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.[1]

Meprodine
Alpha-meprodine
Clinical data
ATC code
  • none
Legal status
Legal status
  • AU: S9 (Prohibited substance)
  • 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
PubChem CID
ChemSpider
UNII
ChEMBL
Chemical and physical data
FormulaC17H25NO2
Molar mass275.392 g·mol−1
3D model (JSmol)
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.[2]

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.

Australia

Meprodine is considered a Schedule 9 prohibited substance in Australia under the Poisons Standard (February 2017).[3] 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.[3]

References
  1. 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.
  2. "Quotas - 2014". Diversion Control Division. Drug Enforcement Administration, U.S. Department of Justice.
  3. "Poisons Standard". Federal Register of Legislation. Australian Government. October 2015.


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