TWEETIO is a family ofphenethylaminepsychedelic drugs.^[1][2][3][4] They areanalogues of the2C drugs (4-substituted 2,5-dimethoxyphenethylamines) in which one or both of themethoxy groups at positions 2 and 5 of thephenyl ring have been lengthened toethoxy groups.^[1][2][4] Examples include2CD-2-ETO (a TWEETIO of2C-D),2CE-5-ETO (a TWEETIO of2C-E), and2CT2-5-ETO (a TWEETIO of2C-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 shorterduration and decreasedpotency, 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 byDarrell Lemaire as potential "smart drugs" in the 1970s or 1980s.^[6][7][8][9] The compounds were described in thescientific literature byAlexander Shulgin via personal communication with Lemaire in the 1990s and 2000s.^[5][1][2][4] It was said by Shulgin in 2003 that thepropoxy analogues had not yet beensynthesized.^[1] In 2023, the propoxy derivativeASR-2001 (2CB-5PrO) was reported by Nick Cozzi and Paul F. Daley of theAlexander Shulgin Research Institute.^{[10][11][12][13][14]} It is under development for potential medical use.^{[10][11][12][13]}

Alexander Shulgin also described some of these compounds in additional detail in his bookPiHKAL (Phenethylamines I Have Known and Loved).^[5]

According to Shulgin in 2011,2CB-5-EtO is not in the publishedscientific literature.^[15] In a 1994literature review however, Shulgin described 2CB-5-EtO as being active but 2-fold lesspotent than2C-B.^[2]

ASR-2001 (2CB-5PrO), a non-hallucinogenic TWEETIO analogue of2C-B with a 5-propoxy group, is under development by theAlexander Shulgin Research Institute for use as a mildstimulant-likemedication for the treatment ofpsychiatric disorders.^{[10][11][12][13][14]}

Another known TWEETIO-related drug, a2C-Eanalogue with a 5-isopropoxy group, is2CE-5iPrO.^[16]

VariousDOx compounds featured extendedmethoxy groups.^[5][15] These includeFlorence (DOM-2ETO),Iris (DOM-5ETO),DOM-2,5-DiEtO,MEM,MME,MEE,EMM,EME,EEM, andEEE, among others.^[5][15] They arederivatives ofDOM and/orTMA-2.^[5][15]

Variousscalines, ormescalineanalogues, featured extendedmethoxy groups.^[5][15] These includeasymbescaline,escaline,metaescaline,metaproscaline,proscaline,symbescaline, andtrisescaline (trescaline), among others.^[5][15]

EMDA-2 (2-ethoxy-4,5-methylenedioxyamphetamine) has been described byAlexander Shulgin as the "TWEETIO" analogue ofMMDA-2.^[5] It is active as apsychedelic, producingclosed-eye visuals and other effects, with apotency of about one-third that of MMDA-2 and aduration of 10 to 12 hours.^[5]

• Substituted methoxyphenethylamine

• PiHKAL TWEETIO Instances and Excerpts

• Alexander Shulgin
• Chemical classes of psychoactive drugs
• TWEETIO (psychedelics)

• CS1 German-language sources (de)
• Articles with short description
• Short description matches Wikidata