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Melgar
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Decarboxylation of amino acids (phenylalanine, tryptophan) in various solvents
I've read a lot of relevant threads on this board, as well as various papers, regarding the decarboxylation of amino acids. Spearmint oil (cavrone)
seemed to keep coming up as a good catalyst, due to its high boiling point and the enone functionality.
My first test was to see if solvent-free conditions could work. Strictly speaking, it wouldn't be entirely solvent-free. A small amount of the
liquid catalyst would be used as the solvent initially, and as the amino acid was decarboxylated, it could act as a solvent for more of the solid
amino acid. Additional quantities of the amino acid could be added as the contents liquefied, and of the available amino acids, the amine products of
phenylalanine and tryptophan would appear to be liquid at decarboxylation temperatures. Testing this appeared to confirm that it would work;
phenylalanine bubbled vigorously and turned yellow when carefully heated over a flame with spearmint oil in a test tube. Almost all of the
phenylalanine in the test tube was successfully decarboxylated in this manner. A test with larger amounts was less clean, however. Bubbles from the
decarboxylation would push the amino acid away from the flask walls, and the mixture of amine and amino acid would solidify if significant amounts of
amino acid were still present. It could possibly be done with a more even heat source, or under microwave irradiation, provided it was done in a
flask that allowed for venting of the evolved CO2 while preventing oxygen from entering the flask. However, this test did seem to indicate that only
a small quantity of solvent should be needed, and then only enough to wet the mixture. The resulting amines would be liquid and could function as
solvent for the reaction after decarboxylation.
The next step was choosing a solvent. I went through my solvents and selected the ones with a boiling point well above water's. That gave me mineral
oil, dimethylformamide, DMSO, tetrachloroethylene, glycerin, propylene glycol, and n-butanol. I ended up testing DMSO, glycerin, and propylene
glycol, because they had known boiling points that were the highest. In each case, a few drops of spearmint oil were added to a test tube, then amino
acid powder was added, then the solvent was added until it wetted the entire powder mass. The test tube was then carefully heated over a methanol
flame.
Glycerin performed the worst. Even hot, it was too thick for bubbles to escape quickly enough to allow the decarboxylation to proceed at a favorable
rate.
Propylene glycol performed quite well. Large quantities of CO2 gas evolved, although darker-colored amine complexes did gradually form.
Decarboxylation was hampered by the amino acid's tendency to float, which made it difficult to accelerate the reaction.
DMSO actually worked very well, and perhaps the best of all of them, despite the spearmint oil forming a layer on the surface. Apparently, the small
amount that did dissolve was enough to catalyze the reaction sufficiently. Also, dimethyl sulfide evolved, but only a small amount. I actually kind
of liked the smell, it smelled like Eastern European food, and reminded me of my Grandma's cooking. The amino acid probably added a meaty smell to it
that reminded me of food, in any case.
I had a flask of tryptophan in xylene, with a catalytic amount of spearmint oil added, that I had attempted to decarboxylate earlier, without luck.
The boiling point was too low to allow decarboxylation to occur at any significant rate. To this, I added about 1/4 its volume of DMSO, and heated.
Bumping immediately became a problem, despite never having been a problem before. Not sure what to do, I added another catalytic amount of spearmint
oil. This actually solved the problem entirely; apparently the catalyst is deactivated somehow by the amino acid over the period of 1-2 weeks or
less. Still, this allowed the entire amount of tryptophan to be decarboxylated over the course of a few hours. After it cooled, a darker oil
collected at the bottom of the flask, with both layers being a shade of orange. I'm guessing that the bottom layer was amine that didn't dissolve in
xylene? When hot, they seemed to be miscible.
I haven't done the workup yet, but figured that since a few other people here have posted about decarboxylation reactions, I'd put down some of my
findings in case it interested anyone. DMSO and spearmint oil seemed to work best, which is a combination I hadn't heard of before. Propylene glycol
with spearmint oil also worked well, and would probably make for an easier workup. Both solvents are also available OTC in large quantities, at a low
cost.
[Edited on 6/13/17 by Melgar]
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AvBaeyer
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Melgar,
Nice post. A note of caution, which I think you have already recognized, without isolation and identification of the reaction products, it is
premature to claim the new conditions "worked." The presence of gas bubbles is indicative of decarboxylation, but was there further reaction of the
amine in these reactions? DMSO at elevated temperature always gives me suspicions. I find your report quite interesting and await further details.
AvB
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Melgar
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Part of the reason that I chose these two amino acids is their characteristic colors and odors, and SWIM's... uh, heh heh, I mean MY
past familiarity with them. Do nostalgic flashbacks to 2007-2008 count as evidence for their successful formation?
As far as DMSO, I gradually increased temperature until decarboxylation proceeded at a satisfactory rate, which was well below its boiling point. I
didn't record temperature at the time, since the only thermometer immediately available was stainless steel, and these reactions were small-scale
proof-of-concept tests that I didn't want to contaminate with metals. I did measure the bath temperature, and both reactions were running well below
150˚C. Reaction progress was easy to monitor, since both amino acids were sparingly soluble in the solvents I used, but amines were liquid at
decarboxylation temperatures, as well as at room temperature. Additionally, I have PEA hydrochloride to test against at least for the
phenylacetaldehyde decarboxylation product.
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Corrosive Joeseph
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Any update on this............?
/CJ
Being well adjusted to a sick society is no measure of one's mental health
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CuReUS
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not directly related to the topic,but how do you remove the NH2 instead of the COOH ?
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Melgar
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Well, the only update I have so far is that proline also works. I suppose I'd need to separate by distillation, but I've had a hell of a time
figuring out a good way to vacuum distill in the small amount of space I have available to me. I've been working on a thermoelectric cooling system,
and trying to fix the magnetic stirrer on my hotplate, but I haven't been able to make much headway on either one. I guess I should just buy a bag of
ice, and use that for cooling until I have something better, and put my hotplate back together without the stirrer so I can at least use it for
something.
I'm leaning towards propylene glycol as being the best solvent to use, because of its 188˚C boiling point, lack of odor and toxicity, and low cost.
It's also a lot less viscous than glycerine, which has similar properties otherwise.
[Edited on 8/3/17 by Melgar]
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JJay
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You don't have enough space to vacuum distill? You can vacuum distill in a space the size of a microwave....
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alking
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Melgar, what temperature was your bath with the DMSO? I recently tried to decarboxylate tryptophan with it and had quite unsatifactory results, I'm
sure some tryptamine was produced, but my effective yield was 0.
The first issue was I seemed to have significant oxidation. Whether this was because I did not flush the system or take measures to ensure an inert
atmosphere or because it reacted with the DMSO I'm not sure, but my bath temperature peaked at 150C. It began decarbing around 120-130C I would guess,
but it's hard to measure. This problem is likely avoidable with lower temperatures and an inert atmosphere, but I can't say for sure w/o confirmation.
The second issue is that at some point between 120-150C it fully solvated the tryptophan. Initially I thought this was a good thing, and it's not
inherently bad, but the downside is that without measuring the CO2 output you can't really tell when the reaction is done. I use a water trap so one
indicator is backflow, but that's not reliable or a good determination to use.
The last and most important issue is the workup. I don't really see it happening here, how do you propose doing so? Even with a very strong vacuum
source you cannot fully strip the DMSO and with a not so strong one there's no point even trying. The efficiency of the solvent in a reaction is
great, but it's worthless if you can't recover the product afterward. I'd imagine this is going to be the case of all high boiling aprotic solvents
unless it's possible to freeze precipitate the tryptamine afterward, and even then it's still rather messy. The only option left is to use a solvent
system to extract it with the DMSO and that just seems like an utter mess to me, you're going to have to throw the DMSO away and I can't imagine the
emulsion you'd have to fight in order to recover the product. Is there a method I'm not aware of? This really does seem like a good solvent for the
reaction, but based on the inability to extract it afterward I think you'd be better off using a stick of butter.
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clearly_not_atara
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I'd be surprised if tryptamine hydrochloride were soluble in DMSO. Is it?
Also, DMSO is boiled away quite often in common usage, so I'm not sure what you're doing wrong. You do need a heat source to get an acceptable rate of
evaporation due to the "heat of boiling" consumed when the DMSO evaporates. If you subject a liquid to vacuum with no heating it can even freeze in
some cases. A warm water bath can be enough heat.
Another method for removing DMSO is to use water and an immiscible solvent:
http://anonym.to/https://www.researchgate.net/post/How_can_I...
| Quote: | 1) take your compound in a beaker and add ice onto it. leave till ice melts.
2) add ethyl acetate/diethyl ether and take mixture in separatory funnel without shaking mixture much.
3) swirl a little but dont shake the separatory funnel. take out water layer. Now you give washing with ice-cold water with good shaking.
4) dry on sodium sulfate and concentrate using rota vapour. |
Essentially what happens here is that the DMSO will migrate into the water layer and the tryptamine will move into the ethyl acetate, diethyl ether,
DCM, chloroform, etc, and then you can wash that layer with water to remove remaining DMSO and evaporate the solvents. You're exploiting DMSO's
affinity for water to get rid of it. This would normally be done after vacuuming as much as possible.
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alking
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I don't have time to look into that now, but I'll check it out later, thanks for the link. I thought hcl reacted with tryptamine in some way though? I
remember reading that tryptamine and DMT I believe cannot form a proper salt with HCl, it tends to be a liquid and prone to oxidation, I assume
because it disassociates for w/e reason. It might still work for an extraction, but I've always thought it was to be avoided.
As to stripping the DMSO I could strip about 25-50% of it and then it became increasingly difficult to do so, I assume because the tryptamine was
binding to it. I'm sure if I had a better vacuum source I could do fine, I'm using a rather abused rotary vane pump, but with anything less I can't
see it being practical to distill out. I'm sure it's nothing with even a basic commercial lab/vacuum source, but keep in mind many of us are lucky to
even have a rotary vane pump.
When I stripped it it came over with a bath temp starting at about 50C (that's the lowest I could pull the vacuum) and peaking at 90C before I cut it
off, I'm not sure how harmful that may have been to the product. My remaining solution, based on volume, seems to be about 50% DMSO, 50% product
(including side products). I was going to try and do an a/b later from this, hopefully there's not too much DMSO remaining to cause a serious
emulsion.
[Edited on 1-9-2017 by alking]
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clearly_not_atara
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A quick Google for "tryptamine hydrochloride" turns up several suppliers selling it, including the one that involves a Greek letter hyphenated with
the name of a monster from Dark Souls 3. On this basis I conclude that it both exists and is stable, so you may be thinking of another salt.
Excessive acidity can destroy indole in the presence of water, so that may be what you heard. But this effect is not unique to HCl, and I don't think
that indole will be protonated by HCl in DMSO, because the pKa of HCl in DMSO is 1.8, meaning that it is weak in DMSO, and the pKa of pyridinium is
3.4, and indole is generally several orders of magnitude less basic than pyridinium, which points to tryptamine being only monoprotonated. However,
extracting indoles with concentrated hydrochloric acid (aq) is to be avoided except at 0 C, because indole is protonated by HCl in water (pKas -3.6
and -5 respectively). Gassing a nonaqueous solvent containing tryptamines with HCl should be okay.
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Melgar
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Quote: Originally posted by alking  | Melgar, what temperature was your bath with the DMSO? I recently tried to decarboxylate tryptophan with it and had quite unsatifactory results, I'm
sure some tryptamine was produced, but my effective yield was 0.
The first issue was I seemed to have significant oxidation. Whether this was because I did not flush the system or take measures to ensure an inert
atmosphere or because it reacted with the DMSO I'm not sure, but my bath temperature peaked at 150C. It began decarbing around 120-130C I would guess,
but it's hard to measure. This problem is likely avoidable with lower temperatures and an inert atmosphere, but I can't say for sure w/o confirmation.
|
My temperatures were similar to yours, and also weren't easy to measure. The tryptophan is practically a foam, and there's hot CO2 bubbles spattering
out all the time. You tend to not need an inert atmosphere though, since the stuff generates its own. You just need plenty of head room and a
restricted opening on your flask. I've done it since with just a stopper and a meter-long length of polyethylene tubing. That way, any suckback will
only suck CO2 and water vapor into the flask.
The DMSO will oxidize the amino acid, forming dimethyl sulfide and an oxidized product. I have since come to the conclusion that propylene glycol is
a superior solvent. After doing this decarboxylation reaction with both solvents, the DMSO would produce a darker product, and give off the familiar
dimethyl sulfide smell. Since there wasn't enough dimethyl sulfide to necessitate evacuation, I can only assume it wasn't a large fraction.
Still, DMSO tends to form complexes with other substances, preventing distillation from it, so I'm reluctant to recommend it anymore, and would
probably instead recommend propylene glycol.
| Quote: | | The second issue is that at some point between 120-150C it fully solvated the tryptophan. Initially I thought this was a good thing, and it's not
inherently bad, but the downside is that without measuring the CO2 output you can't really tell when the reaction is done. I use a water trap so one
indicator is backflow, but that's not reliable or a good determination to use. |
I just let it go until the CO2 bubbles stopped. CO2 bubbles are distinguishable from those produced by boiling in that they don't change size as they
rise through the liquid. They also linger a bit at the surface before popping, whereas the bubbles from boiling don't.
| Quote: | | The last and most important issue is the workup. I don't really see it happening here, how do you propose doing so? Even with a very strong vacuum
source you cannot fully strip the DMSO and with a not so strong one there's no point even trying. The efficiency of the solvent in a reaction is
great, but it's worthless if you can't recover the product afterward. I'd imagine this is going to be the case of all high boiling aprotic solvents
unless it's possible to freeze precipitate the tryptamine afterward, and even then it's still rather messy. The only option left is to use a solvent
system to extract it with the DMSO and that just seems like an utter mess to me, you're going to have to throw the DMSO away and I can't imagine the
emulsion you'd have to fight in order to recover the product. Is there a method I'm not aware of? This really does seem like a good solvent for the
reaction, but based on the inability to extract it afterward I think you'd be better off using a stick of butter. |
Granted, DMSO tends to raise the boiling point of the components of mixtures that it's in, but why wouldn't you just distill the tryptamine out?
Wikipedia says the boiling point is only 137C under 0.15 mmHg. I tried this once from PG and got a lot of bumping, although perhaps with better
boiling chips it wouldn't be as bad.
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alking
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| Quote: | A quick Google for "tryptamine hydrochloride" turns up several suppliers selling it, including the one that involves a Greek letter hyphenated with
the name of a monster from Dark Souls 3. On this basis I conclude that it both exists and is stable, so you may be thinking of another salt.
Excessive acidity can destroy indole in the presence of water, so that may be what you heard. But this effect is not unique to HCl, and I don't think
that indole will be protonated by HCl in DMSO, because the pKa of HCl in DMSO is 1.8, meaning that it is weak in DMSO, and the pKa of pyridinium is
3.4, and indole is generally several orders of magnitude less basic than pyridinium, which points to tryptamine being only monoprotonated. However,
extracting indoles with concentrated hydrochloric acid (aq) is to be avoided except at 0 C, because indole is protonated by HCl in water (pKas -3.6
and -5 respectively). Gassing a nonaqueous solvent containing tryptamines with HCl should be okay. |
It's definitely HCl that I am thinking of, I've read it in at least two, maybe three different places. All were forums and essentially heresay though
so I'd take your source of a supplier selling it over those. My memory is vague, but as you may gather from my description, and likely part of why my
memory is vague, is that no one actually said what happened or why it didn't work, it was always 'It doesn't work for some reason, it does this or
something.' Essential heresay w/o direct experience from anyone making the claim and an incomplete reasoning to support it.
| Quote: |
My temperatures were similar to yours, and also weren't easy to measure. The tryptophan is practically a foam, and there's hot CO2 bubbles spattering
out all the time. You tend to not need an inert atmosphere though, since the stuff generates its own. You just need plenty of head room and a
restricted opening on your flask. I've done it since with just a stopper and a meter-long length of polyethylene tubing. That way, any suckback will
only suck CO2 and water vapor into the flask.
The DMSO will oxidize the amino acid, forming dimethyl sulfide and an oxidized product. I have since come to the conclusion that propylene glycol is
a superior solvent. After doing this decarboxylation reaction with both solvents, the DMSO would produce a darker product, and give off the familiar
dimethyl sulfide smell. Since there wasn't enough dimethyl sulfide to necessitate evacuation, I can only assume it wasn't a large fraction.
Still, DMSO tends to form complexes with other substances, preventing distillation from it, so I'm reluctant to recommend it anymore, and would
probably instead recommend propylene glycol. |
Yeah, that definitely sounds similar to my expeirences. There was significant oxidation and dimethylsulfide formation. The dimethysulfide actually may
be why it was so difficult for me to vacuum distill it in fact, I did not consider that as I did not realize it's BP was so low until looking it up
just now.
| Quote: |
Granted, DMSO tends to raise the boiling point of the components of mixtures that it's in, but why wouldn't you just distill the tryptamine out?
Wikipedia says the boiling point is only 137C under 0.15 mmHg. I tried this once from PG and got a lot of bumping, although perhaps with better
boiling chips it wouldn't be as bad. |
I don't think my vacuum pump is good enough to sublimate the tryptamine. It may be, but I didn't want to risk it and waste time/product trying. If I
couldn't strip the DMSO then I probably can't distill the tryptamine, right? I mean the DMSO would come over first.
In the past when I've experimented with making tryptamine I did so in mineral oil. Usually I do not extract from the mineral oil, I just let the
formed tryptamine crystallize out over 24-48 hr and then solvate what remains between an acetic acid solution and DCM. The DCM is recovered, the
aqeous is basified until the tryptamine precipitates where it is filtered off. From there it's generally fairly pure, but I will then recrystallize it
in some sort of hydrocarbon to get nice white/tan crystals (which oxidize very quickly unless stored under an inert atmosphere).
I'm not very happy with that route, it seems it could be much improved, mainly just due to the solvent used, mineral oil, which is messy and
cumbersome to work with. I'll give PG a try, but other than the oxidation I'd imagine I'd have similar trouble removing it, I don't know. If I could
decarb it with little to no oxidation that would be a huge improvement alone though. I'm currently trying to work up the DMSO trial, it's not going
too bad, but I am having an emulsion to deal with which is taking most of the time so far just waiting for it to break.
[Edited on 3-9-2017 by alking]
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Melgar
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DMSO and PG both boil at around 190C, which is considerably higher than tryptamine. PG can't be reduced (and thus contribute to oxidation) under
ordinary conditions, although it can be oxidized. Probably not as easily as tryptamine though. If you're having a problem with oxidation, have you
tried using an antioxidant? I used to have a problem with oxidation of certain compounds when I'd leave them out to evaporate in recrystallization
dishes, until I started adding small amounts of ascorbic acid to them. BHT would probably work for this reaction, and isn't very expensive.
Even if you can't pull a full vacuum, I'd imagine tryptamine base would have a boiling point less than 150C or so.
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alking
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After working it up my yield was actually near 0%. There was a small amount of tryptamine formed from the, iirc, ~6g of starting material, but it was
so low it was not worth scraping off the filter unfortunately, less than 100mg if even I'd guess. It seems that most of the product oxidized or
otherwise formed some sort side product.
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PartVIII
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I have attempted the decarboxylation of tryptophan with DMSO and obtained 15-20% of theoretical.
The only way I found to remove the DMSO is to distill as much off as possible under high vacuum (<10 mmHg), then carefully perform an acid-base
extraction on the resulting residue. The distillation was carried out after I had already tried nearly every other method to strip the DMSO, so the
vast majority of it was already removed beforehand. Crystallization of the crude freebase (deep orange goo) from acetonitrile was unexpectedly
challenging.
I strongly recommend you ditch DMSO and try the decarboxylation with cyclohexanol (preferably with 0.5-1.0% 2-cyclohexene-1-one). Cyclohexanol can be
easily purchased on ebay and can be recycled via distillation. The synthesis is fairly straight forward:
Reflux AA in cyclohexanol (6mL per 1g Trp) with heavy stirring for 3-4 h or until CO2 evolution ceases. The mixture turns light yellow and turbid when
heated. Wisps of vapor 'pop' out every 5-10 seconds during heavy reflux. Slurry of SM will dissolve and the solution takes on the color of chalky
lemonade . The bath temperature never should reach above 180C. Popping will progressively calm down and become more infrequent. When popping stops,
replace reflux condenser with distillation head and distill off as much solvent as possible without discoloration (~50%).
**Omitting the distillation sacrifices only a small amount of yield and gives much purer product, especially when at atmospheric pressures. In
addition, remember to not heat the flask above 180C**
Filter off crude product and wash with water followed by a small amount of either petroleum or diethyl ether. Doing this gave me reasonably pure
product (NMR). Further purification steps, such as acid/base extraction or distillation, can be performed.
Recrystallization can be done several ways. I dissolved the crude freebase in acetonitrile and adding a several drop of dilute NaOH until the mixture
became turbid. It was left in a beaker covered by a watchglass for almost a week at room temp. Tan colored crystals caked the walls of the beaker.
Product was filtered and dried to yield freebase tryptamine as fluffy tan crystals (60-70% of theoretical).
The procedure this was adapted from reported >90% conversion, but claimed to isolate the amine as the HCl salt without providing details of the
workup or crystallization.
Any suggestions for improvements, especially with respect to the isolation of freebase amines, would be greatly appreciated.
[Edited on 7-9-2017 by PartVIII]
[Edited on 7-9-2017 by PartVIII]
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Mush
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This article is about why cyclohexenon was used as catalyst and why 98% pure cyclohexanol works better than 99% pure.
https://erowid.org/archive/rhodium/chemistry/trp.decarbox.enone.html
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Melgar
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Yep. And for those who don't have easy access to cyclohexenone or cyclohexanol, cavrone, from spearmint oil, has proven to work just as well. As a
bonus, you can buy quite a lot for under $10 on eBay and Amazon.
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turd
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That's crazy talk. DMSO distills long before tryptamine. You need a rather good vacuum to distill the latter.
By the way, it's spelled and pronounced caRVone.
Yes, handling tryptamine(s) can be quite tricky. 
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Melgar
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| Quote: Originally posted by turd |
That's crazy talk. DMSO distills long before tryptamine. You need a rather good vacuum to distill the latter.
By the way, it's spelled and pronounced caRVone.
Yes, handling tryptamine(s) can be quite tricky. |
I wouldn't try to distill much of anything from DMSO, since it tends to raise the boiling point of mixtures. You're right about tryptamine's boiling
point though, I was looking at the vacuum one.
I think my next attempt is just going to be using the amine as the solvent, then adding the amino acid in portions.
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Corrosive Joeseph
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Cyclohexanone to Cyclohexanol with H2O and Sodium Dithionite in 80% yields -
http://parazite.pp.fi/hiveboard/picproxie_docs/000427794-Red...
Synthesis of Cyclohexene from Cyclohexanol by Acid Catalyzed ( E1 ) Elimination (using H3PO4) -
http://academic.keystone.edu/JFalcone/SynthesisCyclohexene.h...
OTC Cyclohexanone......... Attached
/CJ
Attachment: OTC Cyclohexanone.pdf (184kB)
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Melgar
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It's actually technical grade cyclohexanol that apparently works best, due to cyclohexenone (not cyclohexanone) impurities. Of course, cyclohexanol
isn't made commercially via the way you described, so impurities would also be different.
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gatosgr
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What are you using this for? How do you identify the products? Making oligopeptides sounds more useful.
Found the patent for this : https://www.google.com/patents/US20140275569
[Edited on 23-9-2017 by gatosgr]
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Melgar
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One possible workup for DMSO decarboxylation: ion-exchange resin. It might not even have to be acidified. Just dilute with large amounts of water,
then run through a column of polystyrene sulfonate resin. It's orange-colored so a visual check would probably suffice. Rinse the resin with
distilled water, then elute with any ionic substance dissolved in water.
The first step in the process of learning something is admitting that you don't know it already.
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LD5050
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Would DMF be a good choice of solvent to decarboxilate tryptophan with? I was thinking of using DMF for the solvent and for the catylist a few ml of
peppermint oil. I was reading a paper and d-Pulegone found in peppermint and pennyroyal seems to be a good catylist.
UPDATE:
I went ahead and gave this a shot, I mixed 5 grams of tryptophan in 20ml DMF and added 3ml of peppermint oil into a 100ml RBF and set up for reflux.
At first the reaction mixture was milky white the tryptophan did not dissolve into the DMF. When the DMF started to reflux the mixture slowly turned
yellow and had the appearance of a yellow eggnog is how I would describe it.
Approx. 2 hours in the mixture became somewhat transparent and was the color of butterscotch candy. I placed a hose adaptor on top of the reflux
condenser and lead a small tube from the adaptor to a small beaker filled with water to see if I could measure or atleast tell if CO2 was being
produced. I noticed slight bubbling from the tube but not much probably a few bubbles every 5-10 seconds or so. I believe this might be CO2?
I'm now on the fourth hour of reflux and when I removed the hose adaptor from the refluxcondenser I noticed a strong smell of ammonia. Any idea of why
Its producing the smell of ammonia , is this normal?
[Edited on 10-2-2017 by LD5050]
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