fractalicious
Dave
Dear Nexians after repeatedly seeing the results of the paper by 3 University researchers, one of who was reachable I had a conversation with them.
The intent of the the original toxicology paper was to determine the cause of the locomotor ataxia and staggering of goats eating the commonly named Guajillo, and the other grazing trees that might be toxic, and their specific toxins.
The professor said that the testing would never be reaffirmed at by his facility due to very limited research funds and the fact that the trees are not a statewide issue.
The results showed an amazing array of 33 different phenylethlamine alkaloids and 2 steroids if memory serves me correctly. There were also I believe 4 unidentified compounds, a new professional analysis could lend to determination of their unknown structure.
Some time after the paper was written and republished in various journals Trouts I believe Dr. Alexanger Shulgin found the results quite remarkable and possibly quite accurate.
He did mention one distinct posibility for error and joked about dirty glassware from a drug lab, well who read this repeated this over and over to other entheoist's but none ever even seemingly comprehended the real potential problem during the tests that might give some skewed results. This potential error was that the GC-MS insertion process might result in the accidental conversion of ephedrine like compounds to amphetamines this is proven to occur. Ephedrine is a more complex molecule and simple reduction could create methamphetamine in example. If a more complex or as complex molecule occurs in ephedra why not a similar or simpler one,in another plant species, it is however the whole array that's hard to swallow.
OK back to todays conversation with the Doctor. He said that he had never heard from Dr. Shulgin or anything ever about any controversy surrounding the results. He said the primary researcher and her assistant are both unreachable one due to her possible death after protracted illness and being possibly posthumous and that the assistant has not been seen or heard from in many years.
He has the highest confidence that this testing was done competently and properly with the only issues being limitations of the older GC-MS processing equipment at the time. He clearly says that these compounds are identified from known GC-MS signatures in a database and there really is no reasonable explanation for bad results other than accidental conversion through reduction during the insertion process I discussed this and he agreed this might be an issue. It could not explain the full rainbow of compounds a few but not all of them.
The dirty glassware theory is a joke by Shulgin he is saying this is probably dead on and that he was seriously amazed and wanted to confirm these results but could not reach anyone.
What is important is the the professor has agreed to allow me to come to the universities research facility and to harvest samples he suggested waiting till spring but I want to expedite reconfirming the results independently.
I think Shulgin is taking for granted thier limited funds to accomplosish this task, the folks were more into livestock management and loss prevention the entheogenic research, they should have certainly recognized the importance and handed off material and results to another university and this is what the doctorate Professor is willing to help with kindly.
I would like to say that I am a long time plaque psorasis sufferer and only learned of various acacias/mimosa trees properties due to their proven healing powers after refusing to take an injection that could destroy my immune system and several failed topical medicines.
Right now there are clearly some potential toxins in Guajillo. At least 4 unknown compounds were isolated in tests.
In addition my best shot at analysis is probably to simply carefullly collect and deliver leaf, stem, and various bark to the University of Texas and to talk up a few students that might be game to write a paper on these plants and their content and toxicology.
Traveler has kindly granted access to a GC-LS testing facility but I am not familiar with this technology since I can not seem to wiki or google it?
I am going to try to reach the person I have the utmost respect for Dr. Shulgin or his wife Ann, and see if he might either forward these to a friend or himself also do analysis on these samples.
What follows is Dr. Shulgins response to inquiries about the paper:
I am familiar with the literature concerning these two West Texas Acacia species, but not with the plants themselves. I had both these PHYTOCHEMISTRY papers in my Acacia file but I must admit that I have some very mixed feelings about them.
What caught my curiosity immediately was the casual indifference shown to what is certainly an extraordinary discovery. Here, amongst some 40 or so alkaloids found in each of these two species, there were five amphetamines that had heretofore been thought to be inventions of man. Two of these are Schedule II drugs, Amphetamine and Methamphetamine. Two are Schedule I drugs, N,N-Dimethylamphetamine and 4-Methoxyamphetamine. And the fifth one is a major human metabolite of Amphetamine, 4-Hydroxyamphetamine. To my knowledge, none of these had ever before been reported as being natural plant alkaloids. This unprecedented discovery elicited only a passing line of comment in the earlier of the two papers.
My first thoughts as to origin were directed towards the well known natural hydroxylated amphetamines such as norephedrine, ephedrine and N-methylephedrine. I know that ephedrine and pseudoephedrine, frequent precursors in the illegal synthesis of methamphetamine, can be reduced to methamphetamine as an artifact of analysis. The sample insertion conditions of the gas chromatograph can effect this conversion. But then, there was no mention of any of these hydroxylated alkaloids as being present in either Acacia.
Might a contaminated round-bottomed flask have been purchased at a garage sale outside an abandoned meth-lab and served as the source of these "man-made" compounds? Unlikely, even in Texas.
Even more dramatic, one of these amphetamines, the 4-Methoxyamphetamine, is the increasingly notorious PMA that is appearing as one of the lethal "Ecstasy" offerings in the rave scene.
Several months ago I tried to contact, individually, the two principal authors, by both e-mail and personal snail-mail, and I have received no response as yet.
There is certainly precedent for a drug which was originally man-made, to be discovered in a plant. N,N-Dimethyltryptamine (DMT) was first synthesized by Manske, in Canada, in the 1930s. It was over twenty years later that it was discovered in a plant from South America. But such an event usually evokes considerable commentary. Here it seems that an exciting story is being ignored. Am I missing something?
-- Dr. Shulgin
Ok I will quote a couple papers and some info on why studies were done and the results of the first highly disputed results:
Negative impact on testosterone:
Exerpts from:
Effect of dietary phenolic amines on testicular function and luteinizing hormone secretion in male angora goats
Many agriculturally important shrubs of the genus Acacia can contain high concentrations of sympathomimetic phenolic amines. These compounds, which are thought to represent plant chemical defenses against herbivory, can affect different physiological processes of higher animals if they enter into the systemic circulation (Smith, 1977; Evans et al., 1979; Forbes et al., 1995). The sympathomimetic phenolic amines present in A. berlandieri have been implicated in the development of a toxic condition in sheep and goats when this shrub is consumed for extended periods (Camp et al., 1964). Parenteral administration of phenolic amines present in A. berlandieri and A. rigidula impairs reproductive function of female goats (Forbes et al., 1993) and heifers (Carpenter et al., 1994) and suppresses LH release after GnRH administration in wethers (Forbes et al., 1994). Further research is required to determine the occurrence of subtoxic effects in domestic ruminants that regularly consume vegetation with high concentrations of phenolic amines. In the present study, male Angora goats were allowed to graze on a range site dominated by A. berlandieri and A. rigidula to test the hypothesis that consumption of these plants does not affect testicular characteristics or function or systemic LH concentrations.
The results of this study indicate that consumption of phenolic amine-containing vegetation may affect the function of the pituitary-gonadal axis in domestic
goats, as has been suggested in recent studies involving parenteral administration of some of the phenolic amines present in A. berlandieri and A. rigidula (Forbes et al., 1993, 1994; Carpenter et al.,1994).
In terms of testicular characteristics and function, the increase in testosterone secretion by the testes, which normally occurs in male goats as the breeding
season advances (Muduuli et al., 1979; Ritar, 1991; Pe?rez and Mateos, 1995), was clearly suppressed in the PA bucks.
Acute parenteral administration of some of the phenolic amines present in A. berlandieri and A. rigidula inhibited GnRH-stimulated LH secretion in wethers (Forbes et al., 1994).
Increased LH concentrations and augmented LH response to GnRH observed on d 75 in the PA bucks was probably a consequence of reduced negative feedback of testosterone because testosterone was lower in the animals consuming A. berlandieri and A. rigidula. Over the long term, PA males seemed to have a diminished testicular responsiveness to LH. This was reflected during the pre-GnRH period by decreased plasma testosterone despite increased LH and a lack of correlation between plasma concentrations of LH and testosterone. This reduced testicular responsiveness to LH was also evident during the GnRH-stimulated period, as reflected by a decreased testosterone response to GnRH-induced LH release. A possible direct or indirect effect of phenolic amines on testicular function, the latter mediated through their ability to stimulate cortisol secretion (Forbes et al.,1994), may have influenced testicular responsiveness to LH because cortisol has been demonstrated to affect LH-stimulated testicular steroidogenesis (references in Vera-Avila et al., 1996).
Results of the discriminatory analysis indicated that serum testosterone, change in SC, and serum T3 and T4 were the response variables most correlated with treatment when considered independently (independent R2) , and with the exception of T4, when considered in a complete model including all of the other variables (partial R2) . Serum testosterone, serum T3, and change in SC provided most of the discriminatory power (ASCC = .60) that could be achieved by including all variables in the model (ASCC = .64). Thus, according to this analysis, diminished serum testosterone and SC and increased serum T3 concentrations most accurately characterized the differences between PA and CO bucks.
FULL VERSION http://jas.fass.org/cgi/reprint/75/6/1612.pdf
Next on alkaloid results:
Chemistry of Acacia's from South Texas
Acacia species in south Texas contain numerous chemical compounds, many of which have negative effects on animal performance.
Alkaloids, phenolic amines, phytoestrogens, and tannis have been identified in south Texas acacias.
Many of the acacias of south Texas are considered to be valuable forage for deer and domestic livestock. It is known, however, that at least one species, guajillo (Acacia berlandieri) will produce a paralytic condition in sheep and goats called "guajillo wobbles." As part of a larger study investigating the chemistry of south Texas range plants, we determined the chemical composition of the leaves of several south Texas acacias.
Most woody plants contain a variety of chemical compounds a number of which have the advantage to the plant of being toxic to animals that consume them. Many of these defensive compounds are nitrogen-based, though there also are a significant number of nonnitrogenous toxic compounds. Additionally, plants produce compounds which may be repellent or, as in the case of tannins, lower the nutritional value of the plant. Early research, using paper and thin-layer chromatographic techniques, identified several phenolic amines in A. berlandieri, including n-methyl-phenethylamine (NMP), tyramine, nmethyltyramine and hordenine.
The alkaloid fractions (those extractable with 10% HCL) of A. berlandieri and A. rigidula contained a complex mixture of alkaloids including nicotine, nornicotine, anhalamine, mescaline, and 3,4,5-trihydroxy-phenethylamine (demethylated mescaline).
The phenolic amines, such as tyramine, hordenine and N-methyl-B-phenethylamine are powerful activators of the sympathetic nervous system causing the release of cortisol and adrenocorticotropic hormone. In addition to the alkaloids, the plants were also found to contain intricate mixtures of tannins and flavenoids including catechin, fisetin and quercetin.
While tannins and their antinutritional effects have been the subject of much research in recent years, little attention has been paid to the negative effects of consumption of other secondary compounds that are not acutely toxic. However, recent research has shown the negative effects on fertility of consumption of amine-containing forage. Consumption of guajillo and blackbrush was shown to reduce fertility in male goats, and to reduce their ability to handle stressful situations such as transportation.
Table 1. Major Chemical Compounds in South Texas Acacias :
Amines and Alkaloids:
phenethylamine
N,N-dimethylphenethylamine
N,N-dimethyl-"-methylphenethylamine
p-hydroxyamphetamine
tyramine
3-5-dimethoxytyramine
3,4-dimethoxy-5-hydroxy-$-phenethylamine
hordenine
N,N-dimethyldopamine
tryptamine
N,N-dimethyltryptamine
N-methylmescaline
nicotine
anhalamine
peyophorine
nortryptyline
3-"-cumyl-1,3,4-oxadiazolidine-2,5-dione
p-hydroxypipecolamide
4-methyl-2-pyridinamine
N-methylphenethylamine
amphetamine
methamphetamine
p-methoxyamphetamine
N-methyltyramine
candicine
dopamine
N-methyldopamine
3-methoxytyramine
N-methyltryptamine
mescaline
trichocereine
nornicotine
anahalidine
mimosine (methyl ester)
musk ambrette
pipecolamide
1,4-benzezediamine
Phytoestrogens:
octylphenol \
aristolone
(Z)-9-octadecenoic acid
(Z,Z,Z)-9,12,15-octadecatrienoic acid
3b-acetoxy-17-methyl-5a-18-abeoandrost-13-ene
nonylphenol
3b-cholest-5-en-3-ol
(Z,Z)-9,12,-octadecanoic acid
Last but not least some more on toxicology:
Toxic amines and alkaloids from acacia rigidula
Acacia rigidula Benth., blackbrush, is a shrub found growing on rocky ridges in west and southwest Texas and northern Mexico. Consumption of blackbrush and a related species guajillo, Acacia berlandieri Benth., has been associated with a locomotor ataxia known as "limber leg".
A. rigidula has been shown to contain appreciable levels of toxic alkaloids. Sheep and goats grazing on a related species, Acacia berlandieri Benth., guajillo, during periods of drought in the Rio Grande Plains of Texas have developed a locomotor ataxia referred to as "guajillo wobbles" or "limber leg" [2]. Previous analysis of blackbrush had detected and identifed four amines, N-methyl-b-phenethylamine (NMPEA), tyramine, N-methyltyramine, and hordenine, which were also found in guajillo [3].
As a result of this study, an intensive chemical analysis of A. rigidula Benth. was undertaken to identify the amines and alkaloids present in the leaves and stems that would comprise browse material.
Forty-four amines and alkaloids, including the four previously encountered amines, N-methyl-b-phenethylamine, tyramine, N-methyltyramine, and hordenine, were identifed by GC-MS.
The majority of the isolated alkaloids, 18 of the 33 identifed, were related to the parent compound b-phenethylamine. These compounds generally varied in the degree of N-methylation, x-methylation (amphetamine family), and in oxygenation of the aromatic ring (tyramine, dopamine, and mescaline families). The 2-cyclohexylethylamine and the N-cyclohexylethyl-N-methylamine are the saturated analogs of the phenethylamine and NMPEA respectively. Tryptamine, N-methyltryptamine, and N,N-dimethyltryptamine were also isolated from blackbrush.
Other noteworthy alkaloids found in blackbrush include nicotine, nornicotine, and four tetrahydroisoquinoline alkaloids, anhalamine, anhalidine, anhalonidine, and peyophorine. The amides of the amino acids pipecolic acid and p-hydroxypipecolic acid were also detected.
As was previously found with NMPEA the foliage collected in the autumn contained higher quantities of amines and alkaloids [10]. There was also a distinct increase in the number and quantity of methylated analogs present (Table 1).
Several as yet unidentifed amine-containing compounds have been detected but have not yet been identifed. It is also probable that several biosynthetic precursors are present in the mixture but as yet are unresolved and are below the threshold of GC-MS detection.
Phenolic amines, as a group, impact the hypothalamic-pituitary-adrenal axis [11]. The consequent release of ACTH and cortisol results in symphathomimetic action. The number of phenolic amines reported in Table 1 and their concentrations in the plant indicate a substantial toxic load to animals consuming blackbrush. The toxicity of nicotine and nornicotine has been well established [12], as has the psychoactivity of mescaline and its derivatives. None of the compounds identifed appear to have been implicated in locomotor ataxia. However the presence of the amphetamines suggests the possibility for a reduction of monoamine oxidase activity [13]. FULL VERSION: http://www.erowid.org/archive/rhodiu...a.rigidula.pdf
I hope to with help here once and for all confirm or deny and expand accurate analysis of at least the 2 species plus another Acacia Sheffneri.
Here locally in my hometown we have a few more plants of interest but these are quire well studied allready although these will have both seasonal and regional and subspecies variations in content these being Arundo Donax the Reed Cane plant, and both species of Demanthus the rock solid safe Leptobolus and its poorer sister species Illioensis.
Thank you for guidance and advice please no personal requests for plants samples since this inapproproriate just pure research efforts only. If these prove fruitfull for further examination over the coming months I will make an effort to make seed and possibly live seedlings available to members, the seed is almost a year away.
I think Dr. Shulgin pretty much eliminates the potential for error due to accidental reduction conversion of many of the substances since he seems to be saying there is no evidence of the needed more complex molecules they might have been converted from if I am comprehending this correctly.
BTW for the few who are not aware of who Dr. Alexander Shulgin is, please read about phikal, Phenylethlamines I have known and loved he is quite daring having synthesized and himself consumed the results of a myriad of molecules he designed by redistributing various side chains.
Update: Very sad to hear that Dr. Shulgin AKA with endearment as Sasha, has suffered a series of strokes and Ann his wife also is now fighting illness, lets pray for them. He is now 89. Ann is also very ill now apparently and they are taking paypal donations for help with treatment. I feel it a shame to have missed meeting McKenna in Hawaii by a few years, and the Shulgins as they had made SXSW music festival here in 2010 See bit on Dangerous Pictures on website interviews and his interview before McKenna died on their website. I
http://www.shulginresear...ries/the-shulgin-index/
Alexander Shulgin - Wikipedia
I am going to try to contact both the institute and or Sasha his wife, maybe there are others with the institiute staff, that would be willing to help with analysis.
This sentence in the toxicology report very important:
As a result of this study, an intensive chemical analysis of A. rigidula Benth. was undertaken to identify the amines and alkaloids present in the leaves and stems that would comprise browse material.
The researchers had no interest in the cambium of the root, and it was not either qualitively or quantively analysed ever. This could present issues when taking samples pray for success please.
We all known that many of our favorite trees produce little or no desirable content or at least highly varied content in various parts of Mimosa/Acacia Speciestree.
Some parts that are browsable by animals highly toxic lets hope the root cambium proves a good source on n,n, and has far less of these. Anyone shocked by toxicity issues should realise the Mimosa Tenuifolia as spelled in Spanish (also since not circumspect keyword) can have profound effects on developing fetuses of animals eating it.
for all my fellow souls well other than some nasty trolls here and there, ROFL!
The intent of the the original toxicology paper was to determine the cause of the locomotor ataxia and staggering of goats eating the commonly named Guajillo, and the other grazing trees that might be toxic, and their specific toxins.
The professor said that the testing would never be reaffirmed at by his facility due to very limited research funds and the fact that the trees are not a statewide issue.
The results showed an amazing array of 33 different phenylethlamine alkaloids and 2 steroids if memory serves me correctly. There were also I believe 4 unidentified compounds, a new professional analysis could lend to determination of their unknown structure.
Some time after the paper was written and republished in various journals Trouts I believe Dr. Alexanger Shulgin found the results quite remarkable and possibly quite accurate.
He did mention one distinct posibility for error and joked about dirty glassware from a drug lab, well who read this repeated this over and over to other entheoist's but none ever even seemingly comprehended the real potential problem during the tests that might give some skewed results. This potential error was that the GC-MS insertion process might result in the accidental conversion of ephedrine like compounds to amphetamines this is proven to occur. Ephedrine is a more complex molecule and simple reduction could create methamphetamine in example. If a more complex or as complex molecule occurs in ephedra why not a similar or simpler one,in another plant species, it is however the whole array that's hard to swallow.
OK back to todays conversation with the Doctor. He said that he had never heard from Dr. Shulgin or anything ever about any controversy surrounding the results. He said the primary researcher and her assistant are both unreachable one due to her possible death after protracted illness and being possibly posthumous and that the assistant has not been seen or heard from in many years.
He has the highest confidence that this testing was done competently and properly with the only issues being limitations of the older GC-MS processing equipment at the time. He clearly says that these compounds are identified from known GC-MS signatures in a database and there really is no reasonable explanation for bad results other than accidental conversion through reduction during the insertion process I discussed this and he agreed this might be an issue. It could not explain the full rainbow of compounds a few but not all of them.
The dirty glassware theory is a joke by Shulgin he is saying this is probably dead on and that he was seriously amazed and wanted to confirm these results but could not reach anyone.
What is important is the the professor has agreed to allow me to come to the universities research facility and to harvest samples he suggested waiting till spring but I want to expedite reconfirming the results independently.
I think Shulgin is taking for granted thier limited funds to accomplosish this task, the folks were more into livestock management and loss prevention the entheogenic research, they should have certainly recognized the importance and handed off material and results to another university and this is what the doctorate Professor is willing to help with kindly.
I would like to say that I am a long time plaque psorasis sufferer and only learned of various acacias/mimosa trees properties due to their proven healing powers after refusing to take an injection that could destroy my immune system and several failed topical medicines.
Right now there are clearly some potential toxins in Guajillo. At least 4 unknown compounds were isolated in tests.
In addition my best shot at analysis is probably to simply carefullly collect and deliver leaf, stem, and various bark to the University of Texas and to talk up a few students that might be game to write a paper on these plants and their content and toxicology.
Traveler has kindly granted access to a GC-LS testing facility but I am not familiar with this technology since I can not seem to wiki or google it?
I am going to try to reach the person I have the utmost respect for Dr. Shulgin or his wife Ann, and see if he might either forward these to a friend or himself also do analysis on these samples.
What follows is Dr. Shulgins response to inquiries about the paper:
I am familiar with the literature concerning these two West Texas Acacia species, but not with the plants themselves. I had both these PHYTOCHEMISTRY papers in my Acacia file but I must admit that I have some very mixed feelings about them.
What caught my curiosity immediately was the casual indifference shown to what is certainly an extraordinary discovery. Here, amongst some 40 or so alkaloids found in each of these two species, there were five amphetamines that had heretofore been thought to be inventions of man. Two of these are Schedule II drugs, Amphetamine and Methamphetamine. Two are Schedule I drugs, N,N-Dimethylamphetamine and 4-Methoxyamphetamine. And the fifth one is a major human metabolite of Amphetamine, 4-Hydroxyamphetamine. To my knowledge, none of these had ever before been reported as being natural plant alkaloids. This unprecedented discovery elicited only a passing line of comment in the earlier of the two papers.
My first thoughts as to origin were directed towards the well known natural hydroxylated amphetamines such as norephedrine, ephedrine and N-methylephedrine. I know that ephedrine and pseudoephedrine, frequent precursors in the illegal synthesis of methamphetamine, can be reduced to methamphetamine as an artifact of analysis. The sample insertion conditions of the gas chromatograph can effect this conversion. But then, there was no mention of any of these hydroxylated alkaloids as being present in either Acacia.
Might a contaminated round-bottomed flask have been purchased at a garage sale outside an abandoned meth-lab and served as the source of these "man-made" compounds? Unlikely, even in Texas.
Even more dramatic, one of these amphetamines, the 4-Methoxyamphetamine, is the increasingly notorious PMA that is appearing as one of the lethal "Ecstasy" offerings in the rave scene.
Several months ago I tried to contact, individually, the two principal authors, by both e-mail and personal snail-mail, and I have received no response as yet.
There is certainly precedent for a drug which was originally man-made, to be discovered in a plant. N,N-Dimethyltryptamine (DMT) was first synthesized by Manske, in Canada, in the 1930s. It was over twenty years later that it was discovered in a plant from South America. But such an event usually evokes considerable commentary. Here it seems that an exciting story is being ignored. Am I missing something?
-- Dr. Shulgin
Ok I will quote a couple papers and some info on why studies were done and the results of the first highly disputed results:
Negative impact on testosterone:
Exerpts from:
Effect of dietary phenolic amines on testicular function and luteinizing hormone secretion in male angora goats
Many agriculturally important shrubs of the genus Acacia can contain high concentrations of sympathomimetic phenolic amines. These compounds, which are thought to represent plant chemical defenses against herbivory, can affect different physiological processes of higher animals if they enter into the systemic circulation (Smith, 1977; Evans et al., 1979; Forbes et al., 1995). The sympathomimetic phenolic amines present in A. berlandieri have been implicated in the development of a toxic condition in sheep and goats when this shrub is consumed for extended periods (Camp et al., 1964). Parenteral administration of phenolic amines present in A. berlandieri and A. rigidula impairs reproductive function of female goats (Forbes et al., 1993) and heifers (Carpenter et al., 1994) and suppresses LH release after GnRH administration in wethers (Forbes et al., 1994). Further research is required to determine the occurrence of subtoxic effects in domestic ruminants that regularly consume vegetation with high concentrations of phenolic amines. In the present study, male Angora goats were allowed to graze on a range site dominated by A. berlandieri and A. rigidula to test the hypothesis that consumption of these plants does not affect testicular characteristics or function or systemic LH concentrations.
The results of this study indicate that consumption of phenolic amine-containing vegetation may affect the function of the pituitary-gonadal axis in domestic
goats, as has been suggested in recent studies involving parenteral administration of some of the phenolic amines present in A. berlandieri and A. rigidula (Forbes et al., 1993, 1994; Carpenter et al.,1994).
In terms of testicular characteristics and function, the increase in testosterone secretion by the testes, which normally occurs in male goats as the breeding
season advances (Muduuli et al., 1979; Ritar, 1991; Pe?rez and Mateos, 1995), was clearly suppressed in the PA bucks.
Acute parenteral administration of some of the phenolic amines present in A. berlandieri and A. rigidula inhibited GnRH-stimulated LH secretion in wethers (Forbes et al., 1994).
Increased LH concentrations and augmented LH response to GnRH observed on d 75 in the PA bucks was probably a consequence of reduced negative feedback of testosterone because testosterone was lower in the animals consuming A. berlandieri and A. rigidula. Over the long term, PA males seemed to have a diminished testicular responsiveness to LH. This was reflected during the pre-GnRH period by decreased plasma testosterone despite increased LH and a lack of correlation between plasma concentrations of LH and testosterone. This reduced testicular responsiveness to LH was also evident during the GnRH-stimulated period, as reflected by a decreased testosterone response to GnRH-induced LH release. A possible direct or indirect effect of phenolic amines on testicular function, the latter mediated through their ability to stimulate cortisol secretion (Forbes et al.,1994), may have influenced testicular responsiveness to LH because cortisol has been demonstrated to affect LH-stimulated testicular steroidogenesis (references in Vera-Avila et al., 1996).
Results of the discriminatory analysis indicated that serum testosterone, change in SC, and serum T3 and T4 were the response variables most correlated with treatment when considered independently (independent R2) , and with the exception of T4, when considered in a complete model including all of the other variables (partial R2) . Serum testosterone, serum T3, and change in SC provided most of the discriminatory power (ASCC = .60) that could be achieved by including all variables in the model (ASCC = .64). Thus, according to this analysis, diminished serum testosterone and SC and increased serum T3 concentrations most accurately characterized the differences between PA and CO bucks.
FULL VERSION http://jas.fass.org/cgi/reprint/75/6/1612.pdf
Next on alkaloid results:
Chemistry of Acacia's from South Texas
Acacia species in south Texas contain numerous chemical compounds, many of which have negative effects on animal performance.
Alkaloids, phenolic amines, phytoestrogens, and tannis have been identified in south Texas acacias.
Many of the acacias of south Texas are considered to be valuable forage for deer and domestic livestock. It is known, however, that at least one species, guajillo (Acacia berlandieri) will produce a paralytic condition in sheep and goats called "guajillo wobbles." As part of a larger study investigating the chemistry of south Texas range plants, we determined the chemical composition of the leaves of several south Texas acacias.
Most woody plants contain a variety of chemical compounds a number of which have the advantage to the plant of being toxic to animals that consume them. Many of these defensive compounds are nitrogen-based, though there also are a significant number of nonnitrogenous toxic compounds. Additionally, plants produce compounds which may be repellent or, as in the case of tannins, lower the nutritional value of the plant. Early research, using paper and thin-layer chromatographic techniques, identified several phenolic amines in A. berlandieri, including n-methyl-phenethylamine (NMP), tyramine, nmethyltyramine and hordenine.
The alkaloid fractions (those extractable with 10% HCL) of A. berlandieri and A. rigidula contained a complex mixture of alkaloids including nicotine, nornicotine, anhalamine, mescaline, and 3,4,5-trihydroxy-phenethylamine (demethylated mescaline).
The phenolic amines, such as tyramine, hordenine and N-methyl-B-phenethylamine are powerful activators of the sympathetic nervous system causing the release of cortisol and adrenocorticotropic hormone. In addition to the alkaloids, the plants were also found to contain intricate mixtures of tannins and flavenoids including catechin, fisetin and quercetin.
While tannins and their antinutritional effects have been the subject of much research in recent years, little attention has been paid to the negative effects of consumption of other secondary compounds that are not acutely toxic. However, recent research has shown the negative effects on fertility of consumption of amine-containing forage. Consumption of guajillo and blackbrush was shown to reduce fertility in male goats, and to reduce their ability to handle stressful situations such as transportation.
Table 1. Major Chemical Compounds in South Texas Acacias :
Amines and Alkaloids:
phenethylamine
N,N-dimethylphenethylamine
N,N-dimethyl-"-methylphenethylamine
p-hydroxyamphetamine
tyramine
3-5-dimethoxytyramine
3,4-dimethoxy-5-hydroxy-$-phenethylamine
hordenine
N,N-dimethyldopamine
tryptamine
N,N-dimethyltryptamine
N-methylmescaline
nicotine
anhalamine
peyophorine
nortryptyline
3-"-cumyl-1,3,4-oxadiazolidine-2,5-dione
p-hydroxypipecolamide
4-methyl-2-pyridinamine
N-methylphenethylamine
amphetamine
methamphetamine
p-methoxyamphetamine
N-methyltyramine
candicine
dopamine
N-methyldopamine
3-methoxytyramine
N-methyltryptamine
mescaline
trichocereine
nornicotine
anahalidine
mimosine (methyl ester)
musk ambrette
pipecolamide
1,4-benzezediamine
Phytoestrogens:
octylphenol \
aristolone
(Z)-9-octadecenoic acid
(Z,Z,Z)-9,12,15-octadecatrienoic acid
3b-acetoxy-17-methyl-5a-18-abeoandrost-13-ene
nonylphenol
3b-cholest-5-en-3-ol
(Z,Z)-9,12,-octadecanoic acid
Last but not least some more on toxicology:
Toxic amines and alkaloids from acacia rigidula
Acacia rigidula Benth., blackbrush, is a shrub found growing on rocky ridges in west and southwest Texas and northern Mexico. Consumption of blackbrush and a related species guajillo, Acacia berlandieri Benth., has been associated with a locomotor ataxia known as "limber leg".
A. rigidula has been shown to contain appreciable levels of toxic alkaloids. Sheep and goats grazing on a related species, Acacia berlandieri Benth., guajillo, during periods of drought in the Rio Grande Plains of Texas have developed a locomotor ataxia referred to as "guajillo wobbles" or "limber leg" [2]. Previous analysis of blackbrush had detected and identifed four amines, N-methyl-b-phenethylamine (NMPEA), tyramine, N-methyltyramine, and hordenine, which were also found in guajillo [3].
As a result of this study, an intensive chemical analysis of A. rigidula Benth. was undertaken to identify the amines and alkaloids present in the leaves and stems that would comprise browse material.
Forty-four amines and alkaloids, including the four previously encountered amines, N-methyl-b-phenethylamine, tyramine, N-methyltyramine, and hordenine, were identifed by GC-MS.
The majority of the isolated alkaloids, 18 of the 33 identifed, were related to the parent compound b-phenethylamine. These compounds generally varied in the degree of N-methylation, x-methylation (amphetamine family), and in oxygenation of the aromatic ring (tyramine, dopamine, and mescaline families). The 2-cyclohexylethylamine and the N-cyclohexylethyl-N-methylamine are the saturated analogs of the phenethylamine and NMPEA respectively. Tryptamine, N-methyltryptamine, and N,N-dimethyltryptamine were also isolated from blackbrush.
Other noteworthy alkaloids found in blackbrush include nicotine, nornicotine, and four tetrahydroisoquinoline alkaloids, anhalamine, anhalidine, anhalonidine, and peyophorine. The amides of the amino acids pipecolic acid and p-hydroxypipecolic acid were also detected.
As was previously found with NMPEA the foliage collected in the autumn contained higher quantities of amines and alkaloids [10]. There was also a distinct increase in the number and quantity of methylated analogs present (Table 1).
Several as yet unidentifed amine-containing compounds have been detected but have not yet been identifed. It is also probable that several biosynthetic precursors are present in the mixture but as yet are unresolved and are below the threshold of GC-MS detection.
Phenolic amines, as a group, impact the hypothalamic-pituitary-adrenal axis [11]. The consequent release of ACTH and cortisol results in symphathomimetic action. The number of phenolic amines reported in Table 1 and their concentrations in the plant indicate a substantial toxic load to animals consuming blackbrush. The toxicity of nicotine and nornicotine has been well established [12], as has the psychoactivity of mescaline and its derivatives. None of the compounds identifed appear to have been implicated in locomotor ataxia. However the presence of the amphetamines suggests the possibility for a reduction of monoamine oxidase activity [13]. FULL VERSION: http://www.erowid.org/archive/rhodiu...a.rigidula.pdf
I hope to with help here once and for all confirm or deny and expand accurate analysis of at least the 2 species plus another Acacia Sheffneri.
Here locally in my hometown we have a few more plants of interest but these are quire well studied allready although these will have both seasonal and regional and subspecies variations in content these being Arundo Donax the Reed Cane plant, and both species of Demanthus the rock solid safe Leptobolus and its poorer sister species Illioensis.
Thank you for guidance and advice please no personal requests for plants samples since this inapproproriate just pure research efforts only. If these prove fruitfull for further examination over the coming months I will make an effort to make seed and possibly live seedlings available to members, the seed is almost a year away.
I think Dr. Shulgin pretty much eliminates the potential for error due to accidental reduction conversion of many of the substances since he seems to be saying there is no evidence of the needed more complex molecules they might have been converted from if I am comprehending this correctly.
BTW for the few who are not aware of who Dr. Alexander Shulgin is, please read about phikal, Phenylethlamines I have known and loved he is quite daring having synthesized and himself consumed the results of a myriad of molecules he designed by redistributing various side chains.
Update: Very sad to hear that Dr. Shulgin AKA with endearment as Sasha, has suffered a series of strokes and Ann his wife also is now fighting illness, lets pray for them. He is now 89. Ann is also very ill now apparently and they are taking paypal donations for help with treatment. I feel it a shame to have missed meeting McKenna in Hawaii by a few years, and the Shulgins as they had made SXSW music festival here in 2010 See bit on Dangerous Pictures on website interviews and his interview before McKenna died on their website. I
http://www.shulginresear...ries/the-shulgin-index/
Alexander Shulgin - Wikipedia
I am going to try to contact both the institute and or Sasha his wife, maybe there are others with the institiute staff, that would be willing to help with analysis.
This sentence in the toxicology report very important:
As a result of this study, an intensive chemical analysis of A. rigidula Benth. was undertaken to identify the amines and alkaloids present in the leaves and stems that would comprise browse material.
The researchers had no interest in the cambium of the root, and it was not either qualitively or quantively analysed ever. This could present issues when taking samples pray for success please.
We all known that many of our favorite trees produce little or no desirable content or at least highly varied content in various parts of Mimosa/Acacia Speciestree.
Some parts that are browsable by animals highly toxic lets hope the root cambium proves a good source on n,n, and has far less of these. Anyone shocked by toxicity issues should realise the Mimosa Tenuifolia as spelled in Spanish (also since not circumspect keyword) can have profound effects on developing fetuses of animals eating it.
for all my fellow souls well other than some nasty trolls here and there, ROFL!
