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The use of nutmeg as a psychotropic agent

Introduction:

In his search for varied experience and escape from everyday boredom, man has found many substances of plant origin that poison the human organism but that, at the same time, cause pleasurable physical or mental changes. The word "narcotic" technically denotes a stupor-inducing drug, but it has been loosely applied to many of these deliberately-consumed substances. Narcotics are used regularly in nearly all parts of the world, and three observations about these practices are relevant to this paper. First, man seems willing to experiment with almost anything in his environment to find new intoxicants: such bizarre materials as certain glues, morning-glory ( Ipomœa) seeds, cinnamon, and spider webs have all been put to narcotic use.

Second, persons who take narcotics often must tolerate extreme discomfort along with the pleasant effects produced by drugs.

Third, psychological factors profoundly influence individual reactions to narcotic drugs. A person seeking euphoria may find it in a chemical that does little on its own but cause dizziness.

The use of nutmeg as a narcotic illustrates all three points: nutmeg is an obscure drug, causes many alarming symptoms, and brings about pleasant mental changes only in the proper psychological context. Yet nutmeg must be considered a narcotic not only because it can induce stupor but also because many persons now consume it deliberately to escape reality.

Botanical, historical, and commercial notes on Myristica fragrans

Nutmeg and its sister-spice mace are both products of the nutmeg tree, Myristica fragrans Houtt. (Myris- ticaceae). The genus comprises about 100 species found throughout the tropics, especially in the Malayan region; but of these, M. fragrans alone contains enough of an aromatic essential oil to make it valuable for cultivation. Nutmeg is the dried seed of the plant; mace is the dried aril surrounding the shell enclosing the seed.

Upon examination of diversifying the uses of nutmeg, one of its components, trimyristin, was seen as a potential marketable product. Trimyristin is a fat, and it comprises approximately 40% by weight of the nutmeg seed. A by-product of trimyristin is myristic acid, and this carboxylic acid is used commercially in the soap and cosmetic industry.

Another possible marketable product is nutmeg oil. Nutmeg oil, which is the essential or volatile oil of nutmeg, is approximately 12% by weight of the nutmeg seed. A steam distillation plant is under construction in Grenada to obtain the nutmeg oil. However, once the nutmeg oil is removed by the steam distillation, if nothing is done with the remaining components of the nutmeg, then 88% of the nutmeg seed is discarded. Most importantly, the trimyristin which is a potentially marketable product, will be lost. Trimyristin can be sold as any other fat or oil to be used as a source for making fatty acids, fatty alcohols, or glycerol which are used for the soap, cosmetic and oleochemical industries. Moreover, the equipment used to extract trimyristin from nutmeg can also be used to extract other products such as coconut oil from copra. Thus, the marketing potential of trimyristin demands that a pilot study be conducted on its extraction from nutmeg to evaluate the possible commercial production of this fat.

The nutmeg seed is one of four c components of the fruit obtained from the nutmeg tree, Myristica frangans Houtt (Myristicaceae) About 30-55% of the seed consists of oils and 45-60% consists of solid matter including cellulose materials. There are two types of oils: (1) The "essential oil of nutmeg" also called the "volatile oil" accounts for 5-15% of the nutmeg seed and (2) the "fixed oil of nutmeg" sometimes called "nutmeg butter" or expressed oil of nutmeg accounts for 24-40% of the nutmeg seed.14 The relative percentages of the different components will vary depending on the geographical origin of the nutmeg. From this point on, "essential oil", "volatile oil", and "nutmeg oil" will be used interchangeably.

Products of Myristica: their uses and composition

tmeg husks

The pericarp of the nutmeg fruit can be preserved in sugar while unripe, salted and dried as a condiment, or made into jellies. All of these preparations have the flavour of nutmeg.

Nutmeg

Ground nutmeg, a granular orange-brown powder with characteristic aroma, is a widely-known kitchen spice. It has a warm aromatic, slightly bitter taste and is often added to custards, puddings, pies, certain vegetables, and milk drinks like egg-nog. In the past, nutmeg was much used in medicine.

Whole nutmeg, depending on the variety, contains from 5 to 15 per cent of a volatile oil that accounts entirely for the aroma and flavour of the spice.

Fixed oil of nutmeg

The fixed oil of nutmeg is known by many names: nutmeg butter, balsam of nutmegs, "oil of mace ", "butter of mace ", "Banda soap ", and Oleum Myris- ticae Expressum. It is obtained by exposing the nuts to hydraulic pressure and heat.

History of nutmeg as a medicinal agent

Arab physicians seem to have used nutmeg as a drug from the first centuries A.D., although just how they used it is not known. Warburg wrote 1 that Myristica was recommended for a variety of disorders in this early period but was taken mainly for diseases of "the digestive organs, from the mouth to the stomach to the intestines, to the liver and spleen, as well as for freckles and skin blotches ".

Later Arab physicians referred nutmeg to the class of "warm and dry drugs" and elaborated on its applications. By the 11th century, for instance, the spice was praised for its effect on the kidneys, was used to combat pain, vomiting, and lymphatic ailments, and was even considered aphrodisiac 1. According to Ainslie, Vol. I, though, the Arabs were using nutmeg almost solely as a hepatic and tonic by the 19th century. Oddly enough, physicians of the Near East took little notice of mace until the early 1800s when they began to prescribe it as an aphrodisiac and carminative.At the present time, nutmeg is still important in this part of the world. A pharmacologist at the Hebrew University of Jerusalem writes:

"The nutmeg is used by Arabs of Israel and people of its oriental Jewish communities, especially Yemenites, as a drug of their folk medicine, as well as a spice and as an important ingredient in love-potions. It is used against vomiting and to regulate the movements of the bowels; it is good for the liver and for the spleen. It is used in the treatment of tuberculosis, against colds, fever, and, in general, respiratory ailments. It is said to be an antihelminthic and is used for that purpose. It is used against skin diseases like eczema and scabies. It is said to be effective for removing blotches from the face. To increase potentia virilis it is pounded well and added to various foods."

Frequent references in the Vedas to nutmeg indicate that the ancient Hindus knew of the spice from early times. They described it as warmth-producing, stimulating, and good for digestion and also used it in their medicinal preparations. Martius  said that Hindu physicians prescribed it for headache, nerve fevers, cold fevers, foul breath, and intestinal weakness.

In his Materia Indica of 1826, Ainslie wrote that nutmeg "is considered by the natives of India as one of their most valuable medicines ...." Dymock, in 1883, noted that the Moslems of western India used nutmeg as an aphrodisiac. Burkill, in 1935, stressed nutmeg's importance in Indian tonics for dysentery. According to an adviser in the Indian Ministry of Health, nutmeg is still used medicinally in India :

"It is prescribed as an analgesic in neuritic pains, as a sedative in highly tense nervous states, and as a sedative and anti-spasmodic in asthma. In view of its reaction resembling opium, it is used to give relief in the cough and hemoptysis of tuberculosis. In traditional Indian folk and domestic medicine, nutmeg is used in small quantities to induce hypnotic effect in irritable children. It is also administered as an hypnotic and sedative in epileptic convulsions."

Medieval European physicians followed exactly the precepts of Arabian medicine. Consequently, they called nutmeg a warm, dry drug and recommended it for all the maladies listed earlier.

"The importance of nutmeg as a medicine grew hand in hand with the increase in Indian trade during the middle ages; its use spread from the Arabian Empire over Greece and Italy and soon reached central Europe. Nutmeg gradually became a genuine folk remedy, although it was most important as a major ingredient in medicines prepared according to guild rules."

During the 16th and 17th centuries, Western physicians compiled the writings of earlier authorities on nutmeg. This was the great period of the herbalists, and nearly every herbal contained a summary of nutmeg's virtues.

Doctors continued for some time to prescribe Myristica for intestinal illnesses, but by 1800 they realized that any of its effects were the same as those of other aromatics. Then, as modern pharmacy developed, older remedies, nutmeg among them, were relegated to positions of lower and lower priority. In summarizing the medicinal uses of the spice in 1897 :

"Today the employment of nutmeg and mace in medicine is relatively minor. Nutmeg is now used as a stomachic, stimulant, and carminative, especially in

cases of dyspepsia, intestinal catarrh and colic, and as an appetite stimulant, as well as for its ability to control flatulence...."

There is an important omission in the above catalogue of nutmeg uses: sometime later in its history-perhaps as late as the 19th century - - nutmeg became known as an emmenagogue and abortifacient. This use has persisted among women into the present century; in fact, Green (14) in 1959 reported the case of 28-year-old Virginia woman who ate "18.3 g of finely ground nutmeg in an attempt to induce the menses, which had been delayed two days". Some of the older uses of the drug may also be alive in contemporary European and American folk beliefs: McCord, for example, cited a 1962 incident in which a 41-year-old South Carolina man, on the advice of a friend, took two whole nutmegs to relieve a skin infection.

The relevance of medicinal uses of nutmeg to the present discussion of nutmeg as a narcotic is that the toxic properties of Myristica must first have been noticed when patients accidentally took overdoses.

Nutmeg poisoning

Early reports

Several European phy icians of the 16th and 17th centuries described the symptoms of nutmeg poisoning, and many later references to the toxicity of Myristica are traceable to these early observations. In modern writings, the evidence of early commentators is often reduced to the sort of statement that appears in The Wealth of India with no amplification "Excessive doses of nutmeg have a narcotic effect; symptoms of delirium and epileptic convulsions appear after 1-6 hours."

" Nutmeg unites to the medicinal properties of the ordinary aromatics considerable narcotic power. In the quantity of two or three drams (7.7 or 11.6 g), it has been known to produce stupor and delirium, and dangerous if not fatal consequences are said to have followed its free use in India.'

Intoxication following the use of nutmeg as an emmenagogue or abortifacient

By far the greatest numbers of people poisoned by nutmeg have been women - mostly English and American women of the late 19th and early 20th centuries - who took the spice to bring on menstruation or induce abortion. A great many of these cases appeared in the scientific literature of the period, particularly in British medical journals. Commenting on them in 1962 observed:

" It is interesting that of all the instances reviewed in which nutmeg was taken as an abortifacient, this effort was successful in only one patient. Even in this instance, the role of nutmeg was open to question since the abortion followed the ingestion by a period of a month."

There are many other reports , and summarizing all these data, McCord attributed the poisoning symptoms to " a central nervous system depressive effect with periods of stimulation and associated respiratory and cardiovascular difficulties. Occasional case reports have suggested a possible hypersensitivity reaction as illustrated by the presence of facial and periorbital edema with flushing."

Pharmacology of nutmeg

Early studies

Reviewing the findings of earlier workers, Shulgin in 1963 wrote that the myristicin fraction of nutmeg oil "is strongly suspect of representing the effective toxic factor for cats .... "but that it appears "ineffective in duplicating the psychological effects of total nutmeg in man ". He then speculated on possible pharmacological activity of other components of the oil:

"The minor aromatic ethers, eugenol and safrol, have been suggested as possible active components. This seems unlikely, as the amounts ingested from a 5 g nutmeg (0.001 g and 0.003 g respectively) are much below the usual therapeutic levels of these substances (3.0 ml and 0.5 ml respectively). The only component, aside from the myristicin fraction, of the volatile oil from nutmeg that deserves serious consideration as an active agent is the pinenedipentene fraction. Many descriptions of the toxic syndromes of representative terpene medicines parallel the common toxic manifestations of nutmeg (i.e., nausea, cyanosis, stupor, cold extremities, often delirium). [However] actual toxic dosages of oils that are of make-up similar to the hydrocarbon fraction of nutmeg (such as oil of turpentine) are as a rule 20 to 60 times higher than that which would be encountered in nutmeg intoxication."

Conclusion is the best summary of our present knowledge of Myristica; "As yet, no known pharmacology of any known component of oil of nutmeg can explain the syndrome of the whole nutmeg."

Psychopharmacology of mutweg

Speculation on the psychopharmacology of nutmeg must be cautious, since, "the inability to assign to a single component of nutmeg the role of being the toxic factor makes a discussion of the mode of action, by definition, totally theoretical". .

None the less, a few findings are interesting. Truitt and a new group of researchers in 1963 pointed out "a degree of structural resemblance between the chemical formula for myristicin and those of certain sympathomimetic amines ". This similarity, together with nutmeg's stimulant action, suggested that myristicin and nutmeg may act as central monoamine oxidase (MAO) inhibitors. To test this hypothesis, synthetic myristicin and nutmeg oil concentrate were given to rats, and MAO inhibition was established by measuring potentiation of tryptamine convulsions. Controls were run with two potent known MAO inhibitors: tranylcypromine and iproniazid. By these methods, myristicin was shown to produce effects less potent than but parallel to those of the reference drugs. Myristicin was also found to antagonize reserpine ptosis and to increase brain 5-hydroxytryptamine- both of which are changes induced by other MAO inhibitors.

The authors emphasized that this was mere circumstantial evidence, but they felt that nutmeg and myristicin probably were mild MAO inhibitors. Compared to other such compounds, their toxicity is quite low. The authors cited preliminary work with schizophrenic and depressed patients in whom daily administration of ground nutmeg caused "improvements ". They concluded: ''Further study is recommended for more direct evidence of nutmeg and myristicin as enzyme in hibitors and for their utility as anti-depressant drugs."

Shulgin, who has tried to work out the biochemistry of nutmeg's hallucinogenic action, has assumed for the moment that the myristicin fraction of the oil (with its more than 25 per cent content of elemicin) is, indeed, the active principle. He has noted that the metabolism of the aromatic ethers found in essential oil is "virtually unknown" except for a detoxication mechanism by which safrol is converted to piperonylic acid. This reaction indicates a capacity to oxidize an olefinic side chain. Shulgin has suggested that, if this degradative process is "applicable to myristicin, or especially to elemicin, a theoretical intermediate, a vinyl alcohol, could undergo transamination producing the known psychotomimetic drug, 3,4,5-trimethoxy amphetamine (TMA) ". The recent description of the new synthetic hallucinogen - 3-methoxy-4, 5-methylenedioxy amphetamine (MMDA) - which might be derived by an analogous process from myristicin, itself, is even more suggestive of a psychotropic function for this component of nutmeg (fig. 3 b).


FIGURE 3a

Possible production of a known psychomimentic agent from elemicin

FIGURE 3b


Possible production of a known psychotomimetic agent from myristicin.

Thus far, human pharmacological data are inadequate to support the contention that myristicin is psychoactive or that it is an active principle of whole nutmeg. "... some combination of factors in total nutmeg is capable of producing a psychotropic response: the structure of elemicin or myristicin wanting only an ammonia molecule to become a recognized mental agent must be accepted as at least an intriguing coincidence."

The seeds and arils of M. fragrans have powerful narcotic properties. In man, they have frequently caused serious but almost never fatal intoxications. Most Westerners are ignorant of these toxic properties and know nutmeg and mace only as flavouring agents.

Both spices are used as narcotics, probably by significant numbers of people, although information on this use of Myristica is scarce. When taken deliberately as psychotropics, nutmeg and mace often cause reactions quite unlike those described in classical accounts of Myristica poisoning and much more like experiences with Cannabis or other hallucinogenic drugs.

Essential Oil

Although the essential oil is present in lesser amounts than the fixed oil, the essential oil has received most of the investigative research efforts especially during the last twenty years. This is in accord with the fact that the essential oil contains the greater number of individual compounds or components, most of which are valuable in industries. Furthermore, the psychotropic effects of nutmeg as well as most of its other pharmacological properties have been attributed to the compounds found in the essential oil.

The essential oil is obtained from the nutmeg by steam distillation. It is a colourless or pale yellow liquid with a taste and odour of nutmeg. This oil is soluble in alcohol and insoluble in water and has a density, at 25°C of 0.859-0.924. Since it is light and air sensitive, it must be kept cool in a tightly closed container and protected from light.

Components of the Essential Oil

The first major successful analytical works to determine the constituents of nutmeg was performed by Frederick Power and Arthur Henry Salway from 1907 to 1908.17,18 They isolated and identified numerous compounds found in nutmeg. Around the 1960's, more compounds were identified by using modern techniques like gas-liquid chromatography.19

The early articles on the chemistry of nutmeg, including the Merck Index, reported camphene and pinene as the major constituents of the essential oil. More recent articles show sabinene to be the major constituent of the essential oil.20,21 It is still questionable whether sabinene constitutes most of the essential oil because the latest Merck Index still shows camphene and pinene to be the major constituents of the essential oil.From these analyses, a listing of the major components of the essential oil and their relative percentages is provided below. Note that either sabinene or camphene comprise about 50% of the essential oil:


1. Sabinene

(50%)

2. Camphene

(50)%

3. d-Pinene

20%

4. Dipentene

8%

5. d-Linalool

6%

6. d-Borneol

6%

7. i-Terpineol

6%

8. Geraniol

6%

9. Myristcin

4%

10. Safrole

0.6%

11. Eugenol

2%

12. iso Eugenol

2%


Aromatic ethers

Methyl Eugenol

Eugenol

Methyl Iso-Eugenol

Myristicin

Methoxy Eugenol

Elemicin

Safrole

Iso-Eugenol

Iso-Elemicin


Terpenes

Alpha-Terpinene

Myrcene

Gamma-Terpinene

Terpinolene

Alpha-Pinene

Camphene

Beta-Pinene

Uinonene (Dipentene)

Alpha-Phellandrene

Sabinene

Beta-Phellandrene

Delta3-Carene

Alpha-Thujene







Monoterpene Alcohol

Geraniol

4-Terpineol

Alpha-Terpineol

Beta-Terpineol

Citronellol

Linalool

Sesquiterpene

Caryophyllene

Terpinic Esters

Geranyl Acetate

Linalyl Acetate

Bornyl acetate


Acids

Formic

Octanoic

Butyric

Acetic

Aromatic hydrocarbons


P-Cymene

Toluene








The following compounds were identified only on the basis of retention times observed from gas chromatography.

Cumene

Cyclamen Aldehyde

Camphor

Menthone

Menthyl Isovalerate


The structures and physical properties of the major compounds in the essential oil is given in Appendix 1.

Uses of the Essential Oil

Because of its aroma, the essential oil has been used as a natural flavouring extract and as a perfume in the cosmetic industries.22 In particular, the oil has been used as a flavouring agent, replacing ground nutmeg in order to avoid leaving particles in foods and beverages. For example, it has been used to flavour baked goods, beverages, candies, meats and syrups.The essential oil has found widespread use in the cosmetic industry when a spicy odour is required. For example, it has been employed as a flavour in dental creams in combination with peppermint, methyl salicylate and cloves.

In addition to its use in cosmetic industries, nutmeg oil is prominently used in the pharmaceutical industry. Historically, nutmeg has been used as a form of medicine to treat many illnesses ranging from those affecting the nervous system to the digestive system.24 Presently, the nutmeg oil is used by many pharmaceutical companies in their formulations of products to treat different illnesses. In 1992, Procter and Gamble launched a non-drowsy and alcohol-free Vicks cough syrup and the essential oil of nutmeg is a major ingredient. Robinson-Health Care in Britain in 1991 also marketed an impregnated tissue called Easy Breather Tissue which helps to clear congestion, and the essential oil of nutmeg was also an active ingredient. In that same year, Ramedica International Corp. marketed in the USA, a pain relieving ointment called Ramedica Herbal Wonder Balm, and nutmeg oil was again one of the active ingredients. This shows that the essential oil of nutmeg continues its historical importance as a major pharmaceutical ingredient.

Fixed Oil of Nutmeg

Depending upon the method used to obtain the fixed oil of nutmeg from the seed, varying amounts of essential oil will be present in the fixed oil. There are two general ways in which the fixed oil of nutmeg is extracted from nutmeg. In the first process, the ground nutmeg is subjected to intense hydraulic pressure and heat. The other method employs a solvent, for example, diethyl ether. In this process, the ground nutmeg is reflux with diethyl ether, and after filtering off the solid residue, the diethyl ether is distilled off from the filtrate to leave behind the crude fixed oil. These two processes will result in the crude fixed oil containing substantial quantities of essential oil. The quantities of essential oil vary between 10-12%. If the essential oil is removed by steam distillation prior to extracting the crude fixed oil, then the fixed oil of nutmeg will contain only trace amounts of essential oil.

Unlike the liquid essential oil, the fixed oil is a semi-solid, reddish brown material with both the smell and taste of nutmeg. It melts at 45-51°C and has a density of 0.990-0.995. Like most oils, it is completely soluble in hot alcohol, however, sparingly soluble in cold alcohol. The fixed oil is freely soluble in ether and chloroform.The fixed oil of nutmeg has not been subjected to as much investigative research as the essential oil. One possible reason is because of the small number of compounds that are present in the fixed oil.

Hydrolysis or Splitting of Trimyristin to Obtain Myristic Acid

In general, any fat can be broken down to its two major components - a fatty acid component, and a glycerol as the alcohol component. The process is known as hydrolysis or splitting, and the overall reaction involves the addition of water to the fat in order to produce the fatty acid and glycerol (glycerine). There are two methods by which the hydrolysis process can be accomplished: (1) saponification and (2) direct splitting.

With saponification, the fat is heated in a solution of a hydroxide base, for example, sodium or potassium hydroxide, and this produces the metal salt of the carboxylic acid (soap) and glycerol. Acidification of the metal salt or soap with a mineral acid liberates the carboxylic acid and a mineral salt. The process is shown by the reactions below using trimyristin as the fat:

Saponification is usually the method of choice in the laboratory for preparing a carboxylic acid from fat. Saponification is also sometimes used industrially.

In the direct hydrolysis process, the fat is treated with water in the presence of a catalyst to yield directly the carboxylic acid and glycerol. Very high temperatures and pressures are necessary to accomplish this splitting procedure. A mineral acid like sulphuric acid is usually the catalyst used, and at times an alkaline catalyst like zinc oxide, calcium hydroxide or magnesium hydroxide can be used.

Because of the high pressure and. temperature required, this hydrolysis technique is used predominantly in industry.

Conclusion from chemical composition analysis of nutmeg

No in-depth review of the essential oil as a potential marketable commodity will be further discussed since a construction project of a steam distillation plant is in progress in Grenada.

As seen from the discussion on the chemical composition of nutmeg, the most abundant individual compound in nutmeg is trimyristin. Trimyristin, a triglyceride (fat) is approximately 75% by weight of the total fixed and essential oils of nutmeg and 40% by weight of the nutmeg seed. The relative abundance of trimyristin in nutmeg makes it a potentially desirable target for isolation.

At present, the price of the essential oil on the US market is $14/kg and the market size seems to be good. In 1989, nutmeg oil imports to the US were approximately 115,000 kg, and in 1992 nutmeg oil imports were about 192,000 kg valued at about 2 million US dollars.47,48 Recognizing the favourable market trends and prices of nutmeg oil, it would not be advisable to attempt to isolate any individual compounds from nutmeg oil. Nevertheless, one must keep in mind the possibility of extracting compounds from the nutmeg oil in case nutmeg oil faces any severe marketing problems in the near future.

Trimyristin is a favourable potential compound to isolate from nutmeg. In addition to being the most abundant compound in nutmeg, six times that of the essential oil, derivatives of this compound are highly marketable products, specifically myristic acid, myristyl alcohol and glycerol.

Trimyristin is a vegetable fat and can serve as a feedstock for the production of myristic acid, a saturated C14 fatty acid. An evaluation of the economic viability of producing trimyristin as a raw material for the production of myristic acid and glycerol will warrant examination of the market conditions of the vegetable fat industry and other related industries such as the oleochemical industry.


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