Pharmacology - Other possible mescaline containing cacti?

[Maggot Brain]

Swim has heard that beaver tail (or opuntia basilaris) contains mescaline. Has anyone else heard this, or maybe even tried it? Swim lives near large amounts of these cacti (grown by other people and wild) , and never sees torchers or san pedros where he lives (kind of sad considering he lives in southern california).

[Benga]

the following list has circulated a little :

Pharmacology
Species Traditional use Alkaloids
T.atacamensis Traditional use Stimulant
T.bridgesii Possible traditional use Total alkaloids 50mg/100g fresh
Mescaline 25mg/100g fresh
3-Methoxytyramine
3,4-Dimethoxyphenylethylamine
Tyramine
Bridgesigenin A
Bridgesigenin B
Kaempferol
Quercetin
T.cordobensis"Lance" No traditional use. Confirmed active (bioassay). More or less equivalent to pachanoi.
T.cuzcoensis No traditional use. Total alkaloids 50mg/100g fresh
3-Methoxytyramine (>50% of total)
Mescaline 0.5-5mg/100g fresh (1-10% of total)
T.fulvilanus No traditional use. Total alkaloids 50mg/100g fresh
Tyramine (10-50% of total)
N-Methyltyramine(10-50% of total)
Mescaline (traces)
T.grandiflorus No traditional use. Mescaline (bioassay) - white flowered form

T.macrogonus No traditional use. Total alkaloids 10-50mg/100g fresh
Mescaline 5-25mg/100g fresh (10-50% of total)
3-Methoxytyramine (1-10% of total)
3,4-Dimethoxyphenylethylamine (1-10% of total)
Tyramine (1-10% of total)
T.pachanoi Traditional use Total alkaloids 50mg/100g fresh
Mescaline 25mg/100g fresh
3,4-Dimethoxyphenylethylamine (1-10% of total)
3-Hydroxy-4,5-dimethoxyphenylethylamine
3-Methoxytyramine (1-10% of total)
4-Hydroxy-3,5-dimethoxyphenylethylamine
Anhalonidine (traces)
Hordenine (traces)
Tyramine (traces)
T.pasacana Traditional use as ash. Candicine
Hordenine
N-Methyltyramine
Tyramine
T.pallarensis No traditional use. Mescaline (bioassay) - equivalent to pachanoi
T.peruvianus Possible traditional use Total alkaloids 1-10mg/100g fresh
Mescaline (very variable)
Tyramine (50% of total)
3-Methoxytyramine (traces)
3,4-Dimthoxyphenylethylamine
4-Hydroxy-3,5-dimethoxyphenylethylamine
T.peruvianus (KK242) Mescaline 0.817% (dried)
T.scopulicolus No traditional use. Mescaline (bioassay) equal to or better than pachanoi
T.scop."Juul's_Giant" No traditional use. Mescaline (bioassay - variable)
T.strigosus No traditional use. Hordenine 10-50mg/100g fresh
Candicine
Mescaline
Tyramine
T.taquimbalensis No traditional use. Total alkaloids 10-50mg/100g fresh
Mescaline 5-25mg/100g fresh (>50% of total)
Hordenine (1-10% of total)
3,4-Dimethoxyphenylethylamine (traces)
3-Methoxytyramine (traces)
T.tarijensis (T.poco) Traditional use Stimulant
T.terscheckii Traditional use. Total alkaloids 10-50mg/100g fresh
Mescaline 5-25mg/100g fresh
Anhalonine
N,N-Dimethymescaline
T.thelegonoides No traditional use. Hordenine 10-50mg/100g fresh
Mescaline (traces)
T.validus No traditional use. Total alkaloids 50mg/100g fresh
Mescaline 25mg/100g fresh (50% of total)

T.vollianus No traditional use. Mescaline (traces)
T.werdermannianus No traditional use. Total alkaloids 10-50mg/100g fresh
Mescaline 5-25mg/100g fresh
3,4-Dimethoxyphenylethylamine (1-10% of total)
3-Methoxytyramine (1-10% of total)
Tyramine (traces)
4-Hydroxy-3,5-dimethoxyphenylethylamine (traces)

a Gottlieb article states the following :


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Other Peyote-type cacti of central Mexico

There are several cacti which are used by the Tarahumares and other tribes of central Mexico as substitutes for peyote. Many of these cacti are now under investigation for their alkaloidal content and psychopharmacological activity. Progress is somewhat retarded in the studies of the effects of these plants because almost all experimentation has been conducted on laboratory animals rather than humans. Some of these cacti have been found to contain mescaline and other related alkaloids with known sympathomimetic properties. Much further research is needed on these plants and their activity. However, we will attempt to bring the reader up to date on what is known about them at this time. PEYOTILLO:
This small cactus is botanically called PELECYPHORA ASELLIFORMIS. It is also known sometimes as the hatchet cactus because of its oddly flattened tubercules. It is often found growing in the state of San Louis Potosi in central Mexico. The plant contains traces of mescaline too minute to have any effect. It also contains small amounts of anhalidine, anhaladine, hordenine, N-methylmescaline, pellotine, 3-demethyltrichocereine, B-phenethylamine, N-methyl-B-phenethylamine, 3,4-dimethoxy-B-pheneththyl- amine, N-methyl-3,4-dimethoxy-B-phenethylamine, and 4-methoxy-B-phenethy- lamine. Most of these are found in peyote but in much larger quantities.
TSUWIRI:
The botanical name of this cactus is ARIOCARPUS RETUSUS. The Huichol name tsuwiri means False Peyote. These people make long pilgrimages to the sacred places where peyote grows in search of that sacrement. They believe that if a person is has not been properly purified the spirits will lead him to the False Peyote and if he partakes of it, he will suffer madness or at least a bad trip. The plant is known among some tribes as Chautle or Chaute. These names are also used for other Ariocarpus species. This cactus contains hordenine, N-methyltryamine in fairly small amounts (about 0.02 percent) and traces of N-methyl-3,4-dimethoxy-B-phenethylamine, and N-methyl-4-B- phenethylamine. Aside from these alkaloids it also contains a flavone called retusin (3,3',4',7-tetramethoxy-5-hydroxyflavone). Although alkaloid content may very some at different seasons or stages of growth, from the scientific point of view the amounts present in this plant appear insufficient to pro- duce any psychopharmacological response.
SUNAMI:
This plant, ARIOCARPUS FISSURATUS, has been used in folkoric medicine of Mexico and southwestern USA. It is believed to be more potent than peyote and is used in the same manner as that cactus or made into an intoxicating drink. Among some tribes it is known as Chaute (a generic term for Ariocarp- us species), living rock, or dry whiskey. The latter name, however, is often used for peyote and other psychoactive cacti. There are two varieties of A. fissuratus: var. lloydii and var. fissuratus. Both have about the same phytochemical makeup. The plant contains mostly hordenine, less N-methyl- tyramine and some N-methyl-3,4-dimethoxy-B-phenethylamine. Two other species, A. kotschoubeyanus also known as Pata De Venado or Pezuna De Venado, and A. trigonus also contain these alkaloids.
DONANA:
This small cactus, CORYPHANTHA MACROMERIS, from northern Mexico has been found to contain macromerine, a phenethylamine drug reputed to have about 1/5 the potency of mescaline. It also contains normacromerine, N-formylnor- macromerin, tyramine, N-methyltramine, hordenine, N-methyl-3,4-dimethoxy-B- phenethylamine, metanephrine, and synephrine (a macromerine precursor). Other coryphantha species which contain macromerine with most of these other alkaloids include: C. pectinada, C. elephantideus, C. runyonii and C. corn- ifera var. echinus. Most of these alkaloids with the exception of macromerine have also been found in other varieties of C. conifera and in C. durangensis, C. ottonis, C. poselgeriana and C. ramillosa. Considering that there is usually no more than 0.1 percent macromerine in Donana and that a gram or more of this alkaloid may be needed to produce a psychotropic effect, one would have to consume more than a kilo of the dried cactus or 20 pounds of the fresh plant. Clearly this is not possible for most humans. If one wishes to experiment with the hallucinogenic properties of Donana, is is necessary first to make an extraction of the mixed alkaloids. Methods for this are given latter in this guide.
DOLICHOTHELE:
Several tribes occasionally use any one of several species of Dolichothele as a peyote-like sacrament. These include D. baumii, D. longimamma, D. melalenca, D. sphaerica. D. surculosa, and D. uberiforma. Recent investig- ations have revealed in these the presence of small amounts of the alkaloids N-methylphenethylamine, B-O-methylsynephrine, N-methyltryamine, synephrine, hordenine, and dolichotheline (N-isovalerylhistamine).
MISCELLANEOUS:
Several other cacti have been used by the Tarahumares as peyote substitutes. Among these are Obregonia denegrii, Aztekium ritterii, Astrophytum asterias, A. capricorne, A. myriostigma (Bishops cap), and Solisia pectinata. The Tarahumares also consume a cactus which they call Mulato (Mammillaria micro- meris) and claim that it prolongs life, gives speed to runners, and clarifies vison for mystical insights. Another cactus similarly employed is known as Rosapara (Epitheliantha micromeris) is believed by many botanists to be the same species as Mulato, but at a later vegetative stage. The large cactus Pachycereus pecten-aboriginum, known locally as Cawe, has occasionally been used as a narcotic.
What little studies have been carried out on these cacti have revealed the presence of alkaloids most of the other species we have discussed, but no mescaline or macromerine. Many of these alkaloids have some psychopharma- calogical properties, but nothing to compare with those two drugs. Further- more, the amounts of these alkaloids are usually so small as to be insignif- icant. For example, the species Obregonia denegrii contains tyramine 0.003 percent, hordenine 0.002 percent, and N-methyltyramin 0.0002 percent. These are all known sympathomimetics, but the percentages are far too minute to have any value. Several publications in recent years have mentioned the sacramental use of these cacti. As a result thousands of people have obtained these plants from cactus dealers and ingested them, usually with disappointing (and sometimes nauseating) results. Sadly many of these cacti are quite rare. If too many people destroy them experimentally, they may become a seriously endangered species. The most suitable cacti for a true psychedelic experience are peyote, which is for the most part illegal, and several species of Tri- chocereus (such as San Pedro), which are still legal.
SAN PEDRO:
This cactus has gained considerable fame in the past five years after numerous reports that it is hallucinogenic, contains mescaline, and is readily available from cactus nurseries. This plant known botanically as Trichocereus pachanoi, is native to the Andes of Peru and Equador. Unlike the small peyote cactus, San Pedro is large and multi-branched. In it's natural enviorment, it often grows to heights of 10 or 15 feet. It's mescaline content is less than that of peyote (0.3 - 1.2 percent), but because of it's great size and rapid growth, it may provide a more econom- ical source of mescaline than peyote. One plant may easily yield several pounds of pure mescaline upon extraction. San Pedro also contains tyramine, hordenine, 3-methoxytyramine, anhalaninine, anhalonidine, 3,4-dimethoxyphen- ethylamine, 3,4-dimethoxy-4-hydroxy-B-phenethylamine, and 3,5-dimethoxy-4- hydroxy-B-phenethylamine. Some of these are known sympathomimetics. Others have no apparent effects when ingested by themselves. It is possible, how- ever, that in combination with the mescaline and other active compounds they may have a synergistic influence upon one another and subtly alter the qual- itive aspects of the experience. It is also possible that any compounds in the plant which act a mild MAO inhibitors will render a person vulnerable to some of the above mentioned amines which would ordinarily be metabolized before they could take effect.
The effects of San Pedro are in many ways more pleasant than those of peyote. To begin with, it's taste is only slightly bitter and the initial nausea is not as likely to occur. When the full psychotropic experience takes hold it is less overwhelming, more tranquil and not nearly as physical as that from peyote.
San Pedro may be eaten fresh or dried and taken in any of the manners describ- ed for peyote. Cuttings of San Pedro sold in the USA are usually about three feet long by four inches diameter. A piece 4-8 inches long will usually bring about the desired effect. The skin and spines must be removed. The skin should not be thrown away, however. The green tissue close to the skin con- tains a high concentration of mescaline. Some people chew the skin until all the juices are extracted. If you don't what to do this, the skins can be boiled in water for several hours to make a potent tea. The woody core of the cactus cannot be eaten. One can eat around it like a corn cob. The core does not have much alkaloid content, but can be mashed and boiled as a tea for what little is there.
To dry San Pedro slice the cactus into disks (actually stars) 1/2 inch thick and dry thoroughly in the sun or in an oven at 250 degrees F. The spines must be removed either before drying or before chewing. Also one must be careful of the splinters from the woody core.
If a tea is made from fresh San Pedro, the cactus must be either sliced, chopped or crushed before boiling.
San Pedro is a hardy cactus and endures cold climates quite well. It grows at altiudes from sea level to 9000 feet high in the Andes where it is most freq- uently found on western slopes. The soil in this region is very rich in humus and various minerals. This helps in the production of mescaline and other alkaloids.
There are several cacti which look much like San Pedro and have even been mistaken for it by trained botanists. In 1960 when Turner and Heyman disc- overed that San Pedro contained mescaline they erroneously identified the plant as Opunita cylindtica. A few other South American species of Tricho- cereus also contain mescaline with related alkaloids. These include: T. BRIDGESII, T. MACROGONUS, T.TERSCHECKII, and T. WERDERMANNIANUS.
There is evidence that the ritualistic use of San Pedro dates back to 1000 BC. Even today it is used by Curanderos (medicine men) of northern Peru. They prepare a drink called CIMORA from it and take this in a ceremonial setting to diagnose the spiritual or subconscious basis of a patient's illness.

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another study focuses on the following

LANT MATERIAL.-The cacti used in this investigation were obtained from the following sources: Stetsonia coryne, Pachycereus pecten-aboriginum, Trichocereus cuzcoensis,
T. santiaguensis, T. strigosus, T. thelegonoides and T. thelegonus from W. Haage, Erfurt, DDR; T. courantii. T. knuthianus. T. rnanguinii, T. pupureopilosus, T. taquimbalensis and T. tunariensis from H. van Donkelaar, Werkendam, The Netherlands; Pachycereus pecten-aboriginum. Stetsonia coryne, T. santiaguensis. Echinopsis rhodotricha and Pelecyphora aselliformis from K. Edelmann, Reeuwijk, The Netherlands; T. fulvilanus, T. santiaguensis and T. skottsbergii from M. Schleipfer, Augsburg, DBR; T. validus, T. thelegonous were gifts from Dr. J. P. M. Brenan, Royal Botanic Gardens, Kew, UK.
The nomenclature of species as proposed by Backeberg (4) is used. Plants were checked to conform with the macromorphological descriptions given by Backeberg. (4). Reference caccti are maintained in our greenhouse.
ISOLATION AND IDENTIFICATION OF ALKALOIDS.- Methods for isolation and separation of alkaloids have been described earlier (1). The basic technique by which the alkaloids were identified has been fully outlined (1). In essence, the naturally occurring compound was considered as identified, if it showed the same chromatographic behaviour as the reference compound (i) on two gas chromatography columns (SE-30, XE-60, or JxR); (ii) by tlc |chloroform- ethanol conc. ammonia (85:15:0.4) or, for phenols, chloroform ethanol diethylamine, (85:5:10)| and (iii) by gas chromatography- mass spectrometry (glc-rns), giving the same mass spectrum as the reference compound. In addition to the previously used 5% SE-30 and 5% XE-60 columns, a column (6 ft X 1/8 in.) of 3% JxR on Gas Chrom Q (100 120 mesh) was found to be in some ways superior (Varian model 204 or 2100 Aerograph). Preparative glc was carried out using columns of 5% SE-30 on Gas Chrom P (Varian model 202 Aerograph).
SPECIAL CHROMATOGRAPHIC SYSTEMS.- 3-Hydroxy-4-methoxyphenethylamine, the isomeric 4-hydroxy-3-methoxyphenethylamine ("3-methoxytyramine"), and the purified phenolic alkaloid fractions of T. cuzcoensis and Pachycereus pecten-aboriginurn were chromatographed on Whatman no. 1 paper with n-butanol-acetic acid -water (4:1:5) as solvent (13). After spraying with Gibbs' reagent, reference 3 hydroxy-4-methoxyphenethylamine (Rt. 0.45) and the major phenolic alkaloid of P. pecten-aboriginum showed a blue color while the isomer 4-hydroxy-3methoxyphenethylamine and the major phenolic compound from T. cuzcoensis (Rt. 0.45) developed a brown cotor, Gibbs' reagent: 0.1% solution of 2,6-dichloroquinone chlorimide in ethanol followed by 10% sodium carbonate in water.
Reference 4-hydroxy-3-rnetboxyphenethylamine (Rf. 0.60) 3-hydroxy-4-methoxyphenethylamine (Rf. 0.45) and the two isomeric compounds isolated from cacti were well separated by tlc on silica gel G plates with chloroform ethanol diethylamide (85:5:10) as solvent (10).
The identity of 3-hydroxy-4-methoxyphenethylamine and the major phenolic alkaloid or P. pecten-aboriginum was further confirmed by glc using trimethylanilinium hydroxide (5) for on-column methylation of the phenolic groups. In both cases a major compound having the retention time of 3,4-dimethoxyphenethylamine was formed.
RESULTS AND DISCUSSION
Our present screening for cactus alkaloids has largely been motivated by the search for biosynthetic intermediates in the formation of mescaline and related tetrahydroisoquinolines. Indeed, three phenolic'alkaloids, 3-rnethoxytyramine (4-hydroxy-3-methoxyphenethylamine), 3-hydroxy-4,5-dimethoxyphenethlamine and 4-hydroxy-3,5-dimethoxyphenethylamine were identified in cacti (3) and were later shown to be true biosynthetic intermediates (9). Still, some plausible progenitors of the tetrahydroisoquinoline skeleton are lacking. Partly, using "mass fragmentography" (7) to simplify the search for likely, presumably phenolic phenethylamine intermediates, a number of the Trichocercus species, and other cacti listed in table 1 were investigated. Some results with biogenetic implications are reported elsewhere (8). The identification of alkaloids has now been verified mainly by glc-ms and the final results reported here (table 1
Earlier, we have investigated (1) twelve species of the genus Trichocereus, which according to Backeberg comprises in all 38 species. We have now (table 1) examined the alkaloids of 14 more Trichocereus species and identified, in all, eight different phenethylamines (table 1). These are previously all known (1) to occur in the genus Trichocereus, except N-methyl-3-methoxytyramine (N-methyl-4-hydroxy-3-methoxyphenethylamine), which is known only from peyote (8). Mescaline, previously isolated from five Trichocereus species (1), is now identified also in T. cuzcoensis, T. fulvilanus, T. taquimbalensis and T. validus. While it occurred as the major alkaloid in T. taquimbalensis and T. validus, mescaline was only a minor constituent in the two other species. It may also be pointed out that the alkaloid-rich T. cuzcoensis contained 3-methoxytyramine as the predominant alkaloid. The macroscopic appearance of the new mescaline-containing species resembled markedly the previously known species and in fact, based on their appearance they were predicted to contain mescaline.
Stetsonia coryne has previously been known (11) to yield the quarternary alkaloid coryneine (N,N,N-trimethyldopamine). The occurrence of tyramine and N-methyltyramine. plausible biochemical progenitors of coryncine, was thus to be expected (fig. 2). Furthermore, plants from three different sources of this species, which is a not too distant relative of the Trichocereus species, were found to contain beside two other simple phenethylamines small amounts of mescaline. Traces of two phenolic tetrahydroisoquinoline alkaloids, viz. anhalonidine and anhalidine were also identified.
Pachycereus pecten-aboriginum was already in 1929 by Späth and Kuffner (14) shown to contain carnegine. This cactus has now been found to contain several alkaloids as will be reported in a later publication. However, the major compound of the phenolic alkaloid fraction turned out to be a hydroxymethoxyphenethylamine, but surprisingly not the commonly occurring 3-methoxytyramine (4-hydroxy-3-methoxyphenethylamine), but rather the isorneric 3-hydroxy-4-methoxyphenethylamine as described in the experimental section. This latter compound might theoretically be a good precursor of some tetrahydroisoquinoline alkaloids, e.g., carnegine and salsolidine, since it may provide an advantageous para-activation for the ring closure. Experiments on the biosynthesis of carnegine and salsolidine in Carnegiea gigantea have, however, not entirely supported such assumptions (6).
Pelecyphora aselliformis has been reported to contain alkaloids, probably tetrahydroisoquinoline alkaloids. This is now found to be correct with the identification of anhalidine in addition to the ubiquitous hordenine. The structure of one major alkaloid of this species still awaits elucidation. In this connection, it is known (12) that cacti of several genera of Cactaccae, among them pelecyphora, in Mexico are popularly, although for unknown reasons, classed as "peyote". Possibly, the alkaloids of P. aselliformis are responsible for its classification as a "peyote".
Echinopsia rhodotricha was earlier reported (1) not to contain detectable amounts of alkaloids. From a large amount of cacti we have now isolated small amounts of hordenine and tyramine.

Reputation Comments on this post:

Interesting, detailed, response!