LSA (Lysergic Acid Amide) For treating Cluster Headaches .

lsa
LSA (Lysergic Acid Amide)

morning glory


For additional information and answers to your questions on the use of psychedelics for treating cluster headaches, please refer to the Mushroom FAQ and the LSA FAQ. This document answers questions and discusses the specifics of using LSA rather than psilocybin.

Lysergic Acid Amide
Lysergic acid amide (LSA), a relative and precursor to lysergic acid diethylamide (LSD), is found in the seeds of the Hawaiian baby woodrose (Argyreia nervosa) and morning glory (Ipomoea violacea), which can be crushed, eaten, or soaked and drunk to provide a 4 to 8 hour intoxication that is similar to that provided by LSD, though there are reportedly consistent qualitative and quantitative differences (Schultes and Hofmann, 1980). Five to 10 woodrose seeds, which are 0.14% LSA by dry weight (Al-Assmar, 1999), or 150-200 morning glory seeds (0.02% LSA) provide 2 to 5mg of the compound—an active dose (Weber and Ma, 1976). Sleepygrass (Stipa robustum), which grows in the Southwestern United States contains even higher concentrations of LSA, although unlike Ipomoea, which has been used for thousands of years by Central American Indians in shamanic and traditional ceremonies, it appears to have no history of use or abuse in such a manner (Petroski et al., 1992). Morning glory and Hawaiian baby woodrose seeds are available commercially but are usually coated with an emetic to discourage ingestion; instructions for removing this coating are found on the Internet, or the erstwhile user can patiently grow these striking flowers in the garden for later seed harvest.

Al-Assmar S.E., 1999. The seeds of the Hawaiian baby woodrose are a powerful hallucinogen. Archives of Internal Medicine 159(17), 2090. Petroski R.J., Powell R.G., Clay K., 1992. Alkaloids of Stipa robusta (sleepygrass) infected with an Acremonium endophyte. Natural Toxins 1(2), 84-88. Schultes, R.E., Hofmann, A., 1980. The Botany and Chemistry of Hallucinogens, second ed. Charles C. Thomas, Springfield, IL. Weber J.M., Ma T.S., 1976. Microchemical investigations of medicinal plants. XIV. Identification of the alkaloids in the leaves of Ipomoea violacea using preparative thin layer chromatography and solid probe mass spectrometry. Mikrochimica Acta 2-3 Part 1, 227-242.
[Andrew Sewell / John Halpern]

d-lysergic acid amide
LSA is a naturally occurring psychedelic found in many plants such as morning glory, Rivea Corymbosa, and hawaiian baby woodrose seeds.

The following figure shows the chemical structure of LSD and ergoline alkaloids found in seeds of Rivea corymbosa and Ipomoea violacea (Morning Glory). The main hallucinogenic constituents of both seeds are ergine (d-lysergic acid diethylamide) and isoergine, but other related beses occur in minor amounts - chiefly chanoclavine, elymoclavine, and lysergol.

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Common Sources;
Hawaiian Baby Woodrose Seeds
BOTANICAL CLASSIFICATION
Family : Convolvulaceae
Genus : Argyreia
Species : nervosa
Hawaiian Baby Woodrose is a perennial climbing vine with large heart-shaped leaves and white trumpet-shaped flowers. Its large furry seeds grow in seed pods and contain the psychedelic LSA

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To the right is an HBWR seed that has been cracked open with the center pulp in the middle of the three pieces.

Morning Glory Seeds:
BOTANICAL CLASSIFICATION
Family : Convolvulaceae
Genus : Ipomoea
Species : violacea
Ipomoea violacea is a common ornamental vine with heart-shaped leaves and bright white, pink, or purple flowers and small, black seeds that contain LSA.

Rivea Corymbosa seeds:
BOTANICAL CLASSIFICATION
Family : Convolvulaceae
Genus : Rivea (=Turbina)
Species : corymbosa
Rivea corymbosa is a large, woody vine with narrow, heart shaped leaves and white, bell-shaped flowers. The plant has been identified as the Aztec visionary intoxicant oliliuhqui. Oliliuhqui's round seeds contain LSA

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Effects:
LSD-like effects, but less intense, with less visuals. Trip lasts 6-8 hours; tranquil feelings may last additional 12 hours. Sleep is deep and refreshing after trip, however some users may experience a hangover characterized by blurred vision, vertigo, and physical intertia.

History:
Hawaiian Baby Woodrose seeds: Used by the poorer Hawaiians for a high.
Shipping of these seeds became popular, as did a great controversy over the propriety of world-wide distribution.

Rivea Corymbosa seeds: The shamans in Oaxaca, Mexico, where they are cherished for both their history and shamanic use, would ingest 20-30 seeds to communicate with their spirit world.
[BB]

"Rivea corymbosa is a large vine with narrow heart shaped leaves and white bell shaped flowers. The plant is identified as the Aztec visionary intoxicant Ololiuhqui, seeds have a long history of use by the natives of Mexico and is perhaps the most common ethnobotanical used by them. In 1941 Richard Evans Schultes first identified Ololiuhqui as Rivea corymbosa. The plant, Convolvulus corymbosa is from tropical Mexico but is now very common in Cuba and other islands of the West Indies.

The ritual and medicinal use of these seeds "Little Gods" dates back far into the pre-Hispanic period, traditionally the seeds are added to alcohol and left to steep and once drunk the individual can attain hypnotic states. When ingested traditionally they produce a hypnotic state similar to that induce by Ipomoea violacea. Indians report powerful visions, even with very low doses. The main active ingredient ergine has been demonstrated to produce a kind of trance or twilight sleep with dream images."
[psychoactiveherbs dot com][PL]

"Narcotic Properties.-The seeds of Christmas vine were valued as a sacred hallucinogen by Chinantec, Mazatec, Mixtec, Zapotec, and other groups in Southern Mexico in Pre-Columbian times and are still cultivated and used today as aids in divination and witchcraft. It was administered by grinding about 13 seeds, adding water, filtering, and drinking the filtrate in a quiet, secluded place. Hallucinations follow that last about 3 hours, sometimes with aftereffects. The active ingredients are the ergoline alkaloids, lysergic acid amide, and lysergic acid hydroxyethylamide that are closely related to LSD (Schultes and Hoffmann 1992)."
[US Department of Agriculture]
[PL]

Active Constituents:
D-lysergic Acid Amide and related compounds. NOTE: net wisdom has it that extracting LSA from woodrose/mg seeds is an inefficient way to obtain a precursor for LSD.

Lysergic acid amide–containing plants
LSD is the best-known synthetic hallucinogen and is psychoactive at the microgram level. Although LSD does not occur in nature, a close analogue, lysergic acid amide (LSA, ‘‘ergine’’) is found in the seeds of Argyreia nervosa (Hawaiian baby woodrose) and Ipomoea violacea (morning glory). Hallucinogenic activity of LSA occurs with 2–5 mg,which provides a 4- to 8-hr intoxication that reportedly has quantitative as well as qualitative differences from LSD (Schultes & Hofmann, 1980). Seeds are crushed, germinated, eaten whole, or an extract is drunk after the seeds are soaked in water. Five to 10 seeds of Argyreia nervosa or 150–200 seeds (3–6 g) of Ipomoea violacea yield average doses of LSA (Al Assmar, 1999; Borsutzky et al., 2002).
The LSA content of Argyreia nervosa is 0.14% by dry weight of seeds (Chao & Der Marderosian, 1973) and is 0.02% by dry weight in Ipomoea violacea seeds (Miller, 1970). Historically, Ipomoea violacea and related Ipomoea corymbosa seeds were used in Central America for shamanic and ceremonial purposes and the Mazatec of Mexico also continue their usage (Schultes & Hofmann, 1992). Ipomoea spp. are popular annuals grown for their abundant flowers from climbing vines; commercial seeds are usually coated with emetic poisons to discourage intoxication. The highest concentrations of LSA, however, have been found in Stipa robusta (Achnatherum robustum; sleepygrass) growing in the southwest of the United States (USDA, 2004), although there is no history of shamanic tradition with it and no evidence to date that it is commonly ingested for intoxication (Petroski et al., 1992).

J.H. Halpern / Pharmacology & Therapeutics 102 (2004) 131–138 138
Hallucinogens and dissociative agents naturally growing in the United States
John H. Halpern

Scientific Information:
ALKALOIDS are a diverse group of some 5,000 compounds with complex molecular structures. They contain nitrogen as well as carbon, oxygen, and hydrogen. All alkaloids are of plant origin, though some protoalkaloids occur in animals. All are slightly alkaline, hence their name. They are classified into series based on their structures. Many hallucinogenic alkaloids are indoles (see below) or are related to indoles, and the majority have or may have originated in the plant from the amino acid known as tryptophan.
Most medicinal and toxic plants, as well as hallucinogenic plants, owe their biological activity to alkaloids. Examples of widely valued alkaloids are morphine, quinine, nicotine, strychnine, and caffeine.
INDOLES are hallucinogenic alkaloids or related bases, all of them nitrogen-containing compounds. It is most surprising that of the many thousands of organic compounds that act on various parts of the body so few are hallucinogenic. The indole nucleus of the hallucinogens frequently appears in the form of tryptamine derivatives. It is composed of phenyl and pyrrol segments (see diagram following).
Tryptamines may be "simple"—that is, without substitutions—or they may have various "side chains" known as hydroxy (OH), methoxy (CH3), or phosphogloxy (OPO3H) groups in the phenyl ring.
The indole ring is evident not only in the numerous tryptamines (dimethyltryptamine, etc.) but also in the various ergoline alkaloids (ergine and others), in the ibogaine alkoloids, and in the ß-carboline alkaloids (harmine, harmaline, etc.). Lysergic acid diethylamide (LSD) has an indole nucleus. One reason for the significance of the indolic hallucinogens may be their structural similarity to the neurohumoral tryptamine serotonin (5-hydroxydimethyltryptamine), present in the nervous tissue of warm-blooded animals. Serotonin plays a major role in the biochemistry of the central nervous system. A study of the functioning of hallucinogenic tryptamine may experimentally help to explain the function of serotonin in the body.
A chemical relationship similar to that between indolic hallucinogens and serotonin exists between mescaline, an hallucinogenic phenylethylamine base in peyote, and the neurohormone norepinephrine.
These chemical similarities between hallucinogenic compounds and neurohormones with roles in neurophysiology may help to explain hallucinogenic activity and even certain processes of the central nervous system. Other alkaloids—the isoquinolines, tropanes, quinolizidines, and isoxazoles—are more mildly hallucinogenic and may operate differently in the body.
[zauberpilz dot com]

"EXPERIMENTAL STUDIES of the narcotic morning glories began in 1955 when a psychiatrist published notes on self-experimentation with Rivea seeds, showing that they brought on an intoxication accompanied by hallucinations. This announcement prompted chemists to examine the plant, but no active principle could be found until the 1960's. At that time the chemist who discovered LSD analyzed the plant and found several alkaloids closely related to that potently hallucinogenic synthetic compound.
His astonishing discovery met with widespread disbelief, partly because these Iysergic-acid derivatives had hitherto been known in nature only in the primitive fungus ergot (Claviceps purpurea), a parasite on the grains of rye in Europe, when ergot was accidentally ground up in a mill with rye flour and eaten in bread made from the flour, it poisoned whole towns, causing a terrible intoxication and leading frequently to widespread insanity and death. In the Middle Ages, before causes were understood and preventative measures taken, these mysterious mass attacks were called St. Anthony's Fire and were attributed to God's wrath.
Half a dozen of these ergoline alkaloids have been found in seeds of Rivea corymbosa and Ipomoea violacea. The main hallucinogenic constituents of both seeds are ergine (d-lysergic acid diethylamide) and isoergine, but other related beses occur in minor amounts - chiefly chanoclavine, elymoclavine, and lysergol. The total alkaloid content of Ipomoea violacea is five times that of Rivea corymbosa, which explains why the natives use fewer of the Ipomoea seeds in preparing for their rituals. While these alkaloids are not uncommon in numerous morning glories around the world, apparently only in Mexico have the plants been utilized as narcotics."
[zauberpilz dot com]

The ergoline alkaloids can be hydrolysed into Lysergic Acid. That is the reason for infusing the seeds in wine or water for 12-24 hours.

Ergine, also known as d-lysergic acid amide, LSA, and LA-111, is an alkaloid of the ergoline family that occurs in various species of vines of the Convolvulaceae and some species of fungi. As the dominant alkaloid in the hallucinogenic seeds of Rivea corymbosa (ololiuhqui), Argyreia nervosa (Hawaiian baby woodrose) and Ipomoea violacea (tlitliltzin), it is often stated that ergine and/or isoergine (its optical isomer) is responsible for the hallucinogenic activity. [1]

Ergoline Alkaloidal Constituents of Hawaiian Baby Wood Rose are:
  % of Total alkaloid % dry seed weight
Ergine 22.68 0.136
Isoergine 31.36 0.188
Ergometrine 8.20 0.049
Lys. alpha-OH-ethylamide    5.79 0.035
IsoLys. || 3.98 0.024

All these alkaloids listed here can be hydrolysed into Lysergic Acid. That is the reason for infusing the seeds in water or wine for 12-24 hours. Hydrolysis should only be done if the goal is to make LSD, Lysergic acid by itself has little/no psychedelic properties. [2] The "other" alkaloids (non-ergoline) are what makes people sick. Note that the total alkaloids in HBWR are 7 times the LAA% and that the total alkaloids in Ololiuqui are only 2 times the LAA% [3]

  LAA% Total Alks. % by weight
Hawaiian baby wood rose: 0.04 0.30
Ololiuqui: 0.02 0.04

[1]
http://www.answers.com/main/ntquery;jsessionid=247

[2] [3]
http://www.erowid.org/plants/hbw/hbw_info1.shtml

[BB]

Potential Toxicity
There is a definite lack of consensus as to the extent of toxicity associated with the various types of LSA containing seeds available. It is probably safe to say, however, that all LSA containing seeds are 'poisonous' and that the extent of poisoning varies by strain, batch and dose level; but no one really knows to what extent.

The toxicity is generally thought to be due to alkaloids within the seeds themselves, and particularly the outer husks. It is thought that these vary not only by type of seed, but also from plant to plant and even seed to seed (within the same package). Accordingly, selecting five seeds at random on two separate occasions from the same pack may cause very different levels of toxicity.

It is the opinion of many seasoned recreational users that all such seeds contain cyanogenic glucosides. These oxidise readily into cyanide compounds when exposed to the air. In low doses, the body can eventually rid itself of such poisons, but inadvertently taking higher doses can result in symptoms (in no particular order) such as nausea, bluing of the fingers, body load, stomach cramps, leg cramps, vascular constriction, blood vessel damage, elevated heart rate, strong physical and mental lethargy.

There are references to cyanogenic glucosides in other more familiar seeds - such as apple and watermelon - but there appears to be no definitive source for LSA containing seeds. Some of the above symptoms may, of course, actually be caused by the action of the LSA itself.

Some sources also suggest that some seeds may also contain trace elements of strychnine and others suggest that the nausea sometimes associated with the seeds is caused by essential oils within the seeds, but this is generally hearsay. It is also suggested that toxicity may influence the trip level - and there has been much recent debate about this in relation to the inherent efficacy of LSA containing seeds in cluster headache.

It is also believed that for like-for-like dose levels (not seed to seed), Morning Glory seeds are probably more toxic than HBWR, and Rivea Corymbosa are the least toxic. The major alkaloid content of HBWR Argyreia nervosa (Burm. f.) Bojer has been published as follows:

Ergoline Alkaloidal Constituents of Hawaiian Baby Wood Rose are:
  % of Total alkaloid % dry seed weight
Ergine 22.68 0.136
Isoergine 31.36 0.188
Ergometrine 8.20 0.049
Lys. alpha-OH-ethylamide    5.79 0.035
IsoLys. || 3.98 0.024

Source: Jew-Ming Chao and Ara H. Der Marderosian. Journal of Pharmaceutical Sciences 62(4):588-91. 1973

Erowid says this about Hawaiian Baby Woodrose seeds:
"At 0.136% dry weight ergine, then to get a good hit (assuming ergine is 1/10 potency of LSD) we need 100ug x 10 = 1mg ergine. Thus we need 1/1.36 g of seeds for one good hit (assuming the other alkaloids don't make you sick [to your stomach]) or 0.74 grams of HBWR seeds."

The total alkaloids in Hawaiian Baby Woodrose seeds is more than 7 times the Lysergic Acid Amide. The total alkaloids in Rivea Corymbosa seeds is only 2 times the Lysergic Acid Amide. (BB)

One general agreement appears to be that LSA containing seeds SHOULD NOT be taken when pregnant. The active ingredients, possibly including ergonovine, can induce uterine contraction, which can result in abortion, and can restrict blood flow to the fetus.

Removing the outer husk is thought to reduce the likelihood of associated symptoms. Preparation in alcohol is also thought to help, although this is unconvincing especially if pulverising occurs before soaking (dry). Many have suggested using non-polar solvents but these are unlikely to help because LSA and cyanide are both primarily polar-soluble. Fasting before dosing is also thought to help.

Allegedly, in order to minimise unwanted side effects, some Native Central Americans firstly crush the seeds, soak them in cold water, discard the seed mush and drink (having fasted for several hours prior to ingestion).

For more information, if you have a great deal of time on your hands, the following thread is ostensibly about extraction but does drift into other topics.

http://forums.lycaeum.org/cgi-bin/ultimatebb.cgi?ubb=get_topic&f=3&t=001154&p=1
[Lee]

It has been stated that Rivea Corymbosa seeds have the same psychoactive effect as Hawaiian Baby Woodrose seeds but none of the side effects of HBWR seeds like nausea and gravity-pull. When asked about the side effects of Rivea Corymbosa seeds he wrote "No negative feedback has been received in this regard, also none of our research group has experienced any either." He said the best way to ingest Rivea Corymbosa seeds is to crush the seeds and infuse them in wine for 12-24 hours.
[BB]

LSA Cluster Treatment Testimonials:

I have done as many as about 15 seeds and reached the same level but with quite a bit of stomach stress. Important thing is I am still out of cycle and just get a little "twang" here and there. Quite a different world!!! My doctor just checked me out and my bp was 110/70 with a pulse of 56. Which is the best he has ever seen for me, and agrees that the seeds were the answer that started the transformation. Have not done any seeds for a couple of weeks now and am still feeling great...no need to re-dose at this time.
[JKR;2005]

I can only speak from my own experience and that is that O2 continued to work very well for me after LSA dosing. In fact the only CH I had after starting the LSA routine that got over a kip 4 was one where I couldn't get to my O2 until the CH was already at a kip 7. As a related side note, I'm still not thoroughly convinced that the seeds were the sole cause of my recent cycle ending either as it had already gone on much longer than my usual cycles. However....the cycle was MUCH less intense AND never switched over to the opposite side as my cycles also typically do. I am encouraged enough though that I will be using seeds (LSA) going forward for preventative and "if/when" needed to break the onset of my next cycle.
[JL;2005]

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