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Revision as of 14:10, 10 January 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,081 edits Saving copy of the {{drugbox}} taken from revid 452560889 of page Trimeperidine for the Chem/Drugbox validation project (updated: 'CAS_number').  Latest revision as of 16:11, 11 January 2025 edit Arthurfragoso (talk | contribs)Extended confirmed users, Template editors4,591 edits dark mode fix 
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{{Short description|Analgesic drug}}
{{ambox | text = This page contains a copy of the infobox ({{tl|drugbox}}) taken from revid of page ] with values updated to verified values.}}
{{Distinguish|Promedrol}}
{{Drugbox {{Drugbox
| Verifiedfields = changed
| verifiedrevid = 447989848 | verifiedrevid = 470614990
| IUPAC_name = (2S,5R)-1,2,5-trimethyl-4-phenylpiperidin-4-yl propionate | IUPAC_name = (2''S'',5''R'')-1,2,5-Trimethyl-4-phenylpiperidin-4-yl propionate
| image = 2D structure of Trimeperidine.svg | image = Trimeperidine.svg
| image_class = skin-invert-image
| width = 160 | width = 160
| image2 = Trimeperidine ball-and-stick.png
| image_class2 = bg-transparent
| width2 = 250


<!--Clinical data--> <!--Clinical data-->
| tradename = | tradename = Promedol
| Drugs.com = {{drugs.com|international|trimeperidine}} | Drugs.com = {{drugs.com|international|trimeperidine}}
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> | pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
| pregnancy_US = <!-- A / B / C / D / X --> | pregnancy_US = <!-- A / B / C / D / X -->
| pregnancy_category = | pregnancy_category =
| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 --> | legal_AU = S9
| legal_BR = A1
⚫ | legal_CA = <!-- Schedule I -->
| legal_BR_comment = <ref>{{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=] |language=pt-BR |publication-date=2023-04-04}}</ref>
| legal_UK = <!-- Class A -->
| legal_US = <!-- Schedule I --> | legal_CA = Schedule I
| legal_status = | legal_UK = Class A
⚫ | legal_US = Schedule I
⚫ | routes_of_administration =
| legal_DE = Anlage I
⚫ | routes_of_administration =


<!--Pharmacokinetic data--> <!--Pharmacokinetic data-->
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| metabolism = | metabolism =
| elimination_half-life = | elimination_half-life =
| excretion = | excretion =


<!--Identifiers--> <!--Identifiers-->
| CAS_number_Ref = {{cascite|changed|??}}
| CAS_number = <!-- blanked - oldvalue: 64-39-1 -->
| CAS_number = 29606-10-8
| ATC_prefix = none
| ATC_suffix = | ATC_prefix = N02
| ATC_suffix = AB04
| PubChem = 6148 | PubChem = 6148
| DrugBank_Ref = {{drugbankcite|correct|drugbank}} | DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = | DrugBank =
| KEGG = D06268
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 16736164 | ChemSpiderID = 16736164
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<!--Chemical data--> <!--Chemical data-->
| C=17 | H=25 | N=1 | O=2 | C=17 | H=25 | N=1 | O=2
| molecular_weight = 275.39 g/mol
| smiles = C1CN(C)(C)C1(OC(=O)CC)c2ccccc2 | smiles = C1CN(C)(C)C1(OC(=O)CC)c2ccccc2
| InChI = 1/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
| InChIKey = UVITTYOJFDLOGI-KEYYUXOJBX
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | 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 | 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_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = UVITTYOJFDLOGI-KEYYUXOJSA-N | StdInChIKey = UVITTYOJFDLOGI-KEYYUXOJSA-N
| synonyms = Trimeperidine, Promadol | synonyms = Trimeperidine, Promedol
}} }}

'''Trimeperidine''' (trade name '''Promedol''') is an ] ] that is an ] of ]. It was developed in the early 1950s in the USSR during research into the related drug ].<ref>{{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/ }}</ref>

Trimeperidine has four structural ]s, of which two are active, the γ isomer trimeperidine, and the β isomer isopromedol.<ref name="pmid4395897">{{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 }}</ref><ref name="pmid6668">{{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 }}</ref> It is around half the potency of ] as an analgesic,<ref name="pmid13448009">{{cite journal | vauthors = Guseva EN | title = | language = ru | journal = Farmakologiia i Toksikologiia | volume = 19 | issue = Suppl | pages = 17–8 | date = 1956 | pmid = 13448009 }}</ref><ref name="pmid18367">{{cite journal | vauthors = Bender KI, Gerasimova OV | title = | language = ru | journal = Farmakologiia i Toksikologiia | volume = 39 | issue = 5 | pages = 552–6 | date = 1976 | pmid = 18367 }}</ref> and has been widely used for the treatment of pain.<ref name="pmid6901667">{{cite journal | vauthors = Chernukha EA, Rasstrigin NN | title = | language = ru | journal = Fel'dsher I Akusherka | volume = 45 | issue = 6 | pages = 21–7 | date = 1980 | pmid = 6901667 }}</ref><ref name="pmid15206301">{{cite journal | vauthors = Zhirkova IV, Stepanenko SM, Butyleva OI, Zilbert EV, Manerova AF, Golodenko NV | title = | language = ru | journal = Anesteziologiia I Reanimatologiia | issue = 1 | pages = 12–6 | date = 2004 | pmid = 15206301 }}</ref>
Trimeperidine produces similar effects to other opioids, such as ] and ], along with side effects such as ], ]ing, ], and ] 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 ] in the brain.<ref>{{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 }}</ref> 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.

== See also ==
* ]

== References ==
{{Reflist|2}}

{{Opioidergics}}

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