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Important Boiling Points

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spaghettiman

Rising Star
I have done some searching recently, and have been surprised to find
that there seems to be no decent source stating the boiling points of
the freebase forms of some alkaloids of interest:

DMT
5-MeO-DMT
Gramine

Now, the merck index states that DMT has a BP of 60-80C, this is clearly
incorrect. Not at ambient pressures.... this information needs to be
filled in. Shulgun should have measured it for us damnit! he states that
this value is incorrect himself!(TiHKAL)

gramine HCl decomposes at 191C (merck)
gramine freebase melts at ~138(merck) so we know it boils higher than
that. probably much higher

bufotenin has a BP of 320C(merck)

5-MeO-DMT I have not done enough research on, but the BP at atmospheric
pressure seems unavailable, though should be high. here is what i have:

The residue was distilled at the KugelRohr to provide a colorless fraction distilling at 160–170 °C at 0.6 mm/Hg, that crystallized on cooling.There was thus obtained 12.8 g (78%) 5-methoxy-N,N-dimethyltryptamine (5-MeO-DMT) which on recrystallization from hexane had a mp 69–70 °C.
Click to expand...
(TiHKAL)

This is very low pressure. Though, i believe the eroneous values for DMT are from this mixup, 60-80C is correct at very low pressure, a few mm/Hg.


Now, does anyone have any information that can fill any of these gaps?
am i crazy? How the hell has no one measured the BP of DMT at atm?!?!?!?! why
do people still cite the merck value?!

lets make a table of these values, or our best guesses. we want the freebases for use for future sublimation teks for phalaris and other dirty sources.

This subject needs attention... We need a better grasp on these basic properties.

I think DMT vapes around 170-200C at normal atmousphereic pressures. I have no quantitative evidence of this at this time. discuss...
 
New results using a heat gun are suggesting DMT has a BP higher than 300F =~ 150C

swim is starting to think that we are looking at a BP of about 180C. At around this temperature vaporization seems to be happening readily.

This is not the best way to go about this, but i feel we are looking at the ballpark here
 
well here lets think about this...even though water isnt up to its BP its still giving off a lot of moisture..i think what you are looking for is like the flash point where it happens very quickly..

so if i was going to use a sublimator to purify the dmt..i would want to put it on the lowest heat possible and let it run for a long time..im not looking for it to flash into vapor..im looking to selectively separate the dmt from other substances and i think here patience is key...

i like what you are doing here..we really do need more data on this..once we figure this out we can really get to using phalaris grasses and separating the dmt from other possibly harmful chemicals
 
evaporation happens below boiling point too... for it to be the boiling point its going to be the minimum temperature at which the whole mass of liquid wants to become a gas. the liquid starts taking heat now to make it into a gas, maintaining this temperature(the boiling point) until a different azetrope is reached. now the liquid heats until it reaches the new BP at which time it can start pulling heat for the phase change again.

this is how distillation proceeds.

Either way, the merck number is flat out wrong. here are some citations which should have been included previously:

A white oil distilled over at 130–140 °C at 0.1 mm/Hg, and crystallized spontaneously. This distillate weighed 0.77 g, and was recrystallized from boiling hexane after decanting the solution from a small amount of insolubles. There was thus obtained 0.40 g of dimethyltryptamine (DMT) with a mp 67–68 °C.
Click to expand...
(TiHKAL)

The Merck Index gives the very early, very low values of 46 °C and 44.6–46.8 °C and claimes claims that the bp is 60–80 °C with atmospheric pressure being implied. It is clearly in error on both matters.
Click to expand...
(Shulgun, TiHKAL)

edit:
good news benzyme! that must be the real value!

so now we have:
bufotenin: 320C
DMT: 160C
5-MeO-DMT: ???
Gramine: ????

Now i wonder what the heat of vaporization is of any of these chemicals, this would help in verifying these values and extrapolating on them with the Clausius-Clapeyron equation
 
it's actually more appropriate to look at it in terms of theoretical plates than an azeotrope. it's only one compound being considered

*edit* 160 C at 0.6 mmHg is 380 C at ambient pressure
hmm...SWIM never let it reach 160 C at 22 in Hg. he kept it around 149-151 for almost an hour. at 22", it would be closer to 280, 285.


nomograph.gif
 
my previous calculations were incorrect, swim was high. swim didnt convert to kelvin, and swim also was confused on what you were saying.

Now swim has 8611.9 J/mol bassed on 160 at 7.8e-4 atm(your source) and
130 at 1.316e-4 (tihkal)

this gives us:

(r*(log(7.8e-4) - log(1.316e-4)))/((1/403.15) - (1/433.15))
=
86119

which, when we plug into the original equation using the value from your source as the observed pressure and temperature we get :

1/(r*log(7.8e-4)/8.6119e+04 + (1/433.15)) = 618.1226 kelvin

which is 345C

Now the question is, how big is the effect of error in our measurements on this outcome? and right now, swim'd rather smoke another joint than calculate that. stay tuned

also: What about the vaporization temp of the n-oxide? should it be lower?
 
Simple empirical way to measure this: using tempered glassware or Pyrex, put a suitably shaped container in some oil at room temperature. Add a small amount of DMT to the bottom of the glassware. Heat the oil up to around 140 C, measuring constantly with a thermometer, then turn the heat down until the temperature is increasing very slowly. Then watch the DMT to see when it vaporizes, and record the temperature of the oil at that point. The oil should only be a bit hotter than the inside of the glassware if this is done correctly.

Or, put a tiny sample of DMT in a Mel-Temp apparatus, and keep increasing the temperature way past the melting point until it vaporizes. This would probably be much more accurate, and it would require less DMT. I'd do it myself, but then I'd have to take organic chemistry lab AGAIN. That, and it would require me to be in possession of some of my friend's DMT, which is illegal, then smuggle it into the lab and hope that nobody recognizes the smell coming out of my Mel-Temp station!
 
SWIM heated DMT saturated heptane in a water bath to just below the boiling point of water - DMT was clearly smelled and was definitely evaporating. This suggests that the boiling point of DMT is lower than or on par with the boiling point of water. I would set it at 98C personally.
 
Just because enough DMT for you to smell was comming off of that solution doesnt mean you were at the BP of DMT.

when swim makes moonshine a percentage of water is comming off the still even as he takes the heads at a temp well below 100C. does this mean that water boils below 100C?

azetropes form, fluid/gas flow is not clear cut, simple, discrete. The rules arn't always strict for these things. swim smells DMT off a container when its solid, swim smells it strong. its not boiling, but i wouldn't be smelling it if there wasn't some vapor coming off. evolution of vapor does not equate to boiling, no way, no how.

Boiling is when the vapor pressure exceeds the atmospheric pressure.

if you hold some at 98C and it eventually starts to bubble and boil with no heptane, then swim believes you. Or if you boil some heptane/DMT and there is little or no DMT when your done with the heptane. Even that is definitely not conclusive for DMT, it is conclusive for the mixture.
 
azetrope or not, just because DMT vapor is comming off does not mean you have reached the boiling point. Vapor is always coming off, thats why its smelly, BP is when vapor pressure exceeds the atmousphereic pressure. SWIM is gona try to straighten this out with a well documented experiment...
 
Sister has done some work with a nomograph and dmt"s "boiling point".

If the atmospheric BP of dmt is 345°C ( or even worse 160°C at 0.6 torr) then the line on the nomograph indicates that no amount of vacumm will allow this substance to sublime below its MP. So either it is not possible to sublime dmt or the BPs for dmt that are floating around are incorrect. Is there something Sister is missing here, or is it not possible to sublime dmt?
 

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Thank you for clarifying the pressure conversion Benzyme

Although the point (question?) sister was trying to make (ask?) is that with a BP in the high 300's°C no amount of vacuum will take nn-dmt from a solid directly to a gas. It looks like it will reach its melting point long before vacuum will take it to its vapour phase. In which case we are really discussing a distillation rather than a sublimation, aren't we?
 
Dr_Sister said:
...If the atmospheric BP of dmt is 345°C ...
Click to expand...
A boiling point for DMT of 345ºC seems oddly high. Are you sure that’s correct?

The VG site claims that the air temperature in the VG/GVG chamber reaches between 300-400ºF, and this seems about right to me. According to your boiling point value of 345ºC (653ºF), DMT wouldn’t come close to vaporizing in a VG, which is obviously not the case.
 
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