Template talk:Opioids

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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)

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)

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)

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.

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)

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)

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)

"Dithienylbutenyl dimethylamine" deleted

because, it's an incorrect name for dimethylthiambutene.--84.163.86.96 20:29, 18 October 2007 (UTC)

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)

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)

As stated above codeine, morphine and their semi-synthetic derivatives are a class of morphinans which is 4,5-epoxymorphinans, to be precise. 89.230.196.58 (talk) 23:48, 20 November 2009 (UTC)

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)

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)

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)

The original text of the Canadian law had errors. The correction made to the law on 22 Apr 1997 assigned the correct chemical name to oxpheneridine and a new chemical name to the unknown species "carbamethidine." The structural diagrams at isomerdesign.com for these two substances were based on the chemical names in the original, not the correction (they're fixed now). The chemical name for "carbamethidine" corresponds to a known substance "carperidine," and it seems likely that the former name is simply, as suggested by Meodipt, a figment of the Canadian legislators' imagination. Tillbury (talk) 04:55, 26 November 2009 (UTC)

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)

Casomorphin, Dermorphin

Casomorphin, Dermorphin - do these need adding to the template? -- Teutonic Tamer 17:46, 23 February 2008 (UTC)

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)

Oh crap! I had to read this *after* spending the last hour adding a bunch of alkaloids in the poppy :((

Added a bunch of protoberberines, aporphines, papaverrubines, benzophenanthridines and a few morphinans. Good to see u again btw :) Aj1976 (talk) 13:50, 16 August 2008 (UTC)

Do you suggest I move all of them to the "Components of Opium" template? 122.164.55.206 (talk) 01:55, 21 August 2008 (UTC)

Azidomorphine

Hi. I just want you to know that I moved Azidomorphine from the "Codeine-Dionine family" to "Others" within semisynthetics. Reasons are

• 1. Unlike Codeine and related derivatives, Azidomorphine is not 3-alkylated;
  
• 2. the 6- substitute, azide, is a pseudohalide group, thus more closely related to e.g. Chloromorphide and Chlorocodide
  

Hope, that no one has objections...If so, please let me know. Cheers,--84.163.108.175 (talk) 18:04, 25 July 2008 (UTC)

Morpholinylethylmorphine?

Isn't morpholinylethylmorphine the same as pholcodine?--84.163.111.190 (talk) 01:31, 30 July 2008 (UTC)

Yeah mate, same thing. Aj1976 (talk) 13:51, 16 August 2008 (UTC)

Made redirect / mention in article. Nagelfar (talk) 12:08, 25 October 2008 (UTC)

dipropionylmorphine / 3,6-propionylmorphine

What family would a propionyl ester class opioid like dipropionylmorphine fit in? There is no article or place in this template yet for dipropionylmorphine. I hear it crosses the BBB faster than heroin etc. Apparently "3,6-propionylmorphine" has been shown to be preferred in tests of opioid addiction on monkeys by them over heroin. There is yet to be an article on this opioid as well, are they the same? They must at least be very similar. Nagelfar (talk) 15:47, 27 October 2008 (UTC)

Dipropanoylmorphine is already listed, which is the same drug under a different name (propionyl is the US word, propanoyl is the UK/european word for the same ester). 3,6-propionylmorphine is another (mis)named term for the same compound. Meodipt (talk) 11:55, 30 October 2008 (UTC)

Thank you, I updated accordingly. Nagelfar (talk) 20:44, 2 November 2008 (UTC)

Theoretical opioids

Well I created an opioid article from a theoretical opioid at a drug discussion forum, but I don't think I can save it from speedy deletion so I'll put most of what I put in the article here as I found it interesting nonetheless; if it were ever to become widely discussed as a theoretical opioid due to its function it may be notable enough one day to have it's own article, so here it is. (the collapsing table makes it all bolded so just ignore that part):

3-acetyl-6-propanoyl-14-ethoxy-dihydromorphine

3-acetyl-6-propanoyl-14-ethoxy-dihydromorphine is a theoretical super-opioid created for maximum recreational subjective effects. Conceptualized from a knowledge of the mechanisms upon which the molecular structure of existing opioids rely for their mode action becoming subject to use (though not necessarily to higher abuse or habituation due to maximized duration). The action of this opioid relies on its hydroxy in 3-position being initially exposed creating increased lipophilicity while also exposing the lighter acetyl group which allows for a quicker onset of effects. This is coupled with a high potency from the 14-ethoxy and also an enduring activity due to the saturated 7-8 bond. Molecular image of 3-acetyl-6-propanoyl-14-ethoxy-dihydromorphine

Nagelfar (talk) 02:14, 3 November 2008 (UTC)

I think there are quite enough real opioids that do not yet have pages made for them, there is no need to make pages for compounds that have never even been made! Besides that compound is hardly optimised, something like 3-nicotinoyl-6-methylene-14-methoxy-N-(2-(furan-2-yl)ethyl)morphinan would be a better conglomerate of the most active substituents in the literature ;-) Meodipt (talk) 01:06, 4 November 2008 (UTC)

I'm just on the look out for new chemical articles with sourced information, hobbyist discussion may not be the best first party sourcing, however. ;-) Nagelfar (talk) 00:18, 5 November 2008 (UTC)

Apomorphine not an opioid?

Since the template seems to be about opioids, of which morphine happens to be one, what about morphine derivatives that aren't opioids like Apomorphine? Do they actually belong on this template? We have opioids which aren't morphine derivatives like Salvinorin A. If it does belong, shouldn't it be more rightly 'opioids & morphine derivatives'? Nagelfar (talk) 20:34, 6 November 2008 (UTC)

Good point. But Apomorphine isn't an agonist for any of the opioid receptors. It belongs in a class of "Aporphine" alkaloids, distinct from this template, except maybe as part of the Components of Opium category. —Preceding unsigned comment added by Aj1976 (talk • contribs) 11:27, 10 November 2008 (UTC)

OK, but now how many of the "Natural Opiates: Opium Alkaloids" are not opioids either since most of those have no opioid activity? Might it just be easier to make this an opium derivative & opioid template via name move? If not, we'd have to clear out a lot of those and source whether they had opioid activity, without articles on the majority of them, that could be a difficult task. Cyclohexyloxy-α-phenethylamine was just removed due to lack of sourcing as an opioid agonist for example. Nagelfar (talk) 23:06, 10 November 2008 (UTC)

Given the size of the template as it is, I think we should only include substances with known binding to opioid receptors. Otherwise, the template just becomes a mess rather than a navigational aid. St3vo (talk) 03:06, 11 November 2008 (UTC)

Then it appears a great number of these alkloids should be removed. Nagelfar (talk) 00:31, 12 November 2008 (UTC)

Yeah I agree with St3vo, this template should be restricted to opioid receptor ligands, with the natural opiates section containing only those opium alkaloids that are opioid receptor agonists (e.g. morphine, codeine & thebaine), plus a link to the seperate "components of opium" template which should have all the other alkaloids found in opium that are not opioid receptor ligands. This would be a much more logical and neater arrangement, and avoid the redundency of having the various opium alkaloids listed seperately in two different templates. Meodipt (talk) 09:37, 12 November 2008 (UTC)

More semi-synthetics that are prodrugs?

Not very many of the semi-synthetics listed seem to be prodrugs, I notice pretty much just heroin (acetylated morphine) & dipropanoylmorphine. The rest pretty much substitute a section or group on the molecule to change the basic morphinan function and structure. However I have read esterizing oxycodone has been done and works much the same acetylating morphine, making a prodrug form of oxycodone. 14-cinnamyloxycodone is an oxycodone ester. Similar can or have probably been done with other semisynthetics. Nagelfar (talk) 16:09, 18 December 2008 (UTC)

By semi-synthetics that are pro-drugs, I mean semi-synthetic first, then pro-drug additionally, not semi-synthetic by virtue of being pro-drugs. That I only now noticed being confusing. Ester- or ether-izing an otherwise already altered morphine; this may be useful for morphine semi-synthetics that are less liable to quickly cross the BBB but are active, and esterizing/etherizing the 6 position of that less liable or quick semi-synthetic, make it able to more quickly pass through and have a viable pro-drug made of an otherwise not so viable semi-synthetic. Nagelfar (talk) 14:06, 17 October 2009 (UTC)

N,N,3-trimethyl-3-phenylbutan-1-amine (# LS-47438)

N,N,3-trimethyl-3-phenylbutan-1-amine is registered and classed with it's own number: LS-47438. so is attested to. Apparently it is the simplest molecule to follow the "morphine rule". The 2D diagram of the chemical is this or this. Nagelfar (talk) 18:13, 12 February 2009 (UTC)

Template beginning to look sloppy again...

I notice the existence of entries written such as "Poppy Straw Concentrate(PSC) aka Concentrate of Poppy Straw" with two separate links to what would be one page, and this issue recurring throughout the template.

There are so many multiple names for each chemical that this should have to not be the case.

Also familiar names as part of the link or not part of the link has no consistency whatsoever. We have entries such as "Ethylmorphine (Dionine) (Codethyline, Dionine, &c.)" which look are confounded within themselves as to what style we are using here.

Nothing adheres to any wikipedia Manual of Style consistency whether it's slashes separating exact & common names (i.e. "Dihydrodesoxycodeine/Desocodeine") or parenthesis (i.e. "Diacetyldihydromorphine (Dihydroheroin)").

We need to resolve this issue of the template. Nagelfar (talk) 00:27, 5 May 2009 (UTC)

Also shouldn't "Codeine-Barbiturate Salts" go into 'Alkaloid Salts Mixtures' or be removed entirely? (Every brand name permutation, such as oxycodone-APAP mixtures for example, are not given because they are not a chemical in themselves, nor do they have historic provenance such as the opium tinctures). Furthermore how is something such as Codeine Salicylate any different than morphine 'HCl' versus 'tartrate' or freebase? Should such instances also be considered redundant and so removed? Nagelfar (talk) 05:14, 7 May 2009 (UTC)

Quite agreed. I reverted back to the last "good" version as the changes since then were somewhat questionable, lots of redlinks added to the template for compounds that could exist but have never been made or at least are not notable, and the recategorisation had several errors and was not particularly useful. Meodipt (talk) 09:22, 9 May 2009 (UTC)

Looks as if the IP reverted it back, and not even to the version I cleaned up of that, with no discussion or consensus. Nagelfar (talk) 05:00, 5 June 2009 (UTC)

Oxycodone/naloxone & Targin (that redirects the same) has the same issue here in pertinence for Wikipedia. 184.76.53.217 (talk) 07:03, 30 November 2010 (UTC)

Norlaudanosoline and Reticuline

This website: [2] speaks of "Benzylisoquinoline alkaloids present in human neuroblastoma cells" including morphine as one of them (the three given). The page is cited as examples of morphine potentially being an extreme scarce but naturally occuring endogenous ligand. Well the other two "Benzylisoquinoline alkaloids" given in the paper are norlaudanosoline & reticuline; interesting names, "..laudan.." makes me think it is a definite opioid, yet no article entry in Wikipedia yet for either. Could any in the know place them as redlinks where they would go here, if they indeed do? Nagelfar (talk) 12:56, 15 October 2009 (UTC)

Salutaridine is a precursor for reticuline that has an article here on Wikipedia. Nagelfar (talk) 09:03, 17 October 2009 (UTC)

Tropane opioids.

It was brought to my attention that 3-(3-methoxyphenyl)-3-ethoxycarbonyltropane and that the whole class of its derivatives are (may be AFAIK) opioids. Though they are also DARIs. Which makes me wonder if there are enough such substances, stimulants and depressants in one (such as Lefetamine; though it is of a different order than a DARI, it is a DA releaser.) that maybe even another template could be created; simultaneous CNS stimulant/depressant molecules. The stimulant and depressant should also be CNS, they need not be opioid for depressant (maybe GABAergic or such), and the stimulant may be of whatever quality as well; it just must display one or the other. If someone has 5 more so such chemicals we should make a template IMO. Nagelfar (talk) 13:10, 16 October 2009 (UTC)

Tapentadol is another such dual acting stimulant / depressant of the CNS. These are also preparations that maybe could be noted in such another template if made- the likes of Desbutal & Dexamyl, etc. in a separate section thereon. Nagelfar (talk) 09:15, 17 October 2009 (UTC)

Fencamfamine

Fencamfamine keeps being added and removed. It has this very template on its own page; and the argument of it being a ligand seems to be made on its page. 71.34.69.204 (talk) 01:24, 18 October 2009 (UTC)

Referencing each red link with the cite Wikipedia syntax within template.

Doing the reference of each red linked name makes for a long list on the bottom, See my old example here, this is in comparison to this version without such sourcing... I yet however cannot collapse the referenced entries at the bottom without them not showing up and giving an error. http://wiki.riteme.site/wiki/Wikipedia:NavFrame may show how but the few examples that I tried from there did not work. Nagelfar (talk) 05:45, 22 October 2009 (UTC)

If dihydro'heroin' and acetylproprionylmorphine exist, then is dihydroacetylproprionylmorphine a possibility?

Then if 3,6-hydroacetylproprionylmorphine exists, wouldn't this make 6-monohydroacetylproprionylmorphine superior in immediate onset/activation and longer in duration (have 'more legs')? or would just the 6 position being such a freely rotatable ester affect binding or crossing the BBB or be an impossibility due to stability and remaining in such a chemical conformation for any duration unto in vivo administration or for some other reason? Nagelfar (talk) 19:11, 2 July 2010 (UTC)

It seems I misunderstood the conformation of dihydroheroin, the hydrogen is not at the terminus of the ester branch as the name 'dihydroheroin' implies. Though 6-acetylhydromorphine may be the superior metabolite of dihydroheroin, what other complex esterized 6-position morphine monoesters could be made? Nagelfar (talk) 04:18, 10 July 2010 (UTC)

Would an immediately active 6-position ester cocktail composed of something along the lines of: 6-acetylpropionylmorphine, 6-acetylbutyrylmorphine, 6-acetylhydromorphine, 6-acetylbenzoylmorphine, 6-butyrylmorphine, 6-benzoylmorphine, 6-formylmorphine, 6-propanoylmorphine, 6-acetylmorphine, 6-nicotinoylmorphine (ten 6-esters of morphine)... Help duration by slowing down the metabolism via the different ester branch enzyme requirements for metabolization? Nagelfar (talk) 04:32, 10 July 2010 (UTC)

Hydromorphone / Dilaudid, natural not semi-synthetic?

Though it is made by semi-synthetic processes for pharmaceutical grade quantities, Hydromorphone is found in trace amounts in opium latex according to its article page. Should that be of note for this template that it is a trace component found? Many of the active constituents listed hereon as natural to the poppy are likely in trace quantities, why should Dilaudid be omitted because we make it synthetically from a natural base of another constituent molecule, the fact remains it does exist as natural by itself as per evidence, isn't this reasoning correct for what should be included as natural? Nagelfar (talk) 18:19, 22 July 2010 (UTC)

Halogenated Morphine Derivatives

I'm not one to remove the delineation of all real instances of potential opiate article links on a template meant to be an exhaustive list of such. Especially on a website wiki which is most likely to have an eventual informed/informative article on the individual instances as subjects. Though there should be some way to bundle the red-links as invisible until they are blue links. I wish there was a <invisiblered>type command</invisiblered>, (like the "nowiki" command) that made the words in-between [[]] completely vanish until the article is created or made into a redirect. Maybe someone should suggest such in the proper area, and then add such commands to the 'halogenated morphine derivatives' section. Though I don't think such should be made for all red links in such lists, for they inspire one to create such an article, but in big exhaustive areas such as the whole section where minor instances are not simply being filled in, but rather the majority of such are lacking, I think should be the extenuating circumstance for which such a command would be well used. Nagelfar (talk) 06:39, 2 December 2010 (UTC)

Naloxonazine has a mate for a pair in Oxymorphone-3-methoxynaltrexonazine

If someone could remake this image of Oxymorphone-3-methoxynaltrexonazine free GNU (or et cetra) for Wikipedia, it would be a great maintenance of notoriety for the vastly different yet similar morphinan conformations that due to mechanism work in the opposing fashion (in terms of agonism / antagonism, which are to contradict myself here actual quite similar functions in method of action if not result on a body's ecology/ecosystem to use grossly misguided terms of another field). I think this is notable if just to pair it with an example that the bulky multiplied molecular form of Naloxonazine has a twin that doesn't necessitate such a double form being at all times ever an antagonist but a full agonist too. Nagelfar (talk) 00:18, 24 December 2010 (UTC)

Red links removed.

In case a good reference point is needed for what opioids could be added to Wikipedia, the following "red links" were removed from a version of this template hence. Nagelfar (talk) 02:15, 30 October 2011 (UTC)

The red links are still in List of opioids. --ἀνυπόδητος (talk) 06:34, 30 October 2011 (UTC)

Inclusion of articles of combined preparations?

I've noticed multiple articles specifically on combined formulations of opioids used in pharmaceutical medicine. Namely Hydrocodone/paracetamol, Hydrocodone/ibuprofen, Oxycodone/paracetamol, Oxycodone/naloxone, Morphine/naltrexone & Fentanyl/fluanisone. (I could think of Oxycodone/aspirin (Percodan) & Oxycodone/ibuprofen (Combunox) as well). Might there be a manner for integrating these variations into a template exclusively for 'opiate pharmaceutical preparations'? This would likely exclude, and take up, the entire opium segment of this template from here (with the articles such as Laudanum being more similar to the above than to individual molecular entities, such as most the entries in 'opioids' really are.). Nagelfar (talk) 19:52, 2 June 2012 (UTC)

Ethanol

I removed Ethanol from the list. Because Ethanol is not an opioid. Am I wrong? — Preceding unsigned comment added by 94.123.227.9 (talk) 21:41, 18 March 2014 (UTC)

First, I would like to congratulate you on your linking of ethanol with mU activation. http://www.sciencedirect.com/science/article/pii/S0028390805001516 There are thousands of flavors of combinations of activations in our brain. Many effect to accomplish, otherwise, very similar outcomes, by indirectly relying on down-stream influences. To me, alcohol feels like a horrible drug, which I could never get addicted to. On the other hand, some classical opioids have felt so relaxing - so oceanic to me.

Just as many halo saturated halothanes (freons), etc.), have multiple actions (including PRIMARY mU activation) contributing to physiological mechanism, it has been proven that ethanol, at least allostericaly (vivo and vitro) modulates small peptide mU agonists, ethanol is also a dirty solvent, and most likely shares similar dis-associative properties with PCP/DXM/N2O, and others. In fact, the pure mU antagonist, Naltrexone, indicated, primarily (at it's 50mG/Day dose) as an opioid blocker, for alcoholics. Specifically a mU bloacker (mU=of the Morphine Type). http://www.rxlist.com/revia-drug/clinical-pharmacology.htm

It if makes it a bit easier, think of Alcohol as vanlefaxine. They both modulate hormones and nerurtransmitters close to site of action (in brain, mainly), influencing a naloxone reversible mU-opioid antineoception. http://www.ncbi.nlm.nih.gov/pubmed/15157989.

This suggests one of the primary analgesia derived from Effexor, is linked indirectly, through endorphin modulation (enhancement, re-uptake, delays in small peptide destruction), and who knows what else.

It makes perfect sense to me in this day and age of a politically correct, Victorian DEA/FDA, how any (opioid) or dopamine enhancer), wouldn't get a shot in hell at the chance of being seriously scrutinized in a non-objective manner. All but the very rich lose. Some of the biggest looser are the inner city addicts! Also, any addict in the US without access to what has artificially been stopped from reaching quite possible, state-of-art medical status. And all of the MILLIONS who suffer debilitating depression - what about them? Our system (virtually/collectively) tells them they are NOT important.

It is about time our scientists realize a large part of depression for so many (especially, initially, to recover from), is to acknowledge the anhedonia many feel with all these very emotionally blunting and libido sapping(SSRI?SNRI), half-measures, which (coincidentally) only serve to increase sales of the likes of Viagra and other such blockbuster drugs. (Use inferior drugs with rotten sexual side effects.) WOW, do ya THINK there just MIGHT be a small conflict of interest here?!! Boy, them good ole boys ain't stupid. These all too poorly understood SSRI/SNRI's. Somehow, I have a feeling they are not *quite* as miss understood as some apologists would like us to believe they are. Naivety can serve as a two edge sword here, by granting plausible denial-ability, while preserving deep pockets for those who selfishly financially benefit. New studies DRAMATICALLY demonstrate that NMDA Antagonists (Ketamine/PCP/Dextrpmethorphan), can play an important role in the apparent acute abbolishment of m any of the most difficult (to day), treatment of some of our worst, most horribly debilitating depressive symptoms. http://www.biologicalpsychiatryjournal.com/article/S0006-3223%2809%2900519-8/abstract in relieving (especially refractory and difficult to treat, re-curing) depressions. I believe I just read a study regarding Survector's tinaptepine (It's a French/EU anti-depressant DIRECT mU Agonist, which even leading edge researchers within this niche field (*apparently didn't know about*! that is is also a substantial Mu-agonist. Somehow, tolerance does not build up with this molecule. Even with IV abusers.

It's high time we throw out the banksters who have basically ruined our country with their greed - stifling innovation for their own artificial creation of monopolies. They perpetually leave us with a debt which by definition, can NEVER be paid back (in a CLOSED/PRIVATE) system such as ours, in the USA.

 http://www.nature.com/tp/journal/v4/n7/full/tp201430a.html  — Preceding unsigned comment added by 24.118.56.28 (talk) 16:57, 20 March 2015 (UTC) 

Is there consensus in favour of Template:Opioidergics??

I note that Medgirl131 is currently replacing template:Opioids across relevant articles with Template:Opioidergics, created by her, apparently without any discussion with others. Is there any consensus for the implementation of this new template? Medgirl131 undid my reversion 618386506 of her change to Opium with the comment "Template:Opioids will be deprecated in favor of Template:Opioidergics and List of opioids shortly. Sorry for the confusion. Thanks." However I see no record of discussion of this initiative anywhere on WP. Plantsurfer (talk) 08:52, 25 July 2014 (UTC)