4-DesmethylmescalineA. Brossi and S. TeitelOrg. Prep. Proced. Int. 1(3), 171-172 (1969)4-Desmethylmescaline, a potential metabolite of mescaline which occurs as a minor alkaloid in Lophophora williamsii and Trichocerus pachanoi
1, has been prepared from syringaldehyde by a multistep procedure
2. A more convenient route is the facile conversion of mescaline by selective demethylation with mineral acid to afford 4-desmethylmescaline in 64% over-all yield. This procedure is another example of the preferential cleavage of the middle methoxyl that has been demonstrated
3,4 for various alkaloidal systems containing three neighboring methoxy groups.
ExperimentalA solution of 8 g. (32.4 mmole) of mescaline hydrochloride in 100 mL of 20% hydrochloric acid is refluxed for 2 hrs. and evaporated at 40°C under reduced pressure. The residual oil is crystallized from 100 ml. of ethanol to give 2.4 g of 4-desmethylmescaline hydrochloride: mp 249-250°C. ?
EtOHmax sh 230 nm (6500), 272 (1280); nmr (DMSO-d
6, 60-Mc, tetramethylsilane) ? s 2.93 (2CH
2), 3.76 (2CH
3O), 6.53 (2 aromatics), 8.23 (OH and NH
3); tlc (silica gel G, developed with 100:10:5 EtOAc-MeOH:NH
4OH for 11 cm. and detected with Dragendorff's reagent), R
f 0.40; identical in m.m.p., uv, nmr and tlc to an authentic sample
2. Mescaline hydrochloride (4 g.) is recovered by evaporation of the filtrate followed by crystallization from 100 ml. of acetonitrile. The overall yield of 4-desmethylmescaline hydrochloride is thus 64%.
References[1] S. Agurell and J. Lundström, Chem. Commun., 1638 (1968)
[2] F. Benington, R. D. Morin, and L. C. Clarke, Jr., J. Amer, Chem. Soc., 76, 5555 (1954)
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(Rhodium: "Synthesis of Escaline and Homosyringylamine", Novel Discourse)[3] A. Brossi, J. Van Burik, and S. Teitel, Helv. Chim. Acta, 51, 1965 (1968)
[4] A. Brossi, J. O'Brien, and S. Teitel, Helv. Chim. Acta, in press.