The smell of spice

[Infundibulum]

Many people are aware of/like to admit/have read throughout the internet that the spice should have this plastic-like synthetic smell. SWIM's FOAF has made some observations regarding this issue and I think he's mostly convinced that the smell of the spice comes either from some leftovers of naphtha or less likely due to some way naphtha and similar solvents may interact with the spice.

Now, this guy extracts spice (and any other alkaloids using FASA, then he freebases the alkaloids using a calcium hydroxide or sodium carbonate paste. The freebased alkaloids are collected using acetone that quickly evaporates to leave the freebased alkaloids behind.

The latter freebased alkaloids smell of nothing, absolutely nothing to be more precise. One can understand what that is only by testing it (burning in the mouth) or by smoking it.

The method described above results in a total alkaloidal mixture from MHRB. Is it very likely therefore that the "plastic" smell of spice is somehow masked? SWIM thinks this is not the case.

So he got his FASA-derived total freebased alkaloids and washed them with warm naphtha to get the white spice out. The warm naphtha was freeze-precipitated, and the resulting whiteish precipitates were recovered and dried.

When the precipitates were dry and very easy to scrape, he noticed that the spicy plastic smell was there! He dissolved this smelly spice in acetone, and he gave it a good 2 days to dry. The final product, nice white spice was now devoid of its smell!

This reminded him a much earlier observation; his very first extract smelled like plastic. At this stage he was concerned of the presence of sodium hydroxide in his final product. So he dissolved the spice in methanol expecting the sodium hydroxide to fall out undissolved. Nothing really happened, so he evaporated the methanol to recover the spice. When it was totally dry, it was devoid of any smell! Upon trying the product however, he had no doubt of its nature.

So where do these observations lead him? He is concerned that the plasticky smell is some naphtha remains. When this spice is dissolved in acetone or methanol any crystal structures that may retain or trap inside them naphtha are destroyed and hidden solvent residues are free to dissolve in the acetone or methanol. Finally, while acetone or methanol evaporate the previously crystal-trapped smelly residues are given some time to evaporate, leaving smell-free spice.

Alternatively, any naphtha residue retained in the crystal structure of the freebase may "volatise" the spice molecules thus making them smelly.

Are other people aware of similar cases?

 

[Garulfo]

Very interresting hypothesis. My friend will try to verify it...
Smell is also compared to mothball. The french word for mothball is "naphtaline". Naphta-line...
It must be also noted that when the spice is yellow/brown, it smells much stronger than when it is clean. So impurities have also an impact on the smell.
"Fresh" spice (just dried) also smell much stronger than old spice stored since a while, which would corroborate your hypothesis of trapped solvent at nano level in the crystals.

 

[amor_fati]

SWIM's noticed a strong plastic odor from spice that's never even touched naphtha. So unless naphtha, xylene, and toulene all leave something very similar behind or interact with the spice in an extremely similar way, SWIM doubts it has anything to do with naphtha in particular.

 

[endlessness]

SWIM doubt it is any naphtha, as stuff dried thoroughly with vacuum also smells strong

btw, SWIM introduced a funny crazy artist friend to spice yesterday, and this friend gave a good definition of what it smells like: new tennis balls

 

[burnt]

SWIM's noticed a strong plastic odor from spice that's never even touched naphtha. So unless naphtha, xylene, and toulene all leave something very similar behind or interact with the spice in an extremely similar way, SWIM doubts it has anything to do with naphtha in particular.

Naptha contains some aromatic hydrocarbons (things like toluene xylene etc) and since the aromatic hydrocarbons have a high boiling point they could be left behind from incomplete drying of naptha.

So where do these observations lead him? He is concerned that the plasticky smell is some naphtha remains. When this spice is dissolved in acetone or methanol any crystal structures that may retain or trap inside them naphtha are destroyed and hidden solvent residues are free to dissolve in the acetone or methanol. Finally, while acetone or methanol evaporate the previously crystal-trapped smelly residues are given some time to evaporate, leaving smell-free spice.

Alternatively, any naphtha residue retained in the crystal structure of the freebase may "volatise" the spice molecules thus making them smelly.

Are other people aware of similar cases?

It is well known that residual solvents get 'trapped' within crystals. SWIM dries all SWIMs samples under reduced pressure with controlled temperature so most of the solvent should go away. However SWIM also notices residual solvent smell even after drying even when doing it in the rotoevaporator (when SWIM uses toluene). So thats why SWIM always redissolves SWIMs final product in alcohol and then redries it (if aromatic hydrocarbons were used in the extraction, if pure hexane was used this is not a problem as hexane is very volatile and dries easily) that way any residual aromatic hydrocarbon solvents will go away and only a trace amount of ethanol might be left over which makes no difference and the smell is gone.

This works every time in getting rid of the residual solvent smell and should work fine for people who do not have fancy things like rotoevaporators. SWIM recommends that everyone (who can get pure alcohol) who uses aromatic hydrocarbons (toluene or xylene even naptha because it contains such compounds) in their extractions does this as there is a very good chance the stuff does not dry completely or gets trapped within the crystals. But if no solvent is smelled its probably safe. With naptha this is less of an issue as most of it is straigh chain volatile hydrocarbons but toluene and xylene SWIM recommends this be done.

I would also like to make an additional comment on the smell. As infunddiblum pointed out his freebased alkaloids after doing the FASA method have no smell. SWIMs spice has no plastic smell but it does usually have a smell. However the smell is exactly like that of the yellow oil which SWIM cleans out of his spice extracts. Many of us believe this yellow oil is DMT oxide so that is probably the smell that SWIM is smelling as only very little of it in a spice extract would be detectable by the nose. Now that smell the smell of DMT oxide is almost exactly like indole (for the less chemically inclined indole is the main skeleton of tryptamines, the indole ring). So either spice or DMT oxide is what SWIM is smelling and SWIM noticed that it smells similar to indole which makes perfect sense. Warning do not smell indole it is toxic but SWIM was curious and one day smelled it (its strong and scary smelling!, its like the smell of spice extracts x 100).

In conclusion SWIM never smells any weird plastic smell as SWIM believes that is not the smell of spice but the smell of residual solvent. Spice or its degradation product DMT oxide smells like indole more then anything. SWIM can see that smell being described like moth balls or something but SWIM can't remember that smell so all SWIM can really say is that is smells like indole (even though that doesn't mean much to most of the world).

 

[Infundibulum]

Nice input, thanks guys!

It is also likely that, as burnt wrote that dmt-N-oxide may smell more, even thought total alkaloid extraction using xylene coupled to FASA does not really smell at all.

On the other hand, naphtha extracted/re-crystallized product does smell "spicy" and some random drunk guy I met in a pub once claimed that the yellower the product (post-naphtha treatment) the stronger the smell.

SWIM's noticed a strong plastic odor from spice that's never even touched naphtha. So unless naphtha, xylene, and toulene all leave something very similar behind or interact with the spice in an extremely similar way, SWIM doubts it has anything to do with naphtha in particular.

But was that spice obtained by FASA or just by xylene/toluene evaporation? Because for SWIM products resulting from simply evaporation xylene pulls do smell very "plasticky"

Now SWIM's FOAF is inclined to believe that maybe dmt-N-oxide (or even dmt?) is/are more likely to degrade (hence releasing the indolic smell) in situations where residual solvent can remain trapped in the crystals.....

This would be weird in since solvents like xylene or naphtha are used in chemistry by virtue (among many others) that they are fairly inert chemically and less likely to modify/react with the substances dissolved in them.

 

[burnt]

even thought total alkaloid extraction using xylene coupled to FASA does not really smell at all.

Perhaps its because the FASA method is avoiding the n-oxide formation or rather its not extracting it. Because when you make the salt only DMT fumarate should come out. When you freebase that only the spice freebase should be made. So STB and A/B there is almost always n-oxides even if one thinks they cleaned their spice perfectly, SWIM is willing to bet some of it is always there. These compounds are easily detected by the nose detector so a small amount would smell.

Now SWIM's FOAF is inclined to believe that maybe dmt-N-oxide (or even dmt?) is/are more likely to degrade (hence releasing the indolic smell) in situations where residual solvent can remain trapped in the crystals.....

This would be weird in since solvents like xylene or naphtha are used in chemistry by virtue (among many others) that they are fairly inert chemically and less likely to modify/react with the substances dissolved in them.

While the reagents are fairly inert the heating the acids and the bases could cause such things. Also oxygen levels could also be playing a role. Oxygen is pretty much always there so DMT freebase the more air its around the more it will form n-oxides. When its a salt that is less likely to happen because the spice is stable. So when SWIY made spice freebase from the salt it was fresh clean spice.

...Maybe?

 

[lorax]

a friends spice never smells like plastic or solvent. its more like a flowery kind of smell. it smells very sweet and mysterious. a friend has some double preciped and 10x remelted and redried white spice which also smells like this only a little lighter.

 

[lorax]

now SWIM is really afraid of using his spice as it should smell like nothing but still has this flowery smell to it. he now wants to use the FASA conversion method on all of his extracts he made up till now. first he wants to convert 10g of jungle spice to jungle spice fumarate.

 

[burnt]

^^There is not really a reason for concern as its normal for spice extracts to smell. Obtaining absolute purity is not necessary. The point is they shouldn't smell like solvent but should smell like spice (or what we are theorizing spice oxide).

 

[amor_fati]

But was that spice obtained by FASA or just by xylene/toluene evaporation? Because for SWIM products resulting from simply evaporation xylene pulls do smell very "plasticky"

Through FASA. However, SWIM does recall it smelling slightly stronger when still a little wet than when almost completely dry, so perhaps it is due to the spice being volatised (by any sort of solvent, possibly even water) more-so than the actual odor of the solvent.