Trimeperidine

{{Short description|Analgesic drug}}

{{Distinguish|Promedrol}}

{{Drugbox

| Verifiedfields = changed

| verifiedrevid = 470614990

| IUPAC_name = (2S,5R)-1,2,5-Trimethyl-4-phenylpiperidin-4-yl propionate

| image = Trimeperidine.svg

| image_class = skin-invert-image

| width = 160

| image2 = Trimeperidine ball-and-stick.png

| image_class2 = bg-transparent

| width2 = 250

| tradename = Promedol

| Drugs.com = {{drugs.com|international|trimeperidine}}

| pregnancy_AU =

| pregnancy_US =

| pregnancy_category =

| legal_AU = S9

| legal_BR = A1

| legal_BR_comment = {{Cite web |author=Anvisa |author-link=Brazilian Health Regulatory Agency |date=2023-03-31 |title=RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial |trans-title=Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control|url=https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |url-status=live |archive-url=https://web.archive.org/web/20230803143925/https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |archive-date=2023-08-03 |access-date=2023-08-16 |publisher=Diário Oficial da União |language=pt-BR |publication-date=2023-04-04}}

| legal_CA = Schedule I

| legal_UK = Class A

| legal_US = Schedule I

| legal_DE = Anlage I

| routes_of_administration =

| bioavailability =

| protein_bound =

| metabolism =

| elimination_half-life =

| excretion =

| CAS_number_Ref = {{cascite|changed|??}}

| CAS_number = 29606-10-8

| ATC_prefix = N02

| ATC_suffix = AB04

| PubChem = 6148

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| DrugBank =

| KEGG = D06268

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 16736164

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 1M2IB31DTS

| C=17 | H=25 | N=1 | O=2

| smiles = C[C@@H]1CN(C)[C@@H](C)C[C@@]1(OC(=O)CC)c2ccccc2

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 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

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = UVITTYOJFDLOGI-KEYYUXOJSA-N

| synonyms = Trimeperidine, Promedol

}}

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.{{cite journal | vauthors = Nazarov I, Prostakov N, Shvetsov N | title = Geterotsiklicheskie Soedineniya. 39. Sinteticheskie Obezbolivayushchie Veshchestva. 4. Slozhnye Efiry 1, 2, 5-Trimetil-4-Fenil-4-Piperidola S Alifaticheskimi Kislotami-Sintez Promedola I Izopromedola. | language = ru | journal = Zhurnal Obshchei Khimii | date = January 1956 | volume = 26 | issue = 10 | pages = 2798–811 | url = http://genchem.ru/ }}

Trimeperidine has four structural isomers, of which two are active, the γ isomer trimeperidine, and the β isomer isopromedol.{{cite journal | vauthors = Casy AF, McErlane K | title = Analgesic potency and stereochemistry of trimeperidine and its isomers and analogues | journal = The Journal of Pharmacy and Pharmacology | volume = 23 | issue = 1 | pages = 68–9 | date = January 1971 | pmid = 4395897 | doi = 10.1111/j.2042-7158.1971.tb12786.x | s2cid = 35744674 }}{{cite journal | vauthors = Casy AF, Coates JE, Rostron C | title = Reversed ester analogues of pethidine: isomeric 4-acetoxy-1, 2, 6-trimethyl-4-phenylpiperidines | journal = The Journal of Pharmacy and Pharmacology | volume = 28 | issue = 2 | pages = 106–10 | date = February 1976 | pmid = 6668 | doi = 10.1111/j.2042-7158.1976.tb04107.x | s2cid = 19821200 }} It is around half the potency of morphine as an analgesic,{{cite journal | vauthors = Guseva EN | title = [Comparative analgesic effects of promedol, phenadone, tecodine, and morphine] | language = ru | journal = Farmakologiia i Toksikologiia | volume = 19 | issue = Suppl | pages = 17–8 | date = 1956 | pmid = 13448009 }}{{cite journal | vauthors = Bender KI, Gerasimova OV | title = [Relationship between the pain-relieving action of narcotic analgesics and their effect on respiration] | language = ru | journal = Farmakologiia i Toksikologiia | volume = 39 | issue = 5 | pages = 552–6 | date = 1976 | pmid = 18367 }} and has been widely used for the treatment of pain.{{cite journal | vauthors = Chernukha EA, Rasstrigin NN | title = [Anesthesia in labor] | language = ru | journal = Fel'dsher I Akusherka | volume = 45 | issue = 6 | pages = 21–7 | date = 1980 | pmid = 6901667 }}{{cite journal | vauthors = Zhirkova IV, Stepanenko SM, Butyleva OI, Zilbert EV, Manerova AF, Golodenko NV | title = [Method of continuous intravenous postoperative analgesia with promedol in newborn children] | language = ru | journal = Anesteziologiia I Reanimatologiia | issue = 1 | pages = 12–6 | date = 2004 | pmid = 15206301 }}

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.{{cite web | title = Quotas - 2014| url = http://www.deadiversion.usdoj.gov/fed_regs/quotas/2014/fr0825.htm | work = Diversion Control Division | publisher = Drug Enforcement Agency, U.S. Department of Justice }} 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.