Meprodine

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.^[2]

Meprodine

Alpha-meprodine
Clinical data
ATC code	none
Legal status
Legal status	AU: S9 (Prohibited substance) BR: Class A1 (Narcotic drugs)[1] CA: Schedule I DE: Anlage I (Authorized scientific use only) US: Schedule I
Identifiers
IUPAC name (3S,4R)-3-ethyl-1-methyl-4-phenylpiperidin-4-yl propionate
CAS Number	468-51-9 Y
PubChem CID	61119
ChemSpider	16736823 Y
UNII	1177I648L1
KEGG	D12666 Y
ChEMBL	ChEMBL2104027 N
Chemical and physical data
Formula	C17H25NO2
Molar mass	275.392 g·mol−1
3D model (JSmol)	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
NY (what is this?)  (verify)

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.^[3]

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.

Legal Status

Australia

Meprodine is considered a Schedule 9 prohibited substance in Australia under the Poisons Standard (February 2017).^[4] A Schedule 9 substance is a substance which may be abused or misused, the manufacture, possession, sale or use of which should be prohibited by law except when required for medical or scientific research, or for analytical, teaching or training purposes with approval of Commonwealth and/or State or Territory Health Authorities.^[4]

References

1. Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.
2. Morton IK, Hall JM (October 2012). "Meprodine". Concise Dictionary of Pharmacological Agents : Properties and Synonyms. New York: Springer. p. 176. ISBN 978-94-010-5907-7.
3. "Quotas - 2014". Diversion Control Division. Drug Enforcement Administration, U.S. Department of Justice.
4. "Poisons Standard". Federal Register of Legislation. Australian Government. October 2015.