TWEETIO
Group of psychedelic drugs
From Wikipedia, the free encyclopedia
TWEETIO is a family of phenethylamine psychedelic drugs.[1][2][3][4] 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.[1][2][4] 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.[1][2][3][4]

The TWEETIO drugs are said to have been named in a humorous way by pronouncing the simplest structural form of "2-EtO-X".[1][5] Limited human data are available on the TWEETIO compounds.[1][2][5][4] 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-Di-ETO drugs tend to be inactive.[1][2][5]
The TWEETIO compounds were developed by Darrell Lemaire as potential "smart drugs" in the 1970s or 1980s.[6][7][8][9] The compounds were described in the scientific literature by Alexander Shulgin via personal communication with Lemaire in the 1990s and 2000s.[5][1][2][4] It was said by Shulgin in 2003 that the propoxy analogues had not yet been synthesized.[1] In 2023, the propoxy derivative ASR-2001 (2CB-5PrO) was reported by Nick Cozzi and Paul F. Daley of the Alexander Shulgin Research Institute.[10][11][12][13][14] It is under development for potential medical use.[10][11][12][13]
List and properties of TWEETIO drugs
| R4 | Dosage (parent) | R2 | R5 | Code name | Trial dose | Comments of trial |
|---|---|---|---|---|---|---|
| Br- | 12–24 mg | Et- | Me- | 2CB-2-ETO | 15 mg | "30–50 [mg] prolongs action" |
| Et- | Et- | 2CB-DI-ETO | >55 mg | "restless sleep, only" | ||
| Me- | 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-DI-ETO | >55 mg | "mild, 4 hr duration" | ||
| Et- | 10–15 mg | Me- | Et- | 2CE-5-ETO | 15 mg | "16–24 hr duration" |
| 14–22 mg | Et- | Me- | 2CI-2-ETO | 5 mg | "50 mg longer duration only" | |
| MeS- | 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- | 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-DI-ETO | 50 mg | "only longer with higher dose" | ||
| iPrS- | 8–20 mg | Et- | Me- | 2CT4-2-ETO | 25 mg | "dosage affects duration only" |
| PrS- | 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).[5]
According to Shulgin in 2011, 2CB-5-EtO is not in the published scientific literature.[15] In a 1994 literature review however, Shulgin described 2CB-5-EtO as being active but 2-fold less potent than 2C-B.[2]
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.[10][11][12][13][14]
Another known TWEETIO-related drug, a 2C-E analogue with a 5-isopropoxy group, is 2CE-5-iPrO.[16]
Related compounds
DOx compounds
Various DOx compounds featured extended methoxy groups at the 2, 4, and/or 5 positions.[5][15] 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.[5][15][17]
Scalines
Various scalines, or mescaline analogues, featured extended methoxy groups.[5][15] These include asymbescaline, escaline, metaescaline, metaproscaline, proscaline, symbescaline, and trisescaline (trescaline), among others.[5][15]
MDxx compounds
EMDA-2 (2-ethoxy-4,5-methylenedioxyamphetamine) has been described by Alexander Shulgin as the "TWEETIO" analogue of MMDA-2.[5] 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 12 hours.[5]