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Latest revision as of 21:05, 22 October 2023 edit undoKimen8 (talk | contribs)Extended confirmed users5,112 edits change generic short description |
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{{Short description|Stimulant drug of the phenethylamine and amphetamine classes}} |
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{{Drugbox |
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{{Drugbox |
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| verifiedrevid = 390437025 |
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| Watchedfields = changed |
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| verifiedrevid = 447809451 |
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| IUPAC_name = (±)-1-(3,4-dimethylphenyl)propan-2-amine |
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| IUPAC_name = (±)-1-(3,4-dimethylphenyl)propan-2-amine |
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| image = Xylopropamine.svg |
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| image = Xylopropamine.svg |
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| imagename = 1 : 1 mixture (racemate) |
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| chirality = ] |
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| drug_name = Xylopropamine |
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<!--Clinical data--> |
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<!--Clinical data--> |
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| tradename = |
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| tradename = |
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| pregnancy_category = |
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| pregnancy_category = |
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| legal_CA = Schedule I |
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| legal_UK = Class B |
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| legal_US = Schedule I (positional isomer of ]) |
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| legal_status = Rx-only |
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| legal_status = Rx-only |
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| routes_of_administration = Oral |
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| routes_of_administration = Oral |
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<!--Pharmacokinetic data--> |
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<!--Pharmacokinetic data--> |
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| bioavailability = |
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| bioavailability = |
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| metabolism = |
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| metabolism = |
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<!--Identifiers--> |
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<!--Identifiers--> |
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| index_label = |
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| CAS_number = 14543-76-1 |
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| index2_label = Sulfate |
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| CAS_number_Ref = {{cascite|changed|??}} |
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| CAS_number = 102-31-8 |
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| CAS_number2_Ref = {{cascite|changed|??}} |
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| CAS_number2 = 14543-76-1 |
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| ATC_prefix = none |
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| ATC_prefix = none |
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| UNII_Ref = {{fdacite|changed|FDA}} |
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| UNII = 4DB10V9J2I |
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| UNII2_Ref = {{fdacite|changed|FDA}} |
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| UNII2 = B464QNG39U |
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| ATC_suffix = |
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| ATC_suffix = |
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| PubChem = 26727 |
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| PubChem = 26727 |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| DrugBank = |
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| DrugBank = |
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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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| ChemSpiderID = 24901 |
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| smiles = c1c(ccc(c1C)C)CC(N)C |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChI = 1S/C11H17N/c1-8-4-5-11(6-9(8)2)7-10(3)12/h4-6,10H,7,12H2,1-3H3 |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChIKey = ZSZUWPRERIPUBM-UHFFFAOYSA-N |
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<!--Chemical data--> |
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<!--Chemical data--> |
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| C=11 | H=17 | N=1 |
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| C=11 | H=17 | N=1 |
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| molecular_weight = 163.259 g/mol |
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}} |
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}} |
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'''Xylopropamine''' ('''Perhedrin''', '''Esanin'''), also known as '''3,4-dimethylamphetamine''', is a ] ] of the ] and ] classes which was developed and marketed as an ] in the 1950s. |
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'''Xylopropamine''' ('''Perhedrin''', '''Esanin'''), also known as '''3,4-dimethylamphetamine''', is a ] ] of the ] and ] classes which was developed and marketed as an ] in the 1950s.<ref>{{cite patent | country = US | number = 2384700 | title = Alkylated phenyl-isopropyl-amines and process for the manufacture of same | inventor = Schnider O | assign1 = Hoffman La Roche | gdate = 11 September 1945 }}</ref> |
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Xylopropamine was briefly sold as the ] ], but it was not widely marketed. Other related amphetamine derivatives such as ] were also investigated for the same purpose, however these drugs had negative side effects such as high blood pressure and were not very successful, mainly due to the introduction of alternative drugs like ] which had similar efficacy but fewer side effects. |
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Xylopropamine was briefly sold as the ] ], but it was not widely marketed. Other related amphetamine derivatives such as ] were also investigated for the same purpose, however these drugs had negative side effects such as high blood pressure and were not very successful, mainly due to the introduction of alternative drugs like ] which had similar efficacy but fewer side effects. |
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Xylopropamine was also reported as having ]<ref>HARRIS SC, WORLEY RC. Analgesic properties of xylopropamine. Proceedings of the Society for Experimental Biology and Medicine. 1957 Jun;95(2):212-5.</ref> and ]<ref>RANDALL LO, SELITTO JJ, VALDES J. Anti-inflammatory effects of xylopropamine. Archives Internationales de Pharmacodynamie et de Therapie. 1957 Dec 1;113(1-2):233-49.</ref> effects but its side effect profile resulted in it never being further developed for these applications. |
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Xylopropamine was also reported as having ]<ref name="pmid13441687">{{cite journal | vauthors = Harris SC, Worley RC | s2cid = 34027366 | title = Analgesic properties of xylopropamine | journal = Proceedings of the Society for Experimental Biology and Medicine | volume = 95 | issue = 2 | pages = 212–5 | date = June 1957 | pmid = 13441687 | doi = 10.3181/00379727-95-23170 }}</ref> and ]<ref name="pmid13509788">{{cite journal | vauthors = Randall LO, Selitto JJ, Valdes J | title = Anti-inflammatory effects of xylopropamine | journal = Archives Internationales de Pharmacodynamie et de Therapie | volume = 113 | issue = 1–2 | pages = 233–49 | date = December 1957 | pmid = 13509788 }}</ref> effects but its side effect profile resulted in it never being further developed for these applications. |
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== See also == |
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== See also == |
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{{Stimulants}} |
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{{Stimulants}} |
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{{Anorectics}} |
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{{Anorectics}} |
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{{Monoamine releasing agents}} |
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{{Adrenergics}} |
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{{Dopaminergics}} |
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{{Serotonergics}} |
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{{Phenethylamines}} |
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{{Phenethylamines}} |
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