In nutmeg

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". 

Butyric acid, CgHy. COOH, is an oily liquid ha-ving an odour of rancid butter. It has been found in the oils of Eucalyptus globulus, Heracleum giganteum, and in nutmeg, niaouli, and other essential oils. It has the following characters —... 

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. 

Among various sterols, sitosterol was predominant in nutmeg. Other sterols reported... 

Variyar and Bandyopadhyay (1995) determined the phenolic acid profile of nutmeg and mace. The chief phenolic acids in nutmeg were caffeic acid and vanillic acid, whereas ferulic acid and synapic acids predominated in mace. 

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). 

Nutmeg and mace are the two major primary products of M. fragrans and are considered commercially as spices. The constituents of nutmeg can be classified broadly into terpenoids, fatty acids, phenolic acids, lig-nans, neolignans and miscellaneous compounds. The oil content ranges from 3.9 to 16.5% in nutmeg, whereas in mace it varies from 6.0 to 26.1%. The major constituents of the essential oil in nutmeg and mace are sabinene and pinenes. The chief... 

Myristicin forms a colorless to yellowish oil (depending on purity), with a boiling point (at 40 milliliters of mercury) of 173 Celsius. Myristicin exits naturally in nutmeg, carrots, and parsley, from which it can be extracted—especially from the corresponding oils. 

Trimyristin, a solid fat present in nutmeg, is hydrolyzed to give one equivalent of glycerol and three equivalents of myristic acid. Give the structure of trimyristin. 

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).

Ar illode.—A fake accessory seed covering outside of the testa, as in Nutmeg, and arising from the dilatation of the micropyle. 

Myristic acid occurs naturally in nutmeg butter and in most animal and vegetables fats. Synthetically, it may be prepared by electrolysis of methyl hydrogen adipate and decanoic acid or by Maurer oxidation of myristyl alcohol. 

There are various reports hyping elemicin content as being up to 5-6% in nutmeg, but T able XII s numbers are fairly representative of most of what I ve seen in the literature. 

The volatile oils in nutmeg consist of allylbenzene derivatives and terpines. Myristicin, elemicin, and safrole comprise 80% of the allylbenzenes. Myristicin and elemicin may be biotransformed into MMDA (3-methoxy-4,5-dimethylene-dioxampheta-mine) and TMA (3,4,5-trimethoxyamphetamine), respectively, both consisting of a difference of only an amine group added to the side chain. Symptoms occur within 3-8 h, followed by 6-24 h of alternating periods of stupor and delirium. Recovery normally occurs within 24 h but may take several days. 

Sometimes the endosperm and cotyledons are folded around each other and firmly coherent, as in nutmeg (Myristica), in transverse section looking a bit like the molar of a cowt rusdnate. 

Archer, A.W., Determination of safrole and myristicin in nutmeg and mace by high-perfoijnance hquid chromatography, J. Chromatogr., 438, 117, 1988. 

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