Amfepramone

Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]

Overview

Amfepramone (INN)^{[note 1]} is a stimulant drug of the phenethylamine, amphetamine, and cathinone classes that is used as an appetite suppressant.^[2]^[3] It is used in the short-term management of obesity, along with dietary and lifestyle changes.^[2] 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.^[4]

Pharmacology

Amfepramone itself lacks any affinity for the monoamine transporters and instead functions as a prodrug to ethcathinone.^[5] 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.^[5] As a result, ethcathinone and amfepramone can essentially be considered a member of the class of drugs known as norepinephrine releasing agents (NRAs).

Abuse

Amfepramone is believed to have relatively low abuse potential.^[6]^[7]^[8]^[9] but recently there have been reports of teens and adults in the UK abusing this drug, known as “tombstones” to the abusers.

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 ^[10] and as a medicine, it is a Schedule 3 Controlled Drug which requires safe custody. It’s not US FDA approved.

Chemistry

Propiophenone is brominated to produce α-bromopropiophenone.
This is reacted with diethylamine to yield the product, diethylpropion.^[11]^[12]

Notes

↑ 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.

References

↑ ^1.0 ^1.1 “SPC-DOC_PL 16133-0001” (PDF). Medicines Healthcare products Regulatory Agency. Essential Nutrition Ltd. 18 November 2011. Retrieved 18 July 2014.
↑ ^2.0 ^2.1 Brayfield, A, ed. (30 January 2013). “Diethylpropion Hydrochloride”. Martindale: The Complete Drug Reference. London, UK: Pharmaceutical Press. Retrieved 18 July 2014.
↑ Template:Cite document
↑ Arias, HR; Santamaría, A; Ali, SF (2009). “Pharmacological and neurotoxicological actions mediated by bupropion and diethylpropion”. International Review of Neurobiology. 88: 223–55. doi:10.1016/S0074-7742(09)88009-4. PMID 19897080.
↑ ^5.0 ^5.1 Rothman, RB; Baumann, MH (2006). “Therapeutic Potential of Monoamine Transporter Substrates”. Current Topics in Medicinal Chemistry. 6 (17): 1845–1859. doi:10.2174/156802606778249766. PMID 17017961.
↑ Cohen, S (1977). “Diethylpropion (Tenuate): An Infrequently Abused Anorectic”. Psychosomatics. 18 (1): 28–33. doi:10.1016/S0033-3182(77)71101-6. PMID 850721.
↑ 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): 419–427. doi:10.1177/0269881109103113. PMID 19329547.
↑ “Tepanil (diethylpropion hydrochloride) tablet, extended release”. Dailymed. National Institutes of Health.
↑ Caplan, J (May 1963). “Habituation to Diethylpropion (Tenuate)”. Canadian Medical Association Journal. 88: 943–944. PMC 1921278. PMID 14018413.
↑ “Class C Drugs”. Schedule 2 Controlled Drugs. UK Legislation.
↑ US patent 3001910, “Anorexigenic Propiophenones”, issued 1961-09-26, assigned to Temmler-Werke
↑ Template:Cite doi

Template:Anorectics Template:Catecholaminergics Template:Phenethylamines

[2] 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.

[MHRA-1] 1.0 ^1.1 “SPC-DOC_PL 16133-0001” (PDF). Medicines Healthcare products Regulatory Agency. Essential Nutrition Ltd. 18 November 2011. Retrieved 18 July 2014.

[MD-3] 2.0 ^2.1 Brayfield, A, ed. (30 January 2013). “Diethylpropion Hydrochloride”. Martindale: The Complete Drug Reference. London, UK: Pharmaceutical Press. Retrieved 18 July 2014.

[4] Template:Cite document

[5] Arias, HR; Santamaría, A; Ali, SF (2009). “Pharmacological and neurotoxicological actions mediated by bupropion and diethylpropion”. International Review of Neurobiology. 88: 223–55. doi:10.1016/S0074-7742(09)88009-4. PMID 19897080.

[pmid17017961-6] 5.0 ^5.1 Rothman, RB; Baumann, MH (2006). “Therapeutic Potential of Monoamine Transporter Substrates”. Current Topics in Medicinal Chemistry. 6 (17): 1845–1859. doi:10.2174/156802606778249766. PMID 17017961.

[7] Cohen, S (1977). “Diethylpropion (Tenuate): An Infrequently Abused Anorectic”. Psychosomatics. 18 (1): 28–33. doi:10.1016/S0033-3182(77)71101-6. PMID 850721.

[8] 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): 419–427. doi:10.1177/0269881109103113. PMID 19329547.

[9] “Tepanil (diethylpropion hydrochloride) tablet, extended release”. Dailymed. National Institutes of Health.

[10] Caplan, J (May 1963). “Habituation to Diethylpropion (Tenuate)”. Canadian Medical Association Journal. 88: 943–944. PMC 1921278. PMID 14018413.

[11] “Class C Drugs”. Schedule 2 Controlled Drugs. UK Legislation.

[12] US patent 3001910, “Anorexigenic Propiophenones”, issued 1961-09-26, assigned to Temmler-Werke

[13] Template:Cite doi

[note 1]

[2]

[3]

[4]

[5]

[6]

[7]

[8]

[9]

[10]

[11]

[12]