Oxydro
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Solanine
Solanine is a toxic chemical (specifically, a glyco-alkaloid) found in the members of the nightshade family, including potatoes and tomatoes. There is
a much higher concentration than usual in green potatoes—not because the color is caused by solanine (actually chlorophyll causes it) but because
when light hits the potato (which causes chlorophyll to build up) the potato plant makes solanine as a defence mechanism.
See http://en.wikipedia.org/wiki/Solanine for some basic information about solanine.
There is a discussion on y-archive here: http://yarchive.net/food/potato_alkaloids.html
It has been connected to osteoarthritis: http://www.bellybytes.com/bytes/solanine.shtml
A collection of studies on its effects here: http://www.inchem.org/documents/jecfa/jecmono/v30je19.htm
I found some information on its extraction in this article: http://www.solanum.net/download/JAFC-MethodPaper-1996.pdf
Also, from Clarke’s Analysis of Drugs and Poisons:
Synonym. Solatunine
C45H73NO15=868.1
CAS—20562–02–1
A glycoalkaloid present in various species of Solanum, particularly S. tuberosum (Solanaceae).
A white crystalline powder which decomposes at about 285°.
Practically insoluble in water, chloroform and ether; soluble in hot ethanol, dilute acids and amyl alcohol.
Dissociation Constant: pKa6.65 (15°).
Partition Coefficient: Log P(octanol/water), 2.0.
Colour Tests: Mandelin's test—orange→violet→blue; Marquis test—yellow→violet.
[I don't know anything about what partition coefficient and color tests mean]
Thin–layer Chromatography: System TA—Rf 52. (Marquis reagent, positive.)
Does anyone have any more information on this substance? I am interested in extracting it from potato plants, or possibly bittersweet nightshade
(major weed around here), or other nightshade-family plants. No particular reason – although it does induce hallucinations it doesn’t sound like a
nice drug, and although it is toxic, the dose seems to be high enough to make it useless as a poison. But it sounds like an interesting project.
[Edited on 19-12-2004 by Oxydro]
"Our interest's on the dangerous side of things" -- Browning
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JohnWW
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I think solanine, and related compounds, are extracted for use as starting material in the manufacture of steroids, including estrogens and
progestogens for birth control pills, corticosteroids for anti-inflammatory medicines, and anabolic steroids mostly for illegal use to boost sporting
performance. The principal source is Mexican wild yams (dioscoria species).
As well as in potatos, solanine and related compounds are found in other solanum species, including a New Zealand plant, poroporo. However, commercial
production of poroporo for steroid production ceased in New Zealand after several years because it could not compete with Mexican production from wild
yams.
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kclo4
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I Just recently got a Walmart bag full of bittersweet nightshade leafs.
I put them in the freezer to destroy the cell structure, and then in a pot and boiled them with about 2 liters of water, maybe 1.5, I really cant
remember.
Now I have a dark black-green tea like stuff. But I am wondering if the solanine is in the tea, or still in the boiled leafs, it would seem strange
that the solanine would still be in the leafs after about 5 minutes of sitting in to the boiling/near boiling water.
However sense Solanine is not very soluble in water, and i see no crystals (i also added 2 spoon fulls of baking soda to reduce the solanine salts, to
just plain solanine, after the tea had cooled off)
So do you think my solution has lots of solanine in it or very little?
Also it is going to have other alkaloids such as: chaconine, nicotine, tomatine? Maybe atropine and it wouldn't surprise me if it didn't have some
caffeine also, but the most abundant should be solanine.
Does anyone have suggestions about extracting the solanine from the other alkaloids?
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YT2095
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grow some potatoes, but rather than dig them up and eat them, let them produce Fruit, they look like little green tomatoes that form in the bud that
held the flower, 2 of those tiny fruits can kill you!
it`s a much better source than the leaves, Chili peppers are also Nightshade famility as are aubergines.
potato fruits are lethal!
\"In a world full of wonders mankind has managed to invent boredom\" - Death
Twinkies don\'t have a shelf life. They have a half-life! -Caine (a friend of mine)
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kclo4
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That's very Interesting, thank you for that insight. Can potatoes grow indoors as if they were a house plant?
But anyway I have already made the tea from the bittersweet nightshade and all, as I said above. Do you think I have the solanine in the tea? In good
quantities?
edit: I just looked at my dark dark green/ brown solution/tea, and it seems there is a possible white smoky ppt, falling down to the bottom!
this is good in one way or another! 
[Edited on 20-10-2006 by kclo4]
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chiralic
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Location: Venezuela
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Hello:
Below you find several references where you can find information about Toxicology of Steroidals Glycoalkaloids from Solunum species (mainly potato,
tomato and eggplant):
Friedman, M.; McDonald, G. M. Potato glycoalkaloids: chemistry,
analysis, safety, and plant physiology. Crit. Rev. Plant Sci.
1997, 16, 55-132.
Friedman, M. Tomato glycoalkaloids: role in the plant and in
the diet. J. Agric. Food Chem. 2002, 50, 5751-5780.
Kubo, I.; Fukuhara, K. Steroidal glycoalkaloids in Andean
potatoes. AdV. Exp. Med. Biol. 1996, 405, 405-417.
Orgell, W. H.; Vaidya, K. A. Inhibition of human plasma
cholinesterase in Vitro by extracts of solanaceous plants. Science 1958, 128, 1136-1137.
Nishie, K.; Gumbmann, M. R.; Keyl, A. C. Pharmacology of
solanine. Toxicol. Appl. Pharmacol. 1971, 19, 81-92.
Renwick, J. H. Hypothesis: anencephaly and spina bifida are
usually preventable by avoidance of a specific but unidentified
substance present in certain potato tubers. Br. J. PreV. Soc. Med. 1972, 26, 67-88.
Nevin, N. C.; Merrett, J. D. Potato avoidance during pregnancy
in women with previous infant with either anencephaly/and or
spina bifida. Br. J. PreV. Soc. Med. 1975, 29, 111-115.
Harvey, M. H.; Morris, B. A.; McMillan, M.; Marks, V. W.
Potato steroidal alkaloids and neural tube defects: serum
concentration fails to demonstrate a causal relation. Hum. Toxicol. 1986, 5, 249-253.
Friedman, M.; Dao, L. Distribution of glycoalkaloids in potato
plants and commercial potato products. J. Agric. Food Chem.
1992, 40, 419-423.
Mensinga, T. T.; Sips, A. J.; Rompelberg, C. J.; van Twillert,
K.; Meulenbelt, J.; van den Top, H. J.; van Egmond, H. P. Potato
glycoalkaloids and adverse effects in humans: an ascending dose study. Regul. Toxicol. Pharmacol. 2005, 41, 66-72.
Brown, M. S.; McDonald, G. M.; Friedman, M. Sampling leaves
of young potato (Solanum tuberosum) plants for glycoalkaloid
analysis. J. Agric. Food Chem. 1999, 47, 2331-2334.
Valkonen, J. P. T.; Keskitalo, M.; Vasara, T.; Pietila, L. Potato
glycoalkaloids: a burden or a blessing? Crit. ReV. Plant Sci.
1996, 15, 1-20.
Bushway, R. J.; Ponnampalam, R. R-Chaconine and R-solanine
content of potato products and their stability during several
modes of cooking. J. Agric. Food Chem. 1981, 29, 814-817.
Takagi, K.; Toyoda, M.; Fujiyama, Y.; Saito, Y. Effect of cooking
on the contents of R-chaconine and R-solanine of potatoes. J.
Food Hyg. Soc. Jpn. 1990, 31, 67-73.
Regards,
Chiralic
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