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2CB-5-EtO

Pharmaceutical compound From Wikipedia, the free encyclopedia

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][5] It is the derivative of 2C-B in which the methoxy group at the 5 position has been replaced with an ethoxy group.[1]

Other names2CB-5EtO; 2CB-5-ETO; 2CB-5ETO; 2C-B-5-EtO; 2-Methoxy-5-ethoxy-4-bromophenethylamine; 2-Methoxy-4-bromo-5-ethoxyphenethylamine
ATC code
  • None
Quick facts Clinical data, Other names ...
2CB-5-EtO
Clinical data
Other names2CB-5EtO; 2CB-5-ETO; 2CB-5ETO; 2C-B-5-EtO; 2-Methoxy-5-ethoxy-4-bromophenethylamine; 2-Methoxy-4-bromo-5-ethoxyphenethylamine
Routes of
administration
Oral[1]
Drug classPsychoactive drug
ATC code
  • None
Pharmacokinetic data
Duration of actionUnknown[1][2][3][4]
Identifiers
  • 2-(4-bromo-5-ethoxy-2-methoxyphenyl)ethan-1-amine
Chemical and physical data
FormulaC11H16BrNO2
Molar mass274.158 g·mol−1
3D model (JSmol)
  • CCOC1=C(Br)C=C(OC)C(CCN)=C1
  • InChI=1S/C11H16BrNO2/c1-3-15-11-6-8(4-5-13)10(14-2)7-9(11)12/h6-7H,3-5,13H2,1-2H3
  • Key:OOAVAHXKEKAQFF-UHFFFAOYSA-N
Close

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.[2][3] In PiHKAL, Shulgin states that only 2CB-2-EtO and 2CB-2,5-DiEtO are known.[2] 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.[5] Correspondingly, the drug is not included in Daniel Trachsel's 2013 book Phenethylamine: von der Struktur zur Funktion.[4] 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.[3][12][13][14][15] The drug is a controlled substance in Canada under phenethylamine blanket-ban language.[16]

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