Aleph compounds

EXTENSIONS AND COMMENTARY Here is a simple and easily made compound that might well bid fair to be one of the most rewarding and pleasurable of the methoxylated amphetamines. It is fully as potent as its counterpart, TMA-2. This latter compound, with its 2,4,5-trisubstitution pattern, has served as a template from which an immense family of very active and fascinating drugs have arisen. The 2,5-dimethoxy aspect has been kept intact, and modifications in the 4-position have given rise to treasures such as DOM, DOB, DOET, DOI, and the Aleph compounds. And, of course, the entire world of the 2C-X s has exploited this same orientation. 

Characteristics of some psychoactive phenylisopropylamin.es as listed in Burger s Medicinal Chemistry. Substitution of various molecules and molecular groups at various positions in the skeleton nucleus has been extensively tested and results in wide variations in potency (DOB is the strongest, exhibiting some 400 times the strength of mescaline). Those in the middle are the most popular in this series, but the recently-synthesized Aleph compounds, which contain sulfur and emphasize introspection, have also been well received. 

EXTEN SIONS AND COMMENT ARY The three-carbon analog of 2C-T-9 (this would be one of the ALEPH series) has never been made and, for that matter, none of the hi gher numbered 2C-T s have had the amphetamine counterpart s synthesized. They are, as of the present time, unknown compounds. This nifty reaction with di-(t)-butyl disulfide worked so well, that three additional disulfides that were at hand were immediately thrown into the chemical program, with the quick assignment of the names 2C-T-10, 2C-T-11, and 2C-T-12. 

A closely related 2C-T-X compound was also started quite a while later -this was the allylthio homologue of the methallyl material 2C-T-3 or 2C-T-20. Its place in the flow of things is evident from its numbering, 2C-T-16. A mixture of 2,5-dimethoxythiophenol and KOH and allyl chloride in MeOH gave 2,5-dimethoxyphenyl allyl sulfide as a white oil which boiled at 110-125 °C at 0.25 mm/Hg. This, with POCI3 and N-methylformanilide provided 2,5-dimethoxy-4-(allylthio)benzaldehyde which distilled at 140-160 °C at 0.4 mm/Hg and could be recrystallized from MeOH as a pale yellow solid. Reaction of this aldehyde in nitroethane in the presence of ammonium acetate (steam bath for 2.5 h) provided 2,5-dimethoxy-4-allylthio-beta-nitrostyrene as red crystals from acetonitrile. Its mp was 114-115 °C. Anal. (C13H15N04S) C,H. This has not yet been reduced to the final amine, 2,5-dimethoxy-4-allylthiophenethylamine, 2C-T-16. The corresponding amphetamine would be, of course, ALEPH-16. 

EXTENSIONS AND COMMENTARY This material, ORTHO-DOT, can be looked at as the sulfur homologue of TMA-2 with the sulfur atom located in place of the oxygen at the 2-position of the molecule. At what level this compound might show activity is completely unknown, but wherever that might be, it is at a dosage greater than that for the PARA-DOT isomer, ALEPH-1 (or ALEPH), which was fully active at 10 milligrams (ALEPH can be looked at as TMA-2 with... 

EXTENSIONS AND COMMENTARY The earliest work with the sulfur atom was with the three-carbon chain materials, the ALEPHs. It was only after a considerable time of working with them, and trying to come to peace with their property of being so different from person to person as to potency, that the two-carbon homologues were looked at. Although the first of these (this compound, called 2C-T) was prepared at the same time as ALEPH-1, there was a lapse of about four years between their trials. The relatively low potency of 2C-T was a bit discouraging. 

I would like to make an additional point here, about the exploration of qualitative variations. It can be tempting to pursue compounds that make one feel good. These are certainly the ones that are likely to get the most use. However, one of the objectives of psychic exploration is to become more familiar with the components of the psyche, both positive and negative. It appears that Shulgin Shulgin (1991) have been fairly unbiased in this respect. He describes Aleph-1 as producing "the most delicious blends of inflation, paranoia and selfishness"... 

Figure 18.32 Amfetamine counterparts (additional presence of the a-carbon) of 2-C-X and 2C-T-X compounds give rise to the DO-X and ALEPH-X series.

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