Alexander "Sasha" Shulgin's Words

Finshaggy

Well-Known Member
Sasha Shulgin's Words on what is in Your Spice Cabinet:
As the old folk-wisdom says, "Nature is trying to tell us something."
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 phenethylamines. 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 (phenethylamine)? Let's do it by the ring substitution pattern of the phenethylamine, 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 phenethylamine.
(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 phenethylamines. 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.
 

Finshaggy

Well-Known Member
(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 phenethylamine 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.

(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 phenethylamine 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 phenethylamine 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 the Ten Essential phenethylamines, TA.
 

Finshaggy

Well-Known Member
Sasha Shulgin's words on the ambiguity of the word "synthetic":


Some fascinating studies have been done in Germany where the metabolically active mycelium of some Psilocybe species have been administered diethyltryptamine as a potential diet component. Normally, this mushroom species dutifully converts N,N-dimethyltryptamine (DMT) to psilocin, by introducing a 4-hydroxyl group into the molecule by something that is probably called an indole 4-hydroxylase by the biochemists. You put DMT in, and you get 4-hydroxy-DMT out, and this is psilocin. Maybe if you put Mickey Mouse in, you would get 4-hydroxy-Mickey Mouse out. It is as if the mushroom psyche didn't really care what it was working with, it was simply compelled to do its sacred duty to 4-hydroxylate any tryptamine it came across. It was observed that if you put N,N-diethyltryptamine (DET, not a material found in nature) into the growing process, the dutiful and ignorant enzymes would hydroxylate it to 4-hydroxy-N,N-diethyltryptamine (4-HO-DET) a potent drug also not known in nature. This is the title drug of this commentary. What a beautiful burr to thrust into the natural versus synthetic controversy. If a plant (a mushroom mycelium in this case) is given a man-made chemical, and this plant converts it, using its natural capabilities, into a product that had never before been known in nature, is that product natural? What is natural?
Sasha Shulgin's words on Structure Activity Relationship (SAR):


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.
 

Finshaggy

Well-Known Member
Sasha Shulgin's Words on Syllogism and Pharmacology:


What is the train of thought that leads from the structure of a known compound (which is active) to the structure of an unknown one (which may or may not be active)? Certainly the extrapolations involve many what-if's and maybe's. The path can be humorous, it certainly can be tortuous, and it often calls for special things such as faith, insight, and intuition. But can one say that it is logical?

Logic is a tricky thing to evaluate. One of the earliest approaches was laid down by Aristotle, in the form of the syllogism. In it there are three lines consisting of two premises and a conclusion, a form that is called a "mood." All are statements of relationships and, if the premises are true, there are only certain conclusions that may logically follow. For example:

Every man is a lover.
Every chemist is a man.
Therefore, every chemist is a lover.


Letting lover be the major term "a" and letting chemist be the minor term "b" and letting man be the middle term "m", this reduces to:

Every m is a,
Every b is m.
Therefore, every b is a


and it is a valid mood called Barbara.

Of the 256 possible combinations of all's and some's and none's and are's and are-not's, only 24 moods are valid. The reasoning here with MDPH goes:

Some stimulants when given a methylenedioxy ring are MDMA-like.
Some ring-unsubstituted 1,1-dimethylphenylethylamines are stimulants.
Therefore, some ring-unsubstituted 1,1-dimethylphenylethyl
amines when given a methylenedioxy ring are MDMA-like.


In symbolic form this is:

Some m is a, and
Some b is m, then
Some b is a


and this is not one of the 24 valid moods. Given the first premise as some m is a, there is only one valid syllogism form that can follow, and this is known as Disamis, or:

Some m is a, and
Every m is b, then
Some b is a


which translates as:

Some stimulants when given a methylenedioxy group are MDMA-like.
Every stimulant is a ring-unsubstituted 1,1-dimethylphenyl ethylamine.
Therefore, some ring-unsubstituted 1,1-dimethylphenylethyl
amines when given a methylenedioxy group are MDMA-like.


The conclusion is the same. But the second premise is false so the entire reasoning is illogical. What is the false second premise? It is not a fact that every stimulant is a phyntermine.

So much for applying syllogistics to pharmacology.
 

Finshaggy

Well-Known Member
Sasha Shulgin's Words on the Current Drug Laws:


This base, a-ET or etryptamine, was a promising anti-depressant, explored clinically as the acetate salt by Upjohn under the name of Monase. Its central stimulant activity is probably not due to its monoamineoxidase inhibition activity, but appears to stem from its structural relationship to the indolic psychedelics. It was withdrawn from potential commercial use with the appearance of an unacceptable incidence of a medical condition known as agranulocytosis, but the extra mural research into its action, among the lay population, goes on.
One property has been mentioned more than once in anecdotal reports. It appears to serve well, with short term dosage regimens, as an effective tool in kicking dependency on opiates. In chronic use, there is a rather rapid tolerance built up over four or five days, that allows a dosage escalation to a daily load of a gram or more. There might be some discomfort such as sores in the softer tissues of the mouth, but apparently the withdrawal from heroin is easy and effective. Here is a potential tool in addiction treatment that might warrant closer investigation.
Other homologues of a-ET have been synthesized. The a-propylhomologue (a-PT) has been made from tryptophan, and the acetate salt was recrystallized from ethyl acetate/MeOH and melted at 158-158.5 °C. It has not, to my knowledge, ever been tasted. But I suspect that it will take a pretty hefty dosage to get some CNS effect based on the loss of potency with the similar homologation in the Muni Metro series related to MDMA. Rather than lengthening the chain on the alpha-position, some studies have exploited the known potency enhancement that comes from putting a methoxyl group on the 5-position of the indole. This compound, 5-MeO-a-ET, has been made from the 5-methoxyindole-3-aldehyde by coupling with nitropropane (with ammonium acetate) to form the nitrobutene which is a reddish crystalline material, mp 114-116 °C from ethanol. LAH reduction in Et2O/THF gave the desired 5-MeO-a-ET in a 72% yield, mp 201-203 °C as the hydrochloride salt. An alternate synthesis that avoids LAH involves the conversion of 5-methoxyindole to the nitrobutane with 2-nitro-1-butene, followed by reduction with nickel boride to give 5-MeO-a-ET, as the free base in a 52% yield, mp 110-112 °C. As might have been predicted, it was more potent than a-ET by a factor of two with 70 milligrams orally producing a trippy feeling that lasted several hours accompanied with an increased heart beat and difficulty in sleeping. There were no psychedelic effects as such, and no unpleasant side effects. Another compound that has been closely associated with a-ET is a carboline. If a molecule of acetone is brought to react with the amine group and the indolic 2-position, in a condensation that is called a Pictet-Spengler reaction, there would be formed 1,1-dimethyl-3-ethyl-1,2,3,4-tetrahydro-b-carboline. This is a chemical ally of the harmine family of alkaloids, but I have not heard of its having been explored psychedelically. It has been reported to be an impurity of commercial a-ET (including the prescheduling product from the Aldrich Chemical Company) to an extent of some 30%. At these levels, it was suggested that it might play some role in the central action of the parent tryptamine.
a-ET has played yet another role in the evolution of our drug laws, a role that will be found to be of extraordinary importance once it becomes more widely known. This compound may prove pivotal in our ultimate definition of the Analogue Drug Law. I want to talk about: (1) The Controlled Substance Analogue Drug Bill; (2) What happened in a trial in Denver; and (3) What happened in a District Court in Colorado.
During the most political period of the War on Drugs, Congress passed, and the president signed, a new law every two years, on the even-numbered years (the years of congressional re-election) that increased either the definition of what were illegal drugs, or the penalties that follow a conviction for having been associated with them in any way. In 1986, there was a proposed draft of a bill called the "Designer Drug Bill" that had been created within the DEA, and sent on to the Justice Department who, in turn, submitted it to Congress as desired legislation. This was a proposal that would make illegal the tinkering with the structure of a molecule of an illegal drug, to change it in a way that would make it fall outside of the explicit listings of illegal drugs but without significant changes in its pharmacological effects. It was the first time a drug law would define a crime by the activity of a compound as well as by chemical structure. The proposal went to the appropriate legislative committee and, with some modifications, it became law in 1986. There was considerable celebration within the DEA, expressing a "We did it!" kind of satisfaction.
The first three Articles of the Constitution of the United States are entitled: Article. I. The Legislative Department; Article. II. The Executive Department; and Article. III. The Judicial Department. The first of these, consisting of Congress, has the role of writing law and defining the military structure of the nation. The second of these defines the president, who approves the laws of Congress and is the highest military officer. The third of these is invested in the enforcement of these laws. The three departments were defined in a way to assure a balance of power. It is a dangerous step towards a totalitarian state when one special interest group (here the DEA) can, in effect, both write the law and then enforce it.
Here is the text of the Analogue Drug Bill:
(1) The Controlled Substance Analogue Drug Bill. This is contained within Public Law 99-570, the Controlled Substances Analogue Enforcement Act of 1986. This is the so-called "Designer Drug" bill which was intended to allow the prosecution of any act associated with an unscheduled drug, if that drug is analogous either in structure or in action to a scheduled drug, and if it is intended for use in man. Here is the exact wording of this amendment:
(32)(A) Except as provided in subparagraph (B), the term 'controlled substance analogue' means a substance --
(i) the chemical structure of which is substantially similar to the chemical structure of a controlled substance in Schedule I or II;
(ii) which has a stimulant, depressant, or hallucinogenic effect on the central nervous system that is substantially similar to or greater than the stimulant, depressant, or hallucinogenic effect on the central nervous system of a controlled substance in Schedule I or II; or
(iii) with respect to a particular person, which such person represents or intends to have a stimulant, depressant, or hallucino-genic effect on the central nervous system that is substantially similar to or greater than the stimulant, depressant, or hallucinogen effect on the central nervous system of a controlled substance in schedule I or II.
(B) Such term does not include --
(i) a controlled substance;
(ii) any substance for which there is an approved new drug application;
(iii) with respect to a particular person any substance, if an exemption is in effect for investigational use, for that person, under section 505 of the Federal Food, Drug, and Cosmetic Act (21 U.S.C. 355) to the extent conduct with respect to such substance is pursuant to such exemption; or
(iv) any substance to the extent not intended for human consumption before such an exemption takes effect with respect to that substance.
SEC. 203. A controlled substance analogue shall, to the extent intended for human consumption, be treated, for purposes of this title and title III as a controlled substance in Schedule I.
This is the exact wording of the law, and I have discovered that the more times I read it the more convinced I become that, whatever the original intent might have been, it was structured in a way to promote vagueness. I have written elsewhere about the rhetorical nightmare of a double disclaimer, "substantially similar." "Similar" means "pretty much the same." "Substantially identical" would means "pretty much the same." But what does "substantially similar" mean? I like the analogy of seeing two cut glass shakers in the center of the fancy table, one with small holes in the silver screw-down cap containing salt, and the other with slightly larger holes containing pepper. Are these two items substantially similar? If you happen to be a collector of antique crystal glassware, these items are completely identical. If you happen to need to add a condiment to your entree these items are totally different. You must know whose eyes are being looked through to approach the question of "substantial similarity." At a trial a few years ago in Southern California the issue was settled once and for all for a confused jury when a forensic chemist gave an expert opinion that two things were substantially similar when they were greater than 50% identical. Is the right hand more than 50% identical to the right foot? This opinion was patently absurd.
 

Finshaggy

Well-Known Member
(2) What happened in a trial in Denver? A few years ago a young man discovered that the Aldrich Chemical Company offered alpha-ethyltryptamine acetate as a fine chemical. He could buy it in 100g quantities, and package it in 150 milligram capsules to be sold to the street trade as Ecstasy, or MDMA. He could and he did. His actions came to the attention of Law Enforcement, and an opinion was obtained from a DEA chemist that a-ET was not an analogue substance. So the prosecutor decided against pressing charges. But not every one agreed with this not-analogue opinion.
So the chemist solicited the thoughts of his professional colleagues and the answers cam back with as many no's as yes's. The no's were from those who reasoned objectively (scientific, compare the structures) and the yes's were from those who reasoned subjectively (abuse potential, compare the action).
The adventurous a-ET peddler continued, and was again brought to task. The analytical duties went to another chemist, and charges were finally brought under the Analogue Drug Bill. But the earlier opinion was in the record, and the first chemist was brought in by the defense to present these findings at the trial. Clearly there was uncertainty if this was an analogue of anything that was scheduled. The research toxicologist for the home-office of the DEA gave testimony that it was, without question, an analogue. But on cross examination, he was asked just how many times, and for how many different drugs, he had been asked that same question, as an expert witness at a criminal trial. Perhaps twelve, he said. And how many times had he offered the conclusion that the proposed compound had been an analogue of a scheduled drug? In every case. The judge decided that there were some conflicting opinions here, amongst the experts, and dismissed the charges. The defendant was given the warning that this kind of leniency was not common and told to behave himself in the future.
(3) The text of the appellate decision in this matter is a valuable lesson in the fine aspects of grammatical analysis. This is all from 806 F.Supp. 232 (D.Colo., 1992). In way of background it emphasizes that the purpose of the controlled substance analogue statute is to attack underground chemists who tinker with molecules of controlled substances to create new drugs that are not yet illegal. In this case, the defendants were not chemists who created or marketed a designer drug but rather allegedly purchased and distributed a substance that preexisted drugs to which it was a purported analogue. This was probably, in and of itself, sufficient reason to deny the appeal. But the argument developed marvelous new texture as things progressed. As a reminder of the wording of the law (here SS is, of course, substantially similar but this terminology is not addressed in the decision), the three phases of the definitional part of the law can be summarized as follows:
(i) a chemical structure which is SS to ... ;
(ii) which has an effect that is SS to ... ;
(iii) which is represented as having an effect that is SS to ...
The prosecution's reading and analysis of this definition:
"The government's reading of the analogue definition has superficial appeal. As a matter of simple grammar, when an "or" is placed before the last term in a series, each term in the series is usually intended to be disjunctive. Under this reading, a-ET would be an analogue if it satisfies any of the three clauses; however, this reading ignores other grammatical principles that apply in favor of defendant's construction. The operative segments of clauses Iii) and (iii) both begin with the word 'which,' signaling the start of a dependent relative clause modifying a previous noun. In each case the precedent noun is 'chemical structure' found in clause (i). Because both clauses (ii) and (iii) can be read to modify clause (i) the statutory language can be fairly read as requiring the two-pronged definition asserted by the defendants."
The defendant's reading and analysis of this definition:
"Defendant's reading is also bolstered by a deeply rooted rule of statutory construction. A statute must be construed to avoid unintended or absurd results. If I adopt the government's construction and read clause (ii) independently, alcohol or caffeine would be controlled substance analogues because, in a concentrated form, they can have depressent or stimulative effects substantially similar to a controlled substance. Likewise if I read clause (iii) independently, powdered sugar would be an analogue if a defendant represented that it was cocaine, effectively converting this law into a counterfeit drug statute. In both cases the defendant could be prosecuted for selling a controlled substance analogue even though the alleged analogue did not have a chemical structure substantially similar to a schedule I or II controlled substance. Therefore, to prevent this unintended result, clause (i) must apply to any substance that the government contends is a controlled substance analogue."
There is a most instructive bit of history to be considered. In July, 1986, the House of Representatives considered the Designer Drug Enforcement Act of 1986 (H.R. 5246). As with the Senate, the House bill focused on underground chemists who seek to evade the drug laws by slightly altering a controlled substance. The House proposed a two-pronged definition of "analogue" that is virtually identical to the construction advocated by the defendant here. The House bill contained the same three clauses as the current statute, but added the word "and" after clause (i). Congress ultimately adopted the analogue statute as part of the comprehensive "Anti-Drug Abuse Act of 1986." Inexplicably, the analogue definition enacted by Congress dropped the word "and" after clause (i).
This pretty well defines the legislative intent of Congress, and I would give a pretty penny to meet the writer who happened to delete that "and," the one critical word that changed the heart of the law. i would like to know to whom he answered.
Here is a masterpiece of logic which makes some sense out of sloppy law. It must be remembered that the purpose of all of this is to determine if one, or two, or three definitions must be applied to establish just what is an analogue. This court declared that a substance may be a controlled substance analogue only if it satisfies clause (i) and at least one of clauses (ii) or (iii).
There is a fascinating, and potentially most disruptive, appeals ruling made in 1996 concerning the interpretation of this law, in this case involving aminorex and phenethylamine as being analogues of 4-methyl aminorex and methamphetamine, respectively, and thus chargeable as a crime under this analogue statute. This is from the United States District Court for the District of Minnesota, No. 95-2132. In this ruling the Analogue Drug Bill is paraphrased with the following text: "... a drug becomes a controlled substance if it has a chemical structure substantially similar to that of a controlled substance, and either has a substantially similar effect on the user's central nervous system, or a relevant someone represents that it has or intends it to have such an effect." This is fascinating in that the source cited for this quote, 21 U.S.C. SS 802(32)(A), has no such text. And it is potentially disruptive for two reasons. It suggests that an analogue shall become a controlled substance, rather than be treated as if it were a controlled substance. It also introduces a new and undefined term, a "relevant someone." I do not have the legal background to guess the extent that this statement can influence future court challenges in the area of controlled substances analogues. Do, always, keep in mind that the finding that a chemical, in a given situation, is a controlled substance analogue does not make that chemical a controlled substance. The analogue status exists for just the single instance, and the next time the arguments all start over again.
Back to the case involving a-ET. The DEA retreated, licking its wounds, and got its own back by immediately proposing the placement of a-ET into Schedule 1. They succeeded, and Monase is today no longer an FDA-approved antidepressant but it is, instead, a drug with a high potential for abuse. One of the more unexpected forms of abuse can be seen in the costs to the researcher who wished to study it in some legal way. Before it became a scheduled drug, alphaethyltryptamine was what is known as a "fine chemical" and was listed in the catalog of a major chemical company (1993) for a modest $60.90 for a hundred grams. It became a Schedule I drug by emergency scheduling that same year. Recently (1995) I noted that the chemical has been discontinued (as a fine chemical) but has appeared in a catalog from a major supply house for neurological chemicals. Alphaethyl tryptamine now requires a DEA license for purchase, and retailed at $424.00 for 100 milligrams. That calculates out at $424,000.00 for a hundred grams, a price inflation of a factor of almost 7000, or a 700,000% increase. Now THAT is truly drug abuse.
 

Finshaggy

Well-Known Member
Sasha Shulgin's Words on the Temple of True Inner Light:


There is a rather remarkable religious group known as the Temple of the True Inner Light, in New York City, which has embraced as its Eucharist DPT which they refer to as a powerful Angel of the Host. Their communion is confirmed by either the smoking or the drinking of the sacrament, and they have been totally unbothered by any agency of the Federal Government, as far as I know. It is not as if they were unknown. Quite on the contrary, I had on one occasion received a request for information on the drug from a reporter who was writing a story on DPT and its use in the church. I asked him just how he had gotten my name, and he told me that he was given it by someone within the DEA. Someone, sometime, should write an essay on contemporary religions, as to why DPT has flown, why peyote forever struggles, and LSD and marijuana have bombed out, when tied to religion. Is there something about a faith being an "approved" religion? Who gives his approval? Who decides the applicability of the first amendment which explicitly states that, "Congress shall make no law respecting an establishment of religion, or prohibiting the free exercise thereof."

I wish the True Inner Light congregation Godspeed, if you will excuse the expression. My impressions of them from our correspondence have left me totally convinced of their integrity and dedication.
 

curious2garden

Well-Known Mod
Staff member
Do you ever do anything besides copy and paste?
Copied from here: https://steemit.com/science/@marsresident/sasha-shulgin-s-words

Read the commentary, someone copied and pasted trying to make money, hmmm I wonder who that was? Could it be, satan?

Which was ripped from here without attribution:
https://erowid.org/library/books_online/pihkal/pihkal157.shtml

It's a violation of stated copyright:
(https://erowid.org/general/about/about_copyrights.shtml)

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Indagrow

Well-Known Member
This is so that these words survive on past his death for anyone would may be able to use them.
But if it was copied from somewhere then the words already exist. If you truly respect the man and his teaching I wouldnt tarnish his name by tying it to yours
 
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