Nutritional science for mind health products
DSM Nutritional Products
Asked about the source of the DMAA in its supplements - which are among several recently recalled from stores on US army and air force bases amid safety concerns – a USPLabs spokesman said:
“DMAA is, in fact, a constituent of geranium (Pelargonium graveolens) and its derived oil and has been consumed as part of the human diet for more than 100 years.”
He added: “We have enlisted credentialed individuals and organizations to assist us in our endeavors [to prove the above]. As new information is released and published, we will quickly alert consumers regarding our findings.”
He did not however clarify whether the DMAA contained in Jack3d and OxyElite Pro was actually sourced from geranium or was a synthesized copy of a geranium extract, however.
Speculation and conjecture
As for those querying whether DMAA was even in geranium, he said: “There are flaws in the logic that certain individuals who attack the ingredient from an uninformed standpoint have been using. What is currently in circulation about the ingredient is speculation and conjecture professed by competitors and those who are not serious about researching specific and important aspects of geranium and its properties.
“Thus, it is easy for those individuals to irresponsibly allege and disperse false and misleading information which does not help the consumer or the industry. In addition, the processes and methodologies that certain chemists have cited contain critical errors in analytical methods and/or the oils used for these analyses."
He added: “We would welcome the opportunity to discuss these issues directly with any legitimate chemist you have spoken to in order to begin a productive and informative dialogue on this very important research."
DoD: Too soon to tell if there is a relationship with DMAA [and soldier deaths]
His comments came as the Department of Defense continued its probe into the safety of DMAA following the deaths from cardiac arrest of two soldiers using DMAA containing products.
Col. John J. Lammie, MD – director, Health Policy Services, Office of the Surgeon General of the Army, told NutraIngredients-USA that the military had not yet come to any conclusions about DMAA and had ordered a recall of DMAA-containing supplements as a precautionary measure.
He added: “I want to emphasize that no link between DMAA and the medical conditions reported by military medical providers has been validated scientifically by us.
“While the DOD leadership and the USAPHC take these reports very seriously, all of these medical conditions have multiple causes. It is too soon to tell if there is a relationship with DMAA.”
Products held in storage
DMAA-containing supplements recalled by the military are being “held in storage pending the recommendations of DoD leaders after the scientific review is complete”, he said.
"USAPHC is assisting the Office of the Army Surgeon General's Health Policy and Services Directorate in conducting a study of potential health effects of DMAA.
"Medical, dietary and public health specialists are currently developing the methods and tools that will be used in the study. Both providers and service members will provide input. We anticipate it will take several months to conduct the study; timeframes could change, though."
The probe was launched as “two soldiers using DMAA containing products suffered cardiac arrest while exercising”, he said.
”One died immediately after the event, the other after a one month hospitalization. Both were found to have DMAA in their blood. We are reviewing any reports of side effects submitted by providers and reviewing available scientific literature.”
Ongoing debate over the source of DMAA
There is an ongoing debate about whether DMAA, which was first manufactured synthetically by drug giant Eli Lily in the 1940s, is in fact a constituent of geranium, as US supplement makers claim.
The American Herbal Products Association (AHPA) recently told members they should not label DMAA as geranium oil or any part of the geranium plant, while Health Canada has also issued a statement arguing DMAA is not found in geranium and affirming that any products containing it require a drug authorization.
However, a statement released by Barry Lynch, associate director at Cantox Health Sciences International on September 6, claimed that USPLabs has commissioned data "from two independent and highly respected analytical chemistry laboratories" that supports the findings of a 1996 study (Ping, Z.; Jun, Q. & Qing, L. (1996), ‘A Study on the Chemical Constituents of Geranium Oil, Journal of Guizhou Institute of Technology 25 (1): 82–85), that is always referenced as proof that geranium oil contains DMAA.
The data is currently being prepared for submission to peer-reviewed journals for publication, according to Lynch.
12 comments (Comments are now closed)
Geranium Oil Testing
I likewise have no stake in this debate, however I have known Jim Kababick for over 10 years now, and while he is a competitor of mine, I hold his analytical chemistry abilities in high regard, and his scientific integrity is beyond reproach. He certainly has nothing to gain by disputing the presence of DMMA in geranium oil, and risks alienating existing or potential clients, but he has never put business or politics ahead of the data.
Regarding the Ping data, Jim and I have had some extensive discussions on the paper. Since my Ph.D. is in analytical chemistry in the field of chromatography, and I have several dozen peer reviewed publications in chromatographic method development, optimization, and validation, I think I know a little bit of what I talk about. The observations made by Jim are correct - The DMMA, if present, should blow out of the chromatographic column under Ping's conditions, and not be one of the later eluting compounds. Furthurmore, the chromatographic conditions would seem to preclude the use of MS detection techniques due to the excessively high flow rates. The authors of the paper do not seem to be familiar with chromatographic theory, the Van Deemter equation, and method optimization.
As Jim also correctly pointed out, a DMMA level of 0.6% would give the material a strong amine odor; the nose can easily detect these amine compounds down below 0.1%. This is not to say that geranium oil contains no DMMA, but "none" is a relative term. As our instrumental techniques become more and more sensitive, we are getting to the point of being able to detect just about anything in anything. It may be quite possible that DMMA is present at a ppm, ppb, or even ppt levels in geranium oil. What boggles my mind, however, is that entire product lines have been developed containing DMMA in large milligram quantities based on highly questionable analytical data in one publication, and a highly questionable safety record.
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Posted by Mark C. Roman, Ph.D.
24 January 2012 | 00h34
Geranium Oil
I have no stake in either side of the Geranium Oil debate. But, I have utilized Jim Kababicks’ company for testing over a twenty year period.
Unknown to J. Kababick, we have performed round robin on his results many times. Not because we questioned his results, but because verification of analytical results is a core component of our Quality Control strategy. Comparative testing proved Kabaick’s results were always within the parameters of the model we had constructed for our multi lab testing (Round Robin). This is not to say the returned data was always to our liking: but data is what it is. We make course corrections as necessary, and go forward. There are many of us that have performed verification of J.Kabaick’s work- and we still use him.
To not devalue the constructive Geranium debate in the eyes of those of us following this thread, I would suggest criticism of some untested facet which is not the tested facet of J.Kabaick’s integrity.
-Jim Baker
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Posted by Jim Baker
21 January 2012 | 20h19
Science Will Prevail
Clearly, there is legal and regulatory controversy surrounding DMAA. Health Canada, New Zealand and other regulatory agencies have taken their position on this matter. That this agent was developed for commercial use after Benzedrex inhaler was "re-engineered" in the US market speaks to its mode of action.
I write not to offer my opinion on this matter, but instead in reaction to the defamatory comments leveled at Jim Kababick, a scientist of unimpeachable integrity. Having used the services of Flora Research Labs on numerous occassions over the past 10 years, I have been consistently impressed by their objectivity, their thoroughness and their expertise.
Hume wrote many years ago that "reason is slave to the passions" May I respectfully remind us that in matters of analytical chemistry, science will prevail.
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Posted by Michael D Levin
21 January 2012 | 08h26
Replication of Ping study and ethics in science
For almost 20 years now, I have conducted analysis of essential oils utilizing the same analytical column dimensions that Ping et al report in their paper. I was trained by Dr. Walter Jennings & his team at J&W Scientific (now Agilent), the pioneer of modern capillary gas chromatography and one of the world’s preeminent experts in the analysis of volatile oil components in his time. I can assure you that replicating the Ping paper is not even realistic. Capillary columns of that dimension coupled to a mass spectrometer use flow rates of about 1-1.3 mL/minute and higher flows can cause data distortion and problems with analysis (if not column blow outs). Ping reports a flow rate many times higher and I had the paper checked by a PhD chemist from Taiwan who received his PhD in the US who provided the same intel that I was able to gather from the paper. If you look at Van Deemter plots, you will see that based on a given gas viscosity, there is an optimal flow rate that gives the best resolution.
Anyone that knows me knows that I am a scientist of high standards and ethics. Our laboratory work is almost exclusively word of mouth. That is not a successful business model if you are not good at what you do. I also happen to be human. Humans are subject to mistakes. However, I have no qualm about openly admitting mistakes when I make them. We all do at some point in our life and we often learn by them (if we are lucky).
I would be thrilled to find and confirm DMAA in geranium and the reason I ask for the plant material is that if I can detect DMAA in that whole plant material and confirm it was not spiked, I can publish that work and stand behind it solidly. That would make me much more popular than I am now in the sports products circuit and save me a lot of grief and heat that I am taking for my position now. It does not matter to me if it is there or not. What matters to me is good science and getting to the bottom of this issue. Many products that are natural are also made as synthetics. I have no issue there either in most cases. However, I have a big issue when people sell a product as a natural extract and it is synthetic. People should get what they pay for. If it is synthetic DMAA, then say so (some suppliers do). Many people use synthetic Vitamin E, Vitamin C and other synthetic materials like MSM. My issue is that I have not seen data that shows that this compound naturally occurs in geranium. We have one study so far that is out there saying it is (and that is one of the most flawed papers I have ever seen) and hundreds of publications that never mention this compound in geranium and a recent paper that reports that in oils and cold pressed plant material of the same species Ping utilized, there was no DMAA found. The authors of that paper did spiking studies showing that they could far exceed the reported levels of Ping as well and I think that paper is well done. Can one person be right when everyone else is wrong? Yes, I have been in that situation before with my work on benzene methodology. However, as an objective scientist, I have to evaluate the data and the quality of the data in hand and make decisions and revise decision if needed as more data comes in.
This is not a case where I have become rigid in my thinking and am not open to finding out that DMAA may be in the product. I am making my call on what I have seen so far. I recently examined some other summary data suggesting that there may be DMAA in some species of geranium but the data did not include spectral data so we can’t be certain that the peak is actually DMAA. It could just as easily be a co-eluting compound. I would love to gather the materials and repeat the study using spectral data acquisition tools which can add the additional dimension. We also have the capability to isolate and purify the compound if it is there and study the isotope patterns and the isomer ratios as well. Good decisions in science are based on gathering data, evaluating data and drawing conclusions that the data supports. And yes, sometimes we gather new data and then have to make changes to our findings which is perfectly fine. That is the way good science works. That is the way I work. I am a scientist and I am only interested in finding the truth of the matter regardless of what that is.
A final word on amines. I have the pure methylhexaneamine freebase (which is how it would be found in the oil) and like most amines, it has a distinctly unpleasant organoleptic profile. It this amine was at the levels purported in the Ping paper, the rose geranium oil would not smell like roses. At PPB or low PPM levels maybe, not at levels over 0.5%.
Also, I have run the compound and hundreds of geranium oils on that same column chemistry phase. That compound is one of the first compounds to elute which would be expected since it is a low MW compound and highly volatile. Ping has it as one of the last compounds eluting way after his higher MW compounds and the chemistry of this compound can’t account for that. Otherwise it would do the same thing in my column which is the same phase as the one reported by Ping.
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Posted by James Neal-Kababick
20 January 2012 | 10h03
Geranium myopia II
I JUST read Jim Kababick's posting on this piece, where he mentioned IRMS (Isotopic Ratio Mass Spectrometry), a method to determine the origin of a specific chemical(s) (also the method pioneered by Dr. Don Catlin to determine if elevated testosterone in the blood was from the body or a drug). This is what I was referring to as isotopic "fingerprinting" in my (long) comment. Good call, Jim, and my apologies for my OWN myopia!
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Posted by Anthony L. Almada, MSc, FISSN
13 January 2012 | 14h24
Geranium Testing
Yes, and yet again, you do not address the fact that not one of the papers you’re referencing was attempting to replicate the Ping et al., paper as their methodology and materials reflect. You also neglect to mention that not one single paper you’re mentioning ever identified 100% of the components of the geranium oil. You also neglect to mention that volatile amines have only been mentioned one other time in the published literature because they are present in such small (i.e., trace) quantities. You then fail to mention that GC/MS, which all of these papers used, is not suitable for reaching such low detection limits for DMAA in the geranium oil matrix unless very specific methods are used, none of which were in any of the published papers.
You should go and try to replicate the Ping et al. study if you’re so interested in doing so. Why wait for someone to provide you with the material? After all, I don’t think any DMAA-merchandizing company is going to send you any samples any time soon as I believe you’ve made it painfully obvious of your bias. You have consistently shown up and gone out of your way to voice the fact that you don’t believe DMAA is a constituent of the geranium. I actually have a friend in the industry which informed me of something. I won't go into the details other than to ask if you have ever had anyone that sells a DMAA product ask you to evaluate their materials to determine whether it is naturally occurring or not? And if so, what ever came of that?
Of course, I believe none of these companies would offer you any samples now, considering all of this posting and yelling from the rooftops that DMAA doesn’t occur in geranium oil. Interestingly enough, I always notice it's at the same time as another vocal opponent.
But, why would anyone want to send you any samples? Do you really believe you could be impartial? Would you really be ready to admit that you were wrong? That what I believe to be true is actually the case which is that your logic up until this point which you’ve been relying upon to indicate that DMAA isn’t naturally occurring was flawed?
I believe even your statement about IRMS implies that even if DMAA were present in the geranium samples, it MUST be spiked or adulterated, right? Why else would you so quickly mention this type of testing? I don't believe that is being unbiased. That aside, I’m afraid you’re mistaken when you state that it will prove or disprove the authenticity of the claim as isotope values aren’t always a reliable indicator of natural versus synthetic and it requires a very good characterization of authentic samples and that it be within a narrow range, where the two isotopic signatures don’t have overlapping values. Despite what you say, there are many criteria to be met before one can rely upon isotope values. Nonetheless, I’ll bet you’ll see a publication regarding this soon enough.
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Posted by Tim
12 January 2012 | 00h31
Geranium Testing
Yes, and yet again, you do not address the fact that not one of the papers you’re referencing was attempting to replicate the Ping et al., paper as their methodology and materials reflect. You also neglect to mention that not one single paper you’re mentioning ever identified 100% of the components of the geranium oil. You also neglect to mention that volatile amines have only been mentioned one other time in the published literature because they are present in such small (i.e., trace) quantities. You then fail to mention that GC/MS, which all of these papers used, is not suitable for reaching such low detection limits for DMAA in the geranium oil matrix unless very specific methods are used, none of which were in any of the published papers.
You should go and try to replicate the Ping et al. study if you’re so interested in doing so. Why wait for someone to provide you with the material? After all, I don’t think any DMAA-merchandizing company is going to send you any samples any time soon as I believe you’ve made it painfully obvious of your bias. You have consistently shown up and gone out of your way to voice the fact that you don’t believe DMAA is a constituent of the geranium. I actually have a friend in the industry which informed me of something. I won't go into the details other than to ask if you have ever had anyone that sells a DMAA product ask you to evaluate their materials to determine whether it is naturally occurring or not? And if so, what ever came of that?
Of course, I believe none of these companies would offer you any samples now, considering all of this posting and yelling from the rooftops that DMAA doesn’t occur in geranium oil. Interestingly enough, I always notice it's at the same time as another vocal opponent.
But, why would anyone want to send you any samples? Do you really believe you could be impartial? Would you really be ready to admit that you were wrong? That what I believe to be true is actually the case which is that your logic up until this point which you’ve been relying upon to indicate that DMAA isn’t naturally occurring was flawed?
I believe even your statement about IRMS implies that even if DMAA were present in the geranium samples, it MUST be spiked or adulterated, right? Why else would you so quickly mention this type of testing? I don't believe that is being unbiased. That aside, I’m afraid you’re mistaken when you state that it will prove or disprove the authenticity of the claim as isotope values aren’t always a reliable indicator of natural versus synthetic and it requires a very good characterization of authentic samples and that it be within a narrow range, where the two isotopic signatures don’t have overlapping values. Despite what you say, there are many criteria to be met before one can rely upon isotope values. Nonetheless, I’ll bet you’ll see a publication regarding this soon enough.
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Posted by Tim
11 January 2012 | 03h42
Sure
Oh ok, “Shawn”. Please see the response to the other gentleman. In any event, why the manufactured outrage over this ingredient? Why no outrage over certain people in the industry selling prescription only methylxanthine salts as OTC products? Or companies selling compounds which have absolutely zero evidence to support natural occurrence? It is ironic that you call others the “idiots” for bringing heat on the industry as the behavior of individuals making unfounded claims about the legality and/or safety of a compound is what draws negative attention to the industry. I can't help but ask, what is the motivation here? Why consistently try to present things that are not factual and make implications and to be so persistent about it. Again, what is the motivation here?
Though, this begs the question, what will these critics do once DMAA is shown to be naturally occurring without any doubt by what I believe are actual experts in analytical chemistry and geranium oil analysis? Will they admit they were wrong? My guess is that they won’t and will then switch from trying to be an analytical chemistry expert and put on their attorney hat, stating that it’s not legal to sell a synthetic copy of a naturally occurring compound. Oh wait…. It’s interesting they don’t express such outrage over compounds like beta alanine, lycopene and alpha lipoic acid, all of which are produced synthetically. But, unlike the senators that wrote the bill which became DSHEA law, these characters apparently know better. I say they should try running for senate then.
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Posted by Tim
11 January 2012 | 03h41
Nonsense
Some poetry below for you.
No, as someone who actually has an extensive educational background in organic chemistry, I believe unlike you, I do understand enantiomers and diastereomers. I’m glad that you appear to have recently learned what enantiomers are but I’ll go a step further and give you a free lesson. DMAA has two chiral centers; one at the C-1 and one at the C-3. When you say, “forms”, I believe you mean stereoisomers or isomers. There are the (S,R) (R,S) and (S,S) and (R,R). The first two stereoisomers (S,R and R,S) are enantiomers as are (S,S and R,R). The SS, RR and RS, SR are the diastereomers.
Apparently, aside from your organic chem., I believe you also need some work in reading comprehension as the criticism had nothing to do with this. In fact, can you show me where any of that was discussed? Oh, that’s right, you can’t. So, here is what you actually said, “The nearly equal “racemic” ratio is irrefutable evidence that it was not derived from a biological source but from chemical synthesis.” Consequently, you were informed that a racemic ratio (yes, even occurring in two pairs), does not, as you stated, provide irrefutable evidence that anything is synthetic. Racemic mixtures can and do occur in nature quite often. Yes, racemics are not the rule, but are the exception, that is true, but to make such definitive statements as you have is absolute nonsense and shows a lack of education in natural products chemistry.
As for the lack of fragrant smells, I’ll save you the embarrassment and just say that I believe you clearly lack an understanding of the process of extraction and isolation of pure compounds. Though, that is beside the point.
Nice try on trying to slip in, “enantiomeric purity” again. Maybe you don’t understand the meaning of that phrase, but it was actually addressed in the previous discussion. You see, there was a large list of abstracts showing that there are not only racemic mixtures that occur in nature, but even more compounds that consist of unequal (e.g., 80:20, 60:40) amounts of each enantiomer. So, yet again, your assertion that a compound must be enantiomerically pure to be naturally occurring is incorrect. Remember to address this in your response instead of some odd statement about how I don’t know the different between enantiomers and diastereomers.
Oh, here is another gem. I believe you also lack an understanding of how isotopic analysis works. It is no magic solution and requires a good amount of work to determine a given (and narrow) range from a confirmed source to be able to make any determinations. Just FYI.
Last, I thought it was kind of amusing how you have to note that the base compound (DMAA with no salt) smells of ammonia. It is an indication which makes me believe that you’re not very well versed in organic chem as that is a characteristic of volatile amines. I used to pass bottles of spermine and putrescine to students to demonstrate this very rudimentary principle and I expected them to know it.
Oh and like all of these terrible arguments, I should then address your nice backup statement which you’ve included to help cover yourself after you’re proven wrong, which is...I'll paraphrase here is it, “doesn’t matter even if DMAA is naturally occurring because if the commercial version is synthetic, it’s not legal”. It’s interesting that you should claim to know the law better than the two senators that actually sponsored the original bill. They completely disagree with you. But, let me guess, you know what they think better than they do?
Also, I would recommend asking your buddy for some basic lessons in organic chem. I can't help but find it interesting that the same two people just so happen to show up at the same time every day to post nonsensical arguments by chance. Maybe he can also show you his ability to reach part per trillion and part per billion detection limits with his nose.
By the way, you really should be more upfront about the fact that you're a supplement company owner that sells products that compete directly with DMAA-containing supplements. It adds a little more credibility to all of this purported outrage.
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Posted by Tim
11 January 2012 | 03h38
Geranium myopia
Ok. I posted on this topic a few months ago and someone who did not reveal their identity critiqued my comments, implying I did not know stereochemistry (and yet they did not fully grasp enantiomers and diastereomers--DMAA exists in FOUR different forms, as TWO pairs of enantiomers, enantiomers being mirror images of each other, a 3D chemical identity marker).
Well here it is: Let's assume that geranium DOES contain DMAA. So what! What we REALLY need to know is whether the DMAA in dietary supplements is from geranium oil, as ALL marketers have asserted at some time (or to this date). The Ping et al. paper, as anemic and errant as it is (go ask Health Canada), asserts 0.6% by weight of "some" seven carbon chemical, claimed by some to be DMAA. DMAA content in finished goods ranges around 5-25 mg/serving. Anyone familiar with botanical extraction and concentration knows that to achieve a highly pure constituent (from a lower native concentration, like < 1%) is very cost, solvent, and time intensive. Moreover, and far more important to the discussion, is that little thing called enantiomeric purity.
To date, no person nor entity has described chiral separation and characterization (analyzing ALL FOUR forms of DMAA). Two doping studies have identified TWO of the FOUR forms, from biological samples after ingesting DMAA-containing products.
In collaboration with a true, GLOBAL expert on chiral separation, we found the following in a leading DMAA-containing dietary supplement AND in two synthetic chemical standards of DMAA: 1) all four forms of DMAA (both enantiomeric pairs), and 2) virtually EQUAL ratios among each of the two enantiomers comprising each pair.
If DMAA existed as a SINGLE pair of enantiomers, as do some KNOWN and RECOGNIZED constituents of geranium oil, then asserting that a nearly equal ("racemic") ratio of the two enantiomers in a pair affirms SYNTHETIC origin would be dicey, and perhaps incorrect. But TWO pairs of enantiomers, as for DMAA, with racemic ratios, is virtually irrefutable evidence of synthetic origin. Other products are being chirally analyzed now--look for a rapid publication very soon.
Lastly, IF DMAA is being extracted from geranium oil where are the OTHER chemical constituents that are WELL characterized constituents of this fragrant liquid? Sure, one could SPIKE a synthetic DMAA with some fragrant chemicals but a forensic chemist could then apply isotopic "fingerprinting" and determine if BOTH the DMAA and the "geranium signature" chemicals indeed came from the SAME origin. And why do NONE of the Chinese suppliers of DMAA also exhibit BOTANICAL extraction expertise, rather than industrial and pharmaceutical chemical synthesis expertise??
I'm still waiting for convincing evidence, addressing all of the above, to affirm that the DMAA found in dietary supplements is indeed from geranium. All the king's horses and all the king's men couldn't...
BTW: pure DMAA has a distinct, ammonia-like scent...the new smelling salts!
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Posted by Anthony L. Almada, MSc, FISSN
10 January 2012 | 15h32
This Geranium Stinks!
I believe in freedom and love supplements, that believe we should have both.
The problem is the freedom is coupled with responsibility and people who don't act responsibly usually end up costing everyone their freedom.
I've been in this industry long enough to smell is when stuff "stinks." And this one reeks but good.
Seriously, we're dealing with a substance here that we really, really don't need. If not responsible for deaths, it's not helping people stay alive. It's simply not essential to staying awake, getting a pump, getting leaner, living longer, etc...
It's edgy crap and here we are in an argument about geranium oil. And the evidence seems to strongly suggest that the answer is NO... but either way, there's enough doubt that the proof should be in FIRST.
And then we should be able to, responsibly without too much chaos, decide if something is needed, helpful or dangerous.
Oh hell...it's just nuts. So long as it sells it's going to be sold. And nothing it going to change until ethics are mandated which no one is going to like, least of all the consumer.
And keep it up and we'll all be buying Vitamin-C from a pharmacy for $100 month...
Nice work idiots!
Now, get the samples to James Neal-K below...
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Posted by Shawn Phillips
05 January 2012 | 23h52
I would like to see the plant material before processing
I have analyzed geranium oil for almost 20 years now and in my reivew of our data and the data of geranium oil chemistry dating back to 1975, I have not ever seen one instance of this compound found or reported in any peer-reviewed journal on the oil. That said, if it is indeed obtained from geranium, I would like to obtain samples of the whole plant material which I can analyze in our laboratory and also conduct IRMS testing on which will prove or disprove the authenticity of this claim. So far, all data I have obtained fails to support the claim that this compound is naturally found in geranium. However, I am open and willing to research whole plant material to see if it is there. Any takers?
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Posted by James Neal-Kababick
05 January 2012 | 20h06
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