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Wikipedia

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.[2]

Trimeperidine
Clinical data
Other namesTrimeperidine, Promedol
AHFS/Drugs.comInternational Drug Names
ATC code
Legal status
Legal status
Identifiers
  • (2S,5R)-1,2,5-Trimethyl-4-phenylpiperidin-4-yl propionate
CAS Number
  • 29606-10-8 N
PubChem CID
  • 6148
ChemSpider
  • 16736164 Y
UNII
  • 1M2IB31DTS
KEGG
  • D06268
ECHA InfoCard100.000.531
Chemical and physical data
FormulaC17H25NO2
Molar mass275.392 g·mol−1
3D model (JSmol)
  • Interactive image
  • 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 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.[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.

References edit

  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). 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.


trimeperidine, confused, with, promedrol, promedol, opioid, analgesic, that, analogue, prodine, developed, early, 1950s, ussr, during, research, into, related, drug, pethidine, clinical, dataother, names, promedolahfs, drugs, cominternational, drug, namesatc, . Not to be confused with Promedrol 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 2 TrimeperidineClinical dataOther namesTrimeperidine PromedolAHFS Drugs comInternational Drug NamesATC codeN02AB04 WHO Legal statusLegal statusAU S9 Prohibited substance BR Class A1 Narcotic drugs 1 CA Schedule I DE Anlage I Authorized scientific use only UK Class A US Schedule IIdentifiersIUPAC name 2S 5R 1 2 5 Trimethyl 4 phenylpiperidin 4 yl propionateCAS Number29606 10 8 NPubChem CID6148ChemSpider16736164 YUNII1M2IB31DTSKEGGD06268ECHA InfoCard100 000 531Chemical and physical dataFormulaC 17H 25N O 2Molar mass275 392 g mol 13D model JSmol Interactive imageSMILES C C H 1CN C C H C C C 1 OC O CC c2ccccc2InChI 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 YKey UVITTYOJFDLOGI KEYYUXOJSA N Y N Y what is this verify Trimeperidine has four structural isomers of which two are active the g isomer trimeperidine and the b 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 References edit Anvisa 2023 03 31 RDC Nº 784 Listas de Substancias Entorpecentes Psicotropicas 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 Diario Oficial da Uniao published 2023 04 04 Archived from the original on 2023 08 03 Retrieved 2023 08 16 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 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 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 Guseva EN 1956 Comparative analgesic effects of promedol phenadone tecodine and morphine Farmakologiia I Toksikologiia in Russian 19 Suppl 17 8 PMID 13448009 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 Chernukha EA Rasstrigin NN 1980 Anesthesia in labor Fel dsher I Akusherka in Russian 45 6 21 7 PMID 6901667 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 Quotas 2014 Diversion Control Division Drug Enforcement Agency U S Department of Justice nbsp This analgesic related article is a stub You can help Wikipedia by expanding it vte Retrieved from https en wikipedia org w index php title Trimeperidine amp oldid 1198140357, wikipedia, wiki, book, books, library,

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