Trimeperidine

Trimeperidine (Promedol) is an opioid analgesic that is an analogue of prodine. It was developed in the early 1950s in the USSR during research into the related drug pethidine.[1]

Not to be confused with Promedrol.
Trimeperidine
Clinical data
Other namesTrimeperidine, Promedol
AHFS/Drugs.comInternational Drug Names
ATC code
Legal status
Legal status
  • AU: S9 (Prohibited substance)
  • CA: Schedule I
  • DE: Anlage I (Authorized scientific use only)
  • UK: Class A
  • US: Schedule I
Identifiers
IUPAC name
  • (2S,5R)-1,2,5-Trimethyl-4-phenylpiperidin-4-yl propionate
CAS Number
PubChem CID
ChemSpider
UNII
ECHA InfoCard100.000.531
Chemical and physical data
FormulaC17H25NO2
Molar mass275.392 g·mol−1
3D model (JSmol)
SMILES
  • C[C@@H]1CN(C)[C@@H](C)C[C@@]1(OC(=O)CC)c2ccccc2
InChI
  • InChI=1S/C17H25NO2/c1-5-16(19)20-17(15-9-7-6-8-10-15)11-14(3)18(4)12-13(17)2/h6-10,13-14H,5,11-12H2,1-4H3/t13-,14+,17+/m1/s1 Y
  • Key:UVITTYOJFDLOGI-KEYYUXOJSA-N Y
 NY (what is this?)  (verify)

Trimeperidine has four structural isomers, of which two are active, the γ isomer trimeperidine, and the β isomer isopromedol.[2][3] It is around half the potency of morphine as an analgesic,[4][5] and has been widely used for the treatment of pain.[6][7]

Trimeperidine produces similar effects to other opioids, such as analgesia and sedation, along with side effects such as nausea, itching, vomiting and respiratory depression which may be harmful or fatal.

Trimeperidine is in Schedule I of the Controlled Substances Act 1970 of the United States as a Narcotic with ACSCN 9646 with an annual aggregate manufacturing quota of 2 grams as of 2014. The free base conversion ratio for salts includes 0.883 for the hydrochloride. Promedol increases the activity of the reticular activating system in the brain.[8] It is listed under the Single Convention for the Control of Narcotic Substances 1961 and is controlled in most countries in the same fashion as is morphine or heroin.

References
  1. Nazarov I, Prostakov N, Shvetsov N (January 1956). "Geterotsiklicheskie Soedineniya. 39. Sinteticheskie Obezbolivayushchie Veshchestva. 4. Slozhnye Efiry 1, 2, 5-Trimetil-4-Fenil-4-Piperidola S Alifaticheskimi Kislotami-Sintez Promedola I Izopromedola". Zhurnal Obshchei Khimii (in Russian). 26 (10): 2798–811.
  2. Casy AF, McErlane K (January 1971). "Analgesic potency and stereochemistry of trimeperidine and its isomers and analogues". The Journal of Pharmacy and Pharmacology. 23 (1): 68–9. doi:10.1111/j.2042-7158.1971.tb12786.x. PMID 4395897. S2CID 35744674.
  3. Casy AF, Coates JE, Rostron C (February 1976). "Reversed ester analogues of pethidine: isomeric 4-acetoxy-1, 2, 6-trimethyl-4-phenylpiperidines". The Journal of Pharmacy and Pharmacology. 28 (2): 106–10. doi:10.1111/j.2042-7158.1976.tb04107.x. PMID 6668.
  4. Guseva EN (1956). "[Comparative analgesic effects of promedol, phenadone, tecodine, and morphine]". Farmakologiia I Toksikologiia (in Russian). 19 (Suppl): 17–8. PMID 13448009.
  5. Bender KI, Gerasimova OV (1976). "[Relationship between the pain-relieving action of narcotic analgesics and their effect on respiration]". Farmakologiia I Toksikologiia (in Russian). 39 (5): 552–6. PMID 18367.
  6. Chernukha EA, Rasstrigin NN (1980). "[Anesthesia in labor]". Fel'dsher I Akusherka (in Russian). 45 (6): 21–7. PMID 6901667.
  7. Zhirkova IV, Stepanenko SM, Butyleva OI, Zilbert EV, Manerova AF, Golodenko NV (2004). "[Method of continuous intravenous postoperative analgesia with promedol in newborn children]". Anesteziologiia I Reanimatologiia (in Russian) (1): 12–6. PMID 15206301.
  8. "Quotas - 2014". Diversion Control Division. Drug Enforcement Agency, U.S. Department of Justice.


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