Levoamphetamine

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Contents

Levoamphetamine
L-amphetamine.svg
Names
Preferred IUPAC name
(2R)-1-Phenylpropan-2-amine [1]
Other names
l-Amphetamine, Levamfetamine [2]
Identifiers
3D model (JSmol)
2432739
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.005.320 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 205-850-8
1125855
PubChem CID
UNII
  • InChI=1S/C9H13N/c1-8(10)7-9-5-3-2-4-6-9/h2-6,8H,7,10H2,1H3/t8-/m1/s1 Yes check.svgY
    Key: KWTSXDURSIMDCE-MRVPVSSYSA-N Yes check.svgY
  • C[C@@H](N)Cc1ccccc1
  • C[C@@H](N)CC1=CC=CC=C1
Properties
C9H13N
Molar mass 135.2062 g mol−1
log P 1.789
Pharmacology
Oral (as part of Adderall, Evekeo, and generic amphetamine sulfate [3] [4] )
Legal status
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

Levoamphetamine [note 1] is a central nervous system (CNS) stimulant known to increase wakefulness and concentration in association with decreased appetite and fatigue. Pharmaceuticals that contain levoamphetamine are currently indicated and prescribed for the treatment of attention deficit hyperactivity disorder (ADHD), obesity, and narcolepsy in some countries.

Levoamphetamine is the levorotatory stereoisomer of the amphetamine molecule. While pharmaceutical formulations containing enantiopure levoamphetamine are no longer manufactured, levomethamphetamine (levmetamfetamine) is still marketed and sold over-the-counter as a nasal decongestant.

Chemistry

Levoamphetamine is the levorotatory stereoisomer of the amphetamine molecule. Racemic amphetamine contains two optical isomers, dextroamphetamine, and levoamphetamine. [6] [7]

Formulations

Racemic amphetamine

The first patented amphetamine brand, Benzedrine, was a racemic (i.e., equal parts) mixture of the free bases or sulfate salts of both amphetamine enantiomers (levoamphetamine and dextroamphetamine) that was introduced in the United States in 1934 as an inhaler for treating nasal congestion. [3] It was later realized that the amphetamine enantiomers could treat obesity, narcolepsy, and ADHD. [3] [4] Because of the greater central nervous system effect of the dextrorotatory enantiomer (i.e., dextroamphetamine), sold as Dexedrine, prescription of the Benzedrine brand fell and was eventually discontinued. [8] However, in 2012, racemic amphetamine sulfate was reintroduced as the Evekeo brandname. [4] [9]

Adderall

Adderall is a 3.1:1 mixture of dextro- to levo- amphetamine base equivalent pharmaceutical that contains equal amounts (by weight) of four salts: dextroamphetamine sulfate, amphetamine sulfate, dextroamphetamine saccharate and amphetamine (D,L)-aspartate monohydrate. This result is a 76% dextroamphetamine to 24% levoamphetamine, or 34 to 14 ratio. [6] [7]

Evekeo

Evekeo is an FDA-approved medication that contains racemic amphetamine sulfate (i.e., 50% levoamphetamine sulfate and 50% dextroamphetamine sulfate). [4] It is approved for the treatment of narcolepsy, ADHD, and exogenous obesity. [4] The orally disintegrating tablets are approved for the treatment of attention deficit hyperactivity disorder (ADHD) in children and adolescents aged six to 17 years of age. [10]

Others

Products using amphetamine base are now marketed. Dyanavel XR, a liquid suspension form became available in 2015, and contains about 24% levoamphetamine. [11] Adzenys XR, an orally dissolving tablet came to market in 2016 and contains 25% levoamphetamine. [12] [13]

See also

Notes

  1. Synonyms and alternate spellings include: (2R)-1-phenylpropan-2-amine (IUPAC name), levamfetamine (International Nonproprietary Name [INN]), (R)-amphetamine, ()-amphetamine, l-amphetamine, and L-amphetamine. [1] [5]

Related Research Articles

<span class="mw-page-title-main">Amphetamine</span> Central nervous system stimulant

Amphetamine is a central nervous system (CNS) stimulant that is used in the treatment of attention deficit hyperactivity disorder (ADHD), narcolepsy, and obesity. Amphetamine was discovered as a chemical in 1887 by Lazăr Edeleanu, and then as a drug in the late 1920s. It exists as two enantiomers: levoamphetamine and dextroamphetamine. Amphetamine properly refers to a specific chemical, the racemic free base, which is equal parts of the two enantiomers in their pure amine forms. The term is frequently used informally to refer to any combination of the enantiomers, or to either of them alone. Historically, it has been used to treat nasal congestion and depression. Amphetamine is also used as an athletic performance enhancer and cognitive enhancer, and recreationally as an aphrodisiac and euphoriant. It is a prescription drug in many countries, and unauthorized possession and distribution of amphetamine are often tightly controlled due to the significant health risks associated with recreational use.

<span class="mw-page-title-main">Stimulant</span> Overarching term covers many drugs that increase activity of the central nervous system

Stimulants is an overarching term that covers many drugs including those that increase the activity of the central nervous system and the body, drugs that are pleasurable and invigorating, or drugs that have sympathomimetic effects. Stimulants are widely used throughout the world as prescription medicines as well as without a prescription as performance-enhancing or recreational drugs. Among narcotics, stimulants produce a noticeable crash or comedown at the end of their effects. The most frequently prescribed stimulants as of 2013 were lisdexamfetamine (Vyvanse), methylphenidate (Ritalin), and amphetamine (Adderall). It was estimated in 2015 that the percentage of the world population that had used cocaine during a year was 0.4%. For the category "amphetamines and prescription stimulants" the value was 0.7%, and for MDMA 0.4%.

In chemistry, a racemic mixture or racemate, is one that has equal amounts of left- and right-handed enantiomers of a chiral molecule or salt. Racemic mixtures are rare in nature, but many compounds are produced industrially as racemates.

<span class="mw-page-title-main">Methylphenidate</span> Central nervous system stimulant

Methylphenidate, sold under the brand names Ritalin and Concerta among others, is a central nervous system (CNS) stimulant used medically to treat attention deficit hyperactivity disorder (ADHD) and, to a lesser extent, narcolepsy. It is a primary medication for ADHD ; it may be taken by mouth or applied to the skin, and different formulations have varying durations of effect, commonly ranging from 2–4 hours.

<span class="mw-page-title-main">Dextroamphetamine</span> CNS stimulant and isomer of amphetamine

Dextroamphetamine is a potent central nervous system (CNS) stimulant and enantiomer of amphetamine that is prescribed for the treatment of attention deficit hyperactivity disorder (ADHD) and narcolepsy. It is also used as an athletic performance and cognitive enhancer, and recreationally as an aphrodisiac and euphoriant.

An anorectic or anorexic is a drug which reduces appetite, resulting in lower food consumption, leading to weight loss. By contrast, an appetite stimulant is referred to as orexigenic.

<span class="mw-page-title-main">Adderall</span> Drug mixture used mainly to treat ADHD and narcolepsy

Adderall and Mydayis are trade names for a combination drug called mixed amphetamine salts containing four salts of amphetamine. The mixture is composed of equal parts racemic amphetamine and dextroamphetamine, which produces a (3:1) ratio between dextroamphetamine and levoamphetamine, the two enantiomers of amphetamine. Both enantiomers are stimulants, but differ enough to give Adderall an effects profile distinct from those of racemic amphetamine or dextroamphetamine, which are marketed as Evekeo and Dexedrine/Zenzedi, respectively. Adderall is used in the treatment of attention deficit hyperactivity disorder (ADHD) and narcolepsy. It is also used illicitly as an athletic performance enhancer, cognitive enhancer, appetite suppressant, and recreationally as a euphoriant. It is a central nervous system (CNS) stimulant of the phenethylamine class.

<span class="mw-page-title-main">Dexmethylphenidate</span> CNS Stimulant

Dexmethylphenidate, sold under the brand name Focalin among others, is a potent central nervous system (CNS) stimulant used to treat attention deficit hyperactivity disorder (ADHD) in those over the age of five years. It is taken by mouth. The immediate release formulation lasts up to five hours while the extended release formulation lasts up to twelve hours. It is the more active enantiomer of methylphenidate.

<span class="mw-page-title-main">Armodafinil</span> Eugeroic medication

Armodafinil (trade name Nuvigil) is the enantiopure compound of the eugeroic modafinil (Provigil). It consists of only the (R)-(−)-enantiomer of the racemic modafinil. Armodafinil is produced by the pharmaceutical company Cephalon Inc. and was approved by the U.S. Food and Drug Administration (FDA) in June 2007. In 2016, the FDA granted Mylan rights for the first generic version of Cephalon's Nuvigil to be marketed in the U.S.

<span class="mw-page-title-main">Polysubstance use</span> Use of multiple psychoactive substances

Polysubstance use or poly drug use refers to the use of combined psychoactive substances. Polysubstance use may be used for entheogenic, recreational, or off-label indications, with both legal and illegal substances. In many cases one drug is used as a base or primary drug, with additional drugs to leaven or compensate for the side effects, or tolerance, of the primary drug and make the experience more enjoyable with drug synergy effects, or to supplement for primary drug when supply is low.

Dexamyl was a brand name combination drug composed of sodium amobarbital and dextroamphetamine sulfate (Dexedrine) within the same pill. It was widely abused, and is no longer manufactured.

<span class="mw-page-title-main">Orally disintegrating tablet</span> Pill that dissolves on contact with saliva

An orally disintegrating tablet or orally dissolving tablet (ODT) is a drug dosage form available for a limited range of over-the-counter (OTC) and prescription medications. ODTs differ from traditional tablets in that they are designed to be dissolved on the tongue rather than swallowed whole. The ODT serves as an alternative dosage form for patients who experience dysphagia or for where compliance is a known issue and therefore an easier dosage form to take ensures that medication is taken. Common among all age groups, dysphagia is observed in about 35% of the general population, as well as up to 60% of the elderly institutionalized population and 18-22% of all patients in long-term care facilities ODTs may have a faster onset of effect than tablets or capsules, and have the convenience of a tablet that can be taken without water. During the last decade, ODTs have become available in a variety of therapeutic markets, both OTC and by prescription.

A combination drug or a fixed-dose combination (FDC) is a medicine that includes two or more active ingredients combined in a single dosage form. Terms like "combination drug" or "combination drug product" can be common shorthand for an FDC product, although the latter is more precise if in fact referring to a mass-produced product having a predetermined combination of drugs and respective dosages. And it should also be distinguished from the term "combination product" in medical contexts, which without further specification can refer to products that combine different types of medical products—such as device/drug combinations as opposed to drug/drug combinations. When a combination drug product is a "pill", then it may also be a kind of "polypill" or combopill.

<span class="mw-page-title-main">Lisdexamfetamine</span> Central nervous system stimulant prodrug

Lisdexamfetamine, most commonly sold under the brand name Vyvanse and Elvanse among others, is a stimulant medication that is used to treat attention deficit hyperactivity disorder (ADHD) in children and adults, and for moderate-to-severe binge eating disorder in adults. Lisdexamfetamine is taken by mouth. Its effects generally begin within two hours and last for up to 14 hours. In the United Kingdom, it is usually less preferred to methylphenidate for the treatment of children.

Attention deficit hyperactivity disorder management options are evidence-based practices with established treatment efficacy for ADHD.

<span class="mw-page-title-main">Obetrol</span> Diet pill

Obetrol was the brand name of a drug combining several amphetamine salts indicated for the treatment of exogenous obesity. It was originally sold by the American company Obetrol Pharmaceuticals. Obetrol was a popular diet pill in America in the 1950s and 1960s.

Eskatrol was an amphetamine weight loss agent which was removed by the U.S. Food and Drug Administration (FDA) in 1981 after its manufacturer, SmithKline & French (SKF), failed to prove the therapeutic effectiveness (Emax) of the medication. At the time it was among the 200 most widely prescribed drugs in the United States. Others included Dexamyl and Desbutal pills. Eskatrol contained dextroamphetamine sulfate (Dexedrine) and prochlorperazine (Compazine), a typical antipsychotic.

Amphetamine is a stimulant drug.

References

  1. 1 2 "L-Amphetamine". PubChem Compound. United States National Library of Medicine – National Center for Biotechnology Information. 30 December 2017. Retrieved 2 January 2018.
  2. CID 32893 from PubChem
  3. 1 2 3 Heal DJ, Smith SL, Gosden J, Nutt DJ (June 2013). "Amphetamine, past and present – a pharmacological and clinical perspective". J. Psychopharmacol. 27 (6): 479–496. doi:10.1177/0269881113482532. PMC   3666194 . PMID   23539642.
  4. 1 2 3 4 5 "Evekeo- amphetamine sulfate tablet". DailyMed. 14 August 2019. Retrieved 7 April 2020.
  5. "R(-)amphetamine". IUPHAR/BPS Guide to Pharmacology. International Union of Basic and Clinical Pharmacology. Retrieved 2 January 2018.
  6. 1 2 "Adderall XR- dextroamphetamine sulfate, dextroamphetamine saccharate, amphetamine sulfate and amphetamine aspartate capsule, extended release". DailyMed. 17 July 2019. Retrieved 7 April 2020.
  7. 1 2 "Adderall- dextroamphetamine saccharate, amphetamine aspartate, dextroamphetamine sulfate, and amphetamine sulfate tablet". DailyMed. 8 November 2019. Retrieved 7 April 2020.
  8. "Benzedrine: FDA-Approved Drugs". U.S. Food and Drug Administration (FDA). Retrieved 4 September 2015.
  9. "Evekeo: FDA-Approved Drugs". U.S. Food and Drug Administration (FDA). Retrieved 11 August 2015.
  10. "Evekeo ODT- amphetamine sulfate tablet, orally disintegrating". DailyMed. 20 February 2020. Retrieved 7 April 2020.
  11. "Dyanavel XR Prescribing Information". January 2017. Retrieved 14 May 2017.
  12. "Adzenys XR-ODT- amphetamine tablet, orally disintegrating". DailyMed. 22 January 2020. Retrieved 7 April 2020. Adzenys XR-ODT (amphetamine extended-release orally disintegrating tablet) contains a 3 to 1 ratio of d- to l-amphetamine, a central nervous system stimulant.
  13. "Adzenys ER- amphetamine suspension, extended release". DailyMed. 21 January 2020. Retrieved 7 April 2020.