Desmethylprodine

Desmethylprodine
Clinical data
Other names	4-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	13147-09-6;
PubChem CID	61583;
DrugBank	DB01478 ;
ChemSpider	55493 ;
UNII	07SGC963IR;
KEGG	C22797 ;
ChEMBL	ChEMBL279865 ;
CompTox Dashboard (EPA)	DTXSID80157061 ;
Chemical and physical data
Formula	C15H21NO2
Molar mass	247.338 g·mol−1
3D model (JSmol)	Interactive image;
	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 ; Key:BCQMRZRAWHNSBF-UHFFFAOYSA-N ;
	(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]

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

[1] US 2765314, Schmidle CJ, Mansfield RC, "Preparation of Esters", issued 2 October 1956, assigned to Rohm and Haas

[Randall,_Morphine_1957_pp_310-2] Reynolds AK, Randall LO (1957). Morphine & Allied Drugs. p. 310.

[1]

[2]