Amfepramone

Amfepramone
Names
Pronunciationdye eth" il proe' pee on
Trade namesTenuate, Tepanil, others
Other namesDiethylpropion, Diethylcathinone
IUPAC name
  • (RS)-2-diethylamino-1-phenylpropan-1-one
Clinical data
Drug classStimulant[1]
Main usesObesity[2]
Side effectsNervousness, trouble sleeping, headache, dry mouth, sweating, nausea, constipation, thirst[1]
WHO AWaReUnlinkedWikibase error: ⧼unlinkedwikibase-error-statements-entity-not-set⧽
Pregnancy
category
  • AU: B2
    Routes of
    use    		By mouth
    External links
    AHFS/Drugs.comMonograph
    MedlinePlusa682037
    Legal
    License data
    Legal status
    Pharmacokinetics
    Elimination half-life4-6 hours (metabolites)[5]
    ExcretionUrine (>75%)[5]
    Chemical and physical data
    FormulaC13H19NO
    Molar mass205.301 g·mol−1
    3D model (JSmol)
    ChiralityRacemic mixture
    SMILES
    • O=C(c1ccccc1)C(N(CC)CC)C
    InChI
    • InChI=1S/C13H19NO/c1-4-14(5-2)11(3)13(15)12-9-7-6-8-10-12/h6-11H,4-5H2,1-3H3 checkY
    • Key:XXEPPPIWZFICOJ-UHFFFAOYSA-N checkY

    Amfepramone, also known as diethylpropion, is a medication used in the short-term management of obesity.[2] It is used together with diet and exercise.[2] Use is not recommended beyond a few weeks.[2]

    Common side effects include nervousness, trouble sleeping, headache, dry mouth, sweating, nausea, constipation, and thirst.[1] Other side effects may include atrial fibrillation, psychosis, abuse, and pulmonary hypertension.[1] Safety in pregnancy is unclear.[6] It is a stimulant similar to amphetamine.[1]

    Amfepramone was approved for medical use in the United States in 1959.[2] It is available as a generic medication.[7] In the United States 30 pills of 75 mg costs about 20 USD.[7] In the United States it is a Schedule IV controlled substance.[1]

    Medical uses

    Dosage

    The usual dose is 75 mg daily either as 25 mg (immediate release) 1 hour before meals or 75 mg (controlled release) once daily.[1]

    Pharmacology

    Amfepramone itself lacks any affinity for the monoamine transporters and instead functions as a prodrug to ethcathinone.[8] Ethcathinone (and therefore amfepramone as well) is a very weak dopaminergic and serotonergic, and is approximately 10x and 20x stronger on norepinephrine in comparison, respectively.[8] As a result, ethcathinone and amfepramone can essentially be considered a member of the class of drugs known as norepinephrine releasing agents (NRAs).

    Chemistry

    Amfepramone can be synthesized from propiophenone by bromination, followed by reaction with diethylamine.[9][10]

    Amfepramone is most closely chemically related to the antidepressant and smoking cessation aid bupropion (previously called amfebutamone), which has also been developed as a weight-loss medicine when in a combination product with naltrexone.[11]

    Society and culture

    Names

    Another medically-utilized name is diethylpropion (BAN and AAN). Chemical names include: α-methyl-β-keto-N,N-diethylphenethylamine, N,N-diethyl-β-ketoamphetamine and N,N-diethylcathinone. Brand names include: Anorex, Linea, Nobesine, Prefamone, Regenon, Tepanil and Tenuate.

    Legality

    Amfepramone is classified as a Schedule IV controlled substance in the United States. It is also a Schedule IV controlled substance in Canada. In the UK amfepramone is a class C drug [12] and as a medicine, it is a Schedule 3 Controlled Drug which requires safe custody.

    Recreational use

    The authors of several studies of amfepramone claim that the substance has a relatively low potential for causing addiction in users.[13][14][15][16] However, there have been reports of people using this drug recreationally in the UK. Recreational users of amfepramone in the UK refer to amfepramone tablets as "tombstones".

    See also

    References

    1. 1 2 3 4 5 6 7 "Diethylpropion". LiverTox: Clinical and Research Information on Drug-Induced Liver Injury. National Institute of Diabetes and Digestive and Kidney Diseases. 2012. Archived from the original on 6 May 2021. Retrieved 24 December 2021.
    2. 1 2 3 4 5 "Diethylpropion Monograph for Professionals". Drugs.com. Archived from the original on 21 November 2021. Retrieved 24 December 2021.
    3. ↑ "Archive copy" (PDF). Archived (PDF) from the original on 2021-08-27. Retrieved 2021-02-14.{{cite web}}: CS1 maint: archived copy as title (link)
    4. ↑ "Amfepramone-containing medicinal products". European Medicines Agency (EMA). 12 February 2021. Archived from the original on 7 March 2021. Retrieved 12 February 2021.
    5. 1 2 "SPC-DOC_PL 16133-0001" (PDF). Medicines Healthcare products Regulatory Agency. Essential Nutrition Ltd. 18 November 2011. Retrieved 18 July 2014.
    6. ↑ "Diethylpropion Use During Pregnancy". Drugs.com. Archived from the original on 20 November 2021. Retrieved 24 December 2021.
    7. 1 2 "Diethylpropion Prices, Coupons & Savings Tips - GoodRx". GoodRx. Archived from the original on 15 November 2016. Retrieved 24 December 2021.
    8. 1 2 Rothman RB, Baumann MH (2006). "Therapeutic potential of monoamine transporter substrates". Current Topics in Medicinal Chemistry. 6 (17): 1845–59. doi:10.2174/156802606778249766. PMID 17017961. Archived from the original on 2020-10-23. Retrieved 2021-02-14.
    9. ↑ US patent 3001910, Schutte J, "Anorexigenic Propiophenones", issued 1961-09-26, assigned to Temmler-Werke 
    10. ↑ Hyde JF, Browning E, Adams R (1928). "Synthetic Homologs of d,l-Ephedrine". Journal of the American Chemical Society. 50 (8): 2287–2292. doi:10.1021/ja01395a032.
    11. ↑ Arias HR, Santamaría A, Ali SF (2009). "Pharmacological and neurotoxicological actions mediated by bupropion and diethylpropion". New Concepts of Psychostimulant Induced Neurotoxicity. International Review of Neurobiology. Vol. 88. pp. 223–55. doi:10.1016/S0074-7742(09)88009-4. ISBN 9780123745040. PMID 19897080.
    12. ↑ "Class C Drugs". Schedule 2 Controlled Drugs. UK Legislation. Archived from the original on 2012-11-14. Retrieved 2021-02-14.
    13. ↑ Cohen S (1977). "Diethylpropion (tenuate): an infrequently abused anorectic". Psychosomatics. 18 (1): 28–33. doi:10.1016/S0033-3182(77)71101-6. PMID 850721.
    14. ↑ Jasinski DR, Krishnan S (June 2009). "Abuse liability and safety of oral lisdexamfetamine dimesylate in individuals with a history of stimulant abuse". Journal of Psychopharmacology. 23 (4): 419–27. doi:10.1177/0269881109103113. PMID 19329547. S2CID 6138292.
    15. ↑ "Tepanil (diethylpropion hydrochloride) tablet, extended release". Dailymed. National Institutes of Health. Archived from the original on 2020-10-23. Retrieved 2021-02-14.
    16. ↑ Caplan J (May 1963). "Habituation to diethylpropion (Tenuate)". Canadian Medical Association Journal. 88: 943–4. PMC 1921278. PMID 14018413.
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