Nutmeg Myristicin

Stein U, Greyer H, Hentschel H. Nutmeg (myristicin) poisoning—report on a fatal case and a series of cases recorded by a poison information centre. Forensic Sci Int 2001 118(l) 87-90. 

McCord, J.A., and L.P. Jervey. 1962. Nutmeg (myristicin) poisoning.. South Carolina Med. Assoc. 58 436-439. 

MYRISTICIN In moderate amounts in dill, carrot, celery, fennel, mace and nutmeg (no more than 10% tops). Makes up about 40% of the oil of parsnip and can reach up to 50-60% of the oil of parsley leaves and seeds. Give nutmeg a rest folks It just don t have it when compared to parsley and parsnip. 

The synthesis of MMDA in Pihkal is one of the longest and most tedious in the book. If one is going the route via myristicin, the Sisifos work of isolating the tiny amount of essential oil present in nutmeg, followed by fractional distillation to purify the myristicin fraction is also added to the labor of the poor chemist. Therefore I propose a new route to this "essential amphetamine". 

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 —... 

Nutmeg Myristica fragrans Tree Myristicin Elemicin... 

This is the most efficient way to get myristicin from nutmeg. 

This is a material that might be a contributing factor to the pharmacology of nutmeg. The major essential oil from that spice is myristicin, and it is the easiest source of MMDA. It has been reported that the passage of this oil through the liver... 

Nutmeg Myristica fragrans (Myristicaceae) seed 5-16 sabinene (17-28) a-pinene (14-22) P-pinene (9-15) terpinen-4-ol (6-9) myristicin (4-8) elemicin (2) flavour, carminative, aromatherapy although the main constituents are terpenoids, most of the flavour comes from the minor aromatic constituents, myristicin, elemicin, etc myristicin is hallucinogenic (see page 385)... 

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)... 

Nutmeg and mace (Myristica fragrans Houtt) Myristicin, elemicin ... 

Depending on the source, the essential oil of nutmeg contains mainly sabinene (15-50%), a-pinene (10-22%) and (3-pinene (7-18%), with myrcene (0.7-3%), 1,8-cineole (1.5-3.5%), myristicin (0.5-13.5%), limonene (2.7-4.1%), safrole (0.1-3.2%) and terpinen-4-ol (0-11%). The contents depend on whether the oil is of West Indian, Indian or Sri Lankan origin (http //www.chem.uwimona. edu.jm 1104/lectures/nutmeg.html). 

Nutmeg and mace oils from Indonesia, the West Indies and Papua New Guinea showed clear-cut differences in the composition. The oils differed in the composition of the aromatic ether fraction. The most abundant aromatic ether was myristicin in East Indian oils, elemicin in the West Indian oils and safrole in the Papuan oils (Ehlers et al., 1998). Chang Yen et al. (1996) reported that Grenadian nutmeg oils contained more sab-inene and less myristicin and safrole than oils from other geographic regions. 

Nutmeg oil from Papua New Guinea contained a-pinene (22.6%), sabinene (15.8%), P-pinene (15.2%) and myristicin (13.2%) as the chief constituents (Wossa et al., 2004). Sait and Satyaputra (1995) reported that deterpenation of nutmeg oils resulted in lowering of the medicinal quality of the oil due to increase in myristicin concentration. 

Essential oil distilled from the ethnolic extract of nutmeg contained a relatively higher content of terpinen-4-ol, elemicin and myristicin and a lower content of sabinene and pinene compared with the steam-distilled oil (Borges and Pino, 1993). Zhu et al. (1995) reported that nutmeg oil from Guangdong, China, contained 27.63% a-pinene, 26.84% sabinene, 15.52% P-pinene and 7.39% myr-isticine besides the minor constituents. 

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. 

Nutmeg pericarp oil contained 16 monoterpenes (60%), nine monoterpene alcohols (29%), eight aromatic ethers (7%), three sesquiterpenes (1%), six esters (1%) and eight other minor components. The components were similar to those in nutmeg and mace oils but differed substantially in concentration (Table 9.11). The chief constituents were a-pinene, a-ter-pineol and terpinen-4-ol. The sabinene, myristicin and safrole concentrations were much lower, while the terpinen-4-ol and a-terpineol contents were much higher than in nutmeg and mace oils (Choo et al., 1999). The chief volatiles from nutmeg and mace are indicated in Fig. 9.1. 

Another application of nutmeg essential oils is in aromatherapy, which is gaining importance these days. The main constituents of nutmeg and mace - myristicin, elemicin and isoelemicin - when presented in aroma form, act as stress relievers. In Japan, many companies diffuse such aromas through air ventilation systems to improve the work environment, as well as the quality of the air. 

Both nutmeg and mace contain the active ingredient myristicin, which pos-... 

Myristicin, l-allyl-3,4-methylenedioxy-5-methoxybenzene, a naturally occurring alkenylbenzene found in nutmeg, produced neurotoxic effects. Myristicin at > 0.5 mM concentration showed cytotoxicity in human neuroblastoma cells (Lee et al., 2005). 

---