Chemistry:2CB-2-EtO

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2CB-2-EtO, also known as 4-bromo-2-methoxy-5-ethoxyphenethylamine, is a psychedelic drug of the phenethylamine, 2C, and TWEETIO families related to 2C-B.[1][2][3][4] It is the derivative of 2C-B in which the methoxy group at the 2 position has been replaced with an ethoxy group.[1][2][3][4]

According to Alexander Shulgin in his book PiHKAL (Phenethylamines I Have Known and Loved) and other publications, 2CB-2-EtO produces maximal effects at a dose of about 15 mg orally.[1][3][4] Higher doses of 30 to 50 mg orally did not increase its effects any further but only prolonged their duration, from about 3 hours to perhaps 6 hours.[1][3][4] 2CB-2-EtO was said to have not had an intensity that resembled that of 2C-B at any dose.[1] It was also said to be dramatically or about 5-fold less potent than 2C-B.[2] Beyond the preceding, the specific effects of 2CB-2-EtO were not described.[1][2][3][4]

The chemical synthesis of 2CB-2-EtO has been described.[1]

2CB-2-EtO was first described in the literature by Shulgin in PiHKAL in 1991.[1] It was developed and tested by Darrell Lemaire, with publication via personal communication with Shulgin.[3][5][6][7][8] The drug is a controlled substance in Canada under phenethylamine blanket-ban language.[9]

See also

  • TWEETIO (psychedelics)
  • 2CD-5EtO
  • 2CB-5PrO (ASR-2001)

References

  1. ↑ 1.0 1.1 1.2 1.3 1.4 1.5 1.6 1.7 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. (See recipe #23 for the origin of this phrase.) The 2-EtO- homologue of 2C-B is 4-bromo-2-ethoxy-5-methoxyphenethylamine, or 2CB-2ETO. The unbrominated benzaldehyde (2-ethoxy-5-methoxybenzaldehyde) had a melting point of 47.5–48.5 °C, the unbrominated nitrostyrene intermediate a melting point of 76–77 °C, and the final hydrochloride a melting point of 185–186 °C. The hydrobromide salt had a melting point of 168.5–169.5 °C. It seems that one gets about as much effect as can be had, with a dosage of about 15 milligrams, and increases above this, to 30 and to 50 milligrams merely prolong the activity (from about 3 hours to perhaps 6 hours). At no dose was there an intensity that in any way resembled that of 2C-B."
  2. ↑ 2.0 2.1 2.2 2.3 "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." 
  3. ↑ 3.0 3.1 3.2 3.3 3.4 3.5 "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. 
  4. ↑ 4.0 4.1 4.2 4.3 4.4 (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. 
  5. ↑ "Erowid Darrell Lemaire Vault". https://erowid.org/culture/characters/lemaire_darrell/lemaire_darrell.shtml. 
  6. ↑ Morris H (7 December 2016). "The Lazy Lizard School of Hedonism". Hamilton's Pharmacopeia. Season 1. Episode 6. Vice Media. Viceland.
  7. ↑ "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. 
  8. ↑ Lazar (Darrell Lemaire); Hosteen Nez (1990). 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.). https://erowid.org/chemicals/2cd/2cd_smartpills1.pdf. 
  9. ↑ "Controlled Drugs and Substances Act". https://laws-lois.justice.gc.ca/eng/acts/c-38.8/FullText.html. 



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