Structure via PubChem · Public domain (PubChem)
desmethylprodine
Sign in to saveAlso known as MPPP, 1-Methyl-4-phenyl-4-piperidinol propionate, 1-Methyl-4-phenyl-4-propionoxypiperidine, 3-Demethylprodine, PPMP
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. 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. It was reported to have 30 times the activity of pethidine and a greater analgesic effect than morphine in rats, and
Key facts
- Drug.verifiedrevid
- 411133087
- Drug.IUPAC_name
- (1-Methyl-4-phenylpiperidin-4-yl) propanoate
- Drug.image
- Desmethylprodine.svg
- Drug.image_class
- skin-invert-image
- Drug.alt
- Skeletal formula
- Drug.width
- 190px
- Drug.image2
- Desmethylprodine molecule ball.png
- Drug.image_class2
- bg-transparent
- Drug.alt2
- Ball-and-stick model of desmethylprodine
- Drug.legal_BR
- F1
- Drug.legal_US
- Schedule I
- Drug.legal_DE
- Anlage I
- Drug.CAS_number
- 13147-09-6
- Drug.UNII
- 07SGC963IR
- Drug.PubChem
- 61583
- Drug.DrugBank
- DB01478
- Drug.KEGG
- C22797
- Drug.ChemSpiderID
- 55493
via Wikipedia infobox
Chemical data
- Formula
- C15H21NO2
- Molecular weight
- 247.33 g/mol
- IUPAC name
- (1-methyl-4-phenylpiperidin-4-yl) propanoate
- SMILES
- CCC(=O)OC1(CCN(CC1)C)C2=CC=CC=C2
- InChIKey
- BCQMRZRAWHNSBF-UHFFFAOYSA-N
- XLogP
- 2.5
- Polar surface area
- 29.5 Ų
- H-bond donors
- 0
- H-bond acceptors
- 3
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 247.157229
- Has use
- designer drug
Show 3 more facts
- chemical formula
- C₁₅H₂₁NO₂
- canonical SMILES
- CCC(=O)OC1(CCN(CC1)C)C2=CC=CC=C2
- Commons category
- Desmethylprodine
Sources (2)
via Wikidata · CC0
~4 min read
Encyclopedic overview
6 sectionsContents
- History
- Toxic impurity
- Analogs
- See also
- References
- External links
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. 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. 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.
==History== Desmethylprodine was first synthesized in 1947 at Hoffman-LaRoche Laboratories by Albert Ziering and John Lee. They found that it produced effects similar to morphine when administered to rats. Ziering had been searching for synthetic painkillers that were less addictive than morphine. The new drug was a slight variant of pethidine. It was found to be no more effective than pethidine and was never marketed. This research produced the analgesic alphaprodine (Nisentil, Prisilidine), a very closely related compound.
Excerpted from Wikipedia’s “desmethylprodine” article, available under the CC BY-SA 4.0 licence.