Desmethylprodine

Not to be confused with MαPPP (stimulant designer drug), MPTP (neurotoxic impurity of desmethylprodine synthesis) or MPP+ (neurotoxic metabolite of MPTP).
Desmethylprodine
Clinical data
Other names4-propionyloxy-4-phenyl-N-methylpiperidine, MPPP, 3-desmethylprodine
Legal status
Legal status
  • BR: Class F1 (Prohibited narcotics)
  • DE: Anlage I (Authorized scientific use only)
  • US: Schedule I
Identifiers
IUPAC name
  • (1-Methyl-4-phenylpiperidin-4-yl) propanoate
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC15H21NO2
Molar mass247.338 g·mol−1
3D model (JSmol)
SMILES
  • O=C(CC)OC1(CCN(CC1)C)C2=CC=CC=C2
InChI
  • InChI=1S/C15H21NO2/c1-3-14(17)18-15(9-11-16(2)12-10-15)13-7-5-4-6-8-13/h4-8H,3,9-12H2,1-2H3 Y
  • Key:BCQMRZRAWHNSBF-UHFFFAOYSA-N Y
  (verify)

Desmethylprodine or 1-methyl-4-phenyl-4-propionoxypiperidine (MPPP, Ro 2-0718) is an opioid analgesic drug developed in the 1940s by researchers at Hoffmann-La Roche.[1] Desmethylprodine has been labeled by the DEA as a Schedule I drug in the United States. It is an analog of pethidine (meperidine) a Schedule II drug. Chemically, it is a reversed ester of pethidine which has about 70% of the potency of morphine. Unlike its derivative prodine, it does not exhibit optical isomerism.[2] It was reported to have 30 times the activity of pethidine and a greater analgesic effect than morphine in rats, and it was demonstrated to cause central nervous system stimulation in mice.[2]

  1. ^ US 2765314, Schmidle CJ, Mansfield RC, "Preparation of Esters", issued 2 October 1956, assigned to Rohm and Haas 
  2. ^ a b Reynolds AK, Randall LO (1957). Morphine & Allied Drugs. p. 310.
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