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Chemical Guide to classic Psychedelics (DMT, "-N-Oxide, "-Acetate, 5-Meo-", Harmalas, Options
 
Brennendes Wasser
#1 Posted : 1/12/2021 7:20:03 PM

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So while browsing on Page #2 of Google I found some stuff relating to common psychedelics, hope this will be useful!

There is already a page on the wiki, but this data is 90 % new and so I would also like to post it here, as it may be more accessible for people who rarely check the wiki.

Included is data about solubility, which may come in handy when extracting stuff from stuff or also to know what to use and how much for convenient recrystalization.

Also included is data about the vaporization profile. On the Internet you can find all kind of different values for vaporization and even Wikipedia has obviously totally wrong values for DMT (160 °C at 0,0008 bar wtf) and Bufotenin (320 °C at 0,00013 bar wtf). Temperatures given here now are reflecting the actual vaporization point and also give a range of optimal vaporization temperatures, which may be interesting for the community. Twisted Evil
Measurement was done with an IR-Thermometer on a hotplate, so give it +- 5 %.

Also most Compounds have an IR-spectrum included, measured with Attenuated-Total-Reflection-Mode (ATR). Some of these are quite ugly, regarding the Transmission rises above 100 % for sometimes.Confused May be a problem with baseline, but well no drama. No idea what may be useful about that, but its free data. Some have also included an UV/Vis spectrum, measured in Acetonitril.

More compounds may be added in future.
If there is an XXX then this value will come soon.

Current content:

Check the

BIG Analysis on DMT !

Lots of interesting and possibly new stuff unraveled ;o
 

Trippy glass for trippy people.
 
Brennendes Wasser
#2 Posted : 1/12/2021 7:20:47 PM

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DMT




Solubility:

boiling Naphtha (80 °C, C6-C7, 60-80 °C)
XXX g in 1 L
XXX mg in 100 ml

Naphtha (20 °C, C6-C7, 60-80 °C)
XXX g in 1 L
XXX mg in 100 ml

Naphtha in the freezer (-20 °C, C6-C7, 60-80 °C)
1,09 g in 1 L
109 mg in 100 ml


boiling n-Hexane (69 °C)
XXX g in 1 L
XXX mg in 100 ml

n-Hexane (20 °C)
XXX g in 1 L
XXX mg in 100 ml

n-Hexane in the freezer (-20 °C)
XXX g in 1 L
XXX mg in 100 ml

Besides with no extent soluble in Room Temperature Acetone, IPA, Ethanol, Methanol, DCM, Et2O, MEK, Toluene, Xylene, DMF



Phase Transitions:

There are at least 3 reported crystal structure modifications of DMT, coming in different crystal grids and thus different melting points. I just know the one that precipitates already at room temperature more yellow and the one that precipitates at lower temperatures fully white. Hence I believe the later one might be more crystaline as it takes longer and slower precipitation, so the melting point might also be higher.


Measured with IR Thermometer on a hot plate (give it +- 5 %)

Melting Point
58 °C

First fumes starting
100 °C

Strong fumes from
160 °C+

No fumes arising anymore
190 °C

I think 175 °C is optimal for vaporization.


IR-Spectrum (measured in attenuated total reflection method (ATR))




UV-Vis spectrum (0,05 mg/ml in Acetonitril)



Comments:


Not much to say. Dont heat your Spice above 200 °C, this will just cause combustion at some point. Therefore approaches with open flame and Changa will always create unhealthy smoke, that bad charred flavor will just be hidden by the strong DMT-smell. Better use a controlled way of delivering 160 - 200 °C and inhale fresh healthy swiss-alps-DMT.

Also that solubility in the freezer value may now help you to plan your re-x. No more "Maybe you just have to evaporate more Naphtha to get any product? Confused "
Just estimate that ~ 1 mg of Spice will be still held back per 1 ml of Naphtha after freeze-precipitating. This means dont re-x your 100 mg Spice in 100 mg Naphtha Big grin Also if you haven't got any precipitation from 100 ml of Naphtha in the freezer, then you still wont get more than 100 mg from that even if you further reduce ... maybe the problem happened earlier then. Embarrased

That UV/Vis-spectrum is not that interesting, but it shows exactly the Tryptophane-Absorption at 280 nm, which is also used for Protein UV-Detection. Nothing special else though.

If more polymorphs may be accessed with different melting points, these could be measured by XRD and then maybe higher-melting-point-spice will also show greater degrees of crystalinity. It would be senseful if very amorph Spice would be the reason for people observing DMT melting as low as 50 °C and high-crystalinity Spice would be causing 80 °C melting reports. Nevertheless that 58 °C sample looked also quite crystalline ...


Bioassay:

Active
Check the

BIG Analysis on DMT !

Lots of interesting and possibly new stuff unraveled ;o
 
Brennendes Wasser
#3 Posted : 1/12/2021 7:21:32 PM

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DMT-N-Oxide (coming soon)


XXX Picture


Synthesis:

Dispense 1 g of DMT in 2,4 ml of 30 % H2O2 (does not dissolve as this is basically water). Add amounts of Ethanol while stirring until all DMT is dissolved. Should be ~ 7 ml in total. Stirr this mixture for 48 h at Room Temperature until full conversion. Evaporate all solvent, leaving behind DMT-N-Oxide. (source)


Solubility:

boiling n-Hexane (69 °C)
XXX g in 1 L
XXX mg in 100 ml

DMSO (RT)
XXX g in 1 L
XXX mg in 100 ml


Phase Transitions:

Many people have wondered and debated about whether DMT-N-Oxide could be smoked and had an effect. That unusual structure of course must change its properties by far, so normally it would have been expected that a much higher temperature is needed. Also that Amine would normally be important for in-vivo recognition at enzymes / receptors, rendering it possibly inactive for the regular pathway of DMT causing its psychedelic effects, while still being a metabolist of DMT, making it prone to further degradation. People have reported to feel effects upon smoking N-Oxide containing Spice, but this effect may have just been related to the DMT effect, similar to Jungle Spice.


Measured with IR Thermometer on a hot plate (give it +- 5 %)

Melting Point
XXX °C

First fumes starting
XXX °C

Strong fumes from
XXX °C+

No fumes arising anymore
XXX °C

I think XXX °C is optimal for vaporization.


IR-Spectrum (measured in attenuated total reflection method (ATR))

XXX


Comments:


XXX


Bioassay:

XXX
Check the

BIG Analysis on DMT !

Lots of interesting and possibly new stuff unraveled ;o
 
Brennendes Wasser
#4 Posted : 1/12/2021 7:22:18 PM

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DMT-Acetate




Solubility:

Soluble to no extent in water.

Insoluble in all organic solvents. Maybe soluble in DMSO (XXX).


Phase Transitions:

Many people have wondered and debated about whether DMT-Acetate can be smoked direclty. Common sense would tell it is a salt and would take insane heat to vaporize. Also it would be caustic to the throat and lung as it is still 1/4 Acetic Acid. So here there is some actual data about this:


Measured with IR Thermometer on a hot plate (give it +- 5 %)

Melting Point
/

First fumes starting
130 °C

Strong fumes from
165 °C+

No fumes arising anymore
190 °C

I think 175 °C is optimal for vaporization.


IR-Spectrum (measured in attenuated total reflection method (ATR))




Water-Uptake


It was reported only -Fumarate/-Maleate/-Citrate/-Ascorbate salts are the common variants that are not hygroscopic. I'm not sure whether DMT-Acetate really is also hygroscopic, it may just already be an oil in general - it seems to me - even though thats anti-intuitive, being a salt itself.
Still this could be verified very easily by NMR. Water appears in 1H-NMR at 4,67 ppm.


This means you can determine the water content very precisely by calculating:

Integral 4,67 ppm (s) = I(w)

Integral 2,27 ppm (s) (CH3-) = I(D)

1. Calculate Molecule ratio of Water Molecules to D-Acetate-Molecules:

= (0,5*I(w)) / (0,16*I(D)

2. Calculate Mass Fraction of Water Molecules to D-Acetate-Molecules:

100 * (18/248 ) * Molecule ratio = water content [%]

Example: if 1H-NMR shows an Integral of 2,75 at 4,67 ppm (s), then the water content in DMT-Acetate is 10 %. But well thats just a random example and not measured. I would have access for measurement, but I dont feel quite well to do that right now ...


In theory water could also at least qualitatively identified in that IR-spectrum. There should be a big peak at ~ 1600 cm^-1, but that could also be from acetic acid. So not really sure, but I also dont really have a Clue about IR.


Comments:


So it seems that DMT-Acetate can indeed be smoked, just based on having the same vaporization range as Freebase Tryptamines. Quite interesting that there is practically no difference to DMT. It both starts to emit strong vapors above 150 °C and stop vaporizing below 200 °C. Therefore it does not seem to be retarded strongly by the fact that its a salt. Maybe it may be explainable by counting Acetate as a soft ion and not a hard ion like chloride or sulfate.


Bioassay:


A small portion of DMT-Acetate was vaporized according to the optimal vaporization temperature. The vapor was not caustic and no acetic acid smell was present, neither it was unpleasant to the lungs. A regular DMT-like effect was felt. If it had the same potency, hard to say as this oil is hard to weigh. It would be possible to weigh a loaded apparatus and weigh it after the dose was taken. As normally even the tiniest amounts of Acetic Acid are very irritating to the lungs, it seems there is no back dissociation form Acetate to Acetic Acid and the Acetate is not irritating to the lungs. This also means that the DMT will be delivered to the Lungs as a salt and even this protonated form shows some promising metabolism. This is remarkable as other compounds are often blocked for desired physiological pathways when not freebased. Still, being a slushy oil, this is not a convenient form to handle your spice.
Check the

BIG Analysis on DMT !

Lots of interesting and possibly new stuff unraveled ;o
 
Brennendes Wasser
#5 Posted : 1/12/2021 7:23:02 PM

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Bufotenin / 5-OH-DMT




Solubility:

Bufotenine is the most polar common Tryptamine, only surpassed by Psilocybin. Therefore it is completely insoluble in Hexane/Naphtha, but can be soluble in pH > 12 water due to Phenol deprotonation. It is hard to crystalize and will mostly give just an oil. The following solutions can give crystalline products:


1:3 Ethyl Acetate:Naphtha (C6-C7)
Boiling = 7,6 g/l = 760 mg in 100 ml
20 °C = 3,6 g/1 l = 360 mg in 100 ml
- 20 °C = 3,5 g/1 l = 350 mg in 100 ml
Selectively dissolves Bufotenine mostly, not the more polar Alkaloids in Anadenanthera colubrina seeds. (Picture) This mixture will still catch up 2 % of the more polar alkaloids, as you can see here in NMR and GC. Nevertheless its 98 % pure Bufotenin. For 100 % use Xylene. Also when pulling with this on Anadenanthera colubrina seeds, defat first with Naphtha.


Xylene
Boiling = 43 g/l = 4,3 g in 100 ml
- 20 °C = 14,5 g/l = 1,45 g in 100 ml
Selectively dissolves Bufotenine even better, than the more polar Alkaloids. Use Xylene for a 2nd re-x to get pure white crystaline Bufotenine. Nevertheless, it also holds up more Bufotenine still after being in the freezer and harder to evaporate than 1st mixture. (Picture is on top) Why is Xylene a good solvent, even though its way more unpolar than Bufotenin?
69ron gives explanation (cant find source): Xylene can heat Bufotenin above its melting point, then its characteristics drastically change and make it soluble. This can also be used with Limonene, but Limonene is much worse as it needs to be heaten additional 30 °C to 175 °C, which causes partial degradation of Bufotenin.


Ethyl Acetate
Boiling = 280 g/1 l = 28 g in 100 ml
20 °C = 72 g/1 l = 7,2 g in 100 ml
- 20 °C = 50 g/1 l = 5 g in 100 ml
Mentioned for recrystalization in literature. Not recommended, seems to cause a darkening (Picture, right). Also very high solubility overall, means you have to use very minimal amounts of solvent = inconvenient to handle. Furthermore if the Bufotenin has a low purity it will just stay oily after re-x.


Besides with no extent soluble in Room Temperature Acetone, IPA, Ethanol, Methanol, DCM, Et2O, MEK, DMF


Phase Transitions:

Measured with IR Thermometer on a hot plate (give it +- 5 %)

Even though 146 °C is given in literature, both amorph and crystaline Bufotenin gave the following melting point.

Melting Point
108 °C

First fumes starting
160 °C

Bufotenin turning brown (possible phenol -> keton oxidation)
170 °C

Strong fumes from
190 °C+

No fumes arising anymore ...
230 °C

... leaving behind a considerable amount of charred Bufotenin. Seems that it cant be fully evaporated without causing at least partial degradation.

I think 210 °C is optimal for vaporization.


IR-Spectrum (measured in attenuated total reflection method (ATR))

XXX


Comments:


So Bufotenin is hard to crystalize, but easy when using the 2 mentioned solvents. When not heating to 170 °C it seems quite stable and that phenol is not prone to oxidation as people may think. It stays clear white for months even at room temperature.



Bioassay:

The vapor in low concentrations tastes nicely like toasted nuts. In high concentrations it may feel nauseating. But maybe thats just as the overall effect of Bufotenin is a little but nauseating. Seems this cant be avoided, as Bufo is quite similar to Serotonin and therefore causing intense vasoconstriction and tingling in the face and fingers. Not too pleasant. Also face turns quite cold. Red coloring at the face could not be observed. Still other people have reported very promising / intense / interesting experiences when vaped.
Oral consumption seems rather ineffective. 100 mg of Bufo-Fumarate just gave a slight effect, comparable to 1 g of Mushrooms possibly, while still being bad to the stomach.
Check the

BIG Analysis on DMT !

Lots of interesting and possibly new stuff unraveled ;o
 
Brennendes Wasser
#6 Posted : 1/12/2021 7:23:48 PM

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5-MeO-DMT (coming soon)


XXX Picture


Solubility:

boiling n-Hexane (69 °C)
XXX g in 1 L
XXX mg in 100 ml

Besides with no extent soluble in Room Temperature Acetone, IPA, Ethanol, Methanol, DCM, Et2O, MEK, Toluene, Xylene, DMF

5-MeO-DMT is not easy to crystalize, just like 5-OH-DMT. This procedure may work:

XXX


Phase Transitions:

XXX


Measured with IR Thermometer on a hot plate (give it +- 5 %)

Melting Point
XXX °C

First fumes starting
XXX °C

Strong fumes from
XXX °C+

No fumes arising anymore
XXX °C

I think XXX °C is optimal for vaporization.


IR-Spectrum (measured in attenuated total reflection method (ATR))

XXX


Comments:


XXX


Bioassay:

XXX
Check the

BIG Analysis on DMT !

Lots of interesting and possibly new stuff unraveled ;o
 
Brennendes Wasser
#7 Posted : 1/12/2021 7:24:34 PM

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5-AcO-DMT




There is practically no information about 5-AcO-DMT on the Internet (not to be confused with 4-AcO-DMT). Here is some maybe helpful stuff.

Solubility:

boiling n-Hexane (69 °C)
5,0 g in 1 L
500 mg in 100 ml

n-Hexane in the freezer (-20 °C)
1,3 g in 1 L
130 mg in 100 ml

Besides with no extent soluble in Room Temperature Acetone, IPA, Ethanol, Methanol, DCM, Et2O, MEK, Toluene, Xylene, DMF



Phase Transitions:
Measured with IR Thermometer on a hot plate (give it +- 5 %)

Melting Point
83 - 88 °C

First fumes starting
190 °C

No fumes arising anymore
240 °C



IR-Spectrum (measured in attenuated total reflection method (ATR)





UV-Vis spectrum (concentration < 0,01 wt-% in Acetonitril)





Bioassay:

no effect lol


long story:

20 mg 5-AcO-DMT were vaporized over the course of 10 min.
The vapor taste is very smooth and not yukky like 5-OH-DMT. Also it does not turn black upon heating and vaporizes without any residue - just like pure DMT. In contrast this is not the case for 5-OH-DMT. It quickly turns black above 170 °C and only 50 % will vaporize, while the other 50 % will form a black burned layer on the surface, no matter how soft and gently you are heating it.
Seems like the 5-OH is the source of evil regarding the properties of 5-OH-DMT aka. Bufotenine which makes it hard to crystalize and also generates an unconvenient vaporization profile. Therefore the 5-AcO seems to make the molecule much easier to handle in any way.

Nevertheless no effect was felt. Rolling eyes

Vaporization overcomes first-pass-effect by the liver, maybe this is a reason. 5-AcO-DMT should be a prodrug of 5-OH-DMT. De-Acetylation should be fast in the body, but no idea where it takes place - maybe that step is skipped when inhaling vapors. Nevertheless that would mean the prodrug is totally inactive. Compared to Psilocin, its prodrug 4-AcO-DMT is reported to be instantly active when inhaled, suggesting it has an effect itself. Therefore it would be strange if thats not the case for 5-AcO-DMT. Only solution would be: What you see in the first picture is not 5-AcO-DMT, which is nearly impossible, but cant be proven by MS or NMR right now.
Still, it has a distinct Tryptamine / Alkaloid taste. Maybe I should spend some time comparing the IR to this one.

3257 is hard to see, but might be there
(2186 not in literature spectra)
1752 is there
(1698 not in literature spectra - Acetic Acid?)
1373 is there
1216 is there
1168 is there
948 is there

... seems like true 5-AcO-DMT. 2186 + 1698 might be any residual stuff, but their signals are quite strong and in contrast the purity should be super high.
Check the

BIG Analysis on DMT !

Lots of interesting and possibly new stuff unraveled ;o
 
Brennendes Wasser
#8 Posted : 1/12/2021 7:25:19 PM

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Harmala Alkaloids




Solubility:


Many people have debated about Harmala Solubility and what to use if making Changa. Myself I had the feeling like they are soluble in exactly nothing. Here are the most common solvents, from good to bad.


boiling DCM (40 °C)
24,9 g in 1 L
2,5 g in 100 ml

hot DMSO (100 °C)
23,3 g in 1 L
2,3 mg in 100 ml

boiling Methanol (64 °C)
12,7 g in 1 L
1,3 g in 100 ml

boiling Ethanol (78 °C)
8,0 g in 1 L
802 mg in 100 ml

boiling Aceton (56 °C)
3,6 g in 1 L
360 mg in 100 ml

boiling IPA (82 °C)
XXX g in 1 L
XXX mg in 100 ml


Seems like from any good solvent DCM would still be the most healthy one. DMSO is totally healthy, but will never evaporate, so this does not help for Changa people. But if you can be sure to 1000 % evaporate stuff, then Methanol would also be an option. If being more on a safe side, Ethanol is then the best. It is also possible to just prepare everything in an even 1-layer and just sprinkle the Harmalas on top.



Phase Transitions:

Measured with IR Thermometer on a hot plate (give it +- 5 %)

Melting Point
/ sublimating directly

First fumes starting
180 °C

Sublimation while forming small black clumps
205 °C

No fumes arising anymore, leaving behind black residue
240 °C

I think 215 °C is optimal for vaporization.
Interesting, I thought it would be ways above DMT. That means that vaporizers like the Crafty / Mighty can indeed also partioally vaporize Harmalas, it was always stated they could only be used for infused herb. Maybe in future I may test Harmin and Harmalin on their own, for now only the mixture. But they should not differ too much anyways.



IR-Spectrum (measured in attenuated total reflection method (ATR))




Ratio of Harmalin/Harmin

This can be easily determined by 1H-NMR. The additional sp3-Protons of Harmalin give Signals at 3,8 ppm (t) / 3,97 ppm (t) both not being homotop, 2,73 ppm (t).

Ratio is:

XXX

Comments:


XXX

Bioassay:

400 mg Harmala Alkaloids were eaten. Just a quick test to verify whether they indeed also contribute to Nausea. Intense vomiting. Nausea for hours. Really strong effect, like a mixture of LSD / stoned. Walking not easy. All in all bad experience.
Check the

BIG Analysis on DMT !

Lots of interesting and possibly new stuff unraveled ;o
 
Brennendes Wasser
#9 Posted : 1/12/2021 7:26:15 PM

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Salvinorin A (Salvia Divinorum)




Solubility:

boiling IPA (82 °C)
XXX (slightly soluble, just try low amounts)

IPA in fridge (7 °C)
I remember to have read somewhere 1 mg/ml

After dissolving your Salvinorin in boiling IPA to separate it from Chlorophyll, add 3 Volumes of Naphtha to the IPA and place it in the Fridge. This will not only speed up separation, but also further decrease Solubility of Salvinorin in the IPA-Mixture.

By using this method its possible to precipitate nearly all Salvinorin, so better to it multiple times until there is no more greenish colour. But only use a few ml at once for re-x.



Phase Transitions:

Salvinorin is a giant molecule (M = 432 g/mol) and thus should either not vaporize at all or just combust. Still regular vaporization is possible as some people may agree.


Measured with IR Thermometer on a hot plate (give it +- 5 %)

Melting Point
/ sublimating directly

First fumes starting, Salvinorin A turning brown
190 °C

No fumes arising anymore
270 °C

I think 250 °C is optimal for vaporization. Still it will not vaporize 100 %. Seems like that molecule is just too big: Degradation cant be avoided completely.


IR-Spectrum (measured in attenuated total reflection method (ATR))




UV-Vis spectrum (2,7*E-04 mol/L in Acetonitril)



Comments:


Quite unusual that this molecule vaporizes so early. But like with Bufotenin and Harmalas it seems that a clean vaporization is not possible - there are seemingly too many options for that molecule to be also destroyed / broken down while being heaten up. Still, I think Temperatures up to 270 °C are still reachable with electronic vaporizers. Would be quite interesting if people may have success with these and pure Salvinorin.

Also that UV/Vis looks terrible, with negative absorption at some point. Maybe Salvia cannot only create light in your head, but also in Acetonitril. Or there was some problem with the Blank :/ Still as most compounds here, transparent until UV-B Region starting.
Nevertheless there is no real absorption visible, which nicely aligns with the fact that there are no big pi-Electron-Structures in Salvinorin. There is just that Furan Ring, but its rather small so its already expected that all the Tryptamines have a stronger Absorption due to their Indol-"chromophor".


Bioassay:

XXX
Check the

BIG Analysis on DMT !

Lots of interesting and possibly new stuff unraveled ;o
 
Brennendes Wasser
#10 Posted : 1/12/2021 7:27:06 PM

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Whatever Placeholder
Check the

BIG Analysis on DMT !

Lots of interesting and possibly new stuff unraveled ;o
 
downwardsfromzero
#11 Posted : 1/13/2021 2:56:52 PM

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Great work as ever, BW!

I'm thinking of tabulating the data as you complete it.

(As an aside, most of the chemical terminology can be anglicized by adding an -e on the end of the German term:
acetonitrile, ionophore, etc. but phenol and the -OH "-ols" stay the same. "Indol" becomes "indole", however, on account of its lack of an -OH group. Etheric -ols like "cineol" and "anethol" take the -e, so to speak Big grin, and "-in" becomes "-ine" if it's nitrogenous: e.g. "anilin" → aniline, but salvinorin, for example, stays the same. And for some reason, psilocin, baeocystin and psilocybin are random exceptions to this rule - with bufotenin(e) seemingly randomly switching between both camps Laughing

Anyhow, I think your bandwidth is best taken up doing what you do best but the footnote is here for those who may have been wondering about some of the chemistry terms.)
Ora, lege, lege, lege, relege et labora

“There is a way of manipulating matter and energy so as to produce what modern scientists call 'a field of force'. The field acts on the observer and puts him in a privileged position vis-à-vis the universe. From this position he has access to the realities which are ordinarily hidden from us by time and space, matter and energy. This is what we call the Great Work."
― Jacques Bergier, quoting Fulcanelli
 
 
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