Trimeperidine

Last updated
Trimeperidine
Trimeperidine.svg
Trimeperidine ball-and-stick.png
Clinical data
Trade names Promedol
Other namesTrimeperidine, Promedol
AHFS/Drugs.com International Drug Names
ATC code
Legal status
Legal status
Identifiers
  • (2S,5R)-1,2,5-Trimethyl-4-phenylpiperidin-4-yl propionate
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
CompTox Dashboard (EPA)
ECHA InfoCard 100.000.531 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C17H25NO2
Molar mass 275.392 g·mol−1
3D model (JSmol)
  • C[C@@H]1CN(C)[C@@H](C)C[C@@]1(OC(=O)CC)c2ccccc2
  • 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 Yes check.svgY
  • Key:UVITTYOJFDLOGI-KEYYUXOJSA-N Yes check.svgY
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Trimeperidine (trade name 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. [2]

Trimeperidine has four structural isomers, of which two are active, the γ isomer trimeperidine, and the β isomer isopromedol. [3] [4] It is around half the potency of morphine as an analgesic, [5] [6] and has been widely used for the treatment of pain. [7] [8]

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. [9] 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.

Promedol is included into the standard medication kit, which is carried on the battlefield by every Russian military personnel, as a pain-killer in case wounding. [10] [11]


See also

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. 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.
  3. 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.
  4. 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. S2CID   19821200.
  5. Guseva EN (1956). "[Comparative analgesic effects of promedol, phenadone, tecodine, and morphine]". Farmakologiia i Toksikologiia (in Russian). 19 (Suppl): 17–8. PMID   13448009.
  6. 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.
  7. Chernukha EA, Rasstrigin NN (1980). "[Anesthesia in labor]". Fel'dsher I Akusherka (in Russian). 45 (6): 21–7. PMID   6901667.
  8. 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.
  9. "Quotas - 2014". Diversion Control Division. Drug Enforcement Agency, U.S. Department of Justice.
  10. https://www.crisis-medicine.com/ussr-civil-defense-cbrn-kits-aptechka/#:~:text=The%20Soviet%20kit%20consisted%20of,potential%20but%20causes%20less%20vomiting.
  11. "Russian military leadership distributed drugs to soldiers to dull fear: CNS data".