3-Bromomethylphenidate

3-Bromomethylphenidate
Identifiers
	IUPAC name Methyl 2-(3-bromophenyl)-2-(piperidin-2-yl)acetate;
PubChem CID	52947287;
ChemSpider	26350024;
Chemical and physical data
Formula	C14H18BrNO2
Molar mass	312.207 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES COC(=O)C(C1CCCCN1)C2=CC(=CC=C2)Br;
	InChI InChI=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; Key: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.^[1]^[2]^[3]

References

^ Pan D, Gatley SJ, Dewey SL, Chen R, Alexoff DA, Ding YS, Fowler JS (October 1994). "Binding of bromine-substituted analogs of methylphenidate to monoamine transporters". European Journal of Pharmacology. 264 (2): 177–82. doi:10.1016/0014-2999(94)00460-9. PMID 7851480.
^ Deutsch HM, Shi Q, Gruszecka-Kowalik E, Schweri MM (March 1996). "Synthesis and pharmacology of potential cocaine antagonists. 2. Structure-activity relationship studies of aromatic ring-substituted methylphenidate analogs". Journal of Medicinal Chemistry. 39 (6): 1201–9. doi:10.1021/jm950697c. PMID 8632426.
^ Misra M, Shi Q, Ye X, Gruszecka-Kowalik E, Bu W, Liu Z, et al. (October 2010). "Quantitative structure-activity relationship studies of threo-methylphenidate analogs". Bioorganic & Medicinal Chemistry. 18 (20): 7221–38. doi:10.1016/j.bmc.2010.08.034. PMID 20846865.

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[1] Pan D, Gatley SJ, Dewey SL, Chen R, Alexoff DA, Ding YS, Fowler JS (October 1994). "Binding of bromine-substituted analogs of methylphenidate to monoamine transporters". European Journal of Pharmacology. 264 (2): 177–82. doi:10.1016/0014-2999(94)00460-9. PMID 7851480.

[2] Deutsch HM, Shi Q, Gruszecka-Kowalik E, Schweri MM (March 1996). "Synthesis and pharmacology of potential cocaine antagonists. 2. Structure-activity relationship studies of aromatic ring-substituted methylphenidate analogs". Journal of Medicinal Chemistry. 39 (6): 1201–9. doi:10.1021/jm950697c. PMID 8632426.

[3] Misra M, Shi Q, Ye X, Gruszecka-Kowalik E, Bu W, Liu Z, et al. (October 2010). "Quantitative structure-activity relationship studies of threo-methylphenidate analogs". Bioorganic & Medicinal Chemistry. 18 (20): 7221–38. doi:10.1016/j.bmc.2010.08.034. PMID 20846865.

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See also

References