Talk:Dimethyl sulfoxide/Archive 1

Oxidizing agent or antioxidant?

Currently the article contains conflicting statements in this regard. Curious-- does it oxidize terpenes?--Zymatik 22:01, 23 February 2007 (UTC)

In the case of extravasation of doxorubicin, drug reacts with Fe lead to production of ROS which causes severe local vesication/ulcers. Application of DMSO to the area prevents ROS production. That might be what they were getting at in regards to the anti-oxidant bit in the med section. --HH —Preceding unsigned comment added by 207.42.135.25 (talk) 02:39, 1 July 2009 (UTC)

Trivia

Not sure if its appropriate for this article, but the Dead Kennedys have a song called DMSO

Yes, I would agree there, can some moderator reply to this saying whether or not this can be put in a 'Cultural References part of this article?' Stonerwars 07:16, 13 December 2009 (UTC)

Bits of trivia such as this which have no importance to the topic of the article generally should not be added to the article. -- Ed (Edgar181) 14:31, 13 December 2009 (UTC)

LSD

My Organic Chemistry teacher told us that they would mix LSD with DMSO and put it in water pistols. Could this quote be involved in the article somehow: "The Pranksters will smear all the doors, railings, walls, chairs, the heating system, the water fountain, with DMSO... laced with LSD... Dig?... DMSO is close to being an old alchmical ideal, the universal solvent. Put a drop of DMSO on your fingertip and thirty seconds later you can taste it in your mouth. It goes right through your skin and through your system that fast. DMSO with LSD... What a vision! The following night the entire Democratic Party of California will get turned on, zonked out of their apples." - Wolfe, Tom (1968). The Electric Kool-Aid Acid Test, pp. 381. New York: Bantam Books. ISBN 0-553-038064-8

Jhum101 21:19, 22 February 2006 (UTC)

Interesting, though I thought it was pretty easy to absorb LSD already. raptor 13:41, 12 October 2006 (UTC)

Medical

What about the medical uses?

i use it as solvent in my experiment for good interaction between water soluble substance and hydrophobic substance. gobbuster_z

I can not believe wiki has a DMSO article with absolutely NO mention of any of the therapeutic applications of DMSO, the volumes of medical papers on DMSO, nor ANY mention of Dr. Stanley Jacob, known globally as The Father of DMSO.

What gives ?

http://www.dmso.org —Preceding unsigned comment added by 67.161.77.227 (talk) 01:16, 24 September 2007 (UTC)

The article does mention a fair bit about medical applications. Many readers would like Wikipedia to be a source for folk therapies and the like, but Wikipedia takes a sober approach to biochemistry and medicine. But if you've got something to say, especially if it does not fall into the category of pseudoscience, then insert some comments. You are aware that Dr. Stanley Jacob sells DMSO, so editors at Wikipedia would be careful about spam.--Smokefoot 01:30, 24 September 2007 (UTC)

Popular Culture

60 minutes did a segment on DMSO as having several possible healthful effects. It turned out to be a fad (I can remember buying a bottle from the local chemist/pharmacist!) That might be interesting color for the article.

Dimethyl sulfoxide#Safety, WP:NOT

I'm wondering whether the safety section is necessary at all, according to WP:NOT an instruction manual. The reference cited (oxford MSDS) mentioned does not say that DMSO vapor is an irritant. I'm surprised if it is - the boiling point is extremely high. If the section is required, at most a mention of the unusual precautions is necessary. --Rifleman 82 17:04, 24 April 2007 (UTC)

I support contracting the safety section. IMHO, few chemicals require more than 1-3 sentences about safety, especially when there is a link to the MSDS in the ChemBox.--Smokefoot 02:52, 26 October 2007 (UTC)

I disagree, almost every aspect of any wiki entry could be reduced to hyperlinks, but for chemicals a lot of students consult wikipedia and DMSO is so widely used it's important for us to understand just how dangerous it can be, depending on conditions etc. Keep or expand please Yvaud (talk) 00:18, 10 November 2008 (UTC)

CAN SOMEONE PLEASE FIX THE EGREGIOUS IT'S MEANS IT IS PROBLEM!!!!???? How freaking hard is this to understand? —Preceding unsigned comment added by 70.54.203.46 (talk) 15:33, 1 May 2009 (UTC)

I disagree with the dosing measurement of .3 ml/kg simple because ml is volume and kilograms are weight. This is not how volume is measured. It should be a measure of plasma within blood units, or a measure of mg/kg.

Trumanhw (talk) 08:01, 7 January 2010 (UTC)

Dead Kennedys...

The Dead Kennedys wrote a song about this. Should we mention it, and if so, in what manner?98.220.58.62 (talk) 22:33, 11 October 2010 (UTC)

They wrote a song about Dimethyl sulphoxide? Do you have a reference to support that? GiftigerWunsch [BODY DOUBLE] 12:15, 14 October 2010 (UTC)

Bedtime for Democracy is the album it's on.

From a lyrics website: D.M.S.O., crypto wonder drug in vogue. Some people say it cures arthritis; maybe that's why it keeps getting banned. It's absorbed directly through the skin; mix it with lemon juice, touch your fingertips, you'll taste the lemon.98.220.58.62 (talk) 22:04, 25 October 2010 (UTC)

Tasting it?

The opening paragraph says "It has a distinctive property of penetrating the skin very readily, so that one may taste it soon after it comes into contact with the skin." What the heck does this mean? Does it mean that one can 'taste' the chemical with one's fingers? Please rewrite the line so as to be clearer as to the meaning. —Preceding unsigned comment added by 68.62.16.202 (talk) 05:44, 16 November 2010 (UTC)

It penetrates skin quickly...seems pretty clear. When that happens, you can taste it (not "dip finger in it then lick finger", but literally "the sensation of taste happens") because it's now inside you. I can't think of a much clearer wording for this very unusual property of this chemical. DMacks (talk) 05:49, 16 November 2010 (UTC)

Alright, I took a whack at rewriting that sentence. DMacks (talk) 05:52, 16 November 2010 (UTC)

I've just removed the claim since it's unreferenced and sounds like nonsense. Taste is a sensation which occurs by the combination of stimulation of the taste receptors located on the tongue, and the olfactory receptors; neither of these receptors are located in or beneath the skin. The explanation that you can taste it "because it's now inside you" is nonsense, I'm afraid, and without references verifying that you experience a taste after being exposed to the chemical on your skin, preferrably with a convincing explanation of why, it seems like a hoax which went unnoticed. In addition, the ability to be readily absorbed through the skin isn't particularly distinctive; there are a great many compounds to which human skin is permeable. GiftigerWunsch [BODY DOUBLE] 14:46, 17 November 2010 (UTC)

No, the point is, that the DMSO gets into your bloodstream, and since it penetrates the skin, it also comes out of your skin again in the same way. That happens also on the tongue, and gives the sensation of tasting the compound. The relation to the actual taste might be of dimethylsulfide (reduction product of DMSO). But you are right, for nothing of that do I have anything else than WP:OR (I've had the sensation), so it needs some citations. --Dirk Beetstra ^{T C} 14:49, 17 November 2010 (UTC)

We should be able to find a reference for this somewhere: it is a well known phenomenon. Physchim62 (talk) 14:53, 17 November 2010 (UTC)

And indeed it was relatively easy to find a reference for it. Physchim62 (talk) 15:18, 17 November 2010 (UTC)

Beetstra's explanation is a bit more helpful than "it permeates the skin and therefore you can taste it", so I've added it to the article. I don't have access to the book so I don't know whether that is specifically supported by the book; if not perhaps another reference is in order to specifically verify that explanation. GiftigerWunsch [BODY DOUBLE] 16:08, 17 November 2010 (UTC)

Added obvious bit of information

Which no doubt will be removed, even when the fact of the matter is blatant. FX (talk) 22:16, 7 May 2012 (UTC)

Selenium and Tellurium Analogs?

Most of the time, the central atoms of a chemical compound can be replaced by another atom in the same group to form new compounds with similar properties (i.e. sulfuric acid and selenic acid, bromine replacing chlorine in certain salts and biological functions, &c.). Can the sulfur in this compound be replaced by the other chalcogens? (Of course, this excludes oxygen because it only makes two bonds.) Kyoobur9000 (talk) 01:36, 1 November 2012 (UTC)

Seleninylbismethane is CAS# 4371-90-8 and tellurinylbismethane is CAS# 114439-85-9. Dimethyloxopolonium is CAS# 859162-82-6. But oxygen is not as special as you think...the Criegee zwitterion sometimes called a "carbonyl oxide", and is known or postulated to exist for many different substituents (CAS# 202058-26-2 is the dimethyl one). See our sulfoxide article to understand why oxygen does not need to have more than two bonds even in the S case. DMacks (talk) 02:25, 1 November 2012 (UTC)

And should these molecules have pages, or are they so rare or unimportant that it isn't worth Wikipedia-ing them? Kyoobur9000 (talk) 22:39, 5 November 2012 (UTC)

SciFinder only has one ref mentioning the Po case and five for the Te case, almost certainly fail WP:GNG. The Se case has 77 refs--appears to have some synthetic applications and as a good model compound for studies of chemical/physical/spectroscopic trends, and "Dimethyl Selenoxide" is listed in e-EROS. The carbonyl-oxide type of structure in general is (which is why we have a redirect to an article with some content about it). DMacks (talk) 22:49, 5 November 2012 (UTC)

Pain reliever

I get spam touting DMSO as a fantastic pain reliever, e.g., " Contains this incredible compound that was showcased on 60 minutes to some 70 million viewers, hailed by The New York Times in a lead editorial... And savvy doctors like me have been personally using this compound for years...But you haven't heard about it, until now...When the hugely popular TV show 60 minutes airs a story about some secret "miracle compound," you might expect they would trash it. But they didn't." But there is nothing in the article about its use in this area. The first Google hits of "DMSO pain" have articles containing comments on using it for this purpose: http://www.dmso.org/articles/information/muir.htm and http://forum.lef.org/default.aspx?f=41&m=15008 .

Maybe some-one can look into this and present an NPOV comment in the article.Kdammers (talk) 05:31, 30 March 2013 (UTC)

Taste effect

I know wikipedia isn't about original research, but I can say that I used DMSO back in eighties (on potential bruises/sprains) and the near-immediate taste of garlic is startlingly clear. Several of my friends confirmed it as well. FWIW Geoff Canyon (talk) 18:07, 29 November 2013 (UTC)

Structure diagram - bond lengths /angles query

The bond lengths and bond angles here are very different from those quoted by Thomas et al in the 1966 paper ( doi:10.1107/S0365110X66002263)- which happens to be the the reference used for the space filling model. The S⁺–O^– length is really very long! Axiosaurus (talk) 11:18, 1 March 2015 (UTC)

Great catch! I added the dimensions from the paper you found. Many other language Wiki's have the same image. --Smokefoot (talk) 02:20, 3 March 2015 (UTC)

doi:10.1016/S0022-2860(96)09313-1 might have an even shorter one...maybe gas-phase, I can't access the fulltext. I removed the exact dimensions from the lede--waaaay too specific (and possibly disputable based on physical state), and merely retained the note about the overall geometric form. If the structure is that interesting specifically for this chemical, it could have the details in its own section. But it could be more relevant in the more specific sulfoxide article, where the nature of the S–O bond is discussed in detail. DMacks (talk) 03:45, 3 March 2015 (UTC)

Ok, here are the data for the paper you found: 1.485 A (experiment) vs 1.4901 (3-21G*) and 1.485 (6-31G*)

And here is yet another report on the structure http://www.sciencedirect.com/science/article/pii/S002228600100850X. They find 1.4837 A.

--Smokefoot (talk) 04:14, 3 March 2015 (UTC)

I must have made a mistake in this image, but I almost certainly did get the data from a book or journal article because the values are so precise. I can't remember where I got it from - this shows why it's important to provide a source for images! I thought it might've been from Greenwood and Earnshaw, but I looked and it isn't. I just checked the CSD and there are five determinations of the structure of pure DMSO in the crystalline phase. Two are from that 1966 paper and another three are from a high pressure study in 2009 (http://dx.doi.org/10.1021/jp808987k). The S-O distances range from 1.471 to 1.521 Å. I can remake the image with correct dimensions. Thanks for spotting the mistake and finding references, everyone. --Ben (talk) 19:03, 9 March 2015 (UTC)

H3C-O-S-CH3

Perhaps my question was misinterpreted as vandalism, I will restate my question: Why doesn't Dimethyl sulfoxide adopt a configuration that does not violate the octat rule, such as H3C-O-S-CH3?74.111.160.142 (talk) 12:34, 6 October 2015 (UTC)

You can be sure that such a valence isomer has been investigated computationally possibly synthetically from methanolysis of MeSCl. It would not be called dimethyl sulfoxide though. These species are mentioned in sulfenate ester.--Smokefoot (talk) 13:09, 6 October 2015 (UTC)

DMSO is sometimes considered with an electronic nature of H₃C-S(-O)-CH₃ with S having a lone-pair (exact octet) and +1 charge and O having three lone-pairs and –1 charge, which is more comfortable from an octet-rule standpoint and some properties of it are consistent with that charged form (see sulfoxide). The octet rule is not a bright line prohibition, especially for third row and beyond, and there are various explanations for how some structures can appear to violate it and not be unstable (see octet rule and hypervalent molecule). Regarding the other isomers, doi:10.1021/jp980940u is a computational study of their stability and doi:10.1021/jo01051a066 reports that the reaction Smokefoot proposes doesn't give the expected result. DMacks (talk) 01:55, 7 October 2015 (UTC)

"The oldest and most general method for the synthesis of sulfenic acid esters involves the reaction of a sulfenyl halide with an alcohol or phenol." Drabowicz, J.; Kiełbasiński, P.; Łyżwa, P.; Mikołajczyk, M., Science of Synthesis, (2008) 39, 557.--Smokefoot (talk) 22:33, 7 October 2015 (UTC)

I don't have access to that, but my lead-ref is clear that the dimethyl in particular doesn't give good yields under the "obvious" conditions for doing this reaction. Does your ref have special temperature or process-chem methods to get the product isolated well? Instead, the product appears reacts further with CH3SCl in a cascade leading to many other products. At least part of it seems particularly likely for the dimethyl case. For example, doi:10.1021/jo01094a047 says CH₃SCl + HOCH₃ in a 1:2 ratio at –20 °C gave 66% CH₃SO₂SCH₃, and a 2:1 ratio gave 55% CH₃Cl and 70% CH₃SCH₃. DMacks (talk) 03:15, 8 October 2015 (UTC)

DMSO disambiguation

"DMSO" was a disambiguation page that had two articles listed, this one and the "Modeling and Simulation Coordination Office" (M&SCO). I changed the disambiguation page into a redirect to this article because of the overwhelming usage of DMSO for dimethyl sulfoxide over the M&SCO. The M&SCO was created in 2006, when its name was the Defense Modeling and Simulation Office (DMSO). However, the name was changed in 2007 to the "Modeling and Simulation Coordination Office" (M&SCO). Normally, when a term or abbreviation has two uses and one is much more common than the other, the term is redirected to the most common usage and a disambiguation link is put on the top of that article, saying something like:

"DMSO" redirects here, for the U.S. Department of Defense agency, see Modeling and Simulation Coordination Office.

I am usually in favor of disambiguation links, but this usage is a bit obscure, in my opinion. If anyone believes that such a link is appropriate or even if someone does a complete reversion of my actions, I will not stop them. However, I might eventually ask for a discussion to take place in the case of a reversion. If there is some reason that you want to contact me, please use my user talk page. -- Kjkolb (talk) 04:47, 17 February 2016 (UTC)

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The Link for "Aprotic" Solvents leads to "Protic" Solvents

The second sentence in the article reads as follows:

"This colorless liquid is an important polar aprotic solvent that dissolves both polar and nonpolar compounds and is miscible in a wide range of organic solvents as well as water."

However the link embeded in the "aprotic solvent" leads to another article on "Protic Solvent".

Aprotic and Protic Solvents are two entirely different solvents. While an aprotic does not have O-H or N-H bond, protic solvents are rich with those bonds. — Preceding unsigned comment added by Imohams (talk • contribs) 15:21, 16 December 2020 (UTC)

Dolobene^®

The Dolobene^® section is faulty and needs to be removed. The possible dangers of topical DMSO application, especially in cases of laypeople's self-medication are trivialized by that section. The article may cause the impression that Dolobene^® is a licensed drug in Germany. Especially due DMSO's questionable marketing some sort of alternative medicine, wikipedia needs to state that such use is dangerous and without any health benefit.

The legal status of Dolobene^® in Germany

Dolobene^® was never approved or licensed as a Drug, however due to a Grandfather clause the manufacturer could evade a regular approval process, and Dolobene^® was not pulled from the shelves in 1978 with the coming into effect of the Arzneimittelgesetz (AMG). The product was specifically criticized in medical journals as early as 1992. Any reported health effects were clearly attributed to local redness and warming due to vasodilation, both of which do not constitute a health benefit. The advertising was clearly criticized as fraudulent. The authors also warned about systemic side effects of DMSO. Efforts to evade the drug licensing process by defining the product as a Medizinprodukt (medicinal product) failed. On 01/19/2010 the Manufacturer (Merckle Recordati GmbH, 89075 Ulm) asked for all remaining product to be pulled completely, as a valid license could not be obtained.

The brand name Dolobene^® is still used to market similar Products, none of which contain any DMSO. (retrieved 11/16/2021)

I also want to remark, that the section about alternative medicine does -In my opinion- not clearly enough state both the dangers and the fraudulent marketing by retailers like amazon.

89.43.125.246 (talk) 18:19, 16 November 2021 (UTC) Kemiker

Garlic-like taste after dermal contact with DMSO

First things first, in the [4] citation, there is nothing about DMSO. Though I searched and there is not a lof of evidence supporting this. It may or may not be true. I think that should be discussed. Or just use valid source. — Preceding unsigned comment added by Huldakurka (talk • contribs) 18:48, 18 May 2022 (UTC)

Untitled

The link to Reference 2 does not link to a page about DMSO. I'll leave it to you wikipedians to decide what to do about it. 155.254.6.51 (talk) 23:44, 26 December 2019 (UTC)

Safety and study bias

https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6707402/#:~:text=DMSO%20has%20since%20been%20used,and%20many%20more%203%E2%80%93%209

They raten studies on financial bias from (most)1-9(least) and the average was 5 which is terrible. They also note a lack of controls and that safety for human consumption has only been avaluated for skin use in certain compounds and prescription drug use, also in tiny amounts. This is relevant as a huge and misinformed "alternative" health community exists that pushes this stuff. It's possibly safe for many, but we literally have no idea and there are no longterm studies. We do know it can damage the lungs, stomach, and has caused epileptic reaction. I propose this to be added in. I do not have a citation for "alternative" usage unfortunately, but anyone into naturopathy has seen it all over the place recently. Talonx77.11.183.77 (talk) 07:58, 9 February 2023 (UTC)

WP:astroturfing

I'm concerned the article does not give an balanced view of the safety of this chemical. Lack of evidence is given greater prominence than established evidence, and the brief description that the substance is "non toxic" doesn't adequately summarise the sections contents.

Could someone withta greater level of technical knowledge find/arrange sources on this? The most notable risks seem to be that it can break down rapidly into toxic gasses, and that it can cause the skin to absorb environmental contaminants or other chemicals/drugs. 1.145.203.80 (talk) 10:08, 28 July 2023 (UTC)

What class of

What classification does it adhere to again. 72.131.198.14 (talk) 21:54, 28 August 2023 (UTC)

Dead MSDS

MSDS link is dead. No time to find one right now and link it but if I remember I'll come back this weekend and throw on a Sig Aldrich one or whatever. Paritus34251 (talk) 01:17, 14 November 2023 (UTC)

Done. Paritus34251 (talk) 15:49, 20 November 2023 (UTC)

Thanks! Just a quick tweak though...they are now called "SDS" not "MSDS". DMacks (talk) 16:49, 20 November 2023 (UTC)