| Revision as of 18:18, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{drugbox}} taken from revid 465586388 of page 4-Methylamphetamine for the Chem/Drugbox validation project (updated: 'CAS_number'). |
Latest revision as of 21:37, 11 January 2025 edit Arthurfragoso (talk | contribs)Extended confirmed users3,659 edits dark mode fix |
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{{short description|Stimulant and anorectic drug of the amphetamine class}} |
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{{ambox | text = This page contains a copy of the infobox ({{tl|drugbox}}) taken from revid of page ] with values updated to verified values.}} |
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{{cs1 config|name-list-style=vanc|display-authors=6}} |
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{{Drugbox |
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{{Infobox drug |
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| verifiedrevid = 418216592 |
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| Verifiedfields = changed |
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| verifiedrevid = 477222632 |
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| IUPAC_name = 1-(4-methylphenyl)propan-2-amine |
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| IUPAC_name = 1-(4-methylphenyl)propan-2-amine |
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| image = 4-Methylamphetamine.svg |
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| image = 4-Methylamphetamine.svg |
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| image_class = skin-invert-image |
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| image2 = 4-Methylamphetamine molecule ball.png |
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| alt2 = Ball-and-stick model of the 4-methylamphetamine molecule |
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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_status = |
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| legal_CA = Schedule I |
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| legal_UK = Class A |
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| routes_of_administration = |
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| legal_DE = Anlage II |
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| legal_US = ] |
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| routes_of_administration = Oral, intranasal, injection, |
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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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| elimination_half-life = |
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| elimination_half-life = 6-12 hours |
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| excretion = |
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| excretion = Urine |
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<!--Identifiers--> |
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<!--Identifiers--> |
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| CAS_number_Ref = {{cascite|correct|??}} |
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| CAS_number_Ref = {{cascite|changed|??}} |
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| CAS_number = <!-- blanked - oldvalue: 22683-78-9 --> |
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| CAS_number = 64-11-9 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = 9E273KL7HS |
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| ATC_prefix = none |
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| ATC_prefix = none |
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| PubChem = 199116 |
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| PubChem = 199116 |
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<!--Chemical data--> |
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<!--Chemical data--> |
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| C=10 | H=15 | N=1 |
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| C=10 | H=15 | N=1 |
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| molecular_weight = 149.23 g/mol |
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| smiles = NC(Cc1ccc(cc1)C)C |
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| smiles = NC(Cc1ccc(cc1)C)C |
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| InChI = 1/C10H15N/c1-8-3-5-10(6-4-8)7-9(2)11/h3-6,9H,7,11H2,1-2H3 |
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| InChIKey = ZDHZDWSHLNBTEB-UHFFFAOYAG |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/C10H15N/c1-8-3-5-10(6-4-8)7-9(2)11/h3-6,9H,7,11H2,1-2H3 |
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| StdInChI = 1S/C10H15N/c1-8-3-5-10(6-4-8)7-9(2)11/h3-6,9H,7,11H2,1-2H3 |
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| StdInChIKey = ZDHZDWSHLNBTEB-UHFFFAOYSA-N |
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| StdInChIKey = ZDHZDWSHLNBTEB-UHFFFAOYSA-N |
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}} |
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'''4-Methylamphetamine''' ('''4-MA'''; '''PAL-313'''; '''Aptrol'''; '''p-TAP''') is a ] and ] ] of the ] and ] ]es. |
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== Pharmacology == |
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In vitro, it acts as a ] and ] ], ], and ] ] with ] ] values of 53.4nM, 22.2nM, and 44.1nM at the ], ], and ]s, respectively.<ref name="pmid15677348">{{cite journal | vauthors = Wee S, Anderson KG, Baumann MH, Rothman RB, Blough BE, Woolverton WL | title = Relationship between the serotonergic activity and reinforcing effects of a series of amphetamine analogs | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 313 | issue = 2 | pages = 848–854 | date = May 2005 | pmid = 15677348 | doi = 10.1124/jpet.104.080101 | s2cid = 12135483 }}</ref> However, more recent ''in vivo'' studies that involved performing microdialysis on rats showed a different trend. These studies showed that 4-methylamphetamine is much more potent at elevating serotonin (~18 x baseline) relative to ] (~5 x baseline). The authors speculated that this is because 5-HT release dampens DA release through some mechanism. For example, it was suggested that a possible cause for this could be activation of 5HT<sub>2C</sub> receptors since this is known to inhibit DA release. In addition there are alternative explanations such as 5-HT release then going on to encourage GABA release, which has an inhibitory effect on DA neurons.<ref>{{cite journal | vauthors = Di Giovanni G, Esposito E, Di Matteo V | title = Role of serotonin in central dopamine dysfunction | journal = CNS Neuroscience & Therapeutics | volume = 16 | issue = 3 | pages = 179–194 | date = June 2010 | pmid = 20557570 | pmc = 6493878 | doi = 10.1111/j.1755-5949.2010.00135.x }}</ref> |
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== Research == |
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4-MA was investigated as an ] in 1952 and was even given a trade name, '''Aptrol''', but development was apparently never completed.<ref name="pmid14890975">{{cite journal | vauthors = Gelvin EP, McGAVACK TH | title = 2-Amino-1-(p-methylphenyl)-propane (aptrol) as an anorexigenic agent in weight reduction | journal = New York State Journal of Medicine | volume = 52 | issue = 2 | pages = 223–226 | date = January 1952 | pmid = 14890975 }}</ref> More recently it has been reported as a novel ]. |
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In animal studies, 4-MA was shown to have the lowest rate of self-administration out of a range of similar drugs tested (the others being ], ], and ]), likely as a result of having the highest potency for releasing serotonin relative to dopamine.<ref name="pmid15677348"/><ref>{{cite journal | vauthors = Baumann MH, Clark RD, Woolverton WL, Wee S, Blough BE, Rothman RB | title = In vivo effects of amphetamine analogs reveal evidence for serotonergic inhibition of mesolimbic dopamine transmission in the rat | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 337 | issue = 1 | pages = 218–225 | date = April 2011 | pmid = 21228061 | pmc = 3063744 | doi = 10.1124/jpet.110.176271 }}</ref> |
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== Society and culture == |
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More than a dozen deaths were reported throughout Europe in 2012-2013 after consumption of amphetamine ('speed') contaminated with 4-methylamphetamine.<ref>{{cite journal | vauthors = Blanckaert P, van Amsterdam J, Brunt T, van den Berg J, Van Durme F, Maudens K, van Bussel J | title = 4-Methyl-amphetamine: a health threat for recreational amphetamine users | journal = Journal of Psychopharmacology | volume = 27 | issue = 9 | pages = 817–822 | date = September 2013 | pmid = 23784740 | doi = 10.1177/0269881113487950 | s2cid = 35436194 }}</ref><ref>{{Cite journal |title=4-Methyl-amphetamine: A health threat for recreational amphetamine users |url=https://www.researchgate.net/publication/240306373 |journal=ResearchGate}}</ref><ref>{{cite journal | vauthors = Coppola M, Mondola R | title = 4-methylamphetamine (4-MA): chemistry, pharmacology and toxicology of a new potential recreational drug | journal = Mini Reviews in Medicinal Chemistry | volume = 13 | issue = 14 | pages = 2097–2101 | date = December 2013 | pmid = 24195663 | doi = 10.2174/13895575113136660106 }}</ref> |
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== See also == |
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* ] |
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* ] |
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== References == |
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{{Reflist}} |
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{{Stimulants}} |
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{{Anorectics}} |
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{{Monoamine releasing agents}} |
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{{Phenethylamines}} |
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{{DEFAULTSORT:Methylamphetamine, 4-}} |
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] |
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] |
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] |
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] |