TWEETIO is a family of phenethylamine psychedelic drugs. They are analogues of the 2C drugs (4-substituted 2,5-dimethoxyphenethylamines) in which one or both of the methoxy groups at positions 2 and 5 of the phenyl ring have been lengthened to ethoxy groups. Examples include 2CD-2-EtO (a TWEETIO of 2C-D), 2CE-5-EtO (a TWEETIO of 2C-E), and 2CT2-5-EtO (a TWEETIO of 2C-T-2), among many others.
The TWEETIO drugs are said to have been named in a humorous way by pronouncing the simplest structural form of "2-EtO-X". Limited human data are available on the TWEETIO compounds. In any case, some generalizations have been made, including that the 2-EtO compounds tend to have a shorter duration and decreased potency, the 5-EtO drugs tend to have enhanced potency and remarkably increased durations, and the 2,5-DiEtO drugs tend to be inactive.
The TWEETIO compounds were developed by Darrell Lemaire as potential "smart drugs" in the 1970s or 1980s. The compounds were described in the scientific literature by Alexander Shulgin via personal communication with Lemaire in the 1990s and 2000s. It was said by Shulgin in 2003 that the propoxy analogues had not yet been synthesized. In 2023, the propoxy derivative ASR-2001 (2CB-5PrO) was reported by Nick Cozzi and Paul F. Daley of the Alexander Shulgin Research Institute. It is under development for potential medical use.
List and properties of TWEETIO drugs + TWEETIO analogues of selected 2C drugs R4 Parent Parent dose R2 R5 Code name Trial dose Comments of trial Br- 2C-B 12–24 mg Et- Me- 2CB-2-EtO 15 mg "30–50 [mg] prolongs action" Et- Et- 2CB-DiEtO >55 mg "restless sleep, only" Me- 2C-D 20–60 mg Et- Me- 2CD-2-EtO 60 mg "intimate, no intox, 4 hrs" Me- Et- 2CD-5-EtO 50 mg "12 hour duration" Et- Et- 2CD-DiEtO >55 mg "mild, 4 hr duration" Et- 2C-E 10–15 mg Me- Et- 2CE-5-EtO 15 mg "16–24 hr duration" I- 2C-I 14–22 mg Et- Me- 2CI-2-EtO 5 mg "50 mg longer duration only" MeS- 2C-T 60–100 mg Et- Me- 2CT-2-EtO 50 mg "mild, 4 hr duration" Me- Et- 2CT-5-EtO 30 mg "15 hr duration" EtS- 2C-T-2 12–25 mg Et- Me- 2CT2-2-EtO 50 mg "9 hr duration" Me- Et- 2CT2-5-EtO 20 mg "16 hr duration" Et- Et- 2CT2-DiEtO 50 mg "only longer with higher dose" iPrS- 2C-T-4 8–20 mg Et- Me- 2CT4-2-EtO 25 mg "dosage affects duration only" PrS- 2C-T-7 10–30 mg Et- Me- 2CT7-2-EtO 20 mg "fast, out at 5 hrs"
Alexander Shulgin also described some of these compounds in additional detail in his book PiHKAL (Phenethylamines I Have Known and Loved).
According to Shulgin in 2011, 2CB-5-EtO is not in the published scientific literature. In a 1994 literature review however, Shulgin described 2CB-5-EtO as being active but 2-fold less potent than 2C-B.
ASR-2001 (2CB-5PrO), a non-hallucinogenic TWEETIO analogue of 2C-B with a 5-propoxy group, is under development by the Alexander Shulgin Research Institute for use as a mild stimulant-like medication for the treatment of psychiatric disorders.
Another known TWEETIO-related drug, a 2C-E analogue with a 5-isopropoxy group, is 2CE-5-iPrO.
Related compounds DOx compounds Various DOx compounds featured extended methoxy groups at the 2, 4, and/or 5 positions. These include the DOM derivatives Florence (DOM-2-EtO), Iris (DOM-5-EtO), and DOM-2,5-DiEtO and the TMA-2 (DOMeO) derivatives EMM (TMA2-2-EtO), MEM (TMA2-4-EtO), MME (TMA2-5-EtO), EEM (TMA2-2,4-DiEtO), EME (TMA2-2,5-DiEtO), MEE (TMA2-4,5-DiEtO), EEE (TMA2-2,4,5-TriEtO), and MPM (TMA2-4-PrO), among others.
Scalines Various scalines, or mescaline analogues, featured extended methoxy groups. These include asymbescaline, escaline, metaescaline, metaproscaline, proscaline, symbescaline, and trisescaline (trescaline), among others.
MDxx compounds EMDA-2 (2-ethoxy-4,5-methylenedioxyamphetamine) has been described by Alexander Shulgin as the "TWEETIO" analogue of MMDA-2. "The Tweetio homologue of MMDA-2 has been tasted, however. This is 2-ethoxy-4,5-methylenedioxyamphetamine, or EMDA-2. [...] At 135 milligrams, there have been reported eyes-closed visual phenomena, with intense colors. The overall duration is similar to MMDA-2 (some 10 hours) and there are reported sleep disturbances. At 185 milligrams, the feelings were intensified, there were “marvelous eyes-closed visuals (the colors were incredible), good concentration, but distinct body-tingles and rushes.” The time span was about 12 hours from start to finish, but it proved to be impossible to sleep afterwards. This homologue is thus about a third the potency of MMDA-2." It is active as a psychedelic, producing closed-eye visuals and other effects, with a potency of about one-third that of MMDA-2 and a duration of 10 to 12hours.
See also 2C (psychedelics) Substituted methoxyphenethylamine
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