4-Methylmethylphenidate

{{Short description|Stimulant drug}}

{{cs1 config|name-list-style=vanc}}

{{Infobox drug

| verifiedrevid = 421303810

| IUPAC_name = methyl (2R)-2-(4-methylphenyl)-2-[(2R)-piperidin-2-yl]acetate

| image = 4-methylmethylphenidate.png

| image_class = skin-invert-image

| width = 200px

| tradename =

| pregnancy_AU =

| pregnancy_US =

| legal_AU =

| legal_CA = Schedule III

| legal_DE = NpSG

| legal_UK = Class B

| legal_US =

| legal_status =

| routes_of_administration =

| CAS_number_Ref = {{cascite|correct|CAS}}

| CAS_number = 191790-79-1

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 1Y11XUO4EY

| CAS_supplemental =
680996-70-7 (hydrochloride)

| ATC_prefix =

| PubChem = 44296147

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 8281556

| C=15 | H=21 | N=1 | O=2

| smiles = Cc2ccc(cc2)C(C(=O)OC)C1CCCCN1

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 1S/C15H21NO2/c1-11-6-8-12(9-7-11)14(15(17)18-2)13-5-3-4-10-16-13/h6-9,13-14,16H,3-5,10H2,1-2H3/t13-,14-/m0/s1

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = WJZNCJIOIACDBR-KBPBESRZSA-N

}}

threo-4-Methylmethylphenidate (4-MeTMP) is a stimulant drug related to methylphenidate. It is slightly less potent than methylphenidate and has relatively low efficacy at blocking dopamine reuptake despite its high binding affinity, which led to its investigation as a possible substitute drug for treatment of stimulant abuse (cf. nocaine).{{cite journal | vauthors = Wayment HK, Deutsch H, Schweri MM, Schenk JO | title = Effects of methylphenidate analogues on phenethylamine substrates for the striatal dopamine transporter: potential as amphetamine antagonists? | journal = Journal of Neurochemistry | volume = 72 | issue = 3 | pages = 1266–74 | date = March 1999 | pmid = 10037500 | doi = 10.1046/j.1471-4159.1999.0721266.x | doi-access = free }} On the other hand, several other simple ring-substituted derivatives of threo-methylphenidate such as the 4-fluoro and 3-chloro compounds are more potent than methylphenidate both in efficacy as dopamine reuptake inhibitors and in animal drug discrimination assays.{{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 = Schweri MM, Deutsch HM, Massey AT, Holtzman SG | title = Biochemical and behavioral characterization of novel methylphenidate analogs | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 301 | issue = 2 | pages = 527–35 | date = May 2002 | pmid = 11961053 | doi = 10.1124/jpet.301.2.527 }}{{cite journal | vauthors = Davies HM, Hopper DW, Hansen T, Liu Q, Childers SR | title = Synthesis of methylphenidate analogues and their binding affinities at dopamine and serotonin transport sites | journal = Bioorganic & Medicinal Chemistry Letters | volume = 14 | issue = 7 | pages = 1799–802 | date = April 2004 | pmid = 15026075 | doi = 10.1016/j.bmcl.2003.12.097 }}

Image:Methylphenidate derivatives.png (4F-MPH) and 3-chloromethylphenidate (3-CTMP)]]{{clear left}}