3-Bromomethylphenidate

{{Short description|Chemical compound}}

{{drugbox

| drug_name = 3-Bromomethylphenidate

| image = 3-Bromomethylphenidate.svg

| image_class = skin-invert-image

| 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_Ref = {{cascite|correct|CAS}}

| CAS_number = 2865958-69-4

| ChemSpiderID = 26350024

| PubChem = 52947287

| ChEMBL = 1253736

| 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 designer drug. It showed the most potent binding to the dopamine transporter of a series of ring-substituted methylphenidate derivatives, and produced stimulant effects in animal studies.{{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 }}{{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 }}{{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 }}