Amfepramone: Difference between revisions

Amfepramone
Clinical data
Trade names	Tenuate
Other names	Diethylpropion
AHFS/Drugs.com	Monograph
MedlinePlus	a682037
Routes of; administration	Oral
ATC code	A08AA03 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only); DE: Anlage III (Special prescription form required); UK: Class C; US: Schedule IV;
Pharmacokinetic data
Elimination half-life	4-6 hours (metabolites)
Excretion	Urine (>75%)
Identifiers
	IUPAC name (RS)-2-diethylamino-1-phenylpropan-1-one;
CAS Number	134-80-5 ;
PubChem CID	7029;
IUPHAR/BPS	7161;
DrugBank	DB00937 ;
ChemSpider	6762 ;
UNII	19V2PL39NG;
KEGG	D07444 ;
ChEBI	CHEBI:4530 ;
ChEMBL	ChEMBL1194666 ;
CompTox Dashboard (EPA)	DTXSID6022929 ;
ECHA InfoCard	100.001.836
Chemical and physical data
Formula	C13H19NO
Molar mass	205.30 g/mol g·mol−1
3D model (JSmol)	Interactive image;
	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 ; Key:XXEPPPIWZFICOJ-UHFFFAOYSA-N ;
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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.

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

^ ^a ^b "SPC-DOC_PL 16133-0001" (PDF). Medicines Healthcare products Regulatory Agency. Essential Nutrition Ltd. 18 November 2011. Retrieved 18 July 2014.
^ ^a ^b Brayfield, A, ed. (30 January 2013). "Diethylpropion Hydrochloride". Martindale: The Complete Drug Reference. London, UK: Pharmaceutical Press. Retrieved 18 July 2014.
^ "TGA Approved Terminology for Medicines, Section 1 – Chemical Substances" (Document). Therapeutic Goods Administration, Department of Health and Ageing, Australian Government. July 1999. p. 42. {{cite document}}: Unknown parameter |format= ignored (help); Unknown parameter |url= ignored (help)
^ 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.
^ ^a ^b 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.{{cite journal}}: CS1 maint: multiple names: authors list (link)
^ 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.{{cite journal}}: CS1 maint: multiple names: authors list (link)
^ "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
^ Hyde, J. F.; 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.

[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] "SPC-DOC_PL 16133-0001" (PDF). Medicines Healthcare products Regulatory Agency. Essential Nutrition Ltd. 18 November 2011. Retrieved 18 July 2014.

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

[4] "TGA Approved Terminology for Medicines, Section 1 – Chemical Substances" (Document). Therapeutic Goods Administration, Department of Health and Ageing, Australian Government. July 1999. p. 42. {{cite document}}: Unknown parameter |format= ignored (help); Unknown parameter |url= ignored (help)

[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] 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.{{cite journal}}: CS1 maint: multiple names: authors list (link)

[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.{{cite journal}}: CS1 maint: multiple names: authors list (link)

[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] Hyde, J. F.; 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.

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 == Legality ==
 Amfepramone is classified as a [[Controlled Substances Act#Schedule IV controlled substances|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 <ref>{{ cite web | url = http://www.legislation.gov.uk/ukpga/1971/38/schedule/2 | work = Schedule 2 Controlled Drugs | title = Class C Drugs | publisher = UK Legislation }}</ref> and as a medicine, it is a Schedule 3 Controlled Drug which requires safe custody.
-It's not US FDA approved.
 ==Chemistry==

v t e Phenethylamines
Phenethylamines	Psychedelics: 25B-NBOMe 25C-NBOMe 25D-NBOMe 25I-NBOMe 25N-NBOMe 2C-B 2C-B-AN 2C-Bn 2C-Bu 2C-C 2C-CN 2C-CP 2C-D 2C-E 2C-EF 2C-F 2C-G 2C-G-1 2C-G-2 2C-G-3 2C-G-4 2C-G-5 2C-G-6 2C-G-N 2C-H 2C-I 2C-iP 2C-N 2C-NH2 2C-O 2C-O-4 2C-P 2C-Ph 2C-SE 2C-T 2C-T-2 2C-T-3 2C-T-4 2C-T-5 2C-T-6 2C-T-7 2C-T-8 2C-T-9 2C-T-10 2C-T-11 2C-T-12 2C-T-13 2C-T-14 2C-T-15 2C-T-16 2C-T-17 2C-T-18 2C-T-19 2C-T-20 2C-T-21 2C-T-22 2C-T-22.5 2C-T-23 2C-T-24 2C-T-25 2C-T-27 2C-T-28 2C-T-30 2C-T-31 2C-T-32 2C-T-33 2C-TFE 2C-TFM 2C-YN 2C-V Allylescaline DESOXY Escaline Isoproscaline Jimscaline Macromerine MEPEA Mescaline Metaescaline Methallylescaline Proscaline Psi-2C-T-4 TCB-2 Stimulants: Phenylethanolamine Hordenine Phenethylamine Phenpromethamine α-Methylphenethylamine (amphetamine) β-Methylphenethylamine m-Methylphenethylamine N-Methylphenethylamine o-Methylphenethylamine p-Methylphenethylamine Methylphenidate Entactogens: Lophophine MDPEA MDMPEA Others: BOH DMPEA
Amphetamines	Psychedelics: 3C-AL 3C-BZ 3C-E 3C-MAL 3C-P Aleph Beatrice Bromo-DragonFLY D-Deprenyl DMA DMCPA DMMDA DOB DOC DOEF DOET DOI DOM DON DOPR DOTFM Ganesha MMDA MMDA-2 Psi-DOM TMA TeMA ZDCM-04 Stimulants: 2-FA 2-FMA 3-FA 3-FMA Acridorex Alfetamine Amfecloral Amfepentorex Amphetamine (Dextroamphetamine, Levoamphetamine) Amphetaminil Benfluorex Benzphetamine Cathine Clobenzorex Dimethylamphetamine Ephedrine Etilamfetamine Fencamfamin Fencamine Fenethylline Fenfluramine (Dexfenfluramine, Levofenfluramine) Fenproporex Flucetorex Fludorex Formetorex Furfenorex Gepefrine 4-Hydroxyamphetamine Iofetamine Isopropylamphetamine Lefetamine Lisdexamfetamine Mefenorex Metaraminol Methamphetamine (Dextromethamphetamine, Levomethamphetamine) Methoxyphenamine MMA Morforex Norfenfluramine L-Norpseudoephedrine N,alpha-Diethylphenylethylamine Oxifentorex Oxilofrine Ortetamine PBA PCA PFA PFMA PIA PMA PMEA PMMA Phenylpropanolamine Pholedrine Prenylamine Propylamphetamine Pseudoephedrine Sibutramine Tiflorex Tranylcypromine Xylopropamine Zylofuramine Entactogens: 4-FA 4-FMA 4-MA 4-MMA 4-MTA 5-APB 5-APDB 5-EAPB 5-IT 5-MAPB 5-MAPDB 6-APB 6-APDB 6-Chloro-MDMA 6-EAPB 6-IT 6-MAPB 6-MAPDB EDA IAP 2,3-MDA 3,4-MDA (tenamfetamine) MDEA MDHMA MDMA (midomafetamine) MDOH Methamnetamine MMDMA Naphthylaminopropane TAP Others: 3,4-DCA Amiflamine DiFMDA Selegiline (also D-Deprenyl)
Phentermines	Stimulants: Chlorphentermine Cloforex Clortermine Etolorex Mephentermine Pentorex Phentermine Entactogens: MDPH MDMPH Others: Cericlamine
Cathinones	Stimulants: 3-FMC 4-MC 4-BMC 4-CMC 4-EMC 4-FMC 4-MEC 4-MeMABP 4-MPD Amfepramone Benzedrone Brephedrone Buphedrone Bupropion Cathinone Dimethylcathinone Ethcathinone Eutylone Hydroxybupropion Methcathinone Methedrone NEB N-Ethylhexedrone N-Ethylpentedrone Pentedrone Pentylone Radafaxine Entactogens: 3,4-DMMC 3-MMC Butylone Ethylone Methylone Methylenedioxycathinone Mephedrone
Phenylisobutylamines	Entactogens: 4-CAB 4-MAB Ariadne BDB Butylone EBDB Eutylone MBDB Stimulants: Phenylisobutylamine
Phenylalkylpyrrolidines	Stimulants: α-PBP α-PHP α-PPP α-PVP MDPBP MDPPP MDPV 4-MePBP 4-MePHP 4-MePPP MOPPP MOPVP MPBP MPHP MPPP Naphyrone PEP Prolintane Pyrovalerone
Catecholamines (and close relatives)	6-FNE 6-OHDA a-Me-DA a-Me-TRA Adrenochrome Ciladopa D-DOPA (Dextrodopa) Dimetofrine Dopamine Epinephrine Epinine Etilefrine Ethylnorepinephrine Fenclonine Ibopamine Isoprenaline Isoetarine L-DOPA (Levodopa) L-DOPS (Droxidopa) L-Phenylalanine L-Tyrosine m-Tyramine Metanephrine Metaraminol Metaterol Metirosine Methyldopa N,N-Dimethyldopamine Nordefrin (Levonordefrin) Norepinephrine Norfenefrine (m-Octopamine) Normetanephrine Orciprenaline p-Octopamine p-Tyramine Phenylephrine Synephrine
Miscellaneous	AL-LAD Amidephrine Arbutamine Cafedrine Denopamine Desvenlafaxine Diphenidine Dizocilpine Dobutamine Dopexamine Ephenidine Etafedrine ETH-LAD Famprofazone Fluorolintane Hexapradol IP-LAD Lysergic acid amide Lysergic acid 2-butyl amide Lysergic acid 2,4-dimethylazetidide Lysergic acid diethylamide Methoxamine Methoxphenidine MT-45 PARGY-LAD Phenibut PRO-LAD Pronethalol Salbutamol (Levosalbutamol) Solriamfetol Theodrenaline Thiamphenicol UWA-101 Venlafaxine