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Revision as of 15:03, 21 October 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'ChEMBL', 'KEGG').← Previous edit Latest revision as of 01:41, 2 September 2024 edit undo98.178.241.102 (talk) Cats (amph is parent of cathinones). 
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{{Short description|Stimulant drug used as an appetite suppressant}}
{{Drugbox
{{redirect|Keramik}}
{{Use dmy dates|date=August 2022}}
{{Infobox drug
| Verifiedfields = changed | Verifiedfields = changed
| verifiedrevid = 456687601
| Watchedfields = changed
| image = Amfepramone.svg
| verifiedrevid = 401596322
| width = 220
| IUPAC_name = (''RS'')-2-diethylamino-1-phenylpropan-1-one
| alt =
| image = Diethylpropion.png
| chirality = ]
| width = 200px
| imagename = 1 : 1 mixture (racemate)
| drug_name = Amfepramone


<!--Clinical data--> <!-- Clinical data -->
| pronounce =
| tradename = Tenuate
| tradename = Tenuate, Tepanil, Nobesine, others
| Drugs.com = {{drugs.com|monograph|diethylpropion-hydrochloride}} | Drugs.com = {{drugs.com|monograph|diethylpropion-hydrochloride}}
| MedlinePlus = a682037 | MedlinePlus = a682037
| DailyMedID = Diethylpropion
| pregnancy_category = B
| pregnancy_AU = B2
| pregnancy_AU_comment =
| pregnancy_category =
| routes_of_administration = ]
| class =
| ATC_prefix = A08
| ATC_suffix = AA03
| ATC_supplemental =

<!-- Legal status -->
| legal_AU = S4
| legal_AU_comment =
| legal_BR = B2
| legal_BR_comment = <ref>{{Cite web |author=Anvisa |author-link=Brazilian Health Regulatory Agency |date=2023-03-31 |title=RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial |trans-title=Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control|url=https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |url-status=live |archive-url=https://web.archive.org/web/20230803143925/https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |archive-date=2023-08-03 |access-date=2023-08-16 |publisher=] |language=pt-BR |publication-date=2023-04-04}}</ref>
| legal_CA = Schedule G (CDSA IV)
| legal_CA_comment = <ref>{{cite web | title=Tenuate Product information | website=] | date=25 April 2012 | url=https://health-products.canada.ca/dpd-bdpp/info.do?lang=en&code=16693 | access-date=3 August 2022 | archive-date=4 August 2022 | archive-url=https://web.archive.org/web/20220804002602/https://health-products.canada.ca/dpd-bdpp/info.do?lang=en&code=16693 | url-status=live }}</ref><ref>{{cite web | title=Nobesine Product information | website=] | date=25 April 2012 | url=https://health-products.canada.ca/dpd-bdpp/info.do?lang=en&code=9263 | access-date=3 August 2022 | archive-date=4 August 2022 | archive-url=https://web.archive.org/web/20220804002603/https://health-products.canada.ca/dpd-bdpp/info.do?lang=en&code=9263 | url-status=live }}</ref>
| legal_DE = Prescription only (] for higher doses)
| legal_DE_comment =
| legal_NZ = <!-- Class A, B, C -->
| legal_NZ_comment =
| legal_UK = Class C
| legal_UK_comment =
| legal_US = Schedule IV | legal_US = Schedule IV
| legal_US_comment = <ref name="Tepanil FDA label" />
| legal_status =
| legal_EU = Rx-only
| routes_of_administration = Oral
| legal_EU_comment = <ref>{{cite web | url=https://www.ema.europa.eu/en/documents/psusa/amfepramone-list-nationally-authorised-medicinal-products-psusa/00000138/202006_en.pdf | title=Amfepramone. List of nationally authorized medicinal products | archive-url=https://web.archive.org/web/20210827213256/https://www.ema.europa.eu/en/documents/psusa/amfepramone-list-nationally-authorised-medicinal-products-psusa/00000138/202006_en.pdf | archive-date=27 August 2021 |url-status=live }}</ref><ref name="EU Amfepramone">{{cite web | title=Amfepramone-containing medicinal products | website=] (EMA) | date=12 February 2021 | url=https://www.ema.europa.eu/en/medicines/human/referrals/amfepramone-containing-medicinal-products | access-date=12 February 2021 | archive-date=7 March 2021 | archive-url=https://web.archive.org/web/20210307060434/https://www.ema.europa.eu/en/medicines/human/referrals/amfepramone-containing-medicinal-products | url-status=live }}</ref>
| legal_UN = <!-- N I, II, III, IV / P I, II, III, IV -->
| legal_UN_comment =
| legal_status = <!-- For countries not listed above -->


<!--Pharmacokinetic data--> <!-- Pharmacokinetic data -->
| bioavailability = | bioavailability =
| protein_bound = | protein_bound =
| metabolism = | metabolism =
| metabolites =
| elimination_half-life =
| onset =
| excretion =
| elimination_half-life = 4&ndash;6 hours (metabolites)<ref name=MHRA>{{cite web|title=SPC-DOC_PL 16133-0001 |work=Medicines Healthcare products Regulatory Agency |publisher=Essential Nutrition Ltd |date=18 November 2011 |access-date=18 July 2014 |url=http://www.mhra.gov.uk/home/groups/spcpil/documents/spcpil/con1396847771265.pdf }}{{dead link|date=July 2017 |bot=InternetArchiveBot |fix-attempted=yes }}</ref>
| duration_of_action =
| excretion = Urine (>75%)<ref name = MHRA/>


<!--Identifiers--> <!-- Identifiers -->
| CASNo_Ref = {{cascite|correct|CAS}} | CAS_number_Ref = {{cascite|correct|CAS}}
| CAS_number = 134-80-5 | CAS_number = 90-84-6
| CAS_supplemental =
| ATC_prefix = A08
| ATC_suffix = AA03
| PubChem = 7029 | PubChem = 7029
| IUPHAR_ligand = 7161
| DrugBank_Ref = {{drugbankcite|changed|drugbank}}
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB00937 | DrugBank = DB00937
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 6762 | ChemSpiderID = 6762
| UNII_Ref = {{fdacite|correct|FDA}} | UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 19V2PL39NG | UNII = Q94YYU22B8
| KEGG_Ref = {{keggcite|changed|kegg}} | KEGG_Ref = {{keggcite|changed|kegg}}
| KEGG = D03801 | KEGG = D07444
| ChEBI_Ref = {{ebicite|changed|EBI}} | ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 4530 | ChEBI = 4530
| ChEMBL_Ref = {{ebicite|changed|EBI}} | ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = <!-- blanked - oldvalue: 1194666 --> | ChEMBL = 1194666
| NIAID_ChemDB =
| PDB_ligand =
| synonyms = Diethylpropion, Diethylcathinone

<!-- Chemical and physical data -->
| IUPAC_name = (''RS'')-2-diethylamino-1-phenylpropan-1-one
| C=13 | H=19 | N=1 | O=1 | C=13 | H=19 | N=1 | O=1
| SMILES = O=C(c1ccccc1)C(N(CC)CC)C
| molecular_weight = 205.30 g/mol
| smiles = O=C(c1ccccc1)C(N(CC)CC)C
| InChI = 1/C13H19NO/c1-4-14(5-2)11(3)13(15)12-9-7-6-8-10-12/h6-11H,4-5H2,1-3H3
| InChIKey = XXEPPPIWZFICOJ-UHFFFAOYAJ
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C13H19NO/c1-4-14(5-2)11(3)13(15)12-9-7-6-8-10-12/h6-11H,4-5H2,1-3H3 | StdInChI = 1S/C13H19NO/c1-4-14(5-2)11(3)13(15)12-9-7-6-8-10-12/h6-11H,4-5H2,1-3H3
| StdInChI_comment =
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = XXEPPPIWZFICOJ-UHFFFAOYSA-N | StdInChIKey = XXEPPPIWZFICOJ-UHFFFAOYSA-N
| density =
| synonyms = Diethylpropion
| density_notes =
| melting_point =
| melting_high =
| melting_notes =
| boiling_point =
| boiling_notes =
| solubility =
| sol_units =
| specific_rotation =
}} }}
'''Amfepramone''', also known as '''diethylpropion''', is a ] drug of the ], ], and ] ] that is used as an ].<ref name = MD/><ref>{{cite web | title=TGA Approved Terminology for Medicines, Section 1 – Chemical Substances | newspaper=Therapeutic Goods Administration (Tga) | date=July 1999 | publisher=], Department of Health and Ageing, Australian Government | page=42 | url=http://www.tga.gov.au/pdf/medicines-approved-terminology-chemical.pdf | access-date=18 July 2014 | archive-date=11 February 2014 | archive-url=https://web.archive.org/web/20140211201639/http://www.tga.gov.au/pdf/medicines-approved-terminology-chemical.pdf | url-status=live }}</ref> It is used in the short-term management of ], along with dietary and lifestyle changes.<ref name = MD>{{cite web |title=Diethylpropion Hydrochloride |work=Martindale: The Complete Drug Reference |publisher=Pharmaceutical Press |date=30 January 2013 |access-date=18 July 2014 |url=https://www.medicinescomplete.com/mc/martindale/current/1475-e.htm |veditors=Brayfield A |location=London, UK |archive-date=27 August 2021 |archive-url=https://web.archive.org/web/20210827213309/https://about.medicinescomplete.com/wp-content/plugins/revslider/public/assets/js/extensions/revolution.extension.layeranimation.min.js?version=5.4.5 |url-status=live }}</ref> Amfepramone has a similar chemical structure to the antidepressant and ] aid ] (previously called amfebutamone), which has also been developed as a weight-loss medicine when in a combination product with ].<ref>{{cite book | vauthors = Arias HR, Santamaría A, Ali SF | title = New Concepts of Psychostimulant Induced Neurotoxicity | chapter = Pharmacological and neurotoxicological actions mediated by bupropion and diethylpropion | volume = 88 | pages = 223–55 | date = 2009 | pmid = 19897080 | doi = 10.1016/S0074-7742(09)88009-4 | isbn = 9780123745040 | series = International Review of Neurobiology }}</ref>

'''Amfepramone''' (], other names '''diethylcathinone''' and '''diethylpropion''', trade names '''Anorex''', '''Linea''', '''Nobesine''', '''Prefamone''', '''Regenon''', '''Tepanil''', '''Tenuate'''), is a ] ] of the ], ], and ] ]es that is used as an ].


== Pharmacology == == Pharmacology ==
Amfepramone itself lacks any ] for the ]s and instead functions as a ] to ].<ref name="pmid17017961">{{cite journal |doi=10.2174/156802606778249766 |author=Rothman RB, Baumann MH |title=Therapeutic potential of monoamine transporter substrates |journal=Current Topics in Medicinal Chemistry |volume=6 |issue=17 |pages=1845–59 |year=2006 |pmid=17017961 |url=http://www.bentham-direct.org/pages/content.php?CTMC/2006/00000006/00000017/0004R.SGM}}</ref> Ethcathinone (and therefore amfepramone as well) is a very weak ] and ], and is approximately 10x and 20x stronger on ] in comparison, respectively.<ref name="pmid17017961"/> As a result, ethcathinone and amfepramone can essentially be considered ] ] ]s (NRAs). Amfepramone itself lacks any ] for the ]s and instead functions as a ] to ].<ref name="pmid17017961">{{cite journal | vauthors = Rothman RB, Baumann MH | title = Therapeutic potential of monoamine transporter substrates | journal = Current Topics in Medicinal Chemistry | volume = 6 | issue = 17 | pages = 1845–59 | year = 2006 | pmid = 17017961 | doi = 10.2174/156802606778249766 | url = https://zenodo.org/record/1235860 | access-date = 7 September 2020 | archive-date = 23 October 2020 | archive-url = https://web.archive.org/web/20201023101936/https://zenodo.org/record/1235860 | url-status = live }}</ref> Ethcathinone (and therefore amfepramone as well) is a very weak ] and ], and is approximately 10× and 20× stronger on ] in comparison, respectively.<ref name="pmid17017961"/>


== Abuse ==
Amfepramone is believed to have relatively low abuse potential.<ref>{{cite journal |author=Cohen S |title=Diethylpropion (tenuate): an infrequently abused anorectic |journal=Psychosomatics |volume=18 |issue=1 |pages=28–33 |year=1977 |pmid=850721 |url=http://psy.psychiatryonline.org/cgi/pmidlookup?view=long&pmid=850721}}</ref><ref>{{cite journal |author=Jasinski DR, Krishnan S |title=Abuse liability and safety of oral lisdexamfetamine dimesylate in individuals with a history of stimulant abuse |journal=Journal of Psychopharmacology |volume=23 |issue=4 |pages=419–27 |year=2009 |month=June |pmid=19329547 |doi=10.1177/0269881109103113}}</ref><ref>http://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=1611</ref><ref>{{cite journal |author=CAPLAN J |title=Habituation to diethylpropion (Tenuate) |journal=Canadian Medical Association Journal |volume=88 |issue= |pages=943–4 |year=1963 |month=May |pmid=14018413 |pmc=1921278}}</ref>

== Legality ==
Amfepramone is classified as a ] ] in the ].
In the UK Amfepramone is a class C drug.<ref>http://www.statutelaw.gov.uk/content.aspx?LegType=All+Legislation&title=The+Misuse+of+Drugs+Act+1971&searchEnacted=0&extentMatchOnly=0&confersPower=0&blanketAmendment=0&sortAlpha=0&TYPE=QS&PageNumber=1&NavFrom=0&parentActiveTextDocId=1367412&ActiveTextDocId=1367471&filesize=1699</ref>
==Chemistry== ==Chemistry==
Amfepramone can be synthesized from ] by ], followed by reaction with ].<ref>{{ cite patent | country = US | status = patent | number = 3001910 | title = Anorexigenic Propiophenones | inventor = Schutte J | assign1 = Temmler-Werke | gdate = 1961-09-26 }}</ref><ref>{{cite journal | vauthors = Hyde JF, Browning E, Adams R | journal = Journal of the American Chemical Society | volume = 50 | issue = 8 | pages = 2287–2292| title = Synthetic Homologs of d,l-Ephedrine| year = 1928 | doi = 10.1021/ja01395a032 }}</ref>
#] is brominated to produce α-bromopropiophenone.
#This is reacted with ] to yield the product, diethylpropion.


==Society and culture==
Reference: {{US patent|3001910}} {{Cite doi|10.1021/ja01395a032}}
===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. ] include: Anorex, Linea, Nobesine, Prefamone, Regenon, Tepanil and Tenuate.


== See also == === Legal status ===
Amfepramone is classified as a ] ] in the United States. 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 | access-date = 7 February 2012 | archive-date = 14 November 2012 | archive-url = https://web.archive.org/web/20121114181829/http://www.legislation.gov.uk/ukpga/1971/38/schedule/2 | url-status = live }}</ref> and as a medicine, it is a Schedule 3 Controlled Drug which requires safe custody.
* ]

As of June 2022, the safety committee of the ] (EMA) recommends the withdrawal of marketing authorizations for amfepramone.<ref>{{cite web | title=EMA recommends withdrawal of marketing authorisation for amfepramone medicines | website=] (EMA) | date=10 June 2022 | url=https://www.ema.europa.eu/en/news/ema-recommends-withdrawal-marketing-authorisation-amfepramone-medicines | access-date=10 June 2022 | archive-date=10 June 2022 | archive-url=https://web.archive.org/web/20220610152019/https://www.ema.europa.eu/en/news/ema-recommends-withdrawal-marketing-authorisation-amfepramone-medicines | url-status=live }}</ref><ref name="EU Amfepramone" />

=== Recreational use ===
The authors of several studies of amfepramone claim that the substance has a relatively low potential for causing addiction in users.<ref>{{cite journal | vauthors = Cohen S | title = Diethylpropion (tenuate): an infrequently abused anorectic | journal = Psychosomatics | volume = 18 | issue = 1 | pages = 28–33 | year = 1977 | pmid = 850721 | doi = 10.1016/S0033-3182(77)71101-6 | doi-access = free }}</ref><ref>{{cite journal | vauthors = Jasinski DR, Krishnan S | title = Abuse liability and safety of oral lisdexamfetamine dimesylate in individuals with a history of stimulant abuse | journal = Journal of Psychopharmacology | volume = 23 | issue = 4 | pages = 419–27 | date = June 2009 | pmid = 19329547 | doi = 10.1177/0269881109103113 | s2cid = 6138292 }}</ref><ref name="Tepanil FDA label">{{cite web | url = https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=79b15110-e484-4b84-8947-15653746773c | title = Tepanil (diethylpropion hydrochloride) tablet, extended release | work = Dailymed | publisher = National Institutes of Health | access-date = 4 August 2022 | archive-date = 8 May 2021 | archive-url = https://web.archive.org/web/20210508102939/https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=79b15110-e484-4b84-8947-15653746773c | url-status = live }}</ref><ref>{{cite journal | vauthors = Caplan J | title = Habituation to diethylpropion (Tenuate) | journal = Canadian Medical Association Journal | volume = 88 | pages = 943–4 | date = May 1963 | issue = 18 | pmid = 14018413 | pmc = 1921278 }}</ref>


== References == == References ==
{{Reflist|2}} {{Reflist}}


{{Stimulants}}
{{Anorectics}} {{Anorectics}}
{{Monoamine releasing agents}}
{{Neurotoxins}}
{{Adrenergics}}
{{Dopaminergics}}
{{Phenethylamines}} {{Phenethylamines}}
{{Portal bar | Medicine}}


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