Methylphenethylamine

Two mols, for example, 270 grams, of racemic a-methylphenethylamine base are reacted with one mol (150 grams) of d-tartaric acid, thereby forming dl-a-methylphenethylamine d-tartrate, a neutral salt. The neutral salt thus obtained is fully dissolved by the addition of sufficient, say about 1 liter, of absolute ethanol, and heating to about the boiling point. The solution is then allowed to cool to room temperature with occasional stirring to effect crystallization. The crystals are filtered off and will be found to contain a preponderance of the levo enantiomorph. 

The residual solid in the mother liquors is repeatedly and systematically crystallized, yielding a further fraction of 1-a-methylphenethylamine d-tartrate which may be purified by recrystallization. d-a-Methylphenethylamine may be readily recovered from the mother liquors by the addition of tartaric acid thereto for the formation of acid tartrates and separation of d-a-methylphenethylamine d-bitartrate by crystallization. 

N-methyltyramine, the immediate biosynthetic precursor of hordenine, was synthesized and nitrosated in aqueous acid. The major product was U-hydroxy-3-nitro-N-nitroso-N-methylphenethylamine. 

Apparently, minor chemical modifications of the benzilcarboxylic acid containing molecules led to a compound which shows surprising analgesic activity. Condensation of N-methylphenethylamine 74 with... 

The first phenylethylamine of commercial significance to have been synthesized was amphetamine (l-phenyl-2-aminopropane or methylphenethylamine). Amphetamine was developed in 1887 by the Romanian chemist Lazar Edeleanu (1862-1941). For four decades, amphetamine was little more than a laboratory curiosity with no known pharmaceutical use. In 1927, however, the compound was found to have a number of physiological effects It stimulates the... 

Synaptic dopamine transporters are inhibited by various psychotropic alkaloids including the tropane alkaloid cocaine [189, 190], the indole alkaloid ibogaine [191] and by amphetamine (methylphenethylamine) and related compounds [192, 193]. 

The 2-carbon analogue, 2C-BIS-TOM, was prepared from the intermediate aldehyde above, first by reaction with nitromethane to give the nitrostyrene as tomato-colored crystals from EtOAc, mp 145-146 °C. Anal. (CnH 3N02S2) C,H. This was reduced with AH to give 2,5-bis-(methylthio)-4-methylphenethylamine hydrochloride as ivory-colored crystals with a mp of 273-277 °C. 

ARIADNE 4C-DOM BL-3912 DIMOXAMINE l-(2,5-DIMETHOXY-4-METHYLPHENYL)-2-AMINOBUTANE 2,5-DIMETHOXY-a-ETHYL-4-METHYLPHENETHYLAMINE... 

A parallel chemistry to all of this follows the addition of sodium ethoxide (rather than sodium methoxide) to the nitrostyrene. The final product, then, is the ethoxy homologue 2,5-dimethoxy-B-ethoxy-4-methylphenethylamine, or BOED. It is down in human potency by a factor of three, with a normal dosage being 70-75 milligrams. It has a ten hour duration, and is both anorexic and diuretic. There have been no visual effects or insights reported, but rather simply a highly intoxicated state. 

The molecular formula for dextroamphetamine is C9H13N. The full chemical name for dextroamphetamine sulfate, the formulation used in the medication Dexedrine, is d-alpha-methylphenethylamine. 

Although many reversible inhibitors of MAO A have been prepared, largely based on selective reversible inhibitors are rare. A recent example is found in 4-chloro- -methylphenethylamine (133)224. 

Dolichotheline (111) is a histamine-derived alkaloid produced by the cactus Dolichothele sphaerica Britton and Rose (Cactaceae) native to southern Texas and northern Mexico. The alkaloid was first isolated in 1969 by Rosenberg and Paul (160). Spectroscopic data suggested structure 111, 4(5)-(iV-isovalerylaminoethyl)imidazole or 7V -isovalerylhistamine. The structure was proved by synthesis. Refluxing of histamine with isovaleric anhydride yielded 111, identical to the natural product (160). In addition to the major alkaloid dolichotheline, five minor alkaloids have been isolated (161). These were identified as A-methylphenethylamine, /i-O-methylsyn-ephrine, vV-methyltyramine, synephrine, and / -0-ethylsynephrine by IR, NMR, and comparison to authentic materials / -0-ethylsynephrine was probably an artifact of synephrine, since it was not found in a second extraction attempt when no ethanol was used. 

SYNS d-2-AMINO-l-PHENYLPROPANE (7-)-AMPHETAMINE AMSUSTAIN DEPHADREN DEXAMPHETAXHNE DEXEDRINE a-METHYLPHENETHYLAMINE, d-FORM d-l-PHENYL-2-AMINOPROPAN (GERMAN) d-l-PHENYL-2-AMINOPROPANE... 

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