2CD-5EtO

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2CD-5EtO
2CD-5EtO structure.png
Clinical data
Other names2C-D-5-EtO
Identifiers
  • 1-(5-Ethoxy-2-methoxy-4-methylphenyl)-ethan-1-amine
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
Formula C12H19NO2
Molar mass 209.289 g·mol−1
3D model (JSmol)
  • CCOC1=CC(=C(C=C1C)OC)CCN
  • InChI=1S/C12H19NO2/c1-4-15-11-8-10(5-6-13)12(14-3)7-9(11)2/h7-8H,4-6,13H2,1-3H3 Yes check.svgY
  • Key:ZMQDQUPRBYFPSO-UHFFFAOYSA-N Yes check.svgY
 X mark.svgNYes check.svgY  (what is this?)    (verify)

2CD-5EtO is a homologue of the psychedelic phenethylamine 2C-D, where the 5-methoxy group of 2C-D has been lengthened to an ethoxy group. 2CD-5EtO is a representative example of the so-called "tweetio" compounds discovered by Alexander Shulgin and briefly mentioned in his book PiHKAL . They are homologues of the 2C family of drugs, where either one or both of the methoxy groups at the 2,5-positions of the aromatic ring have been replaced by ethoxy. The term tweetio was derived phonetically from the sound of the "2-ETO" derivatives.

Contents

Many tweetio derivatives of various 2C drugs have been synthesized and tested, including the 2-ethoxy homologues 2CD-2EtO, 2CB-2EtO, 2CI-2EtO, 2CT-2EtO, 2CT2-2EtO, 2CT4-2EtO and 2CT7-2EtO, the 5-ethoxy homologues 2CD-5EtO, 2CE-5EtO, 2CB-5EtO, 2CT-5EtO and 2CT2-5EtO, and the 2,5-diethoxy homologues 2CD-diEtO, 2CB-diEtO and 2CT2-diEtO, [1] as well as 2CE-5iPrO. [2] In general, the 2-ethoxy homologues were all several times less potent and somewhat shorter acting than the parent compounds, while the 2,5-diethoxy homologues were far less potent and qualitatively milder even at high doses. [3] The 5-ethoxy homologues however were of a similar potency to the parent compounds and much longer-lasting, with both 2CE-5EtO and 2CT2-5EtO lasting 24 hours or more.

Structures of 2CD-2EtO, 2CE-5EtO and 2CT2-5EtO. Tweetio-examples.png
Structures of 2CD-2EtO, 2CE-5EtO and 2CT2-5EtO.

See also

References

  1. ↑ Laing RR (2003). Hallucinogens: a forensic drug handbook. Academic Press. pp. 85–86. ISBN   978-0-12-433951-4.
  2. ↑ Flanagan TW, Billac GB, Landry AN, Sebastian MN, Cormier SA, Nichols CD (April 2021). "Structure-Activity Relationship Analysis of Psychedelics in a Rat Model of Asthma Reveals the Anti-Inflammatory Pharmacophore". ACS Pharmacology & Translational Science. 4 (2): 488–502. doi:10.1021/acsptsci.0c00063. PMC   8033619 . PMID   33860179.
  3. ↑ Jacob P, Shulgin AT (1994). "Structure-activity relationships of the classic hallucinogens and their analogs". NIDA Research Monograph. 146: 74–91. PMID   8742795.
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