Chemistry:2CB-5-EtO

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2CB-5-EtO, also known as 2-methoxy-5-ethoxy-4-bromophenethylamine, is a psychoactive drug of the phenethylamine, 2C, and TWEETIO families related to the psychedelic drug 2C-B.[1][2] It is the derivative of 2C-B in which the methoxy group at the 5 position has been replaced with an ethoxy group.[1]

Unlike other TWEETIOs, 2CB-5-EtO was not described by Alexander Shulgin in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved) or in his 2003 book chapter on psychedelics.[3][4] In PiHKAL, Shulgin states that only 2CB-2-EtO and 2CB-2,5-DiEtO are known.[3] Similarly, in his 2011 book The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds, Shulgin states that 2CB-5-EtO is not in the published scientific literature.[2] Correspondingly, the drug is not included in Daniel Trachsel's 2013 book Phenethylamine: von der Struktur zur Funktion.[5] However, in a 1994 literature review on psychedelics, Shulgin states that 2CB-5-EtO is, in fact, known and active, with 2-fold lower potency compared to 2C-B, whereas 2CB-2-EtO has 5-fold lower potency than 2C-B.[1] The properties and effects of 2C-B-5-EtO were not otherwise described and remain unclear.[1]

A derivative of 2CB-5-EtO, ASR-2001 (2CB-5-PrO), in which the 5-ethoxy group has been lengthened to a 5-propoxy group, has been developed by the Alexander Shulgin Research Institute (ASRI) and is being investigated for potential medical use as a non-hallucinogenic mild stimulant-like medication.[6][7][8][9][10][11]

2CB-5-EtO was first described in the literature by Shulgin in 1994.[1] It is likely to have been developed and tested by Darrell Lemaire, with publication via personal communication with Shulgin.[4][12][13][14][15] The drug is a controlled substance in Canada under phenethylamine blanket-ban language.[16]

See also

  • TWEETIO (psychedelics)

References

  1. ↑ 1.0 1.1 1.2 1.3 1.4 "Structure-Activity Relationships of the Classic Hallucinogens and Their Analogs". Hallucinogens: An Update. National Institute on Drug Abuse Research Monograph Series. 146. National Institute on Drug Abuse. 1994. pp. 74–91. https://bibliography.maps.org/resources/download/11534. "The two tweetio analogs (2-ethoxy and 5-ethoxy) of both 2C-D and 2C-B have been explored and have dramatically reduced activity. The 5-tweetio (5-ethoxy) compounds are of twofold lessened potency, and the 2-tweetio (2-ethoxy) materials are down by another factor of five. The bis-etios (2,5-diethoxy homologs of 2C-D and 2C-B) are not known to be active at all." 
  2. ↑ 2.0 2.1 The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds. 1. Berkeley: Transform Press. 2011. ISBN 978-0-9630096-3-0. "2C-B-5-EtO [...] (1) [...] (1) Not in the published scientific literature." 
  3. ↑ 3.0 3.1 Shulgin, Alexander; Shulgin, Ann (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628. http://www.erowid.org/library/books_online/pihkal/pihkal.shtml.  "There are two “Tweetios” known that are related to 2C-B. [...] The 2-EtO- homologue of 2C-B is 4-bromo-2-ethoxy-5-methoxyphenethylamine, or 2CB-2ETO. [...] The 2,5-DiEtO- homologue of 2C-B is 4-bromo-2,5-diethoxyphenethylamine, or 2CB-2,5-DIETO. [...]"
  4. ↑ 4.0 4.1 "Basic Pharmacology and Effects". Hallucinogens: A Forensic Drug Handbook. Forensic Drug Handbook Series. Elsevier Science. 2003. pp. 67–137. ISBN 978-0-12-433951-4. https://bibliography.maps.org/resources/download/12634. 
  5. ↑ (in de) Phenethylamine: von der Struktur zur Funktion. Nachtschatten-Science (1 ed.). Solothurn: Nachtschatten-Verlag. 2013. ISBN 978-3-03788-700-4. OCLC 858805226. https://books.google.com/books?id=-Us1kgEACAAJ. 
  6. ↑ "The Heirs to a Vault of Novel Psychedelics Take a Trip Into the Unknown". 2 November 2023. https://doubleblindmag.com/sasha-shulgin-legacy/. 
  7. ↑ "What Happens When You Inherit 500 Psychedelic Compounds?". 30 March 2025. https://doubleblindmag.com/what-happens-when-you-inherit-500-psychedelic-compounds/. 
  8. ↑ "Innovative Approaches in Psychedelics, AI, and Communication: A Multi-Domain Perspective". ACS Medicinal Chemistry Letters 16 (4): 514–516. April 2025. doi:10.1021/acsmedchemlett.5c00114. PMID 40236531. 
  9. ↑ "Alexander Shulgin Research Institute discovers new phenylalkylamine compounds". 19 December 2024. https://www.bioworld.com/articles/715533-alexander-shulgin-research-institute-discovers-new-phenylalkylamine-compounds?v=preview. 
  10. ↑ "Pioneering Psychedelics Scientist Alexander "Sasha" Shulgin's Legacy Lives On Via New Compounds And Research". 10 July 2023. https://www.benzinga.com/markets/cannabis/23/07/33171977/pioneering-psychedelics-scientist-alexander-sasha-shulgins-legacy-lives-on-via-new-compounds-and. 
  11. ↑ Joe Moore (2 April 2024). "Shulgin Farm and the Future of Psychedelic Drug Development (Featuring: Paul F. Daley, Ph.D.)" (Podcast). Psychedelics Today. Event occurs at 16:12–20:45. We have a second lead compound that's a phenethylamine that is actually not psychedelic but it does have effects on mood, concentration, focus, and I've been saying that I think it sort of captures the effect that people are trying to achieve with microdosing, but on two accounts it has much better safety profile. If you push dose, since it has limited efficacy, that's how fully can the receptor systems that it touches be turned on, its efficacy appears to be low, so even if you push dose, there's sort of a ceiling of effect, and it never becomes really psychedelic. So that's a safety factor, you can't overdo it and be all of a sudden tripping at your desk, which is not necessarily a great outcome. [...] So this second compound that we call ASR-2001 is about 100-fold less effective at 2B than at 2A. [...]
  12. ↑ "Erowid Darrell Lemaire Vault". https://erowid.org/culture/characters/lemaire_darrell/lemaire_darrell.shtml. 
  13. ↑ Morris H (7 December 2016). "The Lazy Lizard School of Hedonism". Hamilton's Pharmacopeia. Season 1. Episode 6. Vice Media. Viceland.
  14. ↑ "Notes About Psychoactive Compounds". Radiant Minds: Scientists Explore the Dimensions of Consciousness. Millay. 2010. pp. 201–207. ISBN 978-0-615-29633-3. https://erowid.org/culture/characters/lemaire_darrell/lemaire_darrell_article1.pdf. 
  15. ↑ Certain Exotic Transmitters as Smart Pills or Compounds that Increase the Capacity for Mental Work in Humans: A Story About LAZAR as Told by Hosteen Nez (2nd ed.). 1990. https://erowid.org/chemicals/2cd/2cd_smartpills1.pdf. 
  16. ↑ "Controlled Drugs and Substances Act". https://laws-lois.justice.gc.ca/eng/acts/c-38.8/FullText.html. 



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