatment for attention deficit hyperactivity disorder |journal=Australian Prescriber |volume=18 |issue=3 |pages=60–63 |year=1995 | vauthors = Hazell P |doi-access=free }} or slow release dextroamphetamine preparations may be compounded by individual chemists.{{cite web |url=http://www0.health.nsw.gov.au/PublicHealth/Pharmaceutical/adhd/faqs.asp |title=Pharmaceutical Services |publisher=.health.nsw.gov.au |access-date=5 January 2017 |url-status=dead |archive-url=https://web.archive.org/web/20130505045845/http://www0.health.nsw.gov.au/PublicHealth/Pharmaceutical/adhd/faqs.asp |archive-date=5 May 2013 }} 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.{{cite web |title=Dexamfetamine sulphate - Medicinal forms |url=https://bnf.nice.org.uk/medicinal-forms/dexamfetamine-sulfate.html |website=British National Formulary |publisher=BMJ Group and Pharmaceutical Press (Royal Pharmaceutical Society) |access-date=9 November 2019}} The brand name Dexedrine was available in the United Kingdom prior to UCB Pharma disinvesting the product to another pharmaceutical company (Auden Mckenzie).{{cite journal | title = Dexamfetamine – Prescribe Generically | url = http://www.ipnsm.hscni.net/news/RedAmberNewsNov10.pdf | journal = Red/Amber News | issue = 22 | archive-url = https://web.archive.org/web/20130518094535/http://www.ipnsm.hscni.net/news/RedAmberNewsNov10.pdf | archive-date=18 May 2013 | page = 2 | publisher = Interface Pharmacist Network Specialist Medicines (IPNSM) | date = November 2010 | access-date = 20 April 2012 }}

{{Main|Lisdexamfetamine}}

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.{{cite journal | vauthors = Hutson PH, Pennick M, Secker R | title = Preclinical pharmacokinetics, pharmacology and toxicology of lisdexamfetamine: a novel d-amphetamine pro-drug | journal = Neuropharmacology | volume = 87 | pages = 41–50 | date = December 2014 | pmid = 24594478 | doi = 10.1016/j.neuropharm.2014.02.014 | s2cid = 37893582 }}{{cite web | vauthors = Elayan I | url = https://www.accessdata.fda.gov/drugsatfda_docs/nda/2007/021977s000_PharmToxR.pdf | archive-url = https://web.archive.org/web/20170211130631/http://www.accessdata.fda.gov/drugsatfda_docs/nda/2007/021977s000_PharmToxR.pdf | url-status = dead | archive-date = 11 February 2017 | title = NRP-104 (lisdexamphetamine dimesylate) | work = Pharmacology/Toxicology Review and Evaluation | publisher = U.S. Food and Drug Administration | date = 2006 | pages = 18–19 }} 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%.{{cite journal | vauthors = Mohammadi M, Akhondzadeh S | title = Advances and considerations in attention-deficit/hyperactivity disorder pharmacotherapy | journal = Acta Medica Iranica | volume = 49 | issue = 8 | pages = 487–498 | date = September 2011 | pmid = 22009816 | url = http://acta.tums.ac.ir/index.php/acta/article/view/4380 | access-date = 12 March 2014 }}{{cite journal | vauthors = Heal DJ, Buckley NW, Gosden J, Slater N, France CP, Hackett D | title = A preclinical evaluation of the discriminative and reinforcing properties of lisdexamfetamine in comparison to D-amfetamine, methylphenidate and modafinil | journal = Neuropharmacology | volume = 73 | pages = 348–358 | date = October 2013 | pmid = 23748096 | doi = 10.1016/j.neuropharm.2013.05.021 | s2cid = 25343254 }}{{cite journal | vauthors = Rowley HL, Kulkarni R, Gosden J, Brammer R, Hackett D, Heal DJ | title = Lisdexamfetamine and immediate release d-amfetamine - differences in pharmacokinetic/pharmacodynamic relationships revealed by striatal microdialysis in freely-moving rats with simultaneous determination of plasma drug concentrations and locomotor activity | journal = Neuropharmacology | volume = 63 | issue = 6 | pages = 1064–1074 | date = November 2012 | pmid = 22796358 | doi = 10.1016/j.neuropharm.2012.07.008 | s2cid = 29702399 }}

{{main|Adderall}}

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

• 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%. While the enantiomer ratio by dextroamphetamine salts to levoamphetamine salts is 3:1, the amphetamine base content is 75.9% dextroamphetamine, 24.1% levoamphetamine. {{#tag:ref|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.| group = "note" }}

{{Amphetamine base in marketed amphetamine medications}}

Dextroamphetamine reduces the negative symptoms of schizophrenia, and has been shown to enhance the effects of auditory discrimination training in schizophrenic patients.{{cite journal |vauthors=Lindenmayer JP, Nasrallah H, Pucci M, James S, Citrome L |date=July 2013 |title=A systematic review of psychostimulant treatment of negative symptoms of schizophrenia: challenges and therapeutic opportunities |journal=Schizophrenia Research |volume=147 |issue=2–3 |pages=241–252 |doi=10.1016/j.schres.2013.03.019 |pmid=23619055}}{{cite journal |vauthors=van Kammen DP, Boronow JJ |date=April 1988 |title=Dextro-amphetamine diminishes negative symptoms in schizophrenia |journal=International Clinical Psychopharmacology |volume=3 |issue=2 |pages=111–121 |doi=10.1097/00004850-198804000-00002 |pmid=3294284}}{{cite journal |display-authors=6 |vauthors=Swerdlow NR, Tarasenko M, Bhakta SG, Talledo J, Alvarez AI, Hughes EL, Rana B, Vinogradov S, Light GA |date=July 2017 |title=Amphetamine Enhances Gains in Auditory Discrimination Training in Adult Schizophrenia Patients |journal=Schizophrenia Bulletin |volume=43 |issue=4 |pages=872–880 |doi=10.1093/schbul/sbw148 |pmc=5472129 |pmid=27798224}}{{clear}}

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• {{cite book | url = http://www.inchem.org/documents/pims/pharm/pim178.htm | title = Poison Information Monograph | chapter = PIM 178: Dexamphetamine Sulphate) | publisher = International Programme on Chemical Safety (IPCS) Chemical Safety Information from Intergovernmental organizations (INCHEM) }}

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