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Mescaline solubility and other properties Options
 
69ron
#1 Posted : 2/15/2009 4:42:05 PM

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Mescaline solubility and other properties
Version 1.2


Note: when talking about IPA (isopropyl alcohol), a purity of 99% IPA is assumed. 91% IPA or less cannot substitute for 99% IPA.

Freebase mescaline
Composition: C11H17NO3
Melting point: 35-36°C (Kindler and Peschke, 103)
Boiling point: 180°C (12 mmHg)
XLogP: 0.6 (PubChem)
XLogP3: 0.7 (PubChem)
pKa: 9.56
Appearance: long needle shaped white crystals
Molecular weight: 211.26
Notes: forms mescaline carbonate on prolonged exposure to air
Average dose: 300 to 600 milligrams with a duration of 5 to 12 hours.
Soluble in: alcohol, chloroform, benzene, xylene, toluene, acetone, dichloromethane, highly soluble in isopropyl alcohol, soluble in d-limonene ***
Moderately soluble in: water
Insoluble in: practically insoluble in ether or petroleum ether
LD50: i.p. rats 370 mg/kg

*** SWIM's test's found that freebase mescaline is quite soluble in d-limonene and that mescaline hydrochloride is insoluble in d-limonene. He developed a tech that uses it and got fantastic yields.



Mescaline citrate
Soluble in: water
Insoluble in: xylene, acetone *
* Possible unreliable web source.

Mescaline hydrochloride
Molecular weight: 247.72 (Sigma Aldrich)
Empirical Formula (Hill Notation): C11H17NO3 • HCl (Sigma Aldrich)
CAS Number: 832-92-8
Appearance: colorless crystals, needles
Melting point: 184°C
Moderately soluble in: water, alcohol (Merck Index), methanol (at least 1.0 mg/ml, source Sigma Aldrich solution)
Insoluble in: practically insoluble in toluene and acetone, insoluble in isopropyl alcohol, diethyl ether, and d-limonene***
LD50: i.p. rats 132 mg/kg
Storage temperature: 2-8°C (Sigma Aldrich)
Isolation: when mescaline hydrochloride is extracted from San Pedro, Achuma, or Peruvian torch, it can be isolated from the other alkaloids by washing it in IPA or acetone (use 10 ml per gram of alkaloids, and wash 2-3 times). The non-mescaline alkaloids dissolve in the IPA or acetate, while the mescaline hydrochloride does not. Note that for the cleanest results use about 2 washes of acetone, and then 2 washes with IPA.

*** SWIM's test's found that freebase mescaline is quite soluble in d-limonene and that mescaline hydrochloride is insoluble in d-limonene. He developed a tech that uses it and got fantastic yields.



Mescaline picrate
Melting point: mp 222°C.

Mescaline sulfate dihydrate
Composition: (C11H17NO3)2 • H2SO4 • 2H2O
Appearance: prisms
Melting point: 183–186 °C (361–367 °F)
Molecular Weight: 309.33606
Soluble in: hot water, methanol
Almost insoluble in: near freezing water, alcohol, acetone *
* Possible unreliable web source.



Mescaline fumarate
Composition: unknown (it may be a one to one salt or may not be)
Appearance: unknown
Melting point: unknown
Soluble in: water**, acetone**
Insoluble in: unknown
** This information is from various SWIMs on this forum.

Mescaline acetate
Composition: unknown
Appearance: white free flowing powder with a slight waxy texture ***
Melting point: unknown
Soluble in: water***, isopropyl alcohol***, acetone***, DMSO*** (more than 5 grams/100 ml), boiling MEK***
Insoluble in: xylene, d-limonene, cold MEK (Methyl Ethyl Ketone) ***
*** This information was validated by SWIM and is reliable.
Isolation: when mescaline acetate is extracted from San Pedro, Achuma, or Peruvian torch, it can be isolated from the other alkaloids by washing it in cold MEK (use 10 ml per gram of alkaloids, and wash 2-3 times). The non-mescaline alkaloids dissolve in the MEK, while the mescaline acetate does not. Mescaline acetate can be recrystallized in MEK by boiling the MEK and then freezing it overnight.
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burnt
#2 Posted : 2/15/2009 4:45:56 PM

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I am not sure if you can have mescaline sulfate without the dihydrate part. Unless somehow the salt is formed in an environment devoid of all water. Any idea about this? There is an entry in the merck index on that compound so you don't need the websource although I think its the same as the merck index version I have seen. also HCl could be included its also in the merck index.
 
69ron
#3 Posted : 2/15/2009 5:18:02 PM

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The HCl was there, the formatting wasn't right so it was sort of hidden in the text. I fixed it.

I've seen reference to mescaline acid sulfate and mescaline sulfate dihydrate as if they were actually different compounds. I don’t know if mescaline acid sulfate exists or not without the water. PubChem lists them both under the same entry.

I've removed the mescaline acid sulfate. If its just the same as mescaline sulfate dihydrate there's no point, and since there's no info about it, why have it anyway even it if is a separate form.
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reflexion
#4 Posted : 2/15/2009 5:22:03 PM

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sorry to intrude with such a noobish question. but which form of mescaline is produced by cacti?
orm what is a good solvent to use for making crude cacti extract?
 
69ron
#5 Posted : 2/15/2009 5:30:01 PM

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All good questions.

Unless the cactus flesh was above pH 7, which it’s not, then mescaline must be present in a salt form like mescaline hydrochloride or something similar. The cactus flesh is acidic (around pH 5-6 or so), so the cactus must contain a salt form of mescaline, but I haven’t seen it documented anywhere which salt form it actually is.

From what I read, methanol and ethanol are great solvents to use for a crude cactus extraction. Water produces a thick slimy goo with much more mass to deal with which is almost impossible to filter. Water is not recommended. SWIM has tried all three, and methanol is the best SWIM has tried.


What I want to know is if freebase mescaline is soluble in d-limonene. It would be nice to be able to use d-limonene in an A/B extraction of mescaline. It’s much safer to use than xylene, toluene, or DCM.
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69ron
#6 Posted : 2/15/2009 6:03:32 PM

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Is freebase mescaline soluble in d-limonene? The chemical shape of d-limonene is very similar to toluene, xylene, and benzene, but it's not considered an aromatic hydrocarbon.

d-limonene


toluene


benzene


xylenes


mescaline


Mescaline is known to be poorly soluble in diethyl ether and heptane. Mescaline is fairly polar and so it makes sense for it to be nearly insoluble in such an extremely non-polar solvent like heptane.

Even though diethyl ether is much more polar than heptane, and even more polar than xylene, for some reason mescaline is more soluble in xylene than in diethyl ether, which is quite unusual for an alkaloid. You would expect it to be more soluble in diethyl ether than xylene.

This unusual solubility behavior seems to stem from the shape of the molecules.

Notice the similarity in shape between diethyl ether and heptane, two solvents mescaline is poorly soluble in.

Look at the shape of xylene, benzene, and toluene, three solvents mescaline is very soluble in. Then look at the shape of mescaline. At the center of mescaline is a benzene ring which is identical to the center of those three solvents, and quite similar to the center of d-limonene as well, though not identical.

diethyl ether


heptane
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The Traveler
#7 Posted : 2/15/2009 6:49:42 PM

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Off-topic: these molecule schematics, what are they called? And is there a site explaining these schematics somewhere?


 
psychonaut
#8 Posted : 2/15/2009 8:44:54 PM
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They are called Skeletal Formulas(like structural formulas but specific to organic chemistry). each end point represents a carbon atom and each line between them represents a bond. If the line has a 2nd smaller line next to it, it is a double bond(ie: benzene has 3 double bonds) and 3 lines means a triple bond. Hydrogen atoms are excluded unless attached to another atom(in which case the atomic symbol denotes the atom type). I'm sure googling "skeletal formula" will bring up some results.

Edit: http://www.chemguide.co....g/conventions/draw.html should help.
 
burnt
#9 Posted : 2/16/2009 9:24:40 AM

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Yea the dihydrate and sulfate without dihydrate confuses me a bit. But anyway I think mescaline freebase should be soluble at least partially in d-limonene. Its worth trying.
 
Infundibulum
#10 Posted : 2/16/2009 9:50:48 AM

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SWIM has an indication that mescaline fb is soluble in limonene. He pulled with limonene after pulling some time with xylene and got a fair yield, (150mg msec fumarate from 100g of xylene-exhausted plant material.

Although there were traces of xylene (and as such SWIMs' experiment was more like using a binary solvent, roughly estimated 1 part xylene to 10 partst limo), it did seem that limo could pick up mescaline fb.


Need to calculate between salts and freebases? Click here!
Need to calculate freebase or salt percentage at a given pH? Click here!

 
69ron
#11 Posted : 2/27/2009 7:00:05 PM

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I updated the solubility information to include d-limonene for freebase mescaline and mescaline hydrochloride from many tests SWIM did. D-limonene is a fantastic solvent to use for extracting mescaline. SWIM was amazed by how good it works.

I added mescaline fumarate to the list. Please help add more information and help verify all information about mescaline fumarate and the rest.

If there are any mistakes in the first post, please point them out and I will fix them.

Thank you.
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69ron
#12 Posted : 2/27/2009 7:04:34 PM

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I added mescaline acetate to the first post. Please help me update the information on mescaline acetate. It's so sparse and I'm not sure how accurate it is (as stated in the listing in the first post).
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69ron
#13 Posted : 2/27/2009 7:07:58 PM

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Someone on another forum claims that "crystaline mescaline acetate is inactive". That sounds like false information to me. Can anyone here support that claim?

Google is of little help here. A search for "mescaline acetate" gave only 27 pages. I found many complaints about it not being active or that extractions failed from using vinegar to make mescaline acetate.

Is mescaline acetate soluble in xylene? That would explain all the complaints about using vinegar to salt mescaline.

In SWIM’s tests vinegar didn’t do very well. More tests need to be done though.
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69ron
#14 Posted : 3/13/2009 10:32:02 AM

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I updated the original post's mescaline acetate solubility to include isopropyl alcohol and d-limonene.

SWIM's tests found that mescaline acetate is soluble in: water, 99% isopropyl alcohol.
SWIM's tests found that mescaline acetate is insoluble in: d-limonene, xylene.
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69ron
#15 Posted : 6/6/2009 6:03:57 PM

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I updated the original post's section on mescaline sulfate dihydrate
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burnt
#16 Posted : 6/6/2009 7:35:05 PM

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Hmm yea SWIM is just wondering if its possible to clean up the sulfate the same way as the HCl salt. Maybe there is something to use that is better then acetone or IPA? Or will IPA work?
 
69ron
#17 Posted : 6/6/2009 11:47:52 PM

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I've seen pure white mescaline sulfate that was just recrystallized from ice cold water. Can't you just recrystallize mescaline sulfate in ice cold water? Isn’t that the standard way to purify mescaline sulfate?

You can clean it with ethanol, that's for sure. It's best if the ethanol is ice cold. I assume IPA would work better. Some claim acetone works for it but I haven’t seen that in any respectable text books so I’ve listed that up above as possibly unreliable data.

Personally, I don’t like the idea of using sulfates. It doesn’t seem healthy to me. They are known to cause diarrhea. You know that when the mescaline enters your brain it enters as freebase, not as a sulfate so the sulfuric acid is released from it and ends up in your body. It just doesn’t sound healthy to me. The same thing happens with mescaline HCl, the hydrochloric acid is released before it enters the brain because only freebase mescaline can enter the brain. That’s my understanding anyway. I’d feel better about using an acid that’s better for you especially when using something like mescaline which requires pretty large doses.
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burnt
#18 Posted : 6/7/2009 11:47:00 AM

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^^It might also help with the nausea to use other salts. Who knows. Either way thanks for info.
 
bufoman
#19 Posted : 6/16/2009 10:00:34 PM

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These salts do not leave the digestive tract as the freebase (unionized form) is absorbed in the small intestine. They may be absorbed if they are themselves actively transported thus some salts like oxalate, and fumarate may be but they separate from the alkaloid in the basic pH environment of the small intestine where absorption occurs. I doubt sulfuric acid would be actively transported. Different acids may be responsible for different side effects such as nausea that is an interesting hypothesis.
 
69ron
#20 Posted : 6/17/2009 3:02:39 AM

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The two salt forms which are known to be unhealthy are oxalates and sulfates. You should not use either ever, unless there's no other acid that with work. Oxalates can cause kidney stones and sulfates can lead to digestive problems such as diarrhea.
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