View source for Chemistry:3-Bromomethylphenidate

{{Short description|Chemical compound}}
{{drugbox
| drug_name = 3-Bromomethylphenidate
| image = 3-Bromomethylphenidate.svg
| legal_UK =
| legal_DE = 
| C = 14 | H = 18 | Br = 1 | N = 1 | O = 2
| IUPAC_name = Methyl 2-(3-bromophenyl)-2-(piperidin-2-yl)acetate
| CAS_number = 
| ChemSpiderID      = 26350024<!--there's also 8196266 but choice depends on sterocenters-->
| PubChem = 52947287
| smiles            = COC(=O)C(C1CCCCN1)C2=CC(=CC=C2)Br
| StdInChI=1S/C14H18BrNO2/c1-18-14(17)13(12-7-2-3-8-16-12)10-5-4-6-11(15)9-10/h4-6,9,12-13,16H,2-3,7-8H2,1H3/t12-,13-/m1/s1
| StdInChIKey = JMCTXWAIACSNAZ-CHWSQXEVSA-N
}}

'''3-Bromomethylphenidate''' ('''3-Br-MPH''') is a compound from the phenidate family, which has reportedly been sold as a [[Chemistry:Designer drug|designer drug]]. It showed the most potent binding to the [[Biology:Dopamine transporter|dopamine transporter]] of a series of ring-substituted methylphenidate derivatives, and produced [[Chemistry:Stimulant|stimulant]] effects in animal studies.<ref>{{cite journal | vauthors = Pan D, Gatley SJ, Dewey SL, Chen R, Alexoff DA, Ding YS, Fowler JS | title = Binding of bromine-substituted analogs of methylphenidate to monoamine transporters | journal = European Journal of Pharmacology | volume = 264 | issue = 2 | pages = 177–82 | date = October 1994 | pmid = 7851480 | doi = 10.1016/0014-2999(94)00460-9 }}</ref><ref>{{cite journal | vauthors = Deutsch HM, Shi Q, Gruszecka-Kowalik E, Schweri MM | title = Synthesis and pharmacology of potential cocaine antagonists. 2. Structure-activity relationship studies of aromatic ring-substituted methylphenidate analogs | journal = Journal of Medicinal Chemistry | volume = 39 | issue = 6 | pages = 1201–9 | date = March 1996 | pmid = 8632426 | doi = 10.1021/jm950697c }}</ref><ref>{{cite journal | vauthors = Misra M, Shi Q, Ye X, Gruszecka-Kowalik E, Bu W, Liu Z, Schweri MM, Deutsch HM, Venanzi CA | display-authors = 6 | title = Quantitative structure-activity relationship studies of threo-methylphenidate analogs | journal = Bioorganic & Medicinal Chemistry | volume = 18 | issue = 20 | pages = 7221–38 | date = October 2010 | pmid = 20846865 | doi = 10.1016/j.bmc.2010.08.034 }}</ref>

== See also ==
* [[Chemistry:3,4-Dichloromethylphenidate|3,4-Dichloromethylphenidate]]
* [[Chemistry:4-Fluoromethylphenidate|4-Fluoromethylphenidate]]
* [[Chemistry:4-Methylmethylphenidate|4-Methylmethylphenidate]]
* Methylnaphthidate
* [[Chemistry:4B-MAR|4B-MAR]]

== References ==
{{reflist}}

{{DEFAULTSORT:Bromomethylphenidate, 3-}}
[[Category:2-Benzylpiperidines]]
[[Category:Carboxylate esters]]
[[Category:Designer drugs]]
[[Category:Methyl esters]]
[[Category:Norepinephrine–dopamine reuptake inhibitors]]
[[Category:Stimulants]]


{{Sourceattribution|3-Bromomethylphenidate}}