Amfecloral: Difference between revisions
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Added a pharmacology section featuring the little that is known about amfecloral's metabolism relating to its purported "lack of stimulant effects". |
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{{Short description|Withdrawn appetite suppressant drug}} |
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{{Drugbox |
{{Drugbox |
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| IUPAC_name = 2,2,2-trichloro-''N''-(1-phenylpropan-2-yl)ethanimine |
| IUPAC_name = 2,2,2-trichloro-''N''-(1-phenylpropan-2-yl)ethanimine |
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| image = Amfecloral.png |
| image = Amfecloral.png |
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| tradename = |
| tradename = |
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| pregnancy_category = |
| pregnancy_category = |
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| legal_status = |
| legal_status = In general: unscheduled |
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| routes_of_administration = |
| routes_of_administration = |
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<!--Pharmacokinetic data--> |
<!--Pharmacokinetic data--> |
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| metabolism = |
| metabolism = |
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| elimination_half-life = |
| elimination_half-life = |
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| excretion = |
| excretion = |
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<!--Identifiers--> |
<!--Identifiers--> |
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| CAS_supplemental = <ref name=Ganellin/> |
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| CAS_number_Ref = {{cascite|correct|??}} |
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| CAS_number = 5581-35-1 |
| CAS_number = 5581-35-1 |
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| ATC_prefix = |
| ATC_prefix = none |
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| ATC_suffix = |
| ATC_suffix = |
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| PubChem = 21759 |
| PubChem = 21759 |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| DrugBank = |
| DrugBank = |
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| ChEMBL_Ref = {{ebicite|changed|EBI}} |
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| ChEMBL = 2105544 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 20451 |
| ChemSpiderID = 20451 |
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<!--Chemical data--> |
<!--Chemical data--> |
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| C=11 | H=12 |Cl=3 | N=1 |
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| chemical_formula = C<sub>11</sub>H<sub>12</sub>Cl<sub>3</sub>N |
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| molecular_weight = 264.58 g/mol |
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| smiles = ClC(Cl)(Cl)/C=N/C(Cc1ccccc1)C |
| smiles = ClC(Cl)(Cl)/C=N/C(Cc1ccccc1)C |
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| InChI = 1/C11H12Cl3N/c1-9(15-8-11(12,13)14)7-10-5-3-2-4-6-10/h2-6,8-9H,7H2,1H3/b15-8+ |
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| InChIKey = VBZDETYCYXPOAK-OVCLIPMQBI |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/C11H12Cl3N/c1-9(15-8-11(12,13)14)7-10-5-3-2-4-6-10/h2-6,8-9H,7H2,1H3/b15-8+ |
| StdInChI = 1S/C11H12Cl3N/c1-9(15-8-11(12,13)14)7-10-5-3-2-4-6-10/h2-6,8-9H,7H2,1H3/b15-8+ |
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'''Amfecloral''' ([[International Nonproprietary Name|INN]]), also known as '''amphecloral''' ([[United States Adopted Name|USAN]]), is a [[stimulant]] [[drug]] of the [[substituted phenethylamine|phenethylamine]] and [[substituted amphetamine|amphetamine]] [[chemical class]]es that was used as an [[appetite suppressant]] under the trade name '''Acutran''', but is now no longer marketed.<ref name= |
'''Amfecloral''' ([[International Nonproprietary Name|INN]]), also known as '''amphecloral''' ([[United States Adopted Name|USAN]]), is a [[stimulant]] [[drug]] of the [[substituted phenethylamine|phenethylamine]] and [[substituted amphetamine|amphetamine]] [[chemical class]]es that was used as an [[appetite suppressant]] under the trade name '''Acutran''', but is now no longer marketed.<ref name=Ganellin>{{cite book | title = Dictionary of pharmacological agents, Volumes 1-2 | vauthors = Ganellin CR, Triggle DJ | year = 1996 | publisher = Chapman & Hall | isbn =9780412466304 | page = 67 }}</ref> It was classified as an anorectic drug with little to no stimulant activity in a 1970 review.<ref>{{cite journal | vauthors = Van Rossum JM | title = Mode of action of psychomotor stimulant drugs | journal = International Review of Neurobiology | volume = 12 | pages = 307–83 | date = 1970 | pmid = 4918147 | doi = 10.1016/s0074-7742(08)60065-3 | isbn = 9780123668127 }}</ref> The British Pharmacopoeia Commission approved the name in 1970.<ref>{{cite journal|title=Notes and News|journal=The Lancet|date=October 1970|volume=296|issue=7675|pages=730–732|doi=10.1016/S0140-6736(70)92010-6}}</ref> The raw ingredients used in manufacturing it were [[d-amphetamine]] and [[chloral hydrate]].<ref>{{cite book|last1=McPherson|first1=Edwin M. | name-list-style = vanc |title=Pharmaceutical Manufacturing Encyclopedia |date=2007 |publisher=Elsevier |location=Burlington |isbn=9780815518563 |page=244 |edition=3rd |url=https://books.google.com/books?id=_J2ti4EkYpkC&pg=PA244 }}</ref> |
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== Pharmacology == |
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Amfecloral is metabolised to both d-(S)- and l-(R)-amphetamine and, most likely, also to chloral hydrate.<ref>{{Cite web |title=NCATS Inxight Drugs — AMFECLORAL, (+)- |url=https://drugs.ncats.io/substance/WZS9L0Z92R |access-date=2024-07-16 |website=drugs.ncats.io |language=en}}</ref> Amphetamine is a [[psychostimulant]], whereas chloral hydrate is a [[Sedative hypnotic|sedative/hypnotic]] drug. |
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The extent of metabolism and in-vivo contribution of a chloral hydrate metabolism to its purported "little to no stimulant activity" is unknown. |
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== See also == |
== See also == |
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* [[Amfetaminil]] |
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* [[Amphetamine]] |
* [[Amphetamine]] |
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* [[Clobenzorex]] |
* [[Clobenzorex]] |
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* [[Desbutal]] |
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== References == |
== References == |
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{{Reflist |
{{Reflist}} |
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== External links == |
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* [http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=17397083 PubChem - Substance Summary - Amfecloral] |
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{{Stimulants}} |
{{Stimulants}} |
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{{Depressants}} |
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{{Anorectics}} |
{{Anorectics}} |
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{{Sedatives}} |
{{Sedatives}} |
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{{Monoamine releasing agents}} |
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{{Adrenergics}} |
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{{GABA receptor modulators}} |
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{{Dopaminergics}} |
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{{GABAergics}} |
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{{Phenethylamines}} |
{{Phenethylamines}} |
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[[Category:Anorectics]] |
[[Category:Anorectics]] |
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[[Category: |
[[Category:Substituted amphetamines]] |
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[[Category:Prodrugs]] |
[[Category:Prodrugs]] |
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[[Category:Organochlorides]] |
[[Category:Organochlorides]] |
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[[Category:Norepinephrine-dopamine releasing agents]] |
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{{sedative-stub}} |
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