Template talk:Opioids
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[edit] Spam
A spammer tried inserting links to illegal drug purchasing websites located on the following domain names: mysteria.cz webzdarma.cz fromru.com land.ru atspace.us atspace.biz atspace.org
Spam seems to be a serious issue for drug related articles and templates. I suggest taking more active measures than simply banning dynamic IP addresses, which is rather ineffective.
-Nathan J. Yoder 22:11, 3 May 2005 (UTC)
[edit] Endorphins
Are any forms of endorphins (beta-endorphins) actually prescribed as a drug? It seems to me that refers to the chemicals in the body, not any prescribed drug, so I'll remove it if there's no objections. Nathan J. Yoder 19:39, 23 October 2005 (UTC)
- Well, originally it was the abiguous Endorphins before I edited it to beta-Endorphin. If the template is to be limited to pharmaceutical opioids, thebaine should probably be removed as well. --Bk0 19:44, 23 October 2005 (UTC)
I think it should, then otherwise we have to add things like serotonin and other endogenous opioids. Nathan J. Yoder 09:33, 29 October 2005 (UTC)
Serotonin is not an endogenous opioid. —Preceding unsigned comment added by 70.232.103.145 (talk) 05:12, 27 February 2008 (UTC)
[edit] opioids vs opiates
opioids are endogenous to the human body whereas opiates are exogenous molecules or chemically synthesized molecules. —Preceding unsigned comment added by 128.195.108.249 (talk • contribs)
- Actually, opiates come from the opium poppy, and opioids include opiates as well as synthetic and semi-synthetic drugs (and endogenous chemicals) that bind to the same receptors. --Galaxiaad 00:20, 9 December 2006 (UTC)
[edit] Merge?
I think this template should be merged into Template:Analgesics, as only 3 pages include this one. Template:Analgesics has a far longer list of opioids at the moment anyway. --Galaxiaad 00:28, 9 December 2006 (UTC)
[edit] Opioid Antagonists
Why are Naloxone and Naltrexone listed in the navigational box for Opioids? That's completely wrong, or if you take the stance that opioid antagonists "have something to do with opioids" and therefore belong in the navigational box, it's still grossly misleading.
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- Hello. Opioid antagonists are opioids, though not producing morphine-like effects. Opioids are in wide sense of term all substances having an effect on/throug the opioid receptors, no matter whether agonists, partial agonists, mixed agonist-antagonists, or pure antagonists. They fit perfectly here.--84.163.84.99 18:18, 10 October 2007 (UTC)
[edit] Merge classes "4-Phenylpiperidines" and "Prodine derivatives"
Hi, I would like to propose merging the sub-classes "4-Ph-piperdidine derivatives" and "Prodine derivatives", since their chemical structure and more importantly, their pharmacophore moieties in structures are the same: a quarternary C atom in the position 4- of a 1-substitued piperidine ring, attached to an aromatic ring and another functional group (either carbonyl, or alkanoyloxy/alkoxy group). Comments?--84.163.84.99 18:27, 10 October 2007 (UTC)
The difference is that the pethidines/meperidines form an ester whereas the prodines form a reverse ester. This has impact on the potency. *pethidines/mepedirines: is/should be the name in this context for the remainder of the drugs in 4-phenyl piperidines* Aj1976 16:21, 15 October 2007 (UTC)
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- I see the principal difference, yet as stated above, the pharmacophore portion of their structure is essentialy the same.--84.163.86.96 03:26, 18 October 2007 (UTC)
[edit] "Dithienylbutenyl dimethylamine" deleted
because, it's an incorrect name for dimethylthiambutene.--84.163.86.96 20:29, 18 October 2007 (UTC)
[edit] Bemidones
I don't agree that "Bemidones" should be a family of their own. There are only two compounds in there, ketobemidone and bemidone/hydroxypethidine (two names for the same drug). Also while ketobemidone has NMDA antagonist effects, this just makes it an atypical phenylpiperidine derivative, I don't see that this makes it structurally distinct. Bemidone is m-hydroxy pethidine, so why should it be in a different category to pethidine itself? And I'm not aware of any data showing that bemidone has NMDA antagonist effects anyway.
The chart is ordered by structure rather than by activity, otherwise shouldn't ketobemidone be classed with lefetamine as they both have mu-opioid agonist/NMDA antagonist effects? And for that matter, pethidine, tramadol and tapentadol are all mu-agonist/monoamine reuptake inhibitors. Structurally speaking, ketobemidone, bemidone and pethidine are all 4-phenylpiperidine derivatives and so should go together. Prodines however should be different because of that 3-alkyl group on the piperidine ring which the rest of the 4-phenylpiperidine derivatives don't have.Meodipt 09:13, 22 October 2007 (UTC)
ARYL-PIPERIDINES: These compounds can be combined into three main sub-subgroups. The first contains cocaine and ecgonine which are quite different chemically from the remaining compounds. Ecgonine is a non-aryl modified piperidine which forms part of the cocaine molecule. The second subgroup contains the piperidine carboxylates; pethidine, ethyl pethidine, and prodine and hydroxypethidine, which unlike all others carries a phenol hydroxyl. This subgroup can be further chemically divided into pethidines which are esters of isonipecotic acid, and ?and ?prodines which are piperidol esters of propionic acid. The third group contains four compounds, all arylpiperidylalkanones, i.e., ketobemidones. The ketobemidones are structurally related, the variation being in the alkyl portion of the ketone, e.g., methyl-, ethyl- and propyl-ketobemidones. Acetoxyketobemidone, in addition to being an ethyl ketone, contains an acetoxy substituent on the aryl ring. The important change in this compound is from a phenol to an ester.
Perhaps we should classify it this way....place the bemidones in their own category and rename the 4-ph-piperidines to pethidines/prodines. Either way, the bemidones do belong in a category by themselves. —Preceding unsigned comment added by Aj1976 (talk • contribs) 13:20, 23 October 2007 (UTC)
Oh, and Bemidone IS an NMDA-Ant. —Preceding unsigned comment added by Aj1976 (talk • contribs) 13:26, 23 October 2007 (UTC)
Where did you get that information from, looks like a useful reference. I couldn't find much information about bemidone, although there is lots about ketobemidone. Well...ok I could agree that you could split it up into "pethidines", i.e. 4-phenyl-4-carboethoxypiperidines, "prodines", i.e. 3-alkyl-4-phenyl-piperidin-4-ol esters, and "ketobemidones", i.e. 4-phenyl-4-acylpiperidines. And certainly if there is information about O-acetylketobemidone I think it could use its own page, and same goes for the 4-acetyl and 4-butanoyl analogues. But my point still stands. Bemidone is structurally more closely related to pethidine than it is to ketobemidone, as it is a 4-phenyl-4-carboethoxypiperidine not a 4-phenyl-4-acylpiperidine. So it makes no sense to classify bemidone separately from pethidine. If you want ketobemidone to be in its own category then that makes sense I suppose, but then we should make pages for the other analogues of ketobemidone and I don't have references for them.Meodipt 10:05, 24 October 2007 (UTC)
Ah yes I see, you got that info from the UNODC Bulletin on Narcotics 1954. Well I assume that you noticed in the part you quoted that it says "The second subgroup contains the piperidine carboxylates; pethidine, ethyl pethidine, ?and ?prodine and hydroxypethidine, which unlike all others carries a phenol hydroxyl." So in the reference you cited to support your argument, they have classified hydroxypethidine (otherwise known as bemidone) in the same group as pethidine, and separately from ketobemidone. So yes, ketobemidone should be in its own category, but hydroxypethidine goes with pethidine in the aryl piperidine carboxylates class. Where it says that there are four compounds in the arylpiperidylalkanones class, the compounds they are referring to are the acetyl, propanoyl and butanoyl analogues of ketobemidone (where ketobemidone itself is the propanoyl analogue) and the O-acetyl derivative of ketobemidone, acetoxyketobemidone. "Bemidone" is not included in this class. Meodipt 10:22, 24 October 2007 (UTC)
Hi, Have you checked this site yet: http://www.isomerdesign.com/Cdsa/schedule.php They've classified all the opioids and other scheduled substances by category. The info I have on bemidone came from 3 different places: The (1) UNODC bulletin above (2) Some other reference I'm trying to find, that describes keto-bemidone as being a bridge connecting the pethidine series with the methadone series(3) A clinician friend/colleague in France and.... I forgot what I was going to type *grmbl* :(( (I'll try and get more info on bemidone, but I've been going over your point as well, and I think you are correct in leaving bemidone in the 4-Ph-Piperidines category. I do remember bemidone itself also possessing NMDA-antagonist properties as well as being only 1/3rd the strength of pethidine (I have another reference that states it's analgesic potency as being equal to pethidine and yet another reference that claims it is stronger. Aj1976 13:23, 24 October 2007 (UTC)
Yeah cool. I'll put up pages for the other analogues of ketobemidone so its not all by itself!Meodipt 09:49, 25 October 2007 (UTC)
I have a whole list of benzomorphans as well, but they are all still research drugs (only code names and IUPAC names so I'm not sure if I should add them. Thoughts? (also, pls see the para below about Drotebanol. I really don't know how to classify it. Thebaine derivative? Morphinan? Thanx for adding the analogues of keto-bemidone. You're fast! :P 122.164.54.232 13:15, 25 October 2007 (UTC)
[edit] Problematic overlapping
There is a problematic overlapping issue at hand as codeine, morphinone, oxycodone et al. are also morphinans, but are only classified as derivatives. Could someone more experienced fill this gap?83.5.237.30 23:35, 22 October 2007 (UTC)
Codeine, morphinone and oxycodone are not morphinans, because morphinans have an opiate skeleton with the E ring removed (the one with the -O- ether link). Since codeine, morphinone and oxycodone have an intact E ring, they are opiate derivatives not morphinans.Meodipt 08:26, 23 October 2007 (UTC)
[edit] Classifications
-> Meodipt : Heya, how would you classify Drotebanol (14-Hydroxy-dihydro-6 β-thebainol-4-methylether)? Would you classify it as a Morphinan (since it lacks the 4,5-epoxy bridge)? Structure is here: http://www.unodc.org/images/odccp/bulletin/bulletin_1977-01-01_1_page005_img001_large.gif
Also, I was contemplating adding another 2 categories: 1) 5-Nitro-Benzimidazoles (for etonitazene, clonitazene etc.) 2) Phenazepines (Ethoheptazine etc.) Thoughts? Aj1976 06:54, 25 October 2007 (UTC)
I think the best place for drotebanol would be with the morphinans, it definitely looks most similar to those. Certainly etonitazine and clonitazine should have their own category, and I guess a phenazepines group would make sense too. I kind of feel like there should be another category for tramadol, ciramadol, faxeladol and tapentadol as well, if you read the patents then they are all derived from the same research and are closely related to each other, but their structures are just different enough that there isn't really a convenient label you could stick them all under. I'm kind of unsure about piritramide and bezitramide as well, if you look at the diphenyl-nitrile-propyl group attached to the piperidine nitrogen then they should go together (with diphenoxylate also), but then if you look at the other end of the molecule then bezitramide clearly looks like a cyclised fentanyl derivative, and diphenoxylate is a derivative of pethidine. So not sure how they should be categorised.
I have kind of mixed feelings about all the research compounds as there are just so many of them, my feeling is that when compounds are widely used in research, or are well enough known to have been assigned an INN name or to have been discussed by the UN drug control people, then they are probably notable enough to deserve their own pages, but I don't think every single compound that has ever been reported to be active should have its own page. I guess someone could make a structure-activity relationships page for the opioids, that way a large number of the less notable compounds could all be put together on one page with diagrams showing how they relate to each other and stuff. Maybe I'll get around to it one day...Meodipt 00:39, 26 October 2007 (UTC)
Good deal! I agree with what you say about the research compounds as well as having a category for Tramadol et al. As for Piritramide and Bezitramide, I'm unsure how to classify them too. Bezitramide could be classified as a benzimidazole, together with etonitazene and clonitazene, but the CSA (Controlled Substances Act) puts the latter two drugs in the 5-Nitro-Benzimidazoles category and Piritramide and Bezitramide in a "Pirinitramides" category. I'm really unsure how to proceed with these 4 drugs. Any thoughts on further categorizing the Open-Chain opioids into Amidones, Moramides and Methadols? (also, how 'bout we both work on the SAR page together when we have time?) Aj1976 05:25, 26 October 2007 (UTC)
I don't think the open chain opioids class needs splitting up further (although lefetamine probably shouldn't be in there but I wasn't sure where else to put it). I guess we could make a Pirinitramides class for piritramide and bezitramide though, it seems logical. And think of a good name for the tramadol family, they all have the m-hydroxyphenyl-propyl-dimethylamino backbone but I can't think of a convenient label offhand. I want to get pages made for all the opioids that don't have them yet, which will take a while...but if you want to start an SAR page then go for it, I'll be happy to contribute...Meodipt 13:04, 26 October 2007 (UTC)
[edit] Yet another renaming
Please, rename the "4-Phenylpiperidines" to "Pethidines", since you effectively cleaved up all other 4-phenylpiperidines (ketobemidons and prodines are 4-Ph-piperidines as well...), further, "Open chain derivatives" are "Amidones", since "Alkoxams", "Thiambutenes" etc. are open chain derivatives as well. Or, if you don't have objections, I do so myself, okay? Cheers. --84.163.124.217 17:06, 26 October 2007 (UTC)
Ok, so now "4-phenylpiperidines" has been renamed to "pethidines", where should we put loperamide? It's not a pethidine, a prodine, or a ketobemidone, but it is a 4-phenylpiperidine....when you start making the categories too narrow then the atypical or hybrid drugs no longer fit in anywhere! Is there any way of making subheadings, so that 4-phenylpiperidines could be the broad heading, then pethidines, prodines and ketobemidones could be subheadings? Same would be good for open chain opioids, then the amidones, thiambutenes etc could be subheadings. Meodipt 01:46, 27 October 2007 (UTC)
Sweet I've sorted it into broad headings and subcategories, hope this is ok with everyone, I think it looks good. Meodipt 04:23, 27 October 2007 (UTC)
Good deal! It looks so much better now. :) I've added the Benzimidazoles category (although I feel we should put bezitramide in it, but I'm not fully certain so I'll leave it under the Pirinitramides for now. Cheers. Aj1976 06:18, 27 October 2007 (UTC)
Great job!:) Now it's much better...however, are you sure about classifying propoxyphene and its diastereomers as phenalkoxams? Further, pirinitramides are good as a category for classifing piritramide and bezitramide, however all sources I have to my disposition (mostly german,...) do classify piritramide and bezitramide as "open chain derivatives" (related to methadone), what do you think about moving Pirinitramides as a sub-category under the the open chain derivatives? They are sort of hybrid between 4-phenylpiperidines (piritramide) or fentanyls (bezitramide) and amidons, much like diphenoxylate,..but the pharmacophore (µ-affinity) portion of their molecules should be the 3,3-diphenylpropyl-piperidine moiety... --84.163.89.35 22:08, 27 October 2007 (UTC)
That sounds logical although I'm still not certain whether we should put bezitramide in the benzimidazole category....As for Dextropropoxyphene, it is a Phenalkoxam so perhaps we can have the entry for levopropoxyphene point to it (the entry for propoxyphene already redirects to it), and mention the l isomer's anti-tussive activity on that page as well? (I'm a little drowsy so I hope I'm making sense :D ) Aj1976 06:58, 30 October 2007 (UTC)
I think it would be best keeping bezitramide and piritramide in their own Pirinitramides category as they are both hybrid drugs that don't fit neatly anywhere else, and Pirinitramides seems to be an accepted category for them. As for levopropoxyphene, yeah you might as well turn it into a redirect page if you want, there isn't really any extra information on its own page that would be lost, and its hardly a notable drug in its own right. Meodipt 11:25, 30 October 2007 (UTC)
[edit] Oxpheneridine/Carbamethidine
After some looking around, it appears that these two are the same compound under different names. The diphenyl analogue pictured as "oxpheneridine" on the isomerdesign website does not correspond to the chemical name given, and there is no reference to carbamethidine anywhere apart from the Canadian controlled drug schedules.[1] It would appear this is a mistake made by the drafters of the Canadian law, they have put the same compound in twice, one entry having a chemical name that is incorrect, and they have then invented a new "common" name for the second entry. It is not unusual for legislators to make such a mistake, psilocin for instance is listed on the New Zealand Misuse of Drugs Act twice under different names; this is what happens when people without chemistry training draft laws that concern matters of chemistry. From a search on PubChem and ChemExper, the diphenyl analogue pictured on isomerdesign.com does not appear to be a known compound, although unfortunately I do not have access to a better database such as SciFinder Scholar at present. Meodipt 12:28, 1 November 2007 (UTC)
[edit] SAR-related
I've got a quick question. I've kinda forgotten but am I right in saying that it's not possible to confer antagonist properties to a phenylpiperidine with N- substituents like Allyl, Methylcyclopropyl etc.? Aj1976 05:04, 2 November 2007 (UTC)
Using an allyl, cyclopropylmethyl or cyclobutylmethyl substitution on the nitrogen tends to produce antagonists (or sometimes partial agonists) with the classic opiate derivatives, as well as morphinans and benzomorphans. With oripavines the substitution at the 7-position is more important, if there is a bulky 7-substituent it always produces a partial agonist at least, even if theres a cyclopropylmethyl on the nitrogen (buprenorphine for instance). However with the phenylpiperidines and anilidopiperidines the SAR seems to be somewhat different, or at least those substitutions don't seem to have been tried much, at least in the research I've seen. N-cyclopropylmethyl pethidine or fentanyl might be an antagonist or partial agonist, but I've never seen any mention of them being made, can't imagine those substitutions were never tried though. Meodipt 07:56, 2 November 2007 (UTC)
Yeah, the SAR for Morphinans and benzomorphans are pretty similar. But the open-chain opioids and the ph-piperidines have a couple of key differences. I just found one of my very old lecture notes on it which claimed that for 4-Ph-Piperidines, it's not possible to confer antagonist properties with N-substituents mentioned above...hmmm...I'll continue digging until I find more resources on it. I'm almost done with a basic SAR page. I'm going to upload it over the weekend, but where/how should I link it to the opioids category? Aj1976 13:44, 2 November 2007 (UTC)
I would make a link to it from the Pharmacology section of the Opioid page, and also the Structure-activity relationship page and the Morphinan page. I guess you could put a "see also" section on pages for some individual opioids and put a link to it there, like etonitazene for instance where the page discusses multiple different compounds. Meodipt 01:48, 3 November 2007 (UTC)
Just looked it up, and it would appear that the N-allyl analogue of pethidine has been made, and is called WIN-7681, PubChem 16915. There has been some research done with it, and it appears that it is an antagonist, or at least it reverses the respiratory depressant effects of full agonists.JPET 1955; 113(3):310-318 So this suggests that N-allyl substituents do produce antagonists (or maybe partial agonists) in the 4-Ph-piperidine family at least. Think I should make a page for it? Not that notable a compound I guess, but there has been research done with it, and would expand the SAR info available on wikipedia for people. Meodipt 01:57, 3 November 2007 (UTC)
[edit] Casomorphin, Dermorphin
Casomorphin, Dermorphin - do these need adding to the template? -- Teutonic Tamer 17:46, 23 February 2008 (UTC)
[edit] Components of opium
Components of opium really needs to be split into its own template as it looks very messy as is, this template should be about opioid drugs, and does not need to include other plant components from the opium poppy.Meodipt (talk) 02:26, 3 May 2008 (UTC)
