Finshaggy
Well-Known Member
I found this page that gives dosages, for activators at least
http://herbpedia.wikidot.com/oilahuasca-activators
http://herbpedia.wikidot.com/oilahuasca-activators
Entactogens that can be made by Aminizing your Kitchen's Spice Cabinet
- Thread starter Finshaggy
- Start date
Finshaggy
Well-Known Member
Hungarian Parsley Seed is a better source of Myristicin than Nutmeg. The effects of it when activated properly are said to be like Mescaline and MDMA together. The P450 Enzymes CYP1A2 & CYP3A4 are what break this down and need to be inhibited. CYP2D6 could also play a big role.
Elmicin is something you either need Chromotography type knowledge to get, or you have to buy it in small quantities. When activated properly it is like Mescaline, when activated wrong it is like Melatonin (sleepy). CYP1A1, CYP1B1, CYP1A2, CYP2A6, CYP2C9, CYP2A6, CYP2C9 & CYP2E1 are what are needed to be inhibited to activate this. CYP2D6 could also play an important role.
Safrole is like MDMA when activated properly and like Melatonin when not. CYP2A6, CYP2C9, and CYP2E1 are most important for this. CYP2D6 could also be important.
Methyl Chavicol when activated properly is like a light speedy LSD, when activated wrong it is said to be almost like Marijuana. CYP1A2 and CYP2A6 inhibit it, and CYP2D6 could also be important.
If the CYP2D6 Enzyme is inhibited with all the others, these are possibly visually hallucinogenic Oilahuascas. And the Methyl Chavicol doesn't build a tolerance (the others do) it actually gets stronger for you every time you use it, or you can use less.
Elmicin is something you either need Chromotography type knowledge to get, or you have to buy it in small quantities. When activated properly it is like Mescaline, when activated wrong it is like Melatonin (sleepy). CYP1A1, CYP1B1, CYP1A2, CYP2A6, CYP2C9, CYP2A6, CYP2C9 & CYP2E1 are what are needed to be inhibited to activate this. CYP2D6 could also play an important role.
Safrole is like MDMA when activated properly and like Melatonin when not. CYP2A6, CYP2C9, and CYP2E1 are most important for this. CYP2D6 could also be important.
Methyl Chavicol when activated properly is like a light speedy LSD, when activated wrong it is said to be almost like Marijuana. CYP1A2 and CYP2A6 inhibit it, and CYP2D6 could also be important.
If the CYP2D6 Enzyme is inhibited with all the others, these are possibly visually hallucinogenic Oilahuascas. And the Methyl Chavicol doesn't build a tolerance (the others do) it actually gets stronger for you every time you use it, or you can use less.
Finshaggy
Well-Known Member
There is another mixture that is as simple as the Coffee, Almond, Cinnamon, Vanilla and Nutmeg.
Someone reported having eaten some Nutmeg, but not enough to cause effects. Then took some Calamus Root Extract, but not enough to cause effects. Then smoked some Parsley seed and Dill seed, and reported noticeable Psychedelic effects.
Someone reported having eaten some Nutmeg, but not enough to cause effects. Then took some Calamus Root Extract, but not enough to cause effects. Then smoked some Parsley seed and Dill seed, and reported noticeable Psychedelic effects.
Finshaggy
Well-Known Member
Several allylbenzenes have been proven to form up to 3 alkaloid metabolites after ingestion by several animals.[2][3] They do not form amphetamines in vivo as has been speculated in the past. The alkaloids detected in animal urine are tertiary aminopropiophenones of 3 possible subtypes: dimethylamines, piperidines, and pyrrolidines.[1][2][3][4]
The allylbenzene elemicin has been proven to form all 3 different alkaloid metabolites after ingestion in animals by analyzing urine using gas-liquid chromatography and chemical ionization mass spectrometry.[1]
Safrole is also proven to form all three alkaloid metabolites after ingestion.[2]
Myristicin appears to only form piperidines and pyrrolidines. Dimethylamines of myristicin have not been detected.[3]
Allylbenzene, from which all allylbenzenes are derived, forms piperidine and dimethylamine alkaloids.[4]
Propenylbenzene and its derivatives (asarone, anethole, etc.) do not form alkaloid metabolites.[4]
The allylbenzene elemicin has been proven to form all 3 different alkaloid metabolites after ingestion in animals by analyzing urine using gas-liquid chromatography and chemical ionization mass spectrometry.[1]
Safrole is also proven to form all three alkaloid metabolites after ingestion.[2]
Myristicin appears to only form piperidines and pyrrolidines. Dimethylamines of myristicin have not been detected.[3]
Allylbenzene, from which all allylbenzenes are derived, forms piperidine and dimethylamine alkaloids.[4]
Propenylbenzene and its derivatives (asarone, anethole, etc.) do not form alkaloid metabolites.[4]
Finshaggy
Well-Known Member
From the person who Discovered Oilahuasca
The benzene ring has 6 positions. In the graphical layout given below the following color guide is used:
position 1 = black (the important allyl side chain, required for conversion to an alkaloid)
position 2 = brown (a methoxy group here seems to cause LSD-like mental effects)
position 3 = red
position 4 = green (must be a methoxy or methylenedioxy group for psychedelic activity)
position 5 = blue (a methoxy or methylenedioxy group here seems to enhance visuals)
position 6 = purple (a methoxy group here probably adds speedy effects)
Position 1 has the allyl side chain hanging off of it. It's the same for all allylbenzenes. This is the part of the allylbenzene that reacts in the body to form a dimethylamine, piperidine, or pyrrolidine alkaloid, if digested properly. The details of this are discussed elsewhere.
In order to have psychedelic activity, position 4 must be a methoxy group. It can be tied to another methoxy group on position 5, as it is with myristicin and others. Two methoxy groups tied together are called a methylenedioxy group.
Position 4 cannot be a hydroxy group as it is in eugenol, hydroxychavicol, and chavicol. This can only lead to stimulant effects, not psychedelic effects.
At the bottom of the chart you can see eugenol, hydroxychavicol, and chavicol. These posses no psychedelic activity, even when properly metabolized. These are the only allylbenzenes in the chart that have a hydroxy group on the 4 position.
Above that we have methyl eugenol, chavibitol, and methyl chavicol. Methyl chavicol and methyl eugenol have psychedelic activity when properly metabolized. The effects of chavibitol are unknown, but are probably like a cross between methyl eugenol and methyl chavicol. The 5 position being a methoxy group seems to improve visual effects.
Above that we have croweacin, apiole, and safrole. Apiole and safrole are psychedelic when metabolized properly. Croweacin is a positional isomer of myristicin. It's activity is not known. It's very likely similar to myristicin, but probably more speedy like apiole. The 6 position being a methoxy group seems to add amphetamine style speedy effects.
Above that we have the ever so popular myristicin, and then dillapiole and the rare sarisan. Both myristicin and dillapiole are psychotic when properly metabolized. The activity of sarisan is unknown. It is a positional isomer of myristicin. It has a methoxy group on the 2 position instead of the 3 position. This probably gives it LSD-like mental effects which are attributed to dillapiole and gamma-asarone rather than myristicin.
Above that we have elemicin, 2,3,4,5-tetramethoxy-allylbenzene, and gamma-asarone. Elemicin is the only one of these that's known to have psychedelic activity when properly metabolized. When properly metabolized, it's effects are similar to myristicin, but more like mescaline. It has the same positional substitutions as myristicin, only the 4 and 5 positions are not tied together. Gamma-asarone is a positional isomer of elemicin and is probably the main active psychedelic compound in calamus oil from Nepal. The methoxy group on the 2 position is probably the reason calamus oil from Nepal has LSD-like mental effects shared by dillapiole and absent from most of the other allylbenzenes. I have no idea if 2,3,4,5-tetramethoxy-allylbenzene is active or not.
The benzene ring has 6 positions. In the graphical layout given below the following color guide is used:
position 1 = black (the important allyl side chain, required for conversion to an alkaloid)
position 2 = brown (a methoxy group here seems to cause LSD-like mental effects)
position 3 = red
position 4 = green (must be a methoxy or methylenedioxy group for psychedelic activity)
position 5 = blue (a methoxy or methylenedioxy group here seems to enhance visuals)
position 6 = purple (a methoxy group here probably adds speedy effects)
Position 1 has the allyl side chain hanging off of it. It's the same for all allylbenzenes. This is the part of the allylbenzene that reacts in the body to form a dimethylamine, piperidine, or pyrrolidine alkaloid, if digested properly. The details of this are discussed elsewhere.
In order to have psychedelic activity, position 4 must be a methoxy group. It can be tied to another methoxy group on position 5, as it is with myristicin and others. Two methoxy groups tied together are called a methylenedioxy group.
Position 4 cannot be a hydroxy group as it is in eugenol, hydroxychavicol, and chavicol. This can only lead to stimulant effects, not psychedelic effects.
At the bottom of the chart you can see eugenol, hydroxychavicol, and chavicol. These posses no psychedelic activity, even when properly metabolized. These are the only allylbenzenes in the chart that have a hydroxy group on the 4 position.
Above that we have methyl eugenol, chavibitol, and methyl chavicol. Methyl chavicol and methyl eugenol have psychedelic activity when properly metabolized. The effects of chavibitol are unknown, but are probably like a cross between methyl eugenol and methyl chavicol. The 5 position being a methoxy group seems to improve visual effects.
Above that we have croweacin, apiole, and safrole. Apiole and safrole are psychedelic when metabolized properly. Croweacin is a positional isomer of myristicin. It's activity is not known. It's very likely similar to myristicin, but probably more speedy like apiole. The 6 position being a methoxy group seems to add amphetamine style speedy effects.
Above that we have the ever so popular myristicin, and then dillapiole and the rare sarisan. Both myristicin and dillapiole are psychotic when properly metabolized. The activity of sarisan is unknown. It is a positional isomer of myristicin. It has a methoxy group on the 2 position instead of the 3 position. This probably gives it LSD-like mental effects which are attributed to dillapiole and gamma-asarone rather than myristicin.
Above that we have elemicin, 2,3,4,5-tetramethoxy-allylbenzene, and gamma-asarone. Elemicin is the only one of these that's known to have psychedelic activity when properly metabolized. When properly metabolized, it's effects are similar to myristicin, but more like mescaline. It has the same positional substitutions as myristicin, only the 4 and 5 positions are not tied together. Gamma-asarone is a positional isomer of elemicin and is probably the main active psychedelic compound in calamus oil from Nepal. The methoxy group on the 2 position is probably the reason calamus oil from Nepal has LSD-like mental effects shared by dillapiole and absent from most of the other allylbenzenes. I have no idea if 2,3,4,5-tetramethoxy-allylbenzene is active or not.
Finshaggy
Well-Known Member
Found a report with some measurements:
AFOAF used 5 grams of sassafras bark, 1 gram of lecithin, ground to powder, then mixed with 1 cup of steaming hot milk and 2 ml of vegetable oil. This was left to sit for 2 hours and was then filtered. It was super hard to filter. Decanting would be a better idea.
He then mixed 6 drops of cinnamon bark oil and 3 drops of German chamomile oil into it. The German chamomile would not mix into it and just floated to the top. He mixed it as good as he could and drank it down.
Its been about 3 hours and he feels NICE. There's very obvious euphoria. Sense of touch is enhanced. He feels good. There's no sedation felt at all. It’s mildly psychedelic.
This seemed to work. But he doesn’t know what MDMA really feels like so he can’t compare it to MDMA. It does feel like a phenethylamine though. It’s very different from taking sassafras on its own.
This is a light dose. I think 10-20 grams of bark would be much better.
I would love to hear what others more familiar with MDMA think about this combination. It seems to have worked to produce an MDMA-like effect, but until others more familiar with MDMA test this out, we should take that statement as simply a guess.
AFOAF used 5 grams of sassafras bark, 1 gram of lecithin, ground to powder, then mixed with 1 cup of steaming hot milk and 2 ml of vegetable oil. This was left to sit for 2 hours and was then filtered. It was super hard to filter. Decanting would be a better idea.
He then mixed 6 drops of cinnamon bark oil and 3 drops of German chamomile oil into it. The German chamomile would not mix into it and just floated to the top. He mixed it as good as he could and drank it down.
Its been about 3 hours and he feels NICE. There's very obvious euphoria. Sense of touch is enhanced. He feels good. There's no sedation felt at all. It’s mildly psychedelic.
This seemed to work. But he doesn’t know what MDMA really feels like so he can’t compare it to MDMA. It does feel like a phenethylamine though. It’s very different from taking sassafras on its own.
This is a light dose. I think 10-20 grams of bark would be much better.
I would love to hear what others more familiar with MDMA think about this combination. It seems to have worked to produce an MDMA-like effect, but until others more familiar with MDMA test this out, we should take that statement as simply a guess.
Finshaggy
Well-Known Member
Sasha's Words on this
One of the banes of the archivist is having to choose one pattern of organization over another. The book store owned by a language scholar will have the German poets and playwrights and novelists here, and the French ones over there. Next door, the book store is run by a letters scholar, and the poetry of the world is here, and the plays of the world are there, regardless of the language of origin. The same obtains with spices, and essential oils, and amphetamines. The spice cabinet is a rich source of chemical treasures, each source plant containing a host of com-pounds, some of which are true essential oils. And the next spice from the next plant has some of the same components and some new ones. Does one organize by plant (spice or herb) or by essential oil (amphetamine)? Let's do it by the ring substitution pattern of the amphetamine, and gather the spices and oils as a secondary collection.
(1) The 4-methoxy pattern. The pivotal essential oil is 4-allylanisole, or methyl chavicol, or estragole (called esdragol in the old literature). This allyl compound is found in turpentine, anise, fennel, bay, tarragon, and basil. Its smell is light, and reminiscent of fennel. The propenyl analogue is called anethole, or anise camphor, and it is found in both anise and camphor. It is a waxy solid, and has a very intense smell of anise or fennel. At low concentrations, it is sweet, as in magnolia blossoms, where it is also found. The drinks that turn cloudy with water dilution (Pernod-like liqueurs, and ouzo and roki), are heavy with it, since it was the natural flavoring in the original absinthe. That drink was very popular in the last century, as an intoxicant which produced an altered state of consciousness beyond that which could be ascribed to alcohol alone. It contained wormwood, which proved to be neurologically damaging. The flavorings, such as anethole, are still big things in synthetic liqueurs such as vermouth. Old anethole, when exposed to air and light, gets thick and sticky and yellowish, and becomes quite disagreeable to taste. Maybe it is polymerizing, or maybe oxidizing to stuff that dimerizes. Whatever. These changes are why old spices in the cabinet are best discarded. And adding ammonia to any of these natural product oils produces, in principle, 4-methoxyamphetamine, 4-MA.
(2) The 3,4-dimethoxy pattern. The main actor here is methyleugenol, or 4-allyl-1,2-dimethoxybenzene. This is located in almost every item in the spice cabinet. It is in citronella, bay (which is laurel, which is myrtle), pimiento, allspice, pepper, tree-tea oil, and on and on. It has a faint smell of cloves, and when dilute is immediately mistaken for carnations. The propenyl analogue is, not unreasonably, methylisoeugenol, a bit more scarce, and seems to always be that little minor peak in any essential oil analysis. The compounds missing that methyl group on the 4-oxygen are famous. The allyl material is eugenol, 4-allylguaiacol, and it is in cinnamon, nutmeg, cloves, sassafras and myrrh. You taste it and it burns. You smell it and think immediately of cloves. And its property as an anesthetic, in the form of a clove, is well known in the folk-treatment of toothaches. Actually, flowers of clove (the gillyflower, like the carnation) are the small, pointy things that decorate baked hams and, when stuck into apples, make pomander balls. This anesthetic property has recently led to a drug abuse fad, called clove cigarettes. Very strong, very flavorful, and very corrosive things from Southeast Asia. The eugenol that is present numbs the throat, and allows many strong cigarettes to be smoked without pain. The propenyl analogue is isoeugenol, with a smell that is subtle but very long lasting, used more in soaps and perfumes than in foods. The amine addition to the methyleugenol world produces 3,4-dimethoxyamphetamine, or 3,4-DMA. The isomer with the other methyl group missing is chavibetol (3-hydroxy-4-methoxyallylbenzene) and is found in the pepper leaf that is used with betel nut. A couple of positional rearrangement isomers of methyleugenol are known in the plant world. The 2,4-isomer is called osmorrhizole, and the conjugated form is isoosmorrhizole or nothosmyrnol; both are found in carrot-like vegetables. They, with ammonia, would give 2,4-DMA. And the 3,5-dimethoxyallylbenzene isomer from artemisia (a pungent herb commonly called mugwort) and from sage, would give rise to 3,5-DMA. This is an unexplored isomer which would be both an antidote for opium as well as a stimulant, if the classical reputation of mugwort is transferred to the amphetamine.
(3) The 3,4-methylenedioxy pattern. One of the most famous essential oils is safrole, or 4-allyl-1,2-methylenedioxybenzene. This is the mainstay of sassafras oil, and it and its conjugated isomer isosafrole have a smell that is immediately familiar: root beer! These are among the most widely distributed essential oils, being present in most of the spices, including the heavies such as cinnamon and nutmeg. I am not aware of the 2,3-isomer ever having been found in nature. Adding ammonia to either would give MDA.
(4) The 3-methoxy-4,5-methylenedioxy pattern. The parent compound is myristicin, 5-allyl-1-methoxy-2,3-methylenedioxybenzene, and the source of this is nutmeg (or the botanically parallel material, mace). The nutmeg is the seed of the tree Myristica fragrans and mace is the fibrous covering of the seed. The two spices are virtually identical as to their chemical composition. Myristicin and the conjugated isomer isomyristicin are also found in parsley oil, and in dill. This was the oil that was actually shown to be converted to MMDA by the addition of ammonia by passage through an in vitro liver preparation. So here is the major justification for the equation between the essential oils and the Essential Amphetamines. Care must be taken to make an exact distinction between myristicin (this essential oil) and myristin (the fat) which is really trimyristin or glyceryl trimyristate from nutmeg and coconut. This is the fat from myristic acid, the C-14 fatty acid, and these two similar names are often interchanged even in the scientific literature.
(5) The 2-methoxy-3,4-methylenedioxy pattern. This is the second of the three natural methoxy methylenedioxy orientations. Croweacin is 2-methoxy-3,4-methylenedioxyallylbenzene, and it takes its name from the binomial for the plant Eriostemon crowei from the worlds of rue and the citrus plants. It corresponds to the essential amphetamine MMDA-3a. This oil is found in plants of the Family Rutaceae. My memories of this area of botany are of Ruta graveolens, the common rue, whose small leaves smelled to me, for all the world, like cat urine. This plant has always fascinated me because of a most remarkable recipe that I was given by a very, very conservative fellow-club member, one evening, after rehearsal. He told me of a formula that had provided him with the most complete relief from arthritic pain he had ever known. It was a native decoction he had learned of many years eariler, when he was traveling in Mexico. One took equal quantities of three plants, Ruta graveolens (or our common rue), Rosmarinus officinalis (better known as rosemary), and Cannabis sativa (which is recognized in many households simply as marijuana). Three plants all known in folklore, rue as a symbol for repentance, rosemary as a symbol of remembrance, and pot, well, I guess it is a symbol of a lot of things to a lot of people. Anyway, equal quantities of these three plants are allowed to soak in a large quantity of rubbing alcohol for a few weeks. Then the alcoholic extracts are clarified, and allowed to evaporate in the open air to a thick sludge. This then was rubbed on the skin, where the arthritis was troublesome, and always rubbed in the direction of the extremity. It was not into, but onto the body that it was applied. All this from a very conservative Republican friend!
The methoxy-methylenedioxy pattern is also found in nature with the 2,4,5-orientation pattern. The allyl-2,4,5-isomer is called asaricin. It, and its propenyl-isomer, carpacin, are from the Carpano tree which grows in the Solomon Islands. All these plants are used in folk medicine. These two systems, the 2,3,4- and the 2,4,5-orientations, potentially give rise, with ammonia, to MMDA-3a and MMDA-2.
One of the banes of the archivist is having to choose one pattern of organization over another. The book store owned by a language scholar will have the German poets and playwrights and novelists here, and the French ones over there. Next door, the book store is run by a letters scholar, and the poetry of the world is here, and the plays of the world are there, regardless of the language of origin. The same obtains with spices, and essential oils, and amphetamines. The spice cabinet is a rich source of chemical treasures, each source plant containing a host of com-pounds, some of which are true essential oils. And the next spice from the next plant has some of the same components and some new ones. Does one organize by plant (spice or herb) or by essential oil (amphetamine)? Let's do it by the ring substitution pattern of the amphetamine, and gather the spices and oils as a secondary collection.
(1) The 4-methoxy pattern. The pivotal essential oil is 4-allylanisole, or methyl chavicol, or estragole (called esdragol in the old literature). This allyl compound is found in turpentine, anise, fennel, bay, tarragon, and basil. Its smell is light, and reminiscent of fennel. The propenyl analogue is called anethole, or anise camphor, and it is found in both anise and camphor. It is a waxy solid, and has a very intense smell of anise or fennel. At low concentrations, it is sweet, as in magnolia blossoms, where it is also found. The drinks that turn cloudy with water dilution (Pernod-like liqueurs, and ouzo and roki), are heavy with it, since it was the natural flavoring in the original absinthe. That drink was very popular in the last century, as an intoxicant which produced an altered state of consciousness beyond that which could be ascribed to alcohol alone. It contained wormwood, which proved to be neurologically damaging. The flavorings, such as anethole, are still big things in synthetic liqueurs such as vermouth. Old anethole, when exposed to air and light, gets thick and sticky and yellowish, and becomes quite disagreeable to taste. Maybe it is polymerizing, or maybe oxidizing to stuff that dimerizes. Whatever. These changes are why old spices in the cabinet are best discarded. And adding ammonia to any of these natural product oils produces, in principle, 4-methoxyamphetamine, 4-MA.
(2) The 3,4-dimethoxy pattern. The main actor here is methyleugenol, or 4-allyl-1,2-dimethoxybenzene. This is located in almost every item in the spice cabinet. It is in citronella, bay (which is laurel, which is myrtle), pimiento, allspice, pepper, tree-tea oil, and on and on. It has a faint smell of cloves, and when dilute is immediately mistaken for carnations. The propenyl analogue is, not unreasonably, methylisoeugenol, a bit more scarce, and seems to always be that little minor peak in any essential oil analysis. The compounds missing that methyl group on the 4-oxygen are famous. The allyl material is eugenol, 4-allylguaiacol, and it is in cinnamon, nutmeg, cloves, sassafras and myrrh. You taste it and it burns. You smell it and think immediately of cloves. And its property as an anesthetic, in the form of a clove, is well known in the folk-treatment of toothaches. Actually, flowers of clove (the gillyflower, like the carnation) are the small, pointy things that decorate baked hams and, when stuck into apples, make pomander balls. This anesthetic property has recently led to a drug abuse fad, called clove cigarettes. Very strong, very flavorful, and very corrosive things from Southeast Asia. The eugenol that is present numbs the throat, and allows many strong cigarettes to be smoked without pain. The propenyl analogue is isoeugenol, with a smell that is subtle but very long lasting, used more in soaps and perfumes than in foods. The amine addition to the methyleugenol world produces 3,4-dimethoxyamphetamine, or 3,4-DMA. The isomer with the other methyl group missing is chavibetol (3-hydroxy-4-methoxyallylbenzene) and is found in the pepper leaf that is used with betel nut. A couple of positional rearrangement isomers of methyleugenol are known in the plant world. The 2,4-isomer is called osmorrhizole, and the conjugated form is isoosmorrhizole or nothosmyrnol; both are found in carrot-like vegetables. They, with ammonia, would give 2,4-DMA. And the 3,5-dimethoxyallylbenzene isomer from artemisia (a pungent herb commonly called mugwort) and from sage, would give rise to 3,5-DMA. This is an unexplored isomer which would be both an antidote for opium as well as a stimulant, if the classical reputation of mugwort is transferred to the amphetamine.
(3) The 3,4-methylenedioxy pattern. One of the most famous essential oils is safrole, or 4-allyl-1,2-methylenedioxybenzene. This is the mainstay of sassafras oil, and it and its conjugated isomer isosafrole have a smell that is immediately familiar: root beer! These are among the most widely distributed essential oils, being present in most of the spices, including the heavies such as cinnamon and nutmeg. I am not aware of the 2,3-isomer ever having been found in nature. Adding ammonia to either would give MDA.
(4) The 3-methoxy-4,5-methylenedioxy pattern. The parent compound is myristicin, 5-allyl-1-methoxy-2,3-methylenedioxybenzene, and the source of this is nutmeg (or the botanically parallel material, mace). The nutmeg is the seed of the tree Myristica fragrans and mace is the fibrous covering of the seed. The two spices are virtually identical as to their chemical composition. Myristicin and the conjugated isomer isomyristicin are also found in parsley oil, and in dill. This was the oil that was actually shown to be converted to MMDA by the addition of ammonia by passage through an in vitro liver preparation. So here is the major justification for the equation between the essential oils and the Essential Amphetamines. Care must be taken to make an exact distinction between myristicin (this essential oil) and myristin (the fat) which is really trimyristin or glyceryl trimyristate from nutmeg and coconut. This is the fat from myristic acid, the C-14 fatty acid, and these two similar names are often interchanged even in the scientific literature.
(5) The 2-methoxy-3,4-methylenedioxy pattern. This is the second of the three natural methoxy methylenedioxy orientations. Croweacin is 2-methoxy-3,4-methylenedioxyallylbenzene, and it takes its name from the binomial for the plant Eriostemon crowei from the worlds of rue and the citrus plants. It corresponds to the essential amphetamine MMDA-3a. This oil is found in plants of the Family Rutaceae. My memories of this area of botany are of Ruta graveolens, the common rue, whose small leaves smelled to me, for all the world, like cat urine. This plant has always fascinated me because of a most remarkable recipe that I was given by a very, very conservative fellow-club member, one evening, after rehearsal. He told me of a formula that had provided him with the most complete relief from arthritic pain he had ever known. It was a native decoction he had learned of many years eariler, when he was traveling in Mexico. One took equal quantities of three plants, Ruta graveolens (or our common rue), Rosmarinus officinalis (better known as rosemary), and Cannabis sativa (which is recognized in many households simply as marijuana). Three plants all known in folklore, rue as a symbol for repentance, rosemary as a symbol of remembrance, and pot, well, I guess it is a symbol of a lot of things to a lot of people. Anyway, equal quantities of these three plants are allowed to soak in a large quantity of rubbing alcohol for a few weeks. Then the alcoholic extracts are clarified, and allowed to evaporate in the open air to a thick sludge. This then was rubbed on the skin, where the arthritis was troublesome, and always rubbed in the direction of the extremity. It was not into, but onto the body that it was applied. All this from a very conservative Republican friend!
The methoxy-methylenedioxy pattern is also found in nature with the 2,4,5-orientation pattern. The allyl-2,4,5-isomer is called asaricin. It, and its propenyl-isomer, carpacin, are from the Carpano tree which grows in the Solomon Islands. All these plants are used in folk medicine. These two systems, the 2,3,4- and the 2,4,5-orientations, potentially give rise, with ammonia, to MMDA-3a and MMDA-2.
Finshaggy
Well-Known Member
Continued
(6) The 3,4,5-trimethoxy pattern. Elemicin is the well studied essential oil, 5-allyl-1,2,3-trimethoxybenzene, primarily from the oil of elemi. It is, like myristicin, a component of the Oil of Nutmeg, but it is also found in several of the Oils of Camphor, and in the resin of the Pili in the Philippines. This tree is the source of the Oil of Elemi. I had found a trace component in nutmeg many years ago that proved to be 5-methoxyeugenol, or elemicin without the 4-methyl group; it is also present in the magnolia plant. The aldehyde that corresponds to this is syringaldehyde, and its prefix has been spun into many natural products. Any natural product with a syring somewhere in it has a hydroxy between two methoxys. The amphetamine base from elemicin or isoelemicin would be TMA, the topic of this very recipe.
(7) The 2,4,5-trimethoxy pattern. There is an essential oil called asarone that is 2,4,5-trimethoxy-1-propenylbenzene. It is the trans- or alpha-isomer, and the cis-isomer is known as beta-asarone. It is the isomerization analogue of the much more rare 1-allyl-2,4,5-trimethoxybenzene, gamma-asarone, or euasarone, or sekishone. Asarone is the major component of Oil of Calamus obtained from the rhizomes of Acorus calamus, the common Sweet Flag that grows wild on the edges of swamps throughout North America, Europe, and Asia. It has been used as a flavoring of liqueurs and, as almost every other plant known to man, has been used as a medicine. In fact, in Manitoba this plant was called Rat-root by the Cree Indians in the Lake Winnipeg area known as New Iceland, and Indian-root by the Icelandic pioneers. It was used externally for the treatment of wounds, and internally for most illnesses. There apparently is no report of central effects. The corresponding propanone, acoramone (or 2,4,5-trimethoxyphenylacetone), is also present in Oil of Calamus. The styrene that corresponds to asarone is found in a number of plants, and is surprisingly toxic to brine shrimp. The older literature describes an allyl-trimethoxy benzene called calamol, but it has never been pinned down as to structure. The isolation of gamma-asarone or euasarone from Oil of Xixin (from wild ginger) has given rise to a potential problem of nomenclature. One of the Genus names associated with wild ginger is Asiasarum which looks very much like the name asarone, which comes from the Genus Acorus. And a second Genus of medical plants also called wild ginger is simply called Asarum. There is an Asarum forbesi from central China, and it is known to give a pleasant smell to the body. And there is Asarum seiboldi which is largely from Korea and Manchuria. It has many medical uses, including the treatment of deafness, epilepsy, and rheumatism. The amphetamine that would arise from this natural treasure chest is TMA-2.
( 8 ) The 2,5-dimethoxy-3,4-methylenedioxy pattern. The parent allyl benzene is apiole (with a final "e") or parsley camphor, and it is the major component of parsley seed oil. Its conjugated isomer is called isoapiole, and they are valuable as the chemical precurors to the amination product, DMMDA. Whereas both of these essential oils are white solids, there is a green oily liquid that had been broadly used years ago in medicine, called green, or liquid apiol (without the final "e"). It comes from the seeds of parsley by ether extraction, and when the chlorophyll has been removed, it is known as yellow apiol. With the fats removed by saponification and distillation, the old term for the medicine was apiolin. I would assume that any of these would give rise to white, crystalline apiole on careful distillation, but I have never tried to do it. The commercial Oil of Parsley is so readily available.
(9) The 2,3-dimethoxy-4,5-methylenedioxy pattern. The second of the three tetraoxygenated essential oils is 1-allyl-2,3-dimethoxy-4,5-methylenedioxybenzene, commonly called dillapiole and it comes, not surprisingly, from the oils of any of the several dill plants around the world. It is a thick, almost colorless liquid, but its isomerization product, isodillapiole, is a white crystalline product which melts sharply. This, by the theoretical addition of ammonia, gives DMMDA-2.
(10) The tetramethoxy pattern. The third and last of the tetra-oxygenated essential oils, is 1-allyl-2,3,4,5-tetramethoxybenzene. This is present as a minor component in the oil of parsley, but it is much more easily obtained by synthesis. It, and its iso-compound, and the amination product, are discussed under the last of theTen Essential Amphetamines, TA.
(6) The 3,4,5-trimethoxy pattern. Elemicin is the well studied essential oil, 5-allyl-1,2,3-trimethoxybenzene, primarily from the oil of elemi. It is, like myristicin, a component of the Oil of Nutmeg, but it is also found in several of the Oils of Camphor, and in the resin of the Pili in the Philippines. This tree is the source of the Oil of Elemi. I had found a trace component in nutmeg many years ago that proved to be 5-methoxyeugenol, or elemicin without the 4-methyl group; it is also present in the magnolia plant. The aldehyde that corresponds to this is syringaldehyde, and its prefix has been spun into many natural products. Any natural product with a syring somewhere in it has a hydroxy between two methoxys. The amphetamine base from elemicin or isoelemicin would be TMA, the topic of this very recipe.
(7) The 2,4,5-trimethoxy pattern. There is an essential oil called asarone that is 2,4,5-trimethoxy-1-propenylbenzene. It is the trans- or alpha-isomer, and the cis-isomer is known as beta-asarone. It is the isomerization analogue of the much more rare 1-allyl-2,4,5-trimethoxybenzene, gamma-asarone, or euasarone, or sekishone. Asarone is the major component of Oil of Calamus obtained from the rhizomes of Acorus calamus, the common Sweet Flag that grows wild on the edges of swamps throughout North America, Europe, and Asia. It has been used as a flavoring of liqueurs and, as almost every other plant known to man, has been used as a medicine. In fact, in Manitoba this plant was called Rat-root by the Cree Indians in the Lake Winnipeg area known as New Iceland, and Indian-root by the Icelandic pioneers. It was used externally for the treatment of wounds, and internally for most illnesses. There apparently is no report of central effects. The corresponding propanone, acoramone (or 2,4,5-trimethoxyphenylacetone), is also present in Oil of Calamus. The styrene that corresponds to asarone is found in a number of plants, and is surprisingly toxic to brine shrimp. The older literature describes an allyl-trimethoxy benzene called calamol, but it has never been pinned down as to structure. The isolation of gamma-asarone or euasarone from Oil of Xixin (from wild ginger) has given rise to a potential problem of nomenclature. One of the Genus names associated with wild ginger is Asiasarum which looks very much like the name asarone, which comes from the Genus Acorus. And a second Genus of medical plants also called wild ginger is simply called Asarum. There is an Asarum forbesi from central China, and it is known to give a pleasant smell to the body. And there is Asarum seiboldi which is largely from Korea and Manchuria. It has many medical uses, including the treatment of deafness, epilepsy, and rheumatism. The amphetamine that would arise from this natural treasure chest is TMA-2.
( 8 ) The 2,5-dimethoxy-3,4-methylenedioxy pattern. The parent allyl benzene is apiole (with a final "e") or parsley camphor, and it is the major component of parsley seed oil. Its conjugated isomer is called isoapiole, and they are valuable as the chemical precurors to the amination product, DMMDA. Whereas both of these essential oils are white solids, there is a green oily liquid that had been broadly used years ago in medicine, called green, or liquid apiol (without the final "e"). It comes from the seeds of parsley by ether extraction, and when the chlorophyll has been removed, it is known as yellow apiol. With the fats removed by saponification and distillation, the old term for the medicine was apiolin. I would assume that any of these would give rise to white, crystalline apiole on careful distillation, but I have never tried to do it. The commercial Oil of Parsley is so readily available.
(9) The 2,3-dimethoxy-4,5-methylenedioxy pattern. The second of the three tetraoxygenated essential oils is 1-allyl-2,3-dimethoxy-4,5-methylenedioxybenzene, commonly called dillapiole and it comes, not surprisingly, from the oils of any of the several dill plants around the world. It is a thick, almost colorless liquid, but its isomerization product, isodillapiole, is a white crystalline product which melts sharply. This, by the theoretical addition of ammonia, gives DMMDA-2.
(10) The tetramethoxy pattern. The third and last of the tetra-oxygenated essential oils, is 1-allyl-2,3,4,5-tetramethoxybenzene. This is present as a minor component in the oil of parsley, but it is much more easily obtained by synthesis. It, and its iso-compound, and the amination product, are discussed under the last of theTen Essential Amphetamines, TA.
Finshaggy
Well-Known Member
Cannabinoid Reuptake Inhibitors (CRIs)/Endo-Cannabinoid Reuptake Inhibitors (ECRIs) & Fatty Acid Amide Hydrolayse Inhibitors (FAAH Inhibitors)
Your brain has natural Cannabinoids that it produces to regulate many things, these are called EndoCannabinoids.
Here is a link to the Wiki about EndoCannabinoids function in the brain:
https://en.wikipedia.org/wiki/Endocannabinoid_system
But there is now a Molecule out there that is not a cannabinoid called LY-2183240. What this Molecule is said to do is this:
Acts both as a potent inhibitor of the reuptake of the endocannabinoid anandamide, and as an inhibitor of fatty acid amide hydrolase (FAAH), the primary enzyme responsible for degrading anandamide. This leads to markedly elevated anandamide levels in the brain, and LY-2183240 has been shown to produce both analgesic and anxiolytic effects in animal models.
Here is what Anandamine is (a natural Cannabinoid that your brain produces: http://en.wikipedia.org/wiki/Anandamide
In 1992, in Raphael Mechoulam's lab, the first such compound was identified as arachidonoyl ethanolamine and named anandamide, a name derived from the Sanskrit word for bliss and -amide. Anandamide is derived from the essential fatty acid arachidonic acid. It has a pharmacology similar to THC, although its chemical structure is different. Anandamide binds to the central (CB1) and, to a lesser extent, peripheral (CB2) cannabinoid receptors, where it acts as a partial agonist. Anandamide is about as potent as THC at the CB1 receptor.[41] Anandamide is found in nearly all tissues in a wide range of animals.[42] Anandamide has also been found in plants, including small amounts in chocolate.
AM 404 (Formed in the body when Tylenol is taken)
UCM 707
AM1172
VDM11
VDM13
OMDM1
OMDM2
LY 2183240
LY 2318912
O-2093
Inhibitors of fatty acid amide hydrolase (FAAH)
Carbamate FAAH inhibitors
OL-135
URB 597
URB 532
Bisarylimidazole derivative
Your brain has natural Cannabinoids that it produces to regulate many things, these are called EndoCannabinoids.
Here is a link to the Wiki about EndoCannabinoids function in the brain:
https://en.wikipedia.org/wiki/Endocannabinoid_system
But there is now a Molecule out there that is not a cannabinoid called LY-2183240. What this Molecule is said to do is this:
Acts both as a potent inhibitor of the reuptake of the endocannabinoid anandamide, and as an inhibitor of fatty acid amide hydrolase (FAAH), the primary enzyme responsible for degrading anandamide. This leads to markedly elevated anandamide levels in the brain, and LY-2183240 has been shown to produce both analgesic and anxiolytic effects in animal models.
Here is what Anandamine is (a natural Cannabinoid that your brain produces: http://en.wikipedia.org/wiki/Anandamide
In 1992, in Raphael Mechoulam's lab, the first such compound was identified as arachidonoyl ethanolamine and named anandamide, a name derived from the Sanskrit word for bliss and -amide. Anandamide is derived from the essential fatty acid arachidonic acid. It has a pharmacology similar to THC, although its chemical structure is different. Anandamide binds to the central (CB1) and, to a lesser extent, peripheral (CB2) cannabinoid receptors, where it acts as a partial agonist. Anandamide is about as potent as THC at the CB1 receptor.[41] Anandamide is found in nearly all tissues in a wide range of animals.[42] Anandamide has also been found in plants, including small amounts in chocolate.
AM 404 (Formed in the body when Tylenol is taken)
UCM 707
AM1172
VDM11
VDM13
OMDM1
OMDM2
LY 2183240
LY 2318912
O-2093
Inhibitors of fatty acid amide hydrolase (FAAH)
Carbamate FAAH inhibitors
OL-135
URB 597
URB 532
Bisarylimidazole derivative
Finshaggy
Well-Known Member
Sasha Explains Structure Activity Relationship
There is a sadness felt with most of the published efforts to form sweeping correlations between the structure of a molecule and its biological activity. This relationship is called a SAR, or a Structure Activity Relationship, and there are journals that are dedicated to just this form of analysis.
One needs a large collection of compounds of known structure, and all of them must be of known pharmacological activity. And one needs a computer of some sort. One considers all aspects of the structure such as bond energies, electronic charge densities, molecular lengths, widths and thicknesses, degrees of freedom or of constraint, anything that can be calculated or measured. Then one assigns an independent variable coefficient to everything, constructs some additive equation where these coefficients equal something else, and then compares that something else to the biological activity. Push the "go" button on the computer, and let everything be varied clear across the map, until the calculated solution of the equation makes the best match with the value of pharmacological activity. Then one has a SAR with a statistical measure of goodness of fit, and it then can be used to predict the activity of new structures, which are yet untried, pharmacologically.
And there is the essence of why this entire process is ineffective. Prediction is the heart of this procedure, and prediction is never brought to bear. Let us take a new structure that is not in the original collection of structures, and let us make a prediction as to its, let us say, psychedelic potency. But no one ever tries it out for any of a number of reasons. Maybe the new compound is never synthesized. Or maybe it is synthesized, but never evaluated pharmacologically. The synthesist does not care, or is uninterested, or is restrained by the legal complications that might ensue. Or he does explore it, but chooses not to publish. Almost never is a prediction tested. What is more likely to happen, is that a new input of biological activity and structure variation is uncovered (for which there is no published prediction) and this data is tossed into the mill, and a new set of "more valid" coefficients is calculated, and the SAR becomes touted as a more accurate predictor. But, always remember, that without prediction and challenge, there is no inventive value from the SAR game. It simply organizes what is known, but creates nothing new.
This is a role that I would have loved to see a,N,O-TMS play. At the time of its first synthesis its biological activity was, by definition, completely unknown. Let's cast its shadow up against the structures that were known, and with known activity. What would you predict? The most logical archetype to use as a starting point is the primary amine homologue, a,O-DMS. This is an extremely potent, quite long-lived tryptamine that still ranks up there as the most potent, or nearly so, of all the simple substituted tryptamines. It is orally active. It lasts for many hours. It is completely wild as to visual distortions and illusions. It consistently leads to dramatic, perhaps frightening, but certainly memorable dreams. Three or four milligrams are unmistakably adequate. I would have loved to have had an SAR jock predict what changes would come from the simple addition of an N-methyl group. No one out there predicted this for me, and I have now completely abandoned the art of prediction, at least via the SAR technique. My motto is, make 'em, and taste 'em.
To base structures that are stimulants (amphetamine, for example) an added N-methyl group enhances potency and richness. With MDA, for example, one gets MDMA, not more potent, but of an entirely different form of psychological magic. However, with all the other explored primary amine phenethylamine psychedelics, the potency and the quality of action are effectively lost. With tryptamines, however, the N-methyl groups appear to be needed for full, robust activity. Here, the loss of an N-methyl group might well detract from full potency, and the final unmethylated product (DMT becoming simply tryptamine) will be relatively weak and uninteresting. If a,N,O-TMS had been active at one milligram, then the MDMA explanation is obviously correct. If a,N,O-TMS had been active only at a meager level of twenty milligrams, then the DMT explanation would appear to be correct. It is much less active. It is not spectacular. All you SAR scientists, take this new data, toss it into the maws of computer calculation, and come out with better coefficients.
With this, now, as a challenge, predict for me the potency of a,N,N,O-tetramethylserotonin. Here is a compound that has not been yet synthesized, but which carries the second N-methyl group (yet closer to DMT at the nitrogen atom and probably more potent) and yet a structural kiss of death (as to potency) in the MDA/MDMA world. Will it be up? Will it be down? I am afraid that the "make 'em and taste 'em" procedure is the only one that I can trust.
Good luck
There is a sadness felt with most of the published efforts to form sweeping correlations between the structure of a molecule and its biological activity. This relationship is called a SAR, or a Structure Activity Relationship, and there are journals that are dedicated to just this form of analysis.
One needs a large collection of compounds of known structure, and all of them must be of known pharmacological activity. And one needs a computer of some sort. One considers all aspects of the structure such as bond energies, electronic charge densities, molecular lengths, widths and thicknesses, degrees of freedom or of constraint, anything that can be calculated or measured. Then one assigns an independent variable coefficient to everything, constructs some additive equation where these coefficients equal something else, and then compares that something else to the biological activity. Push the "go" button on the computer, and let everything be varied clear across the map, until the calculated solution of the equation makes the best match with the value of pharmacological activity. Then one has a SAR with a statistical measure of goodness of fit, and it then can be used to predict the activity of new structures, which are yet untried, pharmacologically.
And there is the essence of why this entire process is ineffective. Prediction is the heart of this procedure, and prediction is never brought to bear. Let us take a new structure that is not in the original collection of structures, and let us make a prediction as to its, let us say, psychedelic potency. But no one ever tries it out for any of a number of reasons. Maybe the new compound is never synthesized. Or maybe it is synthesized, but never evaluated pharmacologically. The synthesist does not care, or is uninterested, or is restrained by the legal complications that might ensue. Or he does explore it, but chooses not to publish. Almost never is a prediction tested. What is more likely to happen, is that a new input of biological activity and structure variation is uncovered (for which there is no published prediction) and this data is tossed into the mill, and a new set of "more valid" coefficients is calculated, and the SAR becomes touted as a more accurate predictor. But, always remember, that without prediction and challenge, there is no inventive value from the SAR game. It simply organizes what is known, but creates nothing new.
This is a role that I would have loved to see a,N,O-TMS play. At the time of its first synthesis its biological activity was, by definition, completely unknown. Let's cast its shadow up against the structures that were known, and with known activity. What would you predict? The most logical archetype to use as a starting point is the primary amine homologue, a,O-DMS. This is an extremely potent, quite long-lived tryptamine that still ranks up there as the most potent, or nearly so, of all the simple substituted tryptamines. It is orally active. It lasts for many hours. It is completely wild as to visual distortions and illusions. It consistently leads to dramatic, perhaps frightening, but certainly memorable dreams. Three or four milligrams are unmistakably adequate. I would have loved to have had an SAR jock predict what changes would come from the simple addition of an N-methyl group. No one out there predicted this for me, and I have now completely abandoned the art of prediction, at least via the SAR technique. My motto is, make 'em, and taste 'em.
To base structures that are stimulants (amphetamine, for example) an added N-methyl group enhances potency and richness. With MDA, for example, one gets MDMA, not more potent, but of an entirely different form of psychological magic. However, with all the other explored primary amine phenethylamine psychedelics, the potency and the quality of action are effectively lost. With tryptamines, however, the N-methyl groups appear to be needed for full, robust activity. Here, the loss of an N-methyl group might well detract from full potency, and the final unmethylated product (DMT becoming simply tryptamine) will be relatively weak and uninteresting. If a,N,O-TMS had been active at one milligram, then the MDMA explanation is obviously correct. If a,N,O-TMS had been active only at a meager level of twenty milligrams, then the DMT explanation would appear to be correct. It is much less active. It is not spectacular. All you SAR scientists, take this new data, toss it into the maws of computer calculation, and come out with better coefficients.
With this, now, as a challenge, predict for me the potency of a,N,N,O-tetramethylserotonin. Here is a compound that has not been yet synthesized, but which carries the second N-methyl group (yet closer to DMT at the nitrogen atom and probably more potent) and yet a structural kiss of death (as to potency) in the MDA/MDMA world. Will it be up? Will it be down? I am afraid that the "make 'em and taste 'em" procedure is the only one that I can trust.
Good luck