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| Systematic (IUPAC) name | |
|---|---|
| (2S)-1-phenylpropan-2-amine | |
| Clinical data | |
| Trade names | Dexedrine, Dextrostat, Dexamphetamine |
| AHFS/Drugs.com | monograph |
| MedlinePlus | a605027 |
| Licence data | US Daily Med:link |
| Pregnancy cat. | B3 (AU) C (US) |
| Legal status | Controlled (S8) (AU) Schedule I (CA) Class B (UK) Schedule II (US) |
| Dependence liability | Moderate to High |
| Routes | Oral (only medically-utilized route) |
| Pharmacokinetic data | |
| Bioavailability | Oral 75–100%[1] |
| Metabolism | Hepatic (CYP2D6-mediated hydroxylation)[2] and FMO[3] |
| Half-life | 10-12 hours[4][5] |
| Excretion | Renal (45%);[6] urinary pH-dependent |
| Identifiers | |
| CAS number | 51-64-9 |
| ATC code | N06BA02 |
| PubChem | CID 5826 |
| DrugBank | DB01576 |
| ChemSpider | 5621 |
| UNII | TZ47U051FI |
| KEGG | D03740 |
| ChEBI | CHEBI:4469 |
| ChEMBL | CHEMBL612 |
| Chemical data | |
| Formula | C9H13N |
| Mol. mass | 135.20622 |
|
SMILES
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InChI
|
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| Physical data | |
| Density | 0.913 g/cm³ |
| Boiling point | 201.5 °C (395 °F) |
| Solubility in water | 20 mg/mL (20 °C) |
Dexamphetamine (INN, BAN) or Dextroamphetamine (USAN) is a psychostimulant drug typically used for the treatment of attention deficit-hyperactivity disorder (ADHD) and narcolepsy.
The amphetamine molecule has two stereoisomers: levamphetamine and dexamphetamine. Dexamphetamine is the dextrorotatory, or "right-handed", enantiomer of the amphetamine molecule. Dexamphetamine is available as a generic drug or under several brand names, including Dexedrine and Dextrostat.
Dexamphetamine is also an active metabolite of the prodrug lisdexamphetamine (Vyvanse), as well as of several older N-substituted amphetamine prodrugs used as anorectics, such as clobenzorex (Asenlix), benzphetamine (Didrex), and amphetaminil (Aponeuron). Common side effects include dry mouth, insomnia and headache. Temporary growth rate reduction is also a known side effect in paediatric use.
Contents
- 1 Medical use
- 1.1 Investigational uses
- 2 Adverse effects
- 2.1 Chronic
- 2.2 Psychosis
- 2.3 Withdrawal
- 2.4 Contraindications
- 2.5 Overdose
- 3 Chemistry
- 4 Mechanism of action
- 5 Pharmacokinetics
- 6 History
- 7 Society and culture
- 7.1 Formulations
- 7.1.1 Dexamphetamine sulfate
- 7.1.2 Lisdexampfetamine
- 7.1.3 Mixed amphetamine salts
- 7.2 Military usage
- 7.1 Formulations
- 8 References
- 9 Notes
- 10 Further reading
- 11 External links
Medical use[edit]
Dexedrine Spansule 5, 10 and 15 mg capsules
Dexamphetamine is used for the treatment of ADHD and narcolepsy.[7]
Investigational uses[edit]
Though such use remains out of the mainstream, dexamphetamine has been successfully applied in the treatment of certain categories of depression as well as other psychiatric syndromes.[8] Such alternate uses include reduction of fatigue in cancer patients,[9] antidepressant treatment for HIV patients with depression and debilitating fatigue,[10] and early-stage physiotherapy for severe stroke victims.[11] If physical therapy patients take dexamphetamine while they practice their movements for rehabilitation, they may learn to move much faster than without dexamphetamine, and in practice sessions with shorter lengths.[12]
Adverse effects[edit]
Adverse effects[13][14][15][16][17][18]
Very common (>10% incidence)
- Appetite loss
- Insomnia
- Abdominal pain
Common (1-10% incidence)
- Tachycardia
- Palpitations
- Tremors
- Headache
- Dizziness
- Weight loss
- Dry mouth
- Diarrhoea
- Fever
- Fatigue
- Infection
- Nausea/vomiting
- Dyspepsia (indigestion)
- Nervousness
- Emotional lability
Unknown frequency adverse effects
- Urticaria
- Sexual dysfunction
- Overstimulation
- Restlessness
- Dyskinesia
- Tremor
- Exacerbation of motor and phonic tics and Tourette’s syndrome
- Hyperactivity
Serious adverse effects
- Seizures
- Growth stunting
- Hypertension
- Stroke
- Myocardial infarction (heart attack)
- Psychosis which can occur at therapeutic doses after chronic treatment.
- Mania/Hypomania
- Drug dependence
- Raynaud’s phenomenon
- Cardiomyopathy
- Aggression
- Violence
- Depression
- Suicidality
Recent studies by the FDA indicate that, in children, young adults, and adults, there is no association between serious adverse cardiovascular events (sudden death, myocardial infarction, and stroke) and the use of dexamphetamine or other ADHD stimulants.[19][20][21]
Chronic[edit]
A study on comparative effects between amphetamine mixed salts (commonly known as adderall) and dexamphetamine in children who have been treated for a year or more have shown a temporary decrease in growth rate that does not affect final adult height. Change in weight was reported as slightly greater for amphetamine mixed salts and authors concluded that the result may be clinically insignificant.[22]
Studies on rats show long-term neurological and behavioural changes resulting from prenatal and early postnatal exposure to amphetamines.[23] Warnings from the Patient Medication Guide for Adderall include emergence of new psychotic or manic symptoms, aggression and blurred vision.[24][25]
Psychosis[edit]
Main article: Stimulant psychosis
Abuse of amphetamines can result in a stimulant psychosis which may present with a variety of symptoms (e.g. paranoia,hallucinations, delusions). A Cochrane Collaboration review on treatment for amphetamine, dexamphetamine, and metamphetamine induced psychosis[26] states that about 5-15% of users fail to recover completely.[27] The same review asserts that, based upon at least one trial, antipsychotic medications effectively resolve the symptoms of acute amphetamine psychosis.[26] An amphetamine psychosismay also develop occasionally as a treatment-emergent side effect.[28][28][29]
Withdrawal[edit]
Withdrawal symptoms of dexamphetamine primarily consist of fatigue, depression and an increased appetite. Symptoms may last for days with occasional use and weeks or months with chronic use, with severity dependent on the length of time and the amount of dexamphetamine used. Withdrawal symptoms may also include anxiety, irritability,headaches, agitation, seizures, vomiting, akathisia, hypersomnia (excessive sleeping),vivid or lucid dreams, deep REM sleep and suicidal ideation.[30][31][32]
Contraindications[edit]
Sources[13][14][15]
- Glaucoma
- Moderate-severe hypertension
- Hyperthyroidism
- Epilepsy
- Phaeochromocytoma
- Tourette syndrome
- Psychomotor agitation
- Advanced arteriosclerosis
- Ischaemic heart disease
- Angina pectoris
- Hypersensitivity or idiosyncrasy to the sympathomimetic amines
- During or within 14 days following the administration of monoamine oxidase inhibitors (MAOIs) (hypertensive crisis may occur)[13][14][15][33]
Overdose[edit]
The Physician's 1991 Drug Handbook reports: "Symptoms of overdose include restlessness, tremor, hyperreflexia, tachypnea, confusion, aggressiveness, hallucinations, and panic." Dilated pupils are common with high doses. Repeated high doses may lead to manifestations of acute psychosis. Additionally at least one case report identifies rhabdomyolysis as an associated side effect of dexamphetamine in the presence of other risk factors.[34]
The fatal dose in humans is not precisely known, but in various species of rat generally ranges between 50 and 100 mg/kg, or a factor of 100 over what is required to produce noticeable psychological effects.[35][36] Although the symptoms seen in a fatal overdose are similar to those of metamphetamine, their mechanisms are not identical, as some substances which inhibit dexamphetamine toxicity do not do so for metamphetamine.[37][38]
An extreme symptom of overdose is amphetamine psychosis, characterized by vivid visual, auditory, and sometimes tactile hallucinations. Many of its symptoms are identical to the psychosis-like state which follows long-term sleep deprivation, so it remains unclear whether these are solely the effects of the drug, or due to the long periods of sleep deprivation which are often undergone by the chronic user. Amphetamine psychosis, however, is extremely rare in individuals taking oral amphetamines at therapeutic doses; it is usually seen in cases of prolonged or high-dose intravenous (IV) for non-medicinal uses.[39]
Chemistry[edit]
The molecular structures of both enantiomers of amphetamine: (R)-amphetamine (left) and (S)-amphetamine.
Dexamphetamine is the dextrorotatory stereoisomer of the amphetamine molecule, which can take two different forms. It is a slightly polar, weak base and is lipophilic.[40]
Mechanism of action[edit]
Main article: Amphetamine#Pharmacodynamics
Scientific findings have established that dexamphetamine administration increases the activity of the phosphoinositol cycle via an indirect release of dopamine and Norepinephrine. These results are the first time that this has been confirmed in humans.[41] Because dexamphetamine is a substrate at monoamine transporters, at all doses, dexamphetamine prevents the re-uptake of these neurotransmitters by competing with endogenous monoamines for uptake.[42] At higher doses, when the concentration of dexamphetamine is sufficient, the drug can trigger direct release of norepinephrine and dopamine from the cytoplasmic transmitter pool, that is, dexamphetamine will cause norepinephrine and dopamine efflux via transporter proteins, functionally reversing transporter action, which triggers a cascading release of catecholamines.[42]
Dexamphetamine's binding profile[43]
| Transporter | Ki [nM] |
|---|---|
| SERT | 1765 |
| NET | 7.1 |
| DAT | 110.3 |
Pharmacokinetics[edit]
On average, about one half of a given dose is eliminated unchanged in the urine, while the other half is broken down into various metabolites (mostly benzoic acid).[44] However, the drug's half-life is highly variable because the rate of excretion is very sensitive to urinary pH. Under alkaline conditions, direct excretion is negligible and 95%+ of the dose is metabolized. Having an alkaline stomach will cause the drug to be absorbed faster through the stomach resulting in a higher blood level concentration of amphetamine. Having an alkaline bladder causes dexamphetamine to be excreted more slowly from the blood and into the urine. Alkalinization of the urine can decrease the renal elimination of amphetamines, both potentiating the strength and prolonging the mechanism of action, especially when ingested with sodium bicarbonate.[45]
The main metabolic pathway is:
dexamfephamine phenylacetone benzoic acid hippuric acid.
Another pathway, mediated by enzyme CYP2D6, is:
dexamphetamine p-hydroxyamphetamine p-hydroxynorephedrine.
Although p-hydroxyamphetamine is a minor metabolite (~5% of the dose), it may have significant physiological effects as a norepinephrine analogue.[46]
Subjective effects are increased by larger doses, however, over the course of a given dose there is a noticeable divergence between such effects and drug concentration in the blood.[47] In particular, mental effects peak before maximal blood levels are reached, and decline as blood levels remain stable or even continue to increase.[48][49][50] This indicates a mechanism for development of acute tolerance, perhaps distinct from that seen in chronic use.[51] The long-term effects of amphetamines use on neural development in children has not been well established.[52]
History[edit]
Racemic amphetamine was first synthesized under the chemical name "phenylisopropylamine" in Berlin, 1887 by the Romanian chemist Lazar Edeleanu.[53] 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,[n 1] not a chloride or sulfate salt.
Three years later, in 1935, the medical community became aware of the stimulant properties of amphetamine, specifically dexamphetamine, and in 1937 Smith, Kline, and French introduced tablets under the tradename Dexedrine.[54] In the United States, Dexedrine was approved to treat narcolepsy, attention disorders, depression, and obesity. In Canada, epilepsy and parkinsonism were also approved indications.[55] Dexamphetamine 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 dexamphetamine and amobarbital (a barbiturate) sold under the tradename Dexamyl and, in the 1950s, an extended release capsule (the "Spansule").[56]
It quickly became apparent that dexamphetamine 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. Dexamphetamine, 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.[57]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).[58]
In October 2010, GlaxoSmithKline sold the rights for Dexedrine Spansule to Amedra Pharmaceuticals (a subsidiary of CorePharma).[59]
Society and culture[edit]
Formulations[edit]
Dexamphetamine sulfate[edit]
Dexamphetamine 5 mg generic name tablets
In the United States, an instant-release (IR) tablet preparation of the salt dexamphetamine sulfate is available[clarification needed] under the brand names Dexedrine and Dextrostat, in 5 mg and 10 mg strengths[citation needed], and generic formulations from Teva Pharmaceutical Industries and recently Wilshire Pharmaceuticals. It is also available as a capsule preparation of controlled-release (CR) dexamphetamine sulfate, under the brand names Dexedrine SR and Dexedrine Spansule, in the strengths of 5 mg, 10 mg, and 15 mg. 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 dexamphetamine.[60]
In Australia, dexamphetamine is available in bottles of 100 under the generic name dexamphetamine [sic] as 5 mg instant release sulfate tablets.,[61] or slow release dexamphetamine preparations may be compounded by individual chemists.[62] Similarly, in the United Kingdom it is only available in 5 mg instant release sulfate tablets under the generic name dexamphetamine sulphate [sic] having had been available under the brand name Dexedrine prior to UCB Pharma disinvesting the product to another pharmaceutical company (Auden Mckenzie).[63]
Lisdexampfetamine[edit]
Main article: Lisdexampfetamine
Dexampfetamine is the active metabolite of the prodrug lisdexampfetamine (L-lysine-d-ampfetamine), available by the brand name Vyvanse. Lisdexampfetamine is metabolised in the gastrointestinal tract, while dexampfetamine's metabolism is hepatic.[64] Lisdexampfetamine is therefore an inactive compound until it is converted into an active compound by the digestive system. Although still rated as a Schedule II drug by the U.S. Drug Enforcement Administration, lisdexamphetamine has a slower onset and its route of administration is limited to being taken orally, unlike dexamphetamine, Adderall, and methylphenidate, which can be insufflated to achieve a faster onset with a higher bioavailability[citation needed]. Vyvanse is marketed as once-a-day dosing as it provides a slow release of dexamphetamine into the body. Vyvanse is available as capsules, and in six strengths; 20 mg, 30 mg, 40 mg, 50 mg, 60 mg, and 70 mg. The conversion rate of lisdexamphetamine to dexamphetamine base is 0.2948,[65] thus a 30 mg-strength Vyvanse capsule is molecularly equivalent to 8.844 mg dexamphetamine base.
Mixed amphetamine salts[edit]
Adderall mixed amphetamine salts 30 mg tablets
Main article: Adderall
Another pharmaceutical that contains dexamphetamine is Adderall. The drug formulation of Adderall (both controlled and instant release forms) is:
-
- One-quarter racemic (d,l-)amphetamine aspartate monohydrate
- One-quarter dexamphetamine saccharate
- One-quarter dexamphetamine sulfate
- One-quarter racemic (d,l-)amphetamine sulfate
Adderall is roughly three-quarters dexamphetamine, with it accounting for 72.7% of the amphetamine base in Adderall (the remaining percentage is levoamphetamine).
An experiment with rats suggested Adderall's inclusion of levoamphetamine provides the pharmaceutical with a quicker onset and longer clinical effect compared to pharmaceuticals exclusively formulated of dexamphetamine. One study has shown that although the human brain usually has a preference for dexamphetamine over levoamphetamine, certain children have a better clinical response to levoamphetamine.[66]
Amphetamine exists as two stereoisomers that differ in effects. The l- enantiomer (levoamphetamine) produces more cardiovascular and peripheral effects than the d- enantiomer (dexamphetamine). At low doses, levoamphetamine produces greater arousal than dexamphetamine, acting primarily on norepinephrine. At higher doses, dexamphetamine has stimulant properties that are three to four times as potent as those of levoamphetamine, and acts primarily on dopamine, although few clinical studies of ADHD have documented differences among d-, l- and racemic amphetamine.[67]
Just as dexamphetamine has greater central effects and fewer peripheral effects than levoamphetamine, metamphetamine, which is equipotent to deamphetamine in producing behavioral stimulant effects, has even fewer peripheral effects and greater central effects than dexamphetamine.[67]
In relation to other over-the-counter ADD/ADHD pharmaceuticals, the d- isomer of racemic amphetamine is superior in bioavailibility and CNS stimulation.[68]
Military usage[edit]
The U.S. Air Force uses dexamphetamine 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 affects of the mission and "go-pills".[69][70][71][72] 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.[70]
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Notes[edit]
- ^ Free-base form amphetamine is a volatile oil, hence the efficacy of the inhalers.
Further reading[edit]
- Dexamphetamine 1845887055 at GPnotebook
- Package inserts: "United States". "New Zealand". "Canada".
- Poison Information Monograph (PIM 178: Dexamphetamine Sulphate)
External links[edit]
- Dexedrine Spansule - Official U.S. Website
- Dextroamphetamine consumer information from Drugs.com
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UpToDate Contents
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- 1. 成人の注意欠陥多動性障害（ADHD）に対する薬物療法 pharmacotherapy for adult attention deficit hyperactivity disorder
- 2. ナルコレプシーの治療 treatment of narcolepsy
- 3. 成人における単極性うつ病および初期治療：臨床試験におけるアプローチ unipolar depression in adults and initial treatment investigational approaches
- 4. 癌関連疲労：治療 cancer related fatigue treatment
- 5. 小児および思春期における注意欠陥多動性障害治療薬の薬理学 pharmacology of drugs used to treat attention deficit hyperactivity disorder in children and adolescents
English Journal
- A survey of nonmedical use of tranquilizers, stimulants, and pain relievers among college students: Patterns of use among users and factors related to abstinence in non-users.
- Brandt SA1, Taverna EC2, Hallock RM3.
- Drug and alcohol dependence.Drug Alcohol Depend.2014 Oct 1;143:272-6. doi: 10.1016/j.drugalcdep.2014.07.034. Epub 2014 Aug 7.
- BACKGROUND: This study examined lifetime non-medical prescription drug use among college students at a small liberal arts college in the Northeast. We assessed the motives, frequency of use, sources, and perceived emotional/physical risks of nonmedical prescription drugs. Specifically, we examined t
- PMID 25150402
- How treatable is refractory depression?
- Stewart JW1, Deliyannides DA2, McGrath PJ2.
- Journal of affective disorders.J Affect Disord.2014 Oct;167:148-52. doi: 10.1016/j.jad.2014.05.047. Epub 2014 Jun 4.
- INTRODUCTION: Patients who do not remit following one or more attempts at treatment present a clinical challenge, as well as prolonged suffering and disability. Discouragement is common, so knowledge of likelihood of eventual remission as well as which treatments might ultimately be effective would
- PMID 24972362
- Relationships Between Computer-Based Testing and Behavioral Ratings in the Assessment of Attention and Activity in a Pediatric ADHD Stimulant Crossover Trial.
- Ramtvedt BE1, Sundet K.
- The Clinical neuropsychologist.Clin Neuropsychol.2014 Sep 24:1-16. [Epub ahead of print]
- This study investigated the relationships between computer-based testing and behavioral ratings in the assessment of stimulant-induced changes in attention and activity in a pediatric ADHD crossover trial with methylphenidate, dextroamphetamine, and a placebo. Here 36 children between 9 and 14 years
- PMID 25249305
Japanese Journal
- Ritalin, benzedrine and dexedrine do not transform F 1706 rat cells
- PRICE P. J.
- Cancer Lett. 5, 345-349, 1978
- NAID 30003136261
Related Links
- The official site for DEXEDRINE, DEXEDRINE is a stimulant widely prescribed by physicians for the treatment of ADHD ... What is the most important information I should know about DEXEDRINE? The following have been reported ...
- Learn about the prescription medication Dexedrine (Dextroamphetamine), drug uses, dosage, side effects, drug interactions, warnings, reviews and patient labeling. ... SPANSULE capsules Each SPANSULE sustained-release ...
Related Pictures
★リンクテーブル★
| リンク元 | 「薬物濫用」「デキストロアンフェタミン」 |
「薬物濫用」
- 英
- drug abuse, substance abuse
- 同
- 薬物乱用
- 関
- 薬物依存、薬物嗜癖、物質乱用、物質依存症、薬物使用、接着剤吸引
薬物使用が身体に及ぼす効果
- 濫用 substance abuse：a pattern of abnormal substance use that leads to impairment of occupational, physical, or social functioning(BBS.73)
- 依存 substance dependence：ub stance abuse puls withdrawal symptoms, tolerance, or a pattern of repetitive use(BBS.73)
- 離脱 withdrawal：the development of physical or pschological symptoms after the reduction or cessation of intake of a substance(BBS.73)
- 耐性 tolerance：the need for increased amounts of the substance to achieve the same positive psychological effect(BBS.73)
- 交差耐性 cross-tolerance：the development of tolerance to one substance as the result of using another substance(BBS.73)
薬物
- 1. 中枢神経興奮薬(覚醒剤を含む) stimulants 身体依存はないとされている
- カフェイン caffeine
- ニコチン nicotine
- amphetamines 精神依存有り。身体依存無し
- アンフェタミン amphetamine 精神依存有り。身体依存無し。耐性は連用で出現
- デキストロアンフェタミン dextroamphetamine Dexedrine
- メタンフェタミン methamphetamine Desoxyn speed ice ヒロポン 精神依存有り。身体依存無し。耐性は連用で出現 ← 以前、日本で多く使われた
- メチルフェニデート methylphenidate Ritalin
- methylene dioxymethamphetamine MDMA ecstasy
- 2. sedatives
- alcohol 精神依存有り。身体依存有り。
- barbiturates
- benzodiazepines
- ⇔flumazenil Mazicon Romazicon
- 3. opioids
- 4. hallucinogens and related agents
- cannabis(marijuana(tetrahydrocannabinol THC,hashish) 精神依存有り。身体依存無し 精神依存軽度。耐性は長期使用で軽度出現 大麻草
- lysergic acid diethylamide LSD
- phencyclidine PCP angel dust
- psilocybin
- mescaline
精神依存、身体依存
| 精神依存 | 身体依存 | |
| コカイン、アンフェタミン類(アンフェタミン、メチルフェタミン)、大麻 | ○ | |
| 麻薬(モルヒネ、ヘロイン、コデイン)、バルビツール酸系(フェノバルビタール、チオペンタール)、アルコール | ○ | ○ |