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Long Nguyen
AP Chemistry
May 8, 2015
Dimethyl Sulfoxide: Friend or Foe?
Chemistry has played an essential role in modern science. The field of chemistry itself
extends beyond the mere composition of chemicals; chemical compounds have direct
applications in fields such as engineering, public health, and medicine.

Scientists have

manipulated chemicals to develop cures for diseases and used them as adhesive agents in
structural engineering. These innovative breakthroughs highlight the potential and utility of
chemical compounds: there are virtually limits to what chemistry can achieve. The real concern,
however, is whether or not these chemical compounds can be deemed safe for the public. One
such chemical compound is dimethyl sulfoxide, an organosulfur compound possessing the
chemical formula (CH3)2SO. How viable is this chemical compound for the world beyond
science?
Dimethyl sulfoxide, or DMSO, has a chemical formula of
(CH3)2SO; a central sulfur atom (attached by a pi bond) is doubly
bonded to a topmost oxygen atom, and two methyl (CH 3) groups are
singly bonded (connected by sigma bonds) to the central sulfur atom
(Fig. 1). This chemical compound was first discovered sometime
Fig. 1. The chemical
structure of DMSO.

between the mid- to late-19th century as a by-product of chemical


industries generating paper from wooden pulp.

It has been a

chemical compound of interest and has been studied extensively in chemical literature ever since
the 1860s. Dimethyl sulfoxides most prominent application is in the field of medicine, where it
is widely used for inflammation treatment and step-by-step diagnoses. Its history in medicine as
a pharmaceutical began a century after its discovery, after Dr. Stanley Jacob began investigating
its function in clinical treatments in 1961. As of late, recent breakthroughs in biology have
opened many doors for DMSO.
DMSO applications encompass three main categories: tissue/organ preservation,
penetration-enhancing excipients, and anti-inflammatory pharmaceutical agents. Tissue and
organ preservation rely heavily on DMSO: a solution of 10% DMSO, for instance, is capable of
preserving a frozen cell culture colony for up to three months in cold storage (Fig. 2). DMSOs
properties leave less damage on organic matter in cryogenics: more membranes remain intact,

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smaller ice crystals are formed, and osmotic stress is reduced. In
particular, studies have shown that the inclusion of DMSO in the
cryopreservation of osteochondral tissue allows the tissue to maintain
its function upon thawing. This has heavy implications on the future
of cryogenics; we may one day preserve life with protectants like
DMSO.

Fig. 2. A typical cryogenic


container.

Modern treatments also rely on DMSOs membrane-penetrating properties.

DMSO

expedites chemical delivery within patients by enhancing the diffusion and radius of effect of
known ingredients after their entrance into the skin. After this membrane-penetrating process,
pain is lessened. The final application of DMSO as an anti-inflammatory agent relies mostly on
its characterization as an antioxidant. According to Stephen Edelson, MD, at the Environmental
and Preventive Health Center of Atlanta, doctors use it for all sorts of inflammatory conditions,
from people with rheumatoid arthritis . . . any kind of autoimmune process. These positives to
DMSO highlight the fact that it is an efficient compound in more areas than one. It is, however,
not a complete cure as some would believe. DMSO is merely a symptomatic approach. A
2009 study between multiple science departments at the University of California, Irvine
demonstrated this symptomatic approach by alleviating the scattering of light on the skin.
DMSO, in vivo, increased light absorption by a factor of three when applied topically. These
results will be used in developing molecular imaging techniques.
The positives of DMSO are clear, but what of the negatives? Does DMSO carry with it
possible riskseven worse, death? The extremity of death has not been reported to this day, but
adverse effects have been revealed in multiple studies. Many claim that after using DMSO, a
garlic-like odor soon results from the mouth, causing unpleasantness; this odor is a benign
effect, not bringing any health risks. Other effects, however, have the potential to do real harm.
In a study by Joana Galvao and colleagues at the University College London Institute of
Ophthalmology, DMSO administered in low concentrations (24%) caused neuronal death
involving apoptosis-inducing factor from the mitochondria to the nucleus (Fig. 3). According to
Galvao, These results highlight safety concerns of using low concentrations of DMSO as a
solvent for in vivo administration and in biological assays. She recommends that there be other
ways of solubilizing drugs other than through the use of DMSO. This study shows the real risk
of DMSO. Thousands are cured, but what of the few who are affected by these issues? This low-

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concentration toxicity leads into other concerns as well. Does DMSO do more than just damage
neurons in a localized region, or does it have the potential to harm the entire nervous system?
Jennifer L.

Hanslick and other faculty of Washington Universitys Department of

Psychiatry and Pediatrics discovered in 2009 that DMSO does not merely damage neurons in
localized regions: it can induce widespread apoptosis throughout the central nervous system as
well. In mice of various young ages, DMSO was introduced
to

study

whether

DMSO

could

produce

apoptotic

degeneration in the developing CNS. A large amount of the


staining that Hanslick and her lab members were testing for
was not localized to cell bodies. Because this study was done
in young rats with developing nervous systems, the data could
be extended to young human children. What happens when
these children are exposed to something such as DMSO? The
answer is unclear, but it is likely not a good prospect.

Fig. 3. Apoptosis count for various


DMSO percentages (Galvao et al.).

Fortunately, alternatives to dimethyl sulfoxide do exist should scientists require other


methods of work. Three compounds can be used in DMSOs place: acetonitrile, NMP (NMethylpyrollidone), and DMF (N-dimethylformamide). There is one big significant difference
these three compounds all display reproductive toxicity at slightly to much higher levels than
that of DMSO. For chemical engineering, the three are on par with DMSO. Acetonitrile shares
alkylation, nucleophilic aromatic substitution, and cyanation with DMSO. NMP, like DMSO, is
used in the polymer industry for adhesive and coating purposes. DMF, the most dangerous of the
three, is classified as a carcinogen and is used mostly for the synthesis of materials such as
membranes, carbon fiber, and artificial leather. From their toxic properties, the three have no
practical applications in sensitive areas such as medicine; dosages of acetonitrile, DMF, and
NMP would poison a human fatally. Because of this, the future of these DMSO alternatives is
not clear. Time will be needed to further test them in industry and in vitro.
I believe that DMSO is a fitting chemical compound. For the most part, it is predictable
and fortunately so. Its strength as a commercial solvent and its practicality in lab experiments
make it an excellent chemical compound. The disadvantages to using DMSO, such as its lowdose toxicity and apoptosis-triggering properties, may be hazardous, but they are little in
comparison to the good that DMSO can bring. We must continue to invest ourselves in DMSO

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instead of going against it: we need something like this to advance our knowledge in chemistry
and science.
Works Cited
Bui A, Mcclure R, Chang J, Stoianovici C, Hirshburg J, Yeh A, Choi B. "Revisiting Optical
Clearing with Dimethyl Sulfoxide (DMSO)." Lasers Surg Med. 2009 February ; 41(2):
142148. doi:10.1002/lsm.20742.
Capriotti,Kara,andJosephCapriotti."DimethylSulfoxide:History,Chemistry,andClinical
UtilityinDermatology."JClinAesthetDermatol.2012;5(9):2426..
Egli,R.j,A.Sckell,C.rFraitzl,R.Felix,R.Ganz,W.Hofstetter,andM.Leunig.
"CryopreservationwithDimethylSulfoxideSustainsPartiallytheBiologicalFunctionof
OsteochondralTissue."Bone33.3(2003):35261.
Galvao, J., Davis, B., Tilley, M., Normando, E., Duchen, M. R., Cordeiro, M. F. Unexpected
low-dose toxicity of the universal solvent DMSO. FASEB J. 28, 13171330 (2014).
HanslickJ,LauK,NoguchiK,OlneyJ,ZorumskiC,MennerickS,FarberN."Dimethyl
Sulfoxide(DMSO)ProducesWidespreadApoptosisintheDevelopingCentralNervous
System."NeurobiolDis.2009April;34(1):110.Doi:10.1016/j.nbd.2008.11.006.
Muir,Maya."DMSO:ManyUses,MuchControversy."DMSO.Web.14May2015.
<http://www.dmso.org/articles/information/muir.htm>.
"ReplaceAcetonitrilewithDMSO."GaylordChemical.Web.14May2015.
<http://www.gaylordchemical.com/index.php?page=replaceacetonitrilewithdmso>.
"ReplaceDMFwithDMSO."GaylordChemical.Web.14May2015.
<http://www.gaylordchemical.com/index.php?page=replacedmfwithdmso>
"ReplaceNMPwithDMSO."GaylordChemical.Web.14May2015.
<http://www.gaylordchemical.com/index.php?page=replaceaproblemsolventwith
dmso>.

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