2CB-2-EtO

Pharmaceutical compound
2CB-2-EtO
Clinical data
Other names2C-B-2-ETO; 4-Bromo-5-ethoxy-2-methoxyphenethylamine; 2-Methoxy-4-bromo-5-ethoxyphenethylamine
Routes of
administration		Oral[1]
Drug classSerotonergic psychedelic; Hallucinogen
ATC code
  • None
Pharmacokinetic data
Duration of action3–6 hours[1]
Identifiers
  • 2-(4-bromo-2-ethoxy-5-methoxyphenyl)ethanamine
PubChem CID
  • 86200098
ChemSpider
  • 62909262
Chemical and physical data
FormulaC11H16BrNO2
Molar mass274.158 g·mol−1
3D model (JSmol)
  • Interactive image
  • CCOC1=CC(=C(C=C1CCN)OC)Br
  • InChI=1S/C11H16BrNO2/c1-3-15-10-7-9(12)11(14-2)6-8(10)4-5-13/h6-7H,3-5,13H2,1-2H3
  • Key:FLMAKYQLBBLIAH-UHFFFAOYSA-N

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

References

  1. ^ a b c d e f g h i Shulgin A, Shulgin A (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628. "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. ^ a b c Jacob P, Shulgin AT (1994). "Structure-Activity Relationships of the Classic Hallucinogens and Their Analogs". In Lin GC, Glennon RA (eds.). Hallucinogens: An Update (PDF). National Institute on Drug Abuse Research Monograph Series. Vol. 146. National Institute on Drug Abuse. pp. 74–91. PMID 8742795. Archived from the original on 13 July 2025. 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. ^ a b c d e Shulgin AT (2003). "Basic Pharmacology and Effects". In Laing RR (ed.). Hallucinogens: A Forensic Drug Handbook. Forensic Drug Handbook Series. Elsevier Science. pp. 67–137. ISBN 978-0-12-433951-4. Archived from the original on 13 July 2025.
  4. ^ a b c d Trachsel D, Lehmann D, Enzensperger C (2013). Phenethylamine: von der Struktur zur Funktion [Phenethylamines: From Structure to Function]. Nachtschatten-Science (in German) (1 ed.). Solothurn: Nachtschatten-Verlag. ISBN 978-3-03788-700-4. OCLC 858805226. Archived from the original on 21 August 2025.
  5. ^ "Erowid Darrell Lemaire Vault". erowid.org. Retrieved 14 November 2025.
  6. ^ Morris H (7 December 2016). "The Lazy Lizard School of Hedonism". Hamilton's Pharmacopeia. Season 1. Episode 6. Vice Media. Viceland.
  7. ^ Nez H, Lemaire D (2010). "Notes About Psychoactive Compounds" (PDF). In Targ R, Radin D (eds.). Radiant Minds: Scientists Explore the Dimensions of Consciousness. Millay. pp. 201–207. ISBN 978-0-615-29633-3.
  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.). Archived from the original (PDF) on 9 July 2001.
  9. ^ "Controlled Drugs and Substances Act". Department of Justice Canada. Retrieved 19 January 2026.
  • 2C-B-5-EtO - Isomer Design
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