Psychoactive drugs from plants

David S. Seigler Department of Plant Biology

University of IllinoisUrbana, Illinois 61801 USA

seigler@life.illinois.eduhttp://www.life.illinois.edu/seigler

OUTLINE: PSYCHOACTIVE DRUGS FROM PLANTS

Importance o cultural o medicinal-pharmacological

o economic o abuse-recreational-addiction

Most important drugs o Near Eastern center + ergot (LSD) + cannabis-marihuana + opium-Papaver + Amanita muscaria

o South America + coca + yagé or ayahuasca + virola

• o Africa• + khat• + iboga

• o Mexico• + peyote• + ololiuqui• + Heimia• + Psilocybe

Reading

• CHAPTER 12, pp. 286 ff

Introduction

• A list of commonly known psychoactive drug plants is given on page 287.

• A table giving the psychological classification of major plant-derived psychoactive drugs is given on page 287.

• Many plant-derived compounds can alter one's perception of reality. They may produce feelings of tranquility, invigoration, or "other worldliness". People may use these substances to escape from reality.

• Many of these same compounds are used medicinally.

• Many are quite toxic. Sometimes the toxic and hallucinogenic properties are interrelated or confused.

• Most of the known psychoactive compounds contain nitrogen and many are alkaloids. The best known exception is the active ingredient of marijuana.

• The psychoactive compounds are absorbed into the blood stream and transported to various sites where they exert their effects.

• They may be taken orally, injected, or absorbed through mucous membranes as in the mouth or nose. Many are absorbed through the lungs. Often, the liver is involved in degradation of the compounds.

• When they reach the central nervous system, psychoactive drugs usually act by altering the natural interactions between neurons. The neurons send information by chemical messages.

• The chemical substances involved are called neurotransmitters. They cross the spaces to the adjacent neurons; the spaces are called synapses.

• Specific sites on the adjacent site bind with the neurotransmitter and this interaction triggers a response in the neuron.

• Among the things involved are perception of pain, emotion, and interpretation of audio and visual stimuli.

• Most psychoactive drugs alter or mimic the behavior of four kinds of natural neurotransmitters: acetylcholine, norepinephrine, serotonin, and neuropeptides.

• Several additional modes of action are possible. The action of cannabinoids (such as THC) involves binding to specific endocannabinoid receptors. These receptors normally bind to neuromodulatory lipids in humans.

• In most "primitive" cultures, use of psychotropic substances is within a cultural, religious, or medical context and they are generally not used recreationally. This context generally is lacking in our present day culture in this country.

• Schultes defines hallucinogens as "chemicals that produce, in non-toxic doses, changes in perception, in thought, and in mood, but which seldom produce mental confusion, memory loss, or disorientation for person, place and time".

• Many synthetic hallucinogens also are known, e.g., LSD and heroin.

Cannabis sativa, marihuana near

Rantoul, Illinois

The resinous monoterpenes of Cannabis sativa

(Cannabaceae) have been used in China for

thousands of years. Cannabis is probably

native to central Asia. The plant was used in early times from the Near East to China.

Male (left) and female (right) flowers of Cannabis sativa

Courtesy Dr. J. M. J. de Wet

• This plant is the source of a useful fiber. Seed oils from cannabis are used as edible oils in many Asian cultures.

• The plant has also been used medicinally and for its psychoactive properties.

• Diagram of plant page 293.

• According to USDA sources, cannabis is the number one cash crop in the U.S. today; essentially all of it is grown illegally.

• Cannabis is described in ancient Chinese writings as well as in ancient Hindu texts from India. In India, the psychoactive properties of this plant were discovered.

• It is still debated whether cannabis is hallucinogenic or not. Different cultivars were selected for fiber and drug use.

• Cannabis resin was originally eaten; in India that is the most common way that it is used today. Marco Polo reported the use of hashish in the East.

• By the time of the Crusades, the use of marijuana was found throughout Asia and Africa.

• Smoking (anything) was developed by the American Indians and this process did not get introduced into Europe until the 1500's.

• Cannabis was brought to the New World by the Spanish and the British in efforts to establish a fiber crop.

• In Illinois, this plant was introduced in W.W. I and W.W. II as a source of fiber for ropes. Cannabis has become naturalized and widespread in many areas of the state. Most of the wild cannabis in Illinois has little psychoactive material in it.

Poppies and their products• We have already discussed poppies as medicinal plants.

• Poppies are widely cultivated for the seeds and for seed oil. They are also grown for both legal and illicit sources of opium.

• Morphine and codeine are isolated from crude opium and are widely used for medicinal purposes. Both are addictive.

• The acetylated derivative of morphine, heroin, is even more addictive. Heroin does not occur naturally.

Poppy flower and capsule

Carolina Biological Supply Co.

Incised poppy capsule and latex

Carolina Biological Supply Co.

• Opium has been used for thousands of years as a narcotic. In 3000 B.C., Sumerian tablets describe use of the plant.

• Opium was used by most cultures of the Near East to relieve pain.

• Although often associated with China, the drug was first introduced there by Arab traders in the 7th century A.D.

• The drug was originally used as a treatment for diarrhea much as it is today.

• In the 17th century, the Dutch introduced smoking to Taiwan (Formosa) and people began to mix opium and tobacco as a treatment for malaria. The practice soon became popular in China.

• Although Chinese officials tried to ban the import of opium, first the Portuguese, then the British, forced them to accept this material in trade. This was brought on because the Chinese had little interest in other European goods and the Europeans had to have something to trade for silk, tea, and spices.

• England established opium plantations in India to trade with China.

• During the 1800's there were a series of opium wars in which the British (and later Germany, Russia, France, and the U.S.) took control of some key port cities of China in order to force the Chinese to trade with them. Hong Kong was one of these.

• The use of opium didn't come under control until the Communist government took over in 1949.

• Opium wasn't commonly used in Europe until 1525 when Paracelsus (re-) discovered a way to dissolve it in alcohol. This medicinal preparation, paregoric, became popular.

• Morphine was isolated in 1803 and the purified alkaloid could be given in measured doses.

• Morphine is an potent analgesic and it was widely used in the Civil War. More than 45,000 soldiers returned home as addicts.

Mescal bean, Sophora secundiflora (Fabaceae)

• The seeds of Sophora secundiflora have been used by the American Indians of the Southwestern U.S. as a hallucinogenic drug.

• They are also very toxic.• See diagram page 308.

Mescal bean, Sophora

secundiflora, Fabaceae

Khat, Catha edulis, Celastraceae

• The leaves of khat (kat, qat) have been used for many years in the Arabian peninsula. The leaves are chewed daily by many, and the plant is a major export of Ethiopia to Yemen and a number of nearby countries. Khat is banned in Saudi Arabia.

• Lime is frequently added to hydrolyse the alkaloids and convert them to the free bases. The plant is probably native to Africa?

Courtesy Dr. Abraham Krikorian

Bulletin Narcotics

Coca, Erythroxylum coca, Erythroxylaceae

• Coca has also been discussed under medicinal plants. The leaves of coca have been chewed for thousands of years by Indians of Andean South America.

• The Spanish tried to prohibit coca until they realized that the Indians worked harder with it.

Coca, Erythroxylum coca, Erythroxylaceae

• In this case also, the Indians add lime to the leaves before chewing them.

• Cocaine blocks re-adsorption of norepinephrine in the brain. This makes the user feel invigorated and blocks feelings of fatigue and hunger.

• The leaf form of coca never became popular abroad.

• In 1860, cocaine was isolated and became popular. It became used as a local anesthetic.

• An extract of coca leaves became used in Coca Cola. Later the FDA made the company remove coca alkaloids from the extract.

• As a drug of abuse, cocaine may be sniffed, smoked or injected.

Yagé or ayahuasca, Banisteriopsis spp., Malpighiaceae

• Yagé or ayahuasca, the resinous exudate of the stems of Banisteriopsis spp. is usually made into a drink known as yagé or ayahuasca. B. caapi is one of the most commonly used species and is common in Colombia and Ecuador. The active compounds are harmine and other related alkaloids. Other plants are sometimes added as synergists, i.e., to enhance the activity.

Yagé, Banisteriopsis

caapi, MalpighiaceaeCourtesy Dr. Carl Bouton

Courtesy Dr. Carl Bouton

Psychoactive compounds from cacti

• A number of species of cacti from the New World are known to be hallucinogenic. Among these are peyote or mescal, Lophophora williamsii and Trichocereus pachanoi. The former is from Mexico and the latter from the Andes of South America. Mescaline is the most common alkaloid.

Peyote, Lophophora williamsii, Cactaceae

• The Spanish also tried to suppress the use of these. Many Indians in Mexico and in South America continued use of these plants, however.

• The Native American Church (chartered about 1920) began use of these in religious rites much later (about 1890).

Other hallucinogenic plants

• A snuff made from the powdered pods of Anadananthera peregrina (Fabaceae or Leguminosae) (yopo) has been used by Indians of the Caribbean and of northern South America. The snuff is often mixed with lime (calcium hydroxide).

R. E. Schultes and A. Hofmann, Botany and

Chemistry of Hallucinogens, Thomas, Springfield,

Illinois, 1973

Iboga, Tabernanthe iboga (Apocynaceae)

• Iboga is reported to be used in Africa as a hallucinogen. In Gabon and the adjacent Congo, the plant is used in religious rites and in hunting game. There are also important medical uses for the plant. The active compounds are indole alkaloids.

R. E. Schultes, Hallucinogenic Plants, Golden Press, New York,

1976

Psychoactive substances from the Solanaceae

• In Europe and the Near East, many plants of the Solanaceae were used in a similar manner. Among these were Atropa belladonna, Hyoscyamus spp., Datura spp. (also used by the North American Indians and some Asian peoples), and Mandragora officinarum.

Jimson weed, Daturastramonium, Solanaceae

• Some South American Indians used Brunfelsia grandiflora and Brugmannsia species in a similar manner.

Reina de la noche, Brugmannsia grandiflora, Solanaceae

Withania somnifera, Solanaceae

• Withania somniferum is a Near Eastern plant that has been used both as a psychoactive substance and as a medicinal plant.

Withania somniferum, Solanaceae

• Among the best known of these are Amanita muscaria, the fly agaric. This fungus grows in the temperate zones of Europe and Asia (where it has been widely used) and North America (where it has not been).

• In Siberia, this fungus was used before alcohol became available. The dried mushrooms were sold and were quite expensive. Even the urine from users was recycled.

Hallucinogenic fungi

Fly agaric, Amanita muscaria, a white form

Amanita verna, a highly toxic

species

Psilocybe species• This fungus is mentioned in Sanskrit writings from India.

• In Mexico, members of the genus Psilocybe and other related mushrooms were widespread and commonly used when the Spanish arrived.

• The Spanish tried to suppress use of these fungi. The practice went underground for a couple of centuries. The fungi are usually used in a curative, religious manner.

R. E. Schultes and A. Hofmann, Botany and

Chemistry of Hallucinogens, Thomas, Springfield,

Illinois, 1973

• These hallucinogenic fungi have been used for more than 2000 years in Mexico. About 80 years ago they were rediscovered by western scientists.

• Psilocybin is the active compound in many of these fungi.

Ergot, Claviceps spp., Clavicepitaceae

• Another important group of fungal hallucinogens are the ergot alkaloids that come from Claviceps species on grasses. These compounds are extremely toxic and produce many physiological changes.

• During the Middle Ages they were responsible for much human poisoning. Some of them are also hallucinogenic and are partially responsible for the bizarre actions of the victims of "St. Anthony's fire".

Ololiuqui

• In Mexico, the seeds of a number of Ipomoea and Rivea species (Convolvulaceae) were used in religious-medical applications as well. They contain the same compounds more or less. One important Mexican plant of this type was called "ololiuqui".

R. E. Schultes and A. Hofmann, Botany and

Chemistry of Hallucinogens, Thomas, Springfield,

Illinois, 1973

Peganum harmala is a Near Eastern plant that has been used as a psychoactive material in the past. It has been introduced as a weed and is found in much of the arid subtropical world today. The active compounds are -carboline or harmane alkaloids.

Peganum harmala, Zygophyllaceae

Peganum harmala, Zygophyllaceae