5-Methyltryptamine hydrochloride

Infra-red Spectrum. Principal peaks at wavenumbers 800, 1515, 1612,1587, 1234, 1315 (5-methyltryptamine hydrochloride). 

Codeine Hydrochloride Dequalinium Acetate Fluorometholone Hexamethonium Bromide Riboflavine Stilbazium Iodide Mianserin Hydrochloride Tacrine Hydrochloride Diclofenac Sodium Vinblastine Sulphate Cyclizine Hydrochloride Amiloride Hydrochloride Protoveratrine B Meclofenamate Sodium 5-Methyltryptamine Hydrochloride Dicoumarol Mebendazole Pipradrol Hydrochloride Carbenoxolone Flucytosine Phanquone Phenytoin... 

Methyltryptamine hydrochloride (3-[2-aminoethyl] 5-methylindole hydrochloride) [1010-95-3] M 210.7, m 289-291°(dec), 290-292°, pKEst(i) "3 (protonation of ring NH), pKEst(2) 9.0 (CH2NH2), pKEst(3) 10.9 (acidic indole NH). Recrystd from H2O. The free base has m 93-95° (from C6H6-cyclohexane), and the picrate has m 243°(dec) (from EtOH). [Young J Chem Soc 3493 7958 Gaddum et al. Quart J Exp Physiol 40 49 7955 Rohm Hoppe Seyler s Z Physiol Chem 297 229 1954.]... 

Scale-up results (Table 6.2) show that the process was very reproducible from laboratory scale to pilot-plant scale in terms of yield and quality of the isolated 5-methyltryptamine hydrochloride. 

A typical procedure to prepare the 5-methyltryptamine hydrochloride at the kilo lab scale and at the pilot-plant scale is as follows. 

The acid-catalyzed Pictet-Spengler reaction between tryptamine derivatives and aldehydes is a well-established method for preparing tetrahydro-p-carboline (THpC) derivatives." Our first trials were aimed at using the bisnlfite adduct as the carbonyl sonrce in order to minimize the number of process steps. The reaction was performed by reacting the 5-methyltryptamine hydrochloride with an excess (1.3 eqniv) of the sodium bisulfite adduct in EtOH at reflnx, in the presence of one extra eqnivalent of HCl. The rac-THpC was simply isolated as a hydrochloride salt by filtration of the reaction mixture (Scheme 6.8). 

The addition of an extra equivalent of nonaqneons HCl is necessary to obtain an acceptable yield of 5-methyltryptamine hydrochloride. Withont this extra HCl, the isolated yields dropped to the 15 to 36% range. However, we soon reached the conclnsion that this process had some robusmess issues. 

HC1. The aqueous extracts were pooled, washed with CH2CI2, and made basic by the addition of 25% NaOH. The precipitate that formed was extracted into several small portions of CH2CI2 which were pooled and dried with anhydrous Na2S04. After removal of the drying agent, the solvent was removed under vacuum. To the residue there was added a 1.0 M solution of HC1 in anhydrous Et20 until the mixture was neutral, as determined by external, damp pH paper. The resulting solid was removed by filtration and twice recrystallized from aMeOH/acetone mixed solvent. There was thus obtained N,N-diethyl-2-methyltryptamine hydrochloride (2-Me-DET) as white crystals with a mp 214-216 °C. 

Girgensohnia spp. G. diptera Bge. contains N-methylpiperidine and dipterine, CHH14N2, m.p. 87-8°, [a]D 0° hydrochloride, m.p. 177-8°, picrate, m.p. 189-190°, and picrolonate, m.p. 242-3°, which was later shown to be N-methyltryptamine.i G. oppositiflora Pall, contains N-methylpiperidine and girgensonine, C13H13ON2, m.p. 147-8°, [aJjj 0°. The latter forms a hydrochloride, m.p. 145-8°, and a picrolonate, m.p. 192-4°, and on hydrolysis by alkali yields piperidine, hydrocyanic acid and p-hydroxybenzaldehyde, indicating that it is N-piperidyl-p-hydroxy-phenylacetonitrile, and this has been confirmed by comparison with a synthetic specimen. ( (1) Juraschevski and Stepanova, J. Gen. Chem. Russ., 1939, 9, 2203 Juraschevski, ibid., 1940, 10, 1781. (2) Juraschevski and Stepanova, ibid., 1946, 16, 141). 

EXTENSIONS AND COMMENTARY N-Methyltryptamine (monomethyltryptamine, NMT) is an alkaloid that has been found in the bark, shoots and leaves of several species of Virola, Acacia and Mimosa. However, the major snuffs associated with these plant have been shown to also contain 5-MeO-DMT and are discussed there. NMT has been synthesized in a number of ways. One can react 3-(2-bromoethyl)indole with methylamine. NMT can be isolated as the benzoyl derivative from the methylation of tryptamine with methyl iodide followed by reaction with benzoyl chloride, with the hydrolysis of this amide with alcoholic KOH. It can also be synthesized from indole with oxalyl chloride, with the resulting glyoxyl chloride reacting with methylamine in ether to give indol-3-yl N-methylglyoxalylamide (mp 223-224 °C from IPA) which is obtained in a 68% yield, which is reduced to NMT to give the amine hydrochloride (mp 175-177 °C from ) in a 75% yield. The most simple and direct synthesis is the formamide reduction given above. 

The Fischer indole reaction between 4-methylphenylhydrazine hydrochloride and 4,4-diethoxy-bntylamine affords 5-methyltryptamine with a low yield (average isolated yields = 35%). 

W-Methyl-y3-phenethylamine occurs together with dipterine (W-methyltryptamine) and leptocladine (3 4-dimethyl-3 4 5 6-tetrahydro-4-carboline), in the Chenopodiaceae Arthrophytum leptocladum Popov (16, 17). The colorless oil has b.p. 73—75° (4 mm.) hydrochloride, m.p. 161-162°, picrate 141-142 (from alcohol) picrolonate, m.p. 217—218 (from alcohol) platinichloride, m.p. 220-221 methiodide of the methyl compound, m.p. 227-228°. 

---