Let us break up this name into its component parts, starting at the end:
Note: All of the analytical data included in this document was contributed by K. Trout. The data was contained in Trout's Notes #C-10a "Cactus Chemistry: By Species" This was published in 1999 by Better Days Publishing and is available through both Mind Books or Rainbow Garden Books. I would like to take this opportunity to thank him, and the many people like him, who make the Web a better place to be.
Quite soon after starting the fascinating and never ending journey that is collecting and cultivating cacti and succulents we all hear about Lophophora williamsii, or Peyote, and how you can chew up dried slices of this plant and get "high". This plant has been used by certain tribes, eg. Huichol, of north American Indians in some of their religious ceremonies and is still used today by the Native American Church. We also learn that it is illegal to cultivate this plant in many, if not all, parts of the USA. However, our clever American cousins have learned to get round this by writing a different, usually antiquated, name on the labels.
There is also a south American cactus, Trichocereus pachanoi which has been used in a similar way by some tribes of south American Indians. We then hear that this "high" is caused by something called Mescaline which is a kind of chemical, an Alkaloid. If we are lucky enough to have access to a good range of cactus society journals or cactus books we might be able to find out a bit more about Lophophora, Mescaline and its use as an hallucinogenic drug.
What is often overlooked in these journals and books is these cacti contain not only Mescaline, but many other types of Alkaloid. This vast array of Alkaloids are also found in many genera of cacti, including Echinopsis, Stetsonia, Obregonia, Espostoa, Pelecyphora, Coryphantha, Ariocarpus, Mammillaria, Gymnocalycium, Opuntia and of obvious significance here Turbinicarpus. It is not only genera of cacti which contain Alkaloids, many genera of the Mesembryanthemaceae also contain their share.
Trying to find an accurate definition of what an Alkaloid is can be quite difficult. Every definition I have found is different, sometimes in quite fundamental points. About the best I can come up with is the following:
Alkaloids are bitter tasting, almost always basic, i.e. alkaline, nitrogenous compounds of mostly vegetable origin, which have marked physiological properties. They have a so called "ring" structure. Many are poisonous, although in small doses many are used for medical purposes.
Which in plain English means that they are composed of a ring of 5 or 6 Carbon atoms with other groups of atoms, side groups, attached. Nitrogen is nearly always present, usually as part of the ring structure in which case there are only 5 carbon atoms in the ring or as part of one or more of the side groups.
Although many people are unaware of it, many, if not all of us, are in daily contact with Alkaloids. If we are not taking them into our bodies then we are surely reading about them or seeing them on TV. It is quite interesting to realise how much of human history and culture has been affected by this single group of chemicals and the plants which contain them. Some of these are included in the following table:
| Common name | Chemical name | Formula | Origin | Use |
|---|---|---|---|---|
| Atrophine | α[Hydroxymethyl]benzeneacetic acid 8-methyl-8-azabicyclo[3.2.1]oct-3-yl-ester | C17H23NO3 | Deadly nightshade Atropa belladonna | Eye surgery (dilative), pain relief |
| Caffeine | 1,3,7-Trimethylxanthine | C8H10N4O2 | Coffee Coffea arabica and Tea Camellia sinensis | Stimulant |
| Cocaine | Methyl 3-β-hydroxy-1-α-H, 5-α-H-tropane-2-β-carboxylate benzoate | C17H21NO4 | Coca leaves Erythroxylon coca | Stimulant, Local anaesthetic |
| Codeine | C18H21NO3 | Opium poppy Papaver somniferum | Sedative | |
| Coniine | 2-Propylpiperidine | C8H17N | Hemlock Conium maculatum | Sedative, Poison |
| Curare | Mixture of various Alkaloids | Bark of Strychnos toxifica | Poison for arrow tips | |
| Curarine | Curare derivative | Muscle relaxant | ||
| Ergot alkaloids | Mixture of various Alkaloids | Fungus Claviceps purpurea parastic on Rye Secale cereale | Child birth | |
| Heroin | Diacetylmorphine | Opium poppy | Hallucinogen | |
| LSD | Lysergic acid diethylamide | C20H55N3O | Ergot derivative | Hallucinogen |
| Mescaline | 3,4,5-Trimethoxyphenethylamine | C11H17NO3 | Lophophora sp. etc. | Hallucinogen |
| Morphine | 7,8-Didehydro-4,5-epoxy-17-methyl- (5α,6α)-morphinan-3,6-diol | C17H19NO3 | Opium poppy | Pain relief |
| Nicotine | [-]-1-Methyl-2-[3-pyridyl]-pyrrolidine | C10H14N2 | Tobacco leaves Nicotiana tabacum | Cigarettes |
| Quinine | α-(6-Methoxy-4-quinolyl)-5-vinyl- 2-quinuclidinemethonol | C20H24N2O2 | Cinchona bark | Anti malarial |
| Strychnine | 4,6-Methano-6H,14H-indolo[3,2,1-ij] oxepino[2,3,4-de]pyrrolo [2,3-h,]quinoline, strychnidin-10-one derivative | C21H22N2O2 | Seeds of genus Strychnos, e.g. S. nox vomica | Poison |
OK, proper Chemists and impatient folks can skip this bit, while the rest of us take a diversion into the weird and wacky world of organic chemicals and how you name them.
Lets start with a couple of basic definitions:
Chemists have devised a shorthand way of writing about elements and atoms. They do this by using only one or two letters to indicate the type of element, the first always being capitalised. These letters are usually the first letter in the name of the element, eg. Carbon is C, Hydrogen is H or for most other elements the first letter together with another from the name are used, eg. Chlorine is Cl, Magnesium is Mg. In other elements, letters from its Latin name are used, eg. Sodium is Na (Natrum), Gold is Au (Aurum) etc. This shorthand name is called the elements chemical symbol.
OK, enough of elements and atoms, lets move onto molecules. Atoms of one or more elements combine to form molecules of a substance. We have already seen that Alkaloids are composed of some atoms of Carbon arranged in a ring, nearly always one or more Nitrogen atoms, together with some other elements. In the case of Alkaloids these other elements are Oxygen and Hydrogen. The structure and other properties of a molecule are dependent on the way in which all of the atoms are combined and this depends, in turn, on the way in which these four elements bond together. Each type of element is able to bond with different numbers of atoms. Carbon has 4 bonds, Nitrogen has 3, Oxygen 2 and Hydrogen only one. It's a bit like Hi-Fi's !! i.e., an atom of Carbon can have 4 things plugged into it, whereas Hydrogen can only plug into one other atom.
This shorthand way of writing about elements is also used to simplify writing about molecules. In its most basic form this just consist of adding up the number of atoms of each element and writing down the chemical symbol followed by this number in subscript. We saw above that a molecule of Hydrogen is composed of a single Hydrogen atom, so a molecule of Hydrogen is simply signified by its chemical symbol, H. In Oxygen, 2 atoms combine to form a molecule and is signified by O2. Sucrose is a more complex substance and its "molecular formula" is C12H22O11.
The molecular formula only indicates the relative amounts of each element per molecule and, in fact, different substances can have the same molecular formula. For example, the molecular formula of Sucrose, C12H22O11, is the same as that of Gentiobiose, Lactulose, Palatinose and others. It does not give us any idea how the different atoms are joined together and this is the most important detail. Molecules of Alkaloids are composed of their constituent elements arranged into one or more rings of 5 or 6 Carbon atoms with other smaller component parts. These smaller units are called "side chains", basically because they hang off the side, and have names like Hydroxy- (OH-), Methyl- (CH3-), Ethyl- (C2H5-) etc.
Most of the Alkaloids which have been extensively studied, or are in common usage, will have a Common name, eg. Caffeine, Mescaline, etc. However many of those included in this document do not and are identified by the more complex looking chemical names. These are a formalised way of writing down the component structures of a chemical in a reasonably easy to understand way. If you have a basic knowledge of organic chemistry and one of these names you should be able to draw a diagram of the molecular structure. In the case of Mescaline this name is 3,4,5-Trimethoxyphenethylamine, quite a mouth full ! However it is fairly easy to unravel the gobbledegook once we learn the code.
Let us break up this name into its component parts, starting at the end:
There is not enough space here to go into further detail about any other Alkaloids, but I can recommend the excellent book by Edward F. Anderson, Peyote the divine cactus, which contains a much better overview of Alkaloid chemistry and structure than I could ever give.
First of all lets see the most common Alkaloids found in Lophophora williamsii. Please bear in mind this list only contains 6 of the over sixty Alkaloids known to be present in L. williamsii.
| Lophophora williamsii | |
|---|---|
| Mescaline | 30 % of total alkaloid content (1 % dry weight) |
| Pellotine | 17 % of total alkaloid content |
| Anhalonidine | 14 % of total alkaloid content |
| Glycine | 8 % of total alkaloid content |
| Lophophorine | 5 % of total alkaloid content |
| 3-Hydroxy-4,5-dimethoxyphenethylamine | 1-5 % of total alkaloid content |
The following table lists the types of Alkaloids found in the species of Turbinicarpus which have been analysed so far. At the end there is data for Pelecyphora aselliformis for comparison purposes.
| Turbinicarpus species | Analytical details |
|---|---|
| lophophoroides | Analysis by: Štarha et al.1999 |
| Alkaloid | Quantity present |
| Hordenine | 91.69% [±0.54] of total alkaloid fraction of over 500 mg total alkaloids per 100 gm of fresh plant |
| Anhalonidine | 2.37% [±0.12] of total alkaloid fraction of over 500 mg total alkaloids per 100 gm of fresh plant |
| Tyramine | 1.82% [±0.17] of total alkaloid fraction of over 500 mg total alkaloids per 100 gm of fresh plant |
| Phenethylamine | 1.04% [±0.27] of total alkaloid fraction of over 500 mg total alkaloids per 100 gm of fresh plant |
| O-Methylanhalidine | 0.55% [±0.02] of total alkaloid fraction of over 500 mg total alkaloids per 100 gm of fresh plant |
| N-Methylmescaline | 0.51% [±0.11] of total alkaloid fraction of over 500 mg total alkaloids per 100 gm of fresh plant |
| Pellotine | 0.46% [±0.08] of total alkaloid fraction of over 500 mg total alkaloids per 100 gm of fresh plant |
| Anhalinine | 0.15% [±0.08] of total alkaloid fraction of over 500 mg total alkaloids per 100 gm of fresh plant |
| N-Methyl Tyramine | 0.13% [±0.11] of total alkaloid fraction of over 500 mg total alkaloids per 100 gm of fresh plant |
| Mescaline | Trace detected |
| N,N-Dimethylmescaline | Trace detected |
| pseudomacrochele | Analysis by: Bruhn & Bruhn 1973 |
| Hordenine | Sole alkaloid. 1-10 mg of total alkaloids per 100 gm. fresh. |
| pseudomacrochele ssp. krainzianus | Analysis by: Štarha et al.1999 |
| Hordenine | 49.60% [±0.55] of total alkaloid fraction of 250-500 mg total alkaloids per 100 gm of fresh plant |
| Anhalinine | 29.24% [±0.04] of total alkaloid fraction of 250-500 mg total alkaloids per 100 gm of fresh plant |
| N-Methylmescaline | 3.27% [±0.09] of total alkaloid fraction of 250-500 mg total alkaloids per 100 gm of fresh plant |
| N,N-Dimethylmescaline | 2.89% [±0.15] of total alkaloid fraction of 250-500 mg total alkaloids per 100 gm of fresh plant |
| Mescaline | 2.48% [±0.19] of total alkaloid fraction of 250-500 mg total alkaloids per 100 gm of fresh plant |
| Anhalonidine | 2.44% [±0.13] of total alkaloid fraction of 250-500 mg total alkaloids per 100 gm of fresh plant |
| Phenethylamine | 1.12% [±0.13] of total alkaloid fraction of 250-500 mg total alkaloids per 100 gm of fresh plant |
| Tyramine | 0.98% [±0.18] of total alkaloid fraction of 250-500 mg total alkaloids per 100 gm of fresh plant |
| O-Methylanhalidine | 0.77% [±0.04] of total alkaloid fraction of 250-500 mg total alkaloids per 100 gm of fresh plant |
| Pellotine | 0.36% [±0.08] of total alkaloid fraction of 250-500 mg total alkaloids per 100 gm of fresh plant |
| N-Methyl Tyramine | Trace detected |
| schmiedickeanus | Analysis by: Štarha et al.1999 |
| Hordenine | 43.02% [±1.86] of total alkaloid fraction of 100-250 mg total alkaloids per 100 gm of fresh plant |
| Anhalonidine | 19.86% [±1.41] of total alkaloid fraction of 100-250 mg total alkaloids per 100 gm of fresh plant |
| Anhalinine | 17.19% [±1.00] of total alkaloid fraction of 100-250 mg total alkaloids per 100 gm of fresh plant |
| Pellotine | 9.02% [±0.06] of total alkaloid fraction of 100-250 mg total alkaloids per 100 gm of fresh plant |
| Tyramine | 5.46% [±0.14] of total alkaloid fraction of 100-250 mg total alkaloids per 100 gm of fresh plant |
| O-Methylanhalidine | 2.76% [±0.42] of total alkaloid fraction of 100-250 mg total alkaloids per 100 gm of fresh plant |
| Phenethylamine | 1.1% [±0.12] of total alkaloid fraction of 100-250 mg total alkaloids per 100 gm of fresh plant |
| N-Methylmescaline | 1.02% [±0.21] of total alkaloid fraction of 100-250 mg total alkaloids per 100 gm of fresh plant |
| N,N-Dimethylmescaline | Trace detected |
| N-Methyl Tyramine | Trace detected |
| dickisoniae | Analysis by: Štarha et al.1999 |
| Hordenine | 42.45% [±0.45] of total alkaloid fraction of 250-500 mg total alkaloids per 100 gm of fresh plant |
| Anhalonidine | 22.70% [±1.14] of total alkaloid fraction of 250-500 mg total alkaloids per 100 gm of fresh plant |
| Pellotine | 19.33% [±0.28] of total alkaloid fraction of 250-500 mg total alkaloids per 100 gm of fresh plant |
| Anhalinine | 2.78% [±0.31] of total alkaloid fraction of 250-500 mg total alkaloids per 100 gm of fresh plant |
| Tyramine | 2.59% [±0.13] of total alkaloid fraction of 250-500 mg total alkaloids per 100 gm of fresh plant |
| Phenethylamine | 1.70% [±0.15] of total alkaloid fraction of 250-500 mg total alkaloids per 100 gm of fresh plant |
| O-Methylanhalidine | 1.42% [±0.30] of total alkaloid fraction of 250-500 mg total alkaloids per 100 gm of fresh plant |
| N-Methyl Tyramine | 0.51% [±0.02] of total alkaloid fraction of 250-500 mg total alkaloids per 100 gm of fresh plant |
| schmiedickeanus ssp. flaviflorus | Analysis by: Štarha et al.1999 |
| Hordenine | 92.05% [±0.71] of total alkaloid fraction of 100-250 mg total alkaloids per 100 gm of fresh plant |
| Tyramine | 3.08% [±0.08] of total alkaloid fraction of 100-250 mg total alkaloids per 100 gm of fresh plant |
| O-Methylanhalidine | 2.89% [±0.46] of total alkaloid fraction of 100-250 mg total alkaloids per 100 gm fresh plant |
| Phenethylamine | 1.01% [±0.21] of total alkaloid fraction of 100-250 mg total alkaloids per 100 gm of fresh plant |
| Anhalonidine | 0.88% [±0.12] of total alkaloid fraction of 100-250 mg total alkaloids per 100 gm of fresh plant |
| Pellotine | 0.15% [±0.07] of total alkaloid fraction of 100-250 mg total alkaloids per 100 gm of fresh plant |
| N-Methyl Tyramine | Trace detected |
| Mescaline | Trace detected |
| N-Methylmescaline | Trace detected |
| Anhalinine | Trace detected |
| schmiedickeanus ssp. klinkerianus fa. schwarzii | Analysis by: Štarha et al.1999 |
| Hordenine | 48.81% [±2.72] of total alkaloid fraction of 250-500 mg total alkaloids per 100 gm of fresh plant |
| Anhalinine | 39.57% [±1.14] of total alkaloid fraction of 250-500 mg total alkaloids per 100 gm of fresh plant |
| Tyramine | 2.92% [±0.25] of total alkaloid fraction of 250-500 mg total alkaloids per 100 gm of fresh plant |
| O-Methylanhalidine | 2.82% [±0.41] of total alkaloid fraction of 250-500 mg total alkaloids per 100 gm of fresh plant |
| Mescaline | 1.26% [±0.21] of total alkaloid fraction of 250-500 mg total alkaloids per 100 gm of fresh plant |
| Phenethylamine | 1.07% [±0.42] of total alkaloid fraction of 250-500 mg total alkaloids per 100 gm of fresh plant |
| N-Methylmescaline | 0.98% [±0.24] of total alkaloid fraction of 250-500 mg total alkaloids per 100 gm of fresh plant |
| Anhalonidine | 0.52% [±0.11] of total alkaloid fraction of 250-500 mg total alkaloids per 100 gm of fresh plant |
| Pellotine | 0.41% [±0.11] of total alkaloid fraction of 250-500 mg total alkaloids per 100 gm of fresh plant |
| N-Methyl Tyramine | Trace detected |
| N,N-Dimethylmescaline | Trace detected |
| pseudopectinatus | Analysis by: Štarha et al. 1999 |
| Hordenine | 62.11% [±2.42] of total alkaloid fraction of over 500 mg total alkaloids per 100 gm of fresh plant |
| Over 50% of over 50 mg of total alkaloids per 100 gm of fresh plant (Bruhn & Bruhn 1973) | |
| N-Methyl Tyramine | 25.15% [±1.21] of total alkaloid fraction of over 500 mg total alkaloids per 100 gm of fresh plant |
| Tyramine | 3.18% [±0.19] of total alkaloid fraction of over 500 mg total alkaloids per 100 gm of fresh plant |
| Anhalinine | 2.88% [±0.15] of total alkaloid fraction of over 500 mg total alkaloids per 100 gm of fresh plant |
| Phenethylamine | 0.98% [±0.12] of total alkaloid fraction of over 500 mg total alkaloids per 100 gm of fresh plant |
| O-Methylanhalidine | 1.92% [±0.15] of total alkaloid fraction of over 500 mg total alkaloids per 100 gm of fresh plant |
| N-Methylmescaline | 1.11% [±0.13] of total alkaloid fraction of over 500 mg total alkaloids per 100 gm of fresh plant |
| N,N-Dimethylmescaline | Trace detected |
| alonsoi | Analysis by: Štarha et al. 1999 |
| 6,7-Dimethoxy-1,2-dimethly -1,2,3,4-tetrahydroisoquinoline-8-ol | 0.0075 [±0.0009%] % dry weight |
| N-Methyl Tyramine | 0.0052 [±0.0008%] % dry weight |
| Hordenine | 0.0048 [±0.0008%] % dry weight |
| N-Methyl-3,4-dimethoxyphenethylamine | 0.0020 [±0.0005%] % dry weight |
This data is included because both Turbinicarpus pseudopectinatus and valdezianus have at one time been included in the genus Pelecyphora. According to Neal et al. 1972, P. aselliformis contains 62% water by weight.
| Pelecyphora aselliformis | |||
|---|---|---|---|
| Hordenine | 10-50% of 1-10 mg of total alkaloids per 100 gm fresh | Agurell et al. 1971b | |
| 10-50% of 10-50 mg of total alkaloids per 100 gm fresh. Not major alkaloid. | Bruhn & Bruhn 1973 | ||
| Major alkaloid. 0.00063% dry wt. | Neal et al. 1972; | ||
| 0.0007% [fresh wt] | Štarha 1994 | ||
| Anhalidine | 0.000067% dry wt. | Neal et al. 1972 | |
| 10-50% of 1-10 mg total alkaloids per 100 gm of fresh | Agurell et al. 1971b & Bruhn & Bruhn 1973 | ||
| Less than 0.0001% [fresh wt] | Štarha 1994 | ||
| Pellotine | 0.000009% dry wt. | Neal et al. 1972 | |
| Less than 0.0001% [fresh wt] | Štarha 1994 | ||
| Tyramine | Less than 0.0001% [fresh wt] | Štarha 1994 | |
| N-Methyl Tyramine | 0.0002% [fresh wt] | Štarha 1994 | |
| 3,4-Dimethoxy Phenethylamine | Trace detected | Neal et al. 1972 | |
| 0.0002% [fresh wt] | Štarha 1994 | ||
| N,N-Dimethyl-3-hydroxy- 4,5-dimethoxyphenethyl-amine | 0.00018% dry wt.: Minor alkaloid | Neal et al. 1972 | |
| 10-50% of 10-50 mg of total alkaloids per 100 gm fresh: Major alkaloid | Bruhn & Bruhn 1973 | ||
| Mescaline | 0.003% dry wt. | Siniscalco 1983 | |
| Less than 0.0001% [fresh wt] | Štarha 1994 | ||
| Less than 0.00002% dry wt. | Neal et al. 1972 | ||
| Not observed by other workers (including Agurell et al. 1971b & Bruhn & Bruhn 1973). | |||
| 3,4-Dimethoxy-N-methyl Phenethylamine | Trace detected | Neal et al. 1972 | |
| N-Methylmescaline | Trace detected | Neal et al. 1972 | |
| Quinic acid | tlc & glc by Kringstad & Nordal 1975) | ||
| Unidentified alkaloids reported by Reko 1928. | |||
Note: Phenethylamine, N-Methyl-phenethylamine, 4-Methoxy-phenethylamine and N-Methyl-4-Methoxy-phenethylamine have been erroneously listed for Pelecyphora aselliformis. The cited reference, Neal et al. 1972, ran these 4 alkaloids as their dansyl-derivatives using pure reference compounds. They were not found in the plant.
Probably the first thing we notice about this data is it indicates that species of Turbinicarpus contain little, if any, Mescaline. Which is probably one explanation why they have not been used like Lophophora. It also shows that by far the most common Alkaloid found in species of Turbinicarpus is Hordenine. Two other Alkaloids which are nearly always present are Tyramine and N-Methyltyramine. Both of which are intermediates in the chemical pathway between the Amino acid Tyrosine and Hordenine, i.e., to make Hordenine we must first convert Tyrosine to Tyramine, then Tyramine to N-Methyltyramine and lastly N-Methytyramine to Hordenine. There is similarly a path between Anhalonidine and Pellotine. Which would account for their relatively high amounts.
The only species tested so far which does not have Hordenine as its major Alkaloid is T. alonsoi and even this has Hordenine and N-Methyltyramine in relatively high amounts. If the Alkaloid profile of a particular group of plants is indicative of "relatedness" then possibly T. alonsoi is at the evolutionary outer edge of the genus. Lophophora williamsii and diffusa have been shown to have different alkaloid profiles, in L. williamsii the main Alkaloid is Mescaline, whereas L. diffusa contains predominantly Pellotine. So perhaps the use of Alkaloid profiles as a taxonomic tool is useful.
Before we can really make sense of this data it would be necessary to do far more detailed analysis. What would be important is to:
There are quite a few theories as to why plants contain Alkaloids, in some plants they may take part in the metabolism of Nitrogen, they might be the end products of Nitrogen metabolism temporarily stored in the plants tissues before being discarded. This could possibly account for the diurnal variation found by some workers. However, the most obvious use the plants have for Alkaloids is to discourage animals from eating them. This is accomplished firstly by the bitter taste of the Alkaloids which would possibly convince the animal to look elsewhere for its meal and secondly by means of their physiological properties. This could range from just making the animal sick, to killing it outright.
One of the more interesting possible reasons for having Alkaloids, particularly in xerophytes, is the prevention or control of bacterial attack, i.e., rotting. Huichol Indians, amongst others, were known to rub the juices of fresh Lophophora williamsii on wounds to clean the skin and prevent infection. In 1960 work was done to investigate the possible antibiotic properties of Lophophora williamsii. It was found that an unidentified substance called "Peyocactin" was able to inhibit the action of 18 Penicillin resistant strains of Staphylococcus aureus. "Peyocactin" was later identified as being the alkaloid Hordenine (N,N-Dimethyl-hydroxyphenylethylamine which, as stated above, is the most common Alkaloid found in most Turbinicarpus species. It has also been shown that two other common alkaloids, Tyramine and Pellotine, also have antiseptic properties. This antibiotic nature of these Alkaloids is of particular importance to species of Turbinicarpus when we remember their tendency to split when they receive too much water. What would be interesting is to find out if the amounts of these chemicals increase when a plant has been watered excessively or when the plant is being attacked by Bacteria.
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