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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 = 4–6 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 = D07444		\| 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 = 1194666		\| ChEMBL = 1194666
			\| NIAID_ChemDB =
			\| PDB_ligand =
			\| synonyms = Diethylpropion, Diethylcathinone

	<!--Chemical data-->		<!-- 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}}

	]		]
	]		]
			]
			]
	]		]
			]

			]
	]
	]

Latest revision as of 01:41, 2 September 2024

Stimulant drug used as an appetite suppressant "Keramik" redirects here. For other uses, see Keramik (disambiguation).

Pharmaceutical compound

Amfepramone
Clinical data

Trade names	Tenuate, Tepanil, Nobesine, others
Other names	Diethylpropion, Diethylcathinone
AHFS/Drugs.com	Monograph
MedlinePlus	a682037
License data	US DailyMed: Diethylpropion
Pregnancy category	AU: B2
Routes of administration	By mouth
ATC code	A08AA03 (WHO)
Legal status
Legal status	AU: S4 (Prescription only) BR: Class B2 (Anorectic drugs) CA: Schedule G (CDSA IV) DE: Prescription only (Anlage III for higher doses) UK: Class C US: Schedule IV EU: Rx-only
Pharmacokinetic data
Elimination half-life	4–6 hours (metabolites)
Excretion	Urine (>75%)
Identifiers
IUPAC name (RS)-2-diethylamino-1-phenylpropan-1-one
CAS Number	90-84-6
PubChem CID	7029
IUPHAR/BPS	7161
DrugBank	DB00937
ChemSpider	6762
UNII	Q94YYU22B8
KEGG	D07444
ChEBI	CHEBI:4530
ChEMBL	ChEMBL1194666
CompTox Dashboard (EPA)	DTXSID6022929
ECHA InfoCard	100.001.836
Chemical and physical data
Formula	C₁₃H₁₉NO
Molar mass	205.301 g·mol
3D model (JSmol)	Interactive image
Chirality	Racemic 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 Key:XXEPPPIWZFICOJ-UHFFFAOYSA-N
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Amfepramone, also known as diethylpropion, is a stimulant drug of the phenethylamine, amphetamine, and cathinone classes that is used as an appetite suppressant. It is used in the short-term management of obesity, along with dietary and lifestyle changes. Amfepramone has a similar chemical structure 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.

Pharmacology

Amfepramone itself lacks any affinity for the monoamine transporters and instead functions as a prodrug to ethcathinone. Ethcathinone (and therefore amfepramone as well) is a very weak dopaminergic and serotonergic, and is approximately 10× and 20× stronger on norepinephrine in comparison, respectively.

Chemistry

Amfepramone can be synthesized from propiophenone by bromination, followed by reaction with diethylamine.

Society and culture

Names

Another medically utilized name is diethylpropion (British Approved Name (BAN) and Australian Approved Name (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.

Legal status

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

As of June 2022, the safety committee of the European Medicines Agency (EMA) recommends the withdrawal of marketing authorizations for amfepramone.

Recreational use

The authors of several studies of amfepramone claim that the substance has a relatively low potential for causing addiction in users.

References

Anvisa (31 March 2023). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 4 April 2023). Archived from the original on 3 August 2023. Retrieved 16 August 2023.
"Tenuate Product information". Health Canada. 25 April 2012. Archived from the original on 4 August 2022. Retrieved 3 August 2022.
"Nobesine Product information". Health Canada. 25 April 2012. Archived from the original on 4 August 2022. Retrieved 3 August 2022.
^ "Tepanil (diethylpropion hydrochloride) tablet, extended release". Dailymed. National Institutes of Health. Archived from the original on 8 May 2021. Retrieved 4 August 2022.
"Amfepramone. List of nationally authorized medicinal products" (PDF). Archived (PDF) from the original on 27 August 2021.
^ "Amfepramone-containing medicinal products". European Medicines Agency (EMA). 12 February 2021. Archived from the original on 7 March 2021. Retrieved 12 February 2021.
^ "SPC-DOC_PL 16133-0001" (PDF). Medicines Healthcare products Regulatory Agency. Essential Nutrition Ltd. 18 November 2011. Retrieved 18 July 2014.
^ Brayfield A, ed. (30 January 2013). "Diethylpropion Hydrochloride". Martindale: The Complete Drug Reference. London, UK: Pharmaceutical Press. Archived from the original on 27 August 2021. Retrieved 18 July 2014.
"TGA Approved Terminology for Medicines, Section 1 – Chemical Substances" (PDF). Therapeutic Goods Administration (Tga). Therapeutic Goods Administration, Department of Health and Ageing, Australian Government. July 1999. p. 42. Archived (PDF) from the original on 11 February 2014. Retrieved 18 July 2014.
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.
^ 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 23 October 2020. Retrieved 7 September 2020.
US patent 3001910, Schutte J, "Anorexigenic Propiophenones", issued 1961-09-26, assigned to Temmler-Werke
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.
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Antiobesity agents/Anorectics (A08)

Stimulants

Amphetamines and phenethylamines	4-Methylamphetamine Amfecloral Amfepentorex Amfepramone Amphetamine Amphetaminil Benzphetamine Cathine Cathinone Chlorphentermine Clobenzorex Cloforex Clortermine Dextroamphetamine Dimethylcathinone Ephedrine Ephedra Etilamfetamine Etolorex Fenethylline Fenproporex Fludorex Furfenorex Khat Lisdexamfetamine Mefenorex Methamphetamine Norfenfluramine Pentorex Phentermine (+topiramate) Xylopropamine Zylofuramine
Adrenergic agonists	Albuterol Clenbuterol Ephedrine Ephedra Levopropylhexedrine Synephrine Terbutaline Yohimbine (Yohimbe)
Other	Aminorex Atomoxetine Benfluorex Bupropion (+naltrexone) Dexfenfluramine Dexmethylphenidate Difemetorex Fenbutrazate Fenfluramine (+phentermine) Manifaxine Mazindol Methylphenidate Phendimetrazine Phenethylamine Phenmetrazine Phenylpropanolamine Pipradrol Propylhexedrine Pyrovalerone Sibutramine Tesofensine

Cannabinoid
antagonists

GLP-1, GIP, and / or
glucagon agonists

DACRAs

Cagrilintide (+semaglutide)

5-HT2C
receptor agonists

Absorption inhibitors

Uncouplers

2,4-Dinitrophenol

Others

WHO-EM
Withdrawn from market
Clinical trials:
- Phase III
- Never to phase III

Monoamine releasing agents

DRAsTooltip Dopamine releasing agents

Morpholines: Fenbutrazate Fenmetramide Morazone Morforex Phendimetrazine Phenmetrazine Pseudophenmetrazine
Oxazolines: 4-MAR Aminorex Clominorex Cyclazodone Fenozolone Fluminorex Pemoline Thozalinone
Phenethylamines: 2-OH-PEA 4-CAB 4-FA 4-FMA 4-MA 4-MMA Alfetamine Amfecloral Amfepentorex Amfepramone Amphetamine (Dextroamphetamine Levoamphetamine) Amphetaminil β-Me-PEA BDB BOH Benzphetamine Buphedrone Butylone Cathine Cathinone Clobenzorex Clortermine D-Deprenyl DMA DMMA Dimethylamphetamine Ephedrine Ethcathinone EBDB Ethylone Etilamfetamine Famprofazone Fenethylline Fenproporex Flephedrone Fludorex Furfenorex Hordenine 4-Hydroxyamphetamine Iofetamine (123I) Lisdexamfetamine Lophophine Mefenorex Mephedrone Metamfepramone Methamphetamine Dextromethamphetamine Levomethamphetamine Methcathinone Methedrone MMDA MMDMA MBDB MDA (tenamfetamine) MDEA MDMA (midomafetamine) MDMPEA MDOH MDPEA Methylone Morforex Ortetamine pBA pCA pIA Pholedrine Phenethylamine Pholedrine Phenpromethamine Prenylamine Propylamphetamine Pseudoephedrine Tiflorex Tyramine Xylopropamine Zylofuramine
Piperazines: 2C-B-BZP BZP MBZP MDBZP MeOPP oMPP
Others: 2-ADN 2-AI 2-AT 4-BP 5-APDI 5-IAI Amineptine Clofenciclan Cyclopentamine Cypenamine Cyprodenate Feprosidnine Gilutensin Heptaminol Hexacyclonate Indanorex Isometheptene Methylhexanamine Naphthylaminopropane Octodrine Phthalimidopropiophenone Phenylbiguanide Propylhexedrine

NRAsTooltip Norepinephrine releasing agents

Morpholines: Fenbutrazate Fenmetramide Morazone Morforex Phendimetrazine Phenmetrazine Pseudophenmetrazine
Oxazolines: 4-MAR Aminorex Clominorex Cyclazodone Fenozolone Fluminorex Pemoline Thozalinone
Phenethylamines: 2-OH-PEA 4-CAB 4-FA 4-FMA 4-MA 4-MMA Alfetamine Amfecloral Amfepentorex Amfepramone Amphetamine Dextroamphetamine Levoamphetamine Amphetaminil β-Me-PEA BDB Benzphetamine BOH Buphedrone Butylone Cathine Cathinone Clobenzorex Clortermine Dimethylamphetamine DMA DMMA EBDB Ephedrine Ethcathinone Ethylone Etilamfetamine Famprofazone Fenethylline Fenproporex Flephedrone Fludorex Furfenorex Hordenine 4-Hydroxyamphetamine 5-APDI (IAP) Iofetamine (123I) Lisdexamfetamine Lophophine MBDB MDA (tenamfetamine) MDEA MDMA (midomafetamine) Metamfepramone MDMPEA MDOH MDPEA Mefenorex Mephedrone Mephentermine Methamphetamine Dextromethamphetamine Levomethamphetamine Methcathinone Methedrone Methylone Morforex Naphthylaminopropane Ortetamine pBA pCA Pentorex Phenethylamine Pholedrine Phenpromethamine Phentermine Phenylpropanolamine pIA Prenylamine Propylamphetamine Pseudoephedrine Selegiline (also D-Deprenyl) Tiflorex Tyramine Xylopropamine Zylofuramine
Piperazines: 2C-B-BZP BZP MBZP mCPP MDBZP MeOPP oMPP pFPP
Others: 2-ADN 2-AI 2-AT 2-BP 4-BP 5-IAI Clofenciclan Cyclopentamine Cypenamine Cyprodenate Feprosidnine Gilutensin Heptaminol Hexacyclonate Indanorex Isometheptene Methylhexanamine Octodrine Phthalimidopropiophenone Propylhexedrine Tuaminoheptane

SRAsTooltip Serotonin releasing agents

Aminoindanes: 5-IAI AMMI ETAI MDAI MDMAI MMAI TAI
Aminotetralins: 6-CAT 8-OH-DPAT MDAT MDMAT
Oxazolines: 4-Methylaminorex Aminorex Clominorex Fluminorex
Phenethylamines: 2-Methyl-MDA 4-CAB 4-FA 4-FMA 4-HA 4-MTA 5-APDB 5-Methyl-MDA 6-APDB 6-Methyl-MDA AEMMA Amiflamine BDB BOH Brephedrone Butylone Chlorphentermine Cloforex Amfepramone Metamfepramone DCA Dexfenfluramine DFMDA DMA DMMA EBDB EDMA Ethylone Etolorex Fenfluramine Flephedrone Flucetorex IAP Iofetamine Levofenfluramine Lophophine MBDB MDA (tenamfetamine) MDEA MDHMA MDMA (midomafetamine) MDMPEA MDOH MDPEA Mephedrone Methedrone Methylone MMA MMDA MMDMA MMMA NAP Norfenfluramine 4-TFMA pBA pCA pIA PMA PMEA PMMA TAP
Piperazines: 2C-B-BZP 3-MeOPP BZP DCPP MBZP mCPP MDBZP MeOPP Mepiprazole oMPP pCPP pFPP pTFMPP TFMPP
Tryptamines: 4-Methyl-αET 4-Methyl-αMT 5-CT 5-MeO-αET 5-MeO-αMT 5-MT αET αMT DMT Tryptamine
Others: Indeloxazine Viqualine

Others

DAT modulators: Agonist-like: SoRI-9804
SoRI-20040; Antagonist-like: SoRI-20041

Adrenergic release blockers: Bethanidine
Bretylium
Guanadrel
Guanazodine
Guanethidine
Guanoxan

See also: Receptor/signaling modulators • Monoamine reuptake inhibitors • Adrenergics • Dopaminergics • Serotonergics • Monoamine metabolism modulators • Monoamine neurotoxins

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

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