Isopropylphenidate

Isopropylphenidate (also known as IPH and IPPD) is a piperidine based stimulant drug, closely related to methylphenidate, but with the methyl ester replaced by an isopropyl ester. It has similar effects to methylphenidate but with a longer duration of action,[1][2] and was banned in the UK as a Temporary Class Drug from April 2015 following its unapproved sale as a designer drug.[3]

Not to be confused with isopropylphenidine or N-Isopropyl-N'-phenyl-1,4-phenylenediamine, which is also called IPPD.
Isopropylphenidate
Legal status
Legal status
Identifiers
IUPAC name
  • propan-2-yl 2-phenyl-2-(piperidin-2-yl)acetate
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
FormulaC16H23NO2
Molar mass261.365 g·mol−1
3D model (JSmol)
SMILES
  • C1(=CC=CC=C1)C(C(=O)OC(C)C)C2CCCCN2
InChI
  • InChI=1S/C16H23NO2/c1-12(2)19-16(18)15(13-8-4-3-5-9-13)14-10-6-7-11-17-14/h3-5,8-9,12,14-15,17H,6-7,10-11H2,1-2H3
  • Key:AZVPADMEIMLODT-UHFFFAOYSA-N

It has been researched as potential methylphenidate replacement for ADHD and narcolepsy, because of fewer side effects.[4][2]

See also

References
  1. Markowitz JS, Zhu HJ, Patrick KS (December 2013). "Isopropylphenidate: an ester homolog of methylphenidate with sustained and selective dopaminergic activity and reduced drug interaction liability" (PDF). Journal of Child and Adolescent Psychopharmacology. 23 (10): 648–54. doi:10.1089/cap.2013.0074. hdl:2027.42/140321. PMID 24261661.
  2. US application 20120245201, Markowitz JS, Patrick KS, Zhu H, "Isopropylphenidate for Treatment of Attention-Deficit/Hyperactivity Disorder and Fatigue-Related Disorders and Conditions", published 2012-09-27
  3. "Methylphenidate-based NPS: A review of the evidence of use and harm" (PDF). Advisory Council on the Misuse of Drugs. 31 March 2015.
  4. Florence Levy (July 2014). "Applications of pharmacogenetics in children with attention-deficit/hyperactivity disorder". Pharmgenomics Pers Med: 349–356.
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