Nutmeg compounds

Myristicin, CjjHjgOg, is 4-allyl-6-methoxy-l. 2-methylenedioxybenzene. It is found in oil of nutmeg and in parsley oil. It is a fragrant compound having the following characters —... 

Because it does not have quite the same taste as the much more complex mixture of compounds found in natural vanilla extract, it is most often used with stronger flavors and scents such as chocolate, cloves, nutmeg, or cinnamon. 

Oils may contain toxic compounds. For example, Myristicin is the compound that flavors nutmeg and mace it is also found in black pepper and carrot, parsley, and celery seeds. Used in culinary quantities, myristicin is only a flavoring. In massive doses, it causes hallucination. Thujone, the anise-flavored oil in wormwood, caused an epidemic of brain disease in drinkers addicted to the now-banned liquor absinthe. Sassafras contains a toxic oil similar to thujone, which is why it is no longer used to make root beer. Very high doses of menthol, from peppermint, may cause dangerous irregularities in the heart s rhythm (Weiss, 1997)... 

The volatile oil of nutmeg constitutes the compounds monoterpene hydrocarbons, 61-88% oxygenated monoterpenes, i.e. monoterpene alcohols, monoterpene esters aromatic ethers sesquiterpenes, aromatic monoterpenes, alkenes, organic acids and miscellaneous compounds. Depending on the type, its flavour can vary from a sweetly spicy to a heavier taste. The oil has a clovelike, spicy, sweet, bitter taste with a terpeny, camphor-like aroma. 

There are several reviews on the phytochemical studies of nutmeg (Satyavathy et al., 1987 Thakur et al., 1989 Ross, 2001 Latha et al., 2005). The constituents of nutmeg can be classified broadly into terpenoids, fatty acids, phenolic acids, lignans, neolignans and miscellaneous compounds. 

African nutmeg (Monodora mynstica Dund Gaerth) seeds yielded 4.6% essential oil. The oil contained 75% monoterpene hydrocarbons (Table 9.9). The major components were a-phellandrene (50.4%), a-pinene (5.5%) and myrcene (4.35%). The oil contained 3% sesquiterpene hydrocarbons and oxygenated compounds such... 

It contains the same aroma compounds as nutmeg but in smaller amounts, mainly monoterpenes (87.5%), monoterpene alcohols (5.5%) and other aromatics (7%). Like nutmeg essential oil, the main constituents of mace essential oil are sabinene, a-pinene, (3-pinene, myrcene, limonene, 1,8-cineole, terpinen-4-ol, myristicin, y-terpinene and safrole. Mace oil is more expensive than nutmeg oil. 

The non-volatiles from nutmeg include lignans, phenolic acids, glycosides, sterols and miscellaneous compounds. 

Cluster 5 Nutmeg and MDA, the empathic compounds that create few "visuals, stimulating research into discrete psychedelic effects... 

MDA-like compounds almost always come from the volatile oils found in a small number of plants nutmeg, mace, saffron, calamus, crocus, parsley, dill and sassafras. More than a thousand synthesized compounds fall into this group. Only a few have been tried by humans. 

The oils from nutmeg, dill, parsley seed, calamus, crocus, saffron, vanilla beans, sassafras and other plants contain generous amounts of the precursors to the semi-synthetic MDA-like compounds. Recently dried nutmeg is about 15 percent extractable oil. 

This compound cluster exhibits a two-ring, "open-chained, indolic chemical structure, and in contrast to other psychedelics it is all but inactive when taken orally unless accompanied by certain other compounds. Shortacting tryptamines are closely related to neurotransmitters (such as bufotenine), to MDA (a major botanical source of the snuffs belongs to the nutmeg family), to tryptophan (an essential amino acid produced in human digestion of proteins) and to psilocybin and psilocin (which are tryptamines of longer duration). DMT, the simplest member, occurs normally in the blood, brain and (in higher concentrations) in the cerebrospinal fluid. 

The main products are monolitic terpenes such as alpha-terpineol 32. Minor amounts of bicyclic compounds (34), e.g. borneol 31, can be observed. Some of these products are of commercial importance as fragrances with lilac and nutmeg odor (monocyclic alcohols like alpha-terpineol or 1-terpinene-4-ol) or with campher-like and extremely delicate pepper odor (bicyclic compounds). In current industrial practice, the bicyclic alcohol borneol 31 is synthesized by a multi-step procedure. Much research has been done to develop clean processes which have high selectivity towards one of the products starting directly from alpha-pinene 30. 

Figure 7. Parent ion scans for two isomeric forms of diphenylpropanoids found in nutmeg. The cannon ions at m/z 355, 357, and 371 indicate the presence of both forms of the compound at those masses (X 7).

MyrISTICIE OLEUM. Oil of nutmeg. Called Oil of mace. Myristica moschata. Oleum nuclei fixo-volatile. The compound oil of the kernel. 

Plants - Lignin, tannins, and pigments, flavor components of spices (cinnamon oil, wintergreen oil, bitter almond, nutmeg, cayenne pepper, vanilla bean, clove, and ginger) are derived from coniferyl alcohol. Coniferyl alcohol, in turn, is derived from phenylalanine and tyrosine. Phenylalanine is also a precursor of plant pigments and related polyphenolic compounds called flavonoids. The biosynthetic scheme leads to a class of flavonoids called anthocyanins, which are common flower pigments.. An offshoot of this pathway leads to the synthesis of cocaine. 

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