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词条 Dextroamphetamine
释义

  1. Uses

     Medical  Enhancing performance  Recreational 

  2. Contraindications

  3. Side effects

  4. Overdose

  5. Interactions

  6. Pharmacology

     Pharmacodynamics  Related endogenous compounds  Pharmacokinetics 

  7. History, society, and culture

     Formulations   Dextroamphetamine sulfate    Lisdexamfetamine   Adderall 

  8. Notes

  9. Reference notes

  10. References

  11. External links

{{For|the racemic compound|Amphetamine}}{{Use dmy dates|date=November 2018}}{{Drugbox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 596899008
| INN = Dexamfetamine
| IUPAC_name = (2S)-1-Phenylpropan-2-amine
| image = D-amphetamine.svg
| width = 200px
| pronounce = {{IPAc-en|ˌ|d|ɛ|k|s|t|r|əʊ|æ|m|ˈ|f|ɛ|t|ə|m|iː|n}}
| drug_name =
| tradename = Dexedrine, Metamina, Attentin, Zenzedi, Procentra, Amfexa
| Drugs.com = {{drugs.com|monograph|dextroamphetamine}}
| MedlinePlus = a605027
| licence_EU =
| licence_US = Dextroamphetamine
| pregnancy_AU = B3
| pregnancy_US = C
| legal_AU = S8
| legal_CA = Schedule I
| legal_DE = Anlage III
| legal_UK = Class B
| legal_US = Schedule II
| legal_status =
| dependency_liability = Physical: None
Psychological: Moderate[1]
| addiction_liability = High
| routes_of_administration = By mouth
| bioavailability = Oral: 75–100%[2]
| protein_bound = 15–40%
| metabolism = CYP2D6, DBH,[3] FMO3
| onset = {{abbr|IR|Immediate release}} dosing: 0.5–1.5 hours[4][5]
{{abbr|XR|Extended release}} dosing: 1.5–2 hours[6][7]
| elimination_half-life = 9–11 hours[8]
pH-dependent: 7–34 hours
| duration_of_action = {{abbr|IR|Immediate release}} dosing: 3–6 hours[6][9]
{{abbr|XR|Extended release}} dosing: 8–12 hours[1][6][9]
| excretion = Renal (45%);[10] urinary pH-dependent
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 51-64-9
| ATC_prefix = N06
| ATC_suffix = BA02
| ATC_supplemental =
| PubChem = 5826
| IUPHAR_ligand = 2147
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB01576
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 5621
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = TZ47U051FI
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D03740
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 4469
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 612
| synonyms = D-Amphetamine
| C=9 | H=13 | N=1
| SMILES = C[C@@H](Cc1ccccc1)N
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = InChI=1S/C9H13N/c1-8(10)7-9-5-3-2-4-6-9/h2-6,8H,7,10H2,1H3/t8-/m0/s1
| StdInChI_comment =
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = KWTSXDURSIMDCE-QMMMGPOBSA-N
| density = 0.913
| melting_point =
| melting_notes =
| boiling_point = 201.5
| boiling_notes =
| solubility = 20
}}

Dextroamphetamine{{#tag:ref|Synonyms and alternate spellings include: {{nowrap|(2S)-1-phenylpropan-2-amine}} (IUPAC name), dexamfetamine (INN),[11] dexamphetamine, {{nowrap|(S)-amphetamine}}, {{nowrap|(+)-amphetamine}}, and {{nowrap|D-amphetamine}}.| group = "note" }} is a potent central nervous system (CNS) stimulant and amphetamine enantiomer that is prescribed for the treatment of attention deficit hyperactivity disorder (ADHD) and narcolepsy.[12][23] It is also used as an athletic performance and cognitive enhancer, and recreationally as an aphrodisiac and euphoriant. Dextroamphetamine was also used by military air, tank and special forces as a 'go-pill' during fatigue-inducing missions such as night-time bombing missions or extended combat operations.

The amphetamine molecule exists as two enantiomers,{{#tag:ref|Enantiomers are molecules that are mirror images of one another; they are structurally identical, but of the opposite orientation.[13]|group = "note"}} levoamphetamine and dextroamphetamine. Dextroamphetamine is the dextrorotatory, or 'right-handed', enantiomer and exhibits more pronounced effects on the CNS 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 dimesylate, which is converted into dextroamphetamine after absorption.

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[25] and it releases these neurotransmitters from synaptic vesicles via vesicular monoamine transporter 2.[26] It also shares many chemical and pharmacological properties with human trace amines, particularly phenethylamine and {{nowrap|N-methylphenethylamine}}, the latter being an isomer of amphetamine produced within the human body.

{{TOC limit|3}}

Uses

Medical

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Dextroamphetamine is used to treat attention deficit hyperactivity disorder (ADHD) and narcolepsy (a sleep disorder), and is sometimes prescribed {{nowrap|off-label}} for its past medical indications, such as depression and obesity.[12][23]

{{trim|{{#section-h:Amphetamine|Medical}}}}

Enhancing performance

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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.[14][15][31] Large recreational doses of dextroamphetamine may produce symptoms of dextroamphetamine overdose.[31] Recreational users sometimes open dexedrine capsules and crush the contents in order to snort it or subsequently dissolve it in water and inject it.[16] Injection into the bloodstream can be dangerous because insoluble fillers within the tablets can block small blood vessels.[16] Chronic overuse of dextroamphetamine can lead to severe drug dependence, resulting in withdrawal symptoms when drug use stops.[16]

Contraindications

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Side effects

{{transcluded section|source=Amphetamine}}{{trim|{{#section-h:Amphetamine|Side effects}}}}

Overdose

{{transcluded section|source=Amphetamine}}{{trim|{{#section-h:Amphetamine|Overdose}}}}

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.[37] 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.[17] 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);[17] therefore, concurrent use of both is dangerous.[17] 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.[17] Amphetamine may also decrease the effects of antihypertensives and antipsychotics due to its effects on blood pressure and dopamine respectively.[17] 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.[18][19][20] The human serotonin transporter and norepinephrine transporter do not contain zinc binding sites.[20]|group="note"}}[21]

Pharmacology

Pharmacodynamics

{{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.[22][50] 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).[23][22][24] Amphetamine enantiomers are also substrates for a specific neuronal synaptic vesicle uptake transporter called VMAT2.[26] When amphetamine is taken up by VMAT2, the vesicle releases (effluxes) dopamine, norepinephrine, and serotonin, among other monoamines, into the cytosol in exchange.[25]

Dextroamphetamine (the dextrorotary enantiomer) and levoamphetamine (the levorotary enantiomer) have identical pharmacodynamics, but their binding affinities to their biomolecular targets vary.[50][26] Dextroamphetamine is a more potent agonist of TAAR1 than levoamphetamine.[50] Consequently, dextroamphetamine produces roughly three to four times more central nervous system (CNS) stimulation than levoamphetamine;[27][26] however, levoamphetamine has slightly greater cardiovascular and peripheral effects.[26]

Related endogenous compounds

{{trim|{{#section-h:Amphetamine|Related endogenous compounds}}}}

Pharmacokinetics

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History, society, and culture

{{Main|History and culture of amphetamines}}

Racemic amphetamine was first synthesized under the chemical name "phenylisopropylamine" in Berlin, 1887 by the Romanian chemist Lazar 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,[28] not a chloride or sulfate salt.

Three years later, in 1935, the medical community became aware of the stimulant properties of amphetamine, specifically dextroamphetamine, and in 1937 Smith, Kline, and French introduced tablets under the tradename Dexedrine.[29] In the United States, Dexedrine was approved to treat narcolepsy, attention disorders, and obesity. In Canada indications once included epilepsy and parkinsonism.[30] 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 tradename Dexamyl and, in the 1950s, an extended release capsule (the "Spansule").[31] Preparations containing dextroamphetamine were also used in World War II as a treatment against fatigue.[32]

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.[33] 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).[34]

In October 2010, GlaxoSmithKline sold the rights for Dexedrine Spansule to Amedra Pharmaceuticals (a subsidiary of CorePharma).[35]

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".[36][37][38][39] 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.[37]

Formulations

These represent the current brands in the United States, except Dexedrine instant release tablets. Dexedrine tablets, introduced in 1937, is discontinued but available as Zenzedi and generically;[40][41] Dexedrine listed here represents the extended release "Spansule" capsule which was approved in 1976.[42][43] Amphetamine sulfate tablets, now sold as Evekeo (brand), were originally sold as Benzedrine (brand) sulfate in 1935[44][45] and discontinued sometime after 1982.[46][47]| group = "note" }}
Brand
name		United States
Adopted Name		(D:L) ratioDosage
form		Marketing
start date		Sources
Adderall – 3:1 (salts) tablet 1996 [23][84]
Adderall XR – 3:1 (salts) capsule 2001 [48][49]
Mydayis – 3:1 (salts) capsule 2017 [50]
Adzenys XR amphetamine 3:1 (base) ODT 2016 [51][52]
Dyanavel XR amphetamine 3.2:1 (base) suspension 2015 [53]
Evekeo amphetamine sulfate 1:1 (salts) tablet 2012 [54]
Dexedrine dextroamphetamine sulfate 1:0 (salts) capsule 1976 [48][49]
ProCentra dextroamphetamine sulfate 1:0 (salts) liquid 2010 [49]
Zenzedi dextroamphetamine sulfate 1:0 (salts) tablet 2013 [49]
Vyvanselisdexamfetamine dimesylate1:0 (prodrug) capsule 2007[48]
tablet
 

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 by the brand names of 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.[55] 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.[56] The conversion rate between dextroamphetamine sulfate to amphetamine free base is .728.[57]

In Australia, dexamphetamine is available in bottles of 100 instant release 5 mg tablets as a generic drug.[58] or slow release dextroamphetamine preparations may be compounded by individual chemists.[59] Similarly, in the United Kingdom it is only available in 5 mg instant release sulfate tablets under the generic name dextroamphetamine sulphate having had been available under the brand name Dexedrine prior to UCB Pharma disinvesting the product to another pharmaceutical company (Auden Mckenzie).[60]

Lisdexamfetamine

{{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) (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.[61][62] 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%.[63][64][65]

Adderall

{{main|Adderall}}

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%.[66] 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}}{{clear}}

Notes

1. ^1 {{cite book | vauthors=Stahl SM | title=Prescriber's Guide: Stahl's Essential Psychopharmacology | date=March 2017 | publisher=Cambridge University Press | location=Cambridge, United Kingdom | isbn=9781108228749 | pages=39–44 | edition=6th | chapter-url=https://books.google.com/books?id=9hssDwAAQBAJ&pg=PA39#v=onepage&q&f=false | chapter=Amphetamine (D) | accessdate=8 August 2017 }}
2. ^{{cite encyclopedia| title=Dextromphetamine | url=http://www.drugbank.ca/drugs/DB01576#pharmacology | work=DrugBank | accessdate=5 November 2013 | section=Pharmacology }}
3. ^{{cite book | title=Foye's Principles of Medicinal Chemistry | year=2013 | publisher=Wolters Kluwer Health/Lippincott Williams & Wilkins | location=Philadelphia | isbn=1609133455 | page=648 |vauthors=Lemke TL, Williams DA, Roche VF, Zito W |edition=7th | quote=Alternatively, direct oxidation of amphetamine by DA β-hydroxylase can afford norephedrine.}}
4. ^{{Cite book|title = Primary Care Pediatrics|url = https://books.google.com/books?id=o43u_qWT4asC|publisher = Lippincott Williams & Wilkins|date = 1 January 2001|isbn = 9780781720083|first = Carol|last = Green-Hernandez|first2 = Joanne K.|last2 = Singleton|first3 = Daniel Z.|last3 = Aronzon|page = 243}}|quote = Table 21.2 Medications for ADHD ... D-amphetamine ... Onset: 30 min.
5. ^{{cite web|title = Dexedrine, ProCentra(dextroamphetamine) dosing, indications, interactions, adverse effects, and more|url = http://reference.medscape.com/drug/dexedrine-procentra-dextroamphetamine-342998#10|website = reference.medscape.com|accessdate = 4 October 2015|quote = Onset of action: 1–1.5 hr}}
6. ^1 2 {{cite book | author = Millichap JG | editor = Millichap JG | title = Attention Deficit Hyperactivity Disorder Handbook: A Physician's Guide to ADHD | year = 2010 | publisher = Springer | location = New York, USA | isbn = 9781441913968 | page = 112 | edition = 2nd | chapter = Chapter 9: Medications for ADHD | quote =
Table 9.2 Dextroamphetamine formulations of stimulant medication
Dexedrine [Peak:2–3 h] [Duration:5–6 h] ...
Adderall [Peak:2–3 h] [Duration:5–7 h]
Dexedrine spansules [Peak:7–8 h] [Duration:12 h] ...
Adderall XR [Peak:7–8 h] [Duration:12 h]
Vyvanse [Peak:3–4 h] [Duration:12 h]}}
7. ^{{cite journal | vauthors = Brams M, Mao AR, Doyle RL | title = Onset of efficacy of long-acting psychostimulants in pediatric attention-deficit/hyperactivity disorder | journal = Postgrad. Med. | volume = 120 | issue = 3 | pages = 69–88 | date = September 2008 | pmid = 18824827 | doi = 10.3810/pgm.2008.09.1909 | quote = Onset of efficacy was earliest for d-MPH-ER at 0.5 hours, followed by d, l-MPH-LA at 1 to 2 hours, MCD at 1.5 hours, d, l-MPH-OR at 1 to 2 hours, MAS-XR at 1.5 to 2 hours, MTS at 2 hours, and LDX at approximately 2 hours. ... MAS-XR, and LDX have a long duration of action at 12 hours postdose}}
8. ^{{cite web | title=Adderall IR Prescribing Information | url=http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/011522s042lbl.pdf | publisher = Teva Pharmaceuticals USA, Inc. | work = United States Food and Drug Administration | date=October 2015 | accessdate=18 May 2016 | pages=1–6}}
9. ^1 {{cite journal | vauthors = Mignot EJ | title = A practical guide to the therapy of narcolepsy and hypersomnia syndromes | journal = Neurotherapeutics | volume = 9 | issue = 4 | pages = 739–752 | date = October 2012 | pmid = 23065655 | pmc = 3480574 | doi = 10.1007/s13311-012-0150-9 }}
10. ^{{cite web|title=dextrostat (dextroamphetamine sulfate) tablet [Shire US Inc.]|publisher=Shire US Inc.|work=DailyMed|url=http://dailymed.nlm.nih.gov/dailymed/archives/fdaDrugInfo.cfm?archiveid=1645|date=August 2006|accessdate=8 November 2013|location=Wayne, PA}}
11. ^{{Cite web|url=https://www.ebs.tga.gov.au/ebs/picmi/picmirepository.nsf/pdf?OpenAgent&id=CP-2017-PI-01667-1&d=2018052716114622483|title=Product Information – ASPEN DEXAMFETAMINE|last=|first=|date=13 October 2017|website=www.ebs.tga.gov.au|archive-url=|archive-date=|dead-url=|access-date=27 May 2018}}
12. ^1 {{cite web | title=Dexedrine Prescribing Information | work=United States Food and Drug Administration | publisher=Amedra Pharmaceuticals LLC | date=February 2015 | url=http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/017078s048lbl.pdf | accessdate = 4 September 2015 | pages=1–7}}
13. ^{{cite web|title=Enantiomer|url=http://goldbook.iupac.org/E02069.html|work=IUPAC Goldbook|publisher=International Union of Pure and Applied Chemistry|accessdate=14 March 2014|archiveurl=https://web.archive.org/web/20130317002318/http://goldbook.iupac.org/E02069.html|archivedate=17 March 2013|doi=10.1351/goldbook.E02069|quote=One of a pair of molecular entities which are mirror images of each other and non-superposable.}}
14. ^{{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|accessdate=7 May 2012}}
15. ^{{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 |accessdate=7 May 2012}}
16. ^1 2 3 4 {{cite web|title=National Institute on Drug Abuse. 2009. Stimulant ADHD Medications – Methylphenidate and Amphetamines|url=http://www.drugabuse.gov/publications/drugfacts/stimulant-adhd-medications-methylphenidate-amphetamines|publisher=National Institute on Drug Abuse|accessdate=27 February 2013}}
17. ^1 2 3 4 5 {{cite web | title = Adderall XR Prescribing Information | url = http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/021303s026lbl.pdf | pages = 8–10 | publisher = Shire US Inc | work = United States Food and Drug Administration |date=December 2013 | accessdate = 30 December 2013 }}
18. ^{{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 | 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.}}
19. ^{{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).}}
20. ^1 {{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}}
21. ^{{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}}
22. ^1 {{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 = Mol. Pharmacol. | volume = 60 | issue = 6 | pages = 1181–8 | date = December 2001 | pmid = 11723224 | doi = 10.1124/mol.60.6.1181 }}
23. ^1 {{cite journal | author = Miller GM | title = The emerging role of trace amine-associated receptor 1 in the functional regulation of monoamine transporters and dopaminergic activity | journal = J. Neurochem. | volume = 116 | issue = 2 | pages = 164–76 | date = January 2011 | pmid = 21073468 | pmc = 3005101 | doi = 10.1111/j.1471-4159.2010.07109.x }}
24. ^{{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 = Proc. Natl. Acad. Sci. U.S.A. | volume = 98 | issue = 16 | pages = 8966–71 | date = July 2001 | pmid = 11459929 | pmc = 55357 | doi = 10.1073/pnas.151105198 | bibcode = 2001PNAS...98.8966B }}
25. ^1 2 {{cite journal |vauthors=Eiden LE, Weihe E | title = VMAT2: a dynamic regulator of brain monoaminergic neuronal function interacting with drugs of abuse | journal = Ann. N. Y. Acad. Sci. | volume = 1216 | issue = | pages = 86–98 | date = January 2011 | pmid = 21272013 | doi = 10.1111/j.1749-6632.2010.05906.x |bibcode = 2011NYASA1216...86E | pmc=4183197}}
26. ^1 2 {{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 = 9780071624428 |vauthors=Westfall DP, Westfall TC | section = Miscellaneous Sympathomimetic Agonists | sectionurl = http://www.accessmedicine.com/content.aspx?aID=16661601 | edition = 12th }}
27. ^1 2 3 {{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 }}
28. ^Free-base form amphetamine is a volatile oil, hence the efficacy of the inhalers.
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39. ^‘Go pills’: A war on drugs?, msnbc, 9 January 2003
40. ^{{Cite journal|title = Amphetamine, past and present – a pharmacological and clinical perspective|journal = Journal of Psychopharmacology (Oxford, England)|date = 1 June 2013|issn = 0269-8811|pmc = 3666194|pmid = 23539642|pages = 479–496|volume = 27|issue = 6|doi = 10.1177/0269881113482532|first = David J|last = Heal|first2 = Sharon L|last2 = Smith|first3 = Jane|last3 = Gosden|first4 = David J|last4 = Nutt|quote = Smith, Kline and French synthesised both isomers, and in 1937 commenced marketing of d-amphetamine, which was the more potent of the two isomers, under the trade name of Dexedrine®.}}
41. ^{{cite web|title = Drugs@FDA: FDA Approved Drug Products: Dexedrine|url = http://www.accessdata.fda.gov/scripts/cder/drugsatfda/index.cfm?fuseaction=Search.Overview&DrugName=DEXEDRINE|website = U.S. Food and Drug Administration|accessdate = 30 December 2015|quote = DEXEDRINE ... TABLET;ORAL 5MG Discontinued}}
42. ^{{cite web|title = DEXEDRINE – Official Site For DEXEDRINE – DEXEDRINE Spansule – DEXEDRINE Spansules – DEXEDRINE For ADHD|url = http://dexedrine.net/|website = Official Site For DEXEDRINE|accessdate = 30 December 2015|deadurl = yes|archiveurl = https://web.archive.org/web/20030217042723/http://www.dexedrine.net/|archivedate = 17 February 2003|df = dmy-all}}
43. ^{{cite web|title = Drugs@FDA: Dexedrine: Label and Approval History|url = http://www.accessdata.fda.gov/scripts/cder/drugsatfda/index.cfm?fuseaction=Search.Set_Current_Drug&ApplNo=017078&DrugName=DEXEDRINE&ActiveIngred=DEXTROAMPHETAMINE%2520SULFATE&SponsorApplicant=AMEDRA%2520PHARMS&ProductMktStatus=1&goto=Search.Label_ApprovalHistory|website = U.S. Food and Drug Administration|accessdate = 30 December 2015|quote = 08/02/1976 ... Approval}}
44. ^{{Cite journal|title = Bradley’s Benzedrine Studies on Children with Behavioral Disorders|journal = The Yale Journal of Biology and Medicine|date = 1 March 2011|issn = 0044-0086|pmc = 3064242|pmid = 21451781|pages = 27–33|volume = 84|issue = 1|first = Madeleine P.|last = Strohl|quote = Bradley experimented with Benzedrine sulfate, a drug marketed to doctors by the company Smith, Kline & French (SKF) between 1935 and 1937...}}
45. ^{{Cite journal|title = Amphetamine, past and present – a pharmacological and clinical perspective|journal = Journal of Psychopharmacology (Oxford, England)|date = 1 June 2013|issn = 0269-8811|pmc = 3666194|pmid = 23539642|pages = 479–496|volume = 27|issue = 6|doi = 10.1177/0269881113482532|first = David J|last = Heal|first2 = Sharon L|last2 = Smith|first3 = Jane|last3 = Gosden|first4 = David J|last4 = Nutt|quote = Smith, Kline and French introduced Benzedrine onto the market in 1935 as a treatment for narcolepsy (for which it is still used today), mild depression, post-encephalitic Parkinsonism and a raft of other disorders.}}
46. ^{{Cite journal|title = Amphetamine, past and present – a pharmacological and clinical perspective|journal = Journal of Psychopharmacology (Oxford, England)|date = 1 June 2013|issn = 0269-8811|pmc = 3666194|pmid = 23539642|pages = 479–496|volume = 27|issue = 6|doi = 10.1177/0269881113482532|first = David J|last = Heal|first2 = Sharon L|last2 = Smith|first3 = Jane|last3 = Gosden|first4 = David J|last4 = Nutt|quote = The use of Benzedrine to treat ADHD declined dramatically after Gross (1976) reported that the racemate was significantly less clinically effective than Dexedrine. Currently, the only use of l-amphetamine in ADHD medications is in mixed salts/mixed enantiomers amphetamine...}}
47. ^{{cite web|url = http://www.accessdata.fda.gov/scripts/cder/drugsatfda/index.cfm?fuseaction=Search.Label_ApprovalHistory#apphist|title = FDA Approved Drug Products: Label and Approval History (Benzedrine)|website = www.accessdata.fda.gov|access-date = 11 March 2016|quote = Action Date 5/11/1982, Supplement Number 007, Approval Type Chemistry}}
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49. ^1 2 3 4 {{cite web | title = National Drug Code Amphetamine Search Results | url = http://www.accessdata.fda.gov/scripts/cder/ndc/results.cfm?beginrow=1&numberperpage=160&searchfield=amphetamine&searchtype=ActiveIngredient&OrderBy=ProprietaryName | work = National Drug Code Directory|publisher=United States Food and Drug Administration | accessdate = 16 December 2013 | archiveurl = https://web.archive.org/web/20131216080856/http://www.accessdata.fda.gov/scripts/cder/ndc/results.cfm?beginrow=1&numberperpage=160&searchfield=amphetamine&searchtype=ActiveIngredient&OrderBy=ProprietaryName | archivedate=16 December 2013}}
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Reference notes

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References

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External links

  • [https://www.drugs.com/pro/dextroamphetamine.html Dextroamphetamine consumer information from Drugs.com]
  • Poison Information Monograph (PIM 178: Dexamphetamine Sulphate)
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