Meprodine

Meprodine

Alpha-meprodine
Clinical data
ATC code	none
Legal status
Legal status	CA: Schedule I DE: Anlage I (Controlled) US: Schedule I
Identifiers
IUPAC name (3S,4R)-3-ethyl-1-methyl-4-phenylpiperidin-4-yl propionate
CAS Number	468-51-9
PubChem (CID)	61119
ChemSpider	16736823 Y
ChEMBL	CHEMBL2104027
Chemical and physical data
Formula	C17H25NO2
Molar mass	275.39 g/mol
3D model (Jmol)	Interactive image
SMILES CC[C@H]1CN(C)CC[C@@]1(OC(=O)CC)c2ccccc2
InChI InChI=1S/C17H25NO2/c1-4-14-13-18(3)12-11-17(14,20-16(19)5-2)15-9-7-6-8-10-15/h6-10,14H,4-5,11-13H2,1-3H3/t14-,17-/m0/s1 Y Key:ODEGQXRCQDVXSJ-YOEHRIQHSA-N Y
(verify)

Meprodine is an opioid analgesic that is an analogue of pethidine (meperidine). It is closely related to the drug prodine, the only difference being that meprodine has an ethyl group rather than a methyl at the 3-position of the piperidine ring.

As with prodine, there are two isomers of meprodine, alpha-meprodine and beta-meprodine, with the alpha isomer having been more widely used. Alphameprodine (ACSCN 9604) and betameprodine (ACSCN 9608) are both Schedule I Narcotic controlled substances in the United States, both with annual aggregate manufacturing quotas of 2 grammes as of 2014.^[1]

Meprodine has similar effects to other opioids, and produces analgesia, sedation and euphoria. Side effects can include itching, nausea and potentially serious respiratory depression which can be life-threatening.

References