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    Chemistry and Physical Properties
    by Murple, Feb 6, 2001

    2C-T-2 and 2C-T-7 are two closely related chemicals in a series of phenethylamine compounds created by Alexander Shulgin. The 2C prefix derives from the fact that these compounds are the two carbon phenethylamine homologues of previously made three carbon amphetamines, having the alpha-methyl group removed. Shulgin named most of the 2C compounds by adding the last letter of the amphetamine prototype's name, for example 2C-B from DOB and 2C-I from DOI. The 2C-T series is based on the three carbon ALEPH series (described in detail in Shulgin's book, PiHKAL), and the T comes from the fact that the original name for ALEPH-1 was DOT (T standing for "thio", from it's sulfur atom). There are a whole series of 2C-T compounds which have been made or theorized, and the numbering of the series was assigned in the order the chemicals were thought up, rather than due to any structural properties.

    Click to enlarge
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    So far, the only syntheses which have been published are Shulgin's methods as described in PIHKAL. Shulgin's recipes for 2C-T-2 and 2C-T-7 have been included as appendices to this paper.

    Physical Properties

    2C-T-2's full name is 2,5-dimethoxy-4-ethylthiophenthylamine, and 2C-T-7's is 2,5-dimethoxy-4-(n)-propylthiophenethylamine. Both chemicals generally come in the form of a hydrochloride salt, which are white crystalline powders. As free bases, both chemicals are a clear white oil. 2C-T-2 has the molecular formula C12H19NO2S and a molecular weight of 241.3476. 2C-T-7, has the molecular formula C13H21NO2S and its molecular weight is 255.3744. 2C-T-2 has a boiling point of 120-130 Celsius (at 300 microns). 2C-T-7 has a boiling point of 140-150 Celsius at 251 microns.

    Both chemicals react to Marquis reagent, the principal ingredient in ecstasy testing kits, by producing an orange-red color reaction (similar to the color of uncooked salmon). 2C-T-2 produces a slightly more orange color, and 2C-T-7 a slightly more red color, but the difference is minute.

    Regarding the stability of these chemicals, in 2000, Shulgin re-examined the original discovery samples of 2C-T-7 and the closely related 2C-T-4, to make sure that the propyl and isopropyl groups, respectively, had not been compromised. These samples were at the time well into their second decade. Both samples were still white, and the spectra showed clean when checked by mass spectroscopy. When asked about the possibility of long term storage of 2C-T-2 and 2C-T-7, he said "I feel that the solids are stable with time." It is probably advisable to store the chemicals in air-tight, light-proof containers (such as amber glass vials with good caps) in a cool, dry location.

    Since these chemicals have become more widely available, some people have been dissolving them in solvents to allow for measuring doses out by liquid volume. The two most popular solvents for this purpose have been water and ethyl alcohol. There have been mixed reports as to the solubility of 2C-T-2 and 2C-T-7. Some have reported that when making solutions using water, with time, the drugs recrystallize and settle to the bottom. Reports of both unexpectedly strong and weak reactions raise questions about just how soluble these chemicals are. One factor which needs to be accounted for as well is that the solvents being used are not pure. Although advocates of this measurement technique recommend using distilled water, it is possible that people are also using plain bottled water and even unfiltered tap water. Some people use high proof liquor such as vodka or grain alcohol as a solvent. This offers the advantage of protecting against biological contaminants, and appears to offer somewhat better solubility. Regardless of which solvent is used, the impurities present in both liquor and water could conceivably alter the ability of the phenethylamines to enter and remain in solution, and could potentially react with them chemically. Another factor which could alter the ability of the chemicals to remain in solution is the temperature at which the solution is stored. Solutions which are stable at room temperature may separate out if stored in the refrigerator. The long term molecular stability of 2C-T-2 and 2C-T-7 in solution has never been explored, and there is the possibility that they may be less stable when stored in solution versus being stored in pure form.

    Related Chemicals

    Shulgin has thought up and named twenty-four compounds in the 2C-T series of phenethylamines. Nine of these have been synthesized and evaluated up to active doses, two have been synthesized but have not had their activities discovered, and the rest have never been made. There is also a twenty-fifth chemical in this series which not only was never made, but never officially assigned a 2C-T-X code name.

    2C-T 5-dimethoxy-4-methylthiophenethylamine
    The original compound in the series. It is a psychedelic described by Shulgin as "generic" in dosages of 60 to 100 mg. In contrast to this evaluation, one person interviewed while collecting 2C-T-2 and 2C-T-7 experience reports for this paper mentioned having used this drug as well. He said "I actually prefer 2-CT despite it's lower potency (100 mg) because it doesn't seem to engage your mind as much - like DMT, it's just watch the fireworks." Having tried several drugs in the 2C-T series, he observes, "As the aliphatic chain gets longer the effects seem to become less visual and more mind-manifesting (in the sense that thought processes become more important. For instance 2-CT can be floridly visual with patterns and color changes similar to mescaline, whereas 2-CT-7 is rarely very visual with some exceptions (colors get brighter, contrast is accented))." He also stated that his partner got more nausea from 2C-T than other drugs in this series, but pointed out that "she has a pretty sensitive stomach." While the low potency is a negative, it has the advantage of producing a short trip of only 3 to 5 hours.
    2C-T-2 2,5-dimethoxy-4-ethylthiophenethylamine
    As a principal subject of this paper, this drug will be discussed elsewhere.
    2C-T-3 2,5-dimethoxy-4-(beta-methallylthio)phenethylamine
    Has never been synthesized.
    2C-T-4 2,5-dimethoxy-4-isopropylthiophenethylamine
    An active psychedelic at dosages of 8 to 20 mg and results in a long 12 to 18 hour trip. It apparently produces some cross-tolerance with 2C-B. An entire chapter of Shulgin's PIHKAL is devoted to a detailed description of a powerful experience of a 2C-T-4 trip.
    2C-T-5 2,5-dimethoxy-4-cyclohexylthiophenethylamine
    Has never been synthesized.
    2C-T-6 2,5-dimethoxy-4-phenylthiophenethylamine
    Has never been synthesized.
    2C-T-7 2,5-dimethoxy-4-(n)-propylthiophenethylamine
    As a principal subject of this paper, this drug will be discussed elsewhere.
    2C-T-8 2,5-dimethoxy-4-cyclopropylmethylthiophenethylamine
    Active in the 30-50 mg dose range, giving a 12 to 18 hour trip which Shulgin describes by saying "there are as many negatives as there are positives."
    2C-T-9 2,5-dimethoxy-4-(t)-butylthiophenethylamine
    Active in the 60 to 100 mg dose range, and gives effects lasting 12 to 18 hours. With this one, heavy body load seems to dominate over the mild psychedelic effects.
    2C-T-10 2,5-dimethoxy-4-(2-pyridylthio)phenethylamine
    Synthesis was abandoned before completion.
    2C-T-11 2,5-dimethoxy-4-(4-bromophenylthio)phenethylamine
    Synthesis was abandoned before completion.
    2C-T-12 2,5-dimethoxy-4-(1-morpholinothio)phenethylamine
    Synthesis was abandoned before completion.
    2C-T-13 2,5-dimethoxy-4-(2-methoxyethylthio)phenethylamine
    A psychedelic at 25 to 40 mg, giving a 6 to 8 hour trip. In the paper "Structure-Activity Relationships of the Classic Hallucinogens and Their Analogs" by Alexander Shulgin and Peyton Jacob III, this compound was erroneously listed in as 2C-T-24. When asked about this, Shulgin said that this is simply a misprint.
    2C-T-14 2,5-dimethoxy-4-(2-methylthioethylthio)phenethylamine
    Has been synthesized but, no human testing has been done, and its activity is unknown.
    2C-T-15 2,5-dimethoxy-4-cyclopropylthiophenethylamine
    Has been synthesized and preliminary tests have been done, with some threshold effects lasting several hours being noted from 6-30 mg. Its activity remains unknown. It has been given the nickname "Sesqui" by Shulgin, derived from the fact that 15-carbon terpenes are known by the term "sesquiterpene," and this is the fifteenth drug in the 2C-T series.
    2C-T-16 2,5-dimethoxy-4-allylthiophenethylamine
    Has never been synthesized.
    2C-T-17 2,5-dimethoxy-4-(s)-butylthiophenethylamine
    Produces a 10 to 15 hour psychedelic trip without significant sensory changes when taken in dosages of 60 to 100 mg. Shulgin has given this compound the nickname "Nimitz" - a name derived from State Highway 17 in California (now Interstate 880), known as the Nimitz Freeway.
    2C-T-18 2,5-dimethoxy-4-cyclobutylthiophenethylamine
    Synthesis was abandoned before completion.
    2C-T-19 2,5-dimethoxy-4-(n-butylthio)phenethylamine
    Synthesis was abandoned before completion.
    2C-T-20 2,5-dimethoxy-4-(beta-methallylthio)phenethylamine
    This is another name for 2C-T-3. The reason for this is that the homologous three carbon amphetamine (ALEPH-3) had been started, abandoned, and forgotten about. Several years later, Shulgin decided to try making the three carbon homologue again, and assigned a new number to the forgotten project. A new number was assigned to the corresponding 2C-T as well, before remembering the original ALEPH-3 project. As noted above, it has never been synthesized.
    2C-T-21 2,5-dimethoxy-4-(2-fluoroethylthio)phenethylamine
    In doses from 8 to 12 mg, is a mild psychedelic without much body load that lasts 7 to 10 hours. In "Thanatos to Eros," Myron Stolaroff describes this drug as being a "wonderful energizer" rather than a psychedelic, saying that it "raises mood and spirit, raises the energy level, increases wit and sense of humor, facilitates communication, and in general provides an excellent good time." The anonymous contributor mentioned above under 2C-T said of 2C-T-21 that it is "perhaps one of the best," and that it "allows you to do just about anything while feeling emotionally open and motivated." More to the point was his closing remark on it, "Amazing stuff!" One other interesting bit of trivia about this drug is that it was the first psychedelic drug synthesized which contained six separate elements (C, H, N, O, S, and F). This was the last drug in the 2C-T series to be synthesized and investigated.
    2C-T-21.5 2,5-dimethoxy-4-(2,2-difluoroethylthio)phenethylamine
    A humorously named compound thought up while writing PIHKAL. Although it has not been synthesized, Shulgin writes "I will wager mucho that it will be very potent."
    2C-T-22 2,5-dimethoxy-4-(2,2,2-trifluoroethylthio)phenethylamine
    Synthesis was abandoned before completion.
    2C-T-23 2,5-dimethoxy-4-cyclopentylthiophenethylamine
    Synthesis was abandoned before completion.
    2C-T-24 2,5-dimethoxy-4-diethylaminothiophenethylamine
    In addition to the named 2C-T compounds, Shulgin also wrote about this chemical in PIHKAL. It has been theorized by never synthesized. Although never officially named so by its inventor, it seems logical to assign the name 2C-T-24 to this compound, in case it ever gets synthesized and explored and needs to be referred to by a simpler name.

    After all this, Shulgin decided that while the 2C-T family of drugs was pharmacologically interesting, it no longer seemed too challenging from a creative chemistry perspective. Realizing that others could pick up with them where he left off, using the knowledge in PIHKAL, he abandoned further research with the 2C-T series. Information gleaned from this research went on to bear other interesting fruit, however. Seduced by the unexpected enhancement of activity achieved by substituting sulfur for oxygen, Shulgin turned his attention back to mescaline and its derivatives escaline and meta-escaline. He spent several months synthesizing sulfur analogues of these, a process culminating in the creation and evaluation of all five possible compounds. The results were positive. 3-Thioescaline (3-TE) was found active in the 60 to 80 mg range, and 4-TE in the 20 to 30 mg range. 3-Thio-meta-escaline (3-TME) as well as 4-TME were both found active in the range of 60 to 100 mg. 5-TME has been run up to 200 mg, and if it is active, the dosage must be higher than this. Including an ethoxy group into the mescaline molecule and then inserting a sulfur atom was found to be able to increase the potency up to twenty times that of mescaline (as in the case of 4-TE). Further offspring of this line of research can be found in PIHKAL, including thioproscaline (which exhibited some unpleasant effects) and 4-thiobuscaline (which appears to be primarily a euphoriant). Shulgin then went on to explore this ethoxy/thio substitution in the tryptamine world, documenting some of his finds in TIHKAL.

    Regarding further explorations of the 2C-T series: if anyone has continued this research as Shulgin hoped, the results have not been made publically available. This field is ripe for picking.

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