2C (substance group)

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2C ( 2C-x ) is the group name of the psychedelic phenethylamines , which have a methoxy group in the second and fifth positions of the phenethylamine stem structure . Most of these substances have a lipophilic substituent in the fourth position (para-substituted) , which influences the potency and the degradation of the substance. Many of these 2C substances were first synthesized by Alexander Shulgin in the 1970 / 80s and described in his book PIHKAL ( Phenethylamines I Have Known And Loved ). Shulgin is also the namesake of this group of substances, which names the two carbon atoms ( carbon ) between the benzene ring and the amino group . Some of these 2C substances are used as ligands in the elucidation of structure-activity relationships in the 5-HT 2A / 2C receptors .

Table overview

General structural formula of the 2C substances
Surname R 3 R 4 Structural formula
2C-B - H. - Br 4-bromo-2,5-dimethoxyphenethylamine.svg
2C-C -H - Cl 2,5-dimethoxy-4-chlorophenethylamine.svg
2C-D -H - CH 3 2,5-dimethoxy-4-methylphenethylamine.svg
2C-E -H - CH 2 CH 3 2,5-dimethoxy-4-ethylphenethylamine.svg
2C-F -H - F 2,5-dimethoxy-4-fluorophenethylamine.svg
2C-G -CH 3 -CH 3 3,4-dimethyl-2,5-dimethoxyphenethylamine.svg
2C-G-3 - (CH 2 ) 3 - 2C-G-3-Chemdraw.png
2C-G-4 - (CH 2 ) 4 - 2C-G-4-Chemdraw.png
2C-GN - (CH) 4 - 2C-GN-Chemdraw.png
2C-H -H -H 2,5-dimethoxyphenethylamine.svg
2C-I -H - I. 2,5-dimethoxy-4-iodophenethylamine.svg
2C-N -H - NO 2 2,5-dimethoxy-4-nitrophenethylamine.svg
2C-O -H - OCH 3 2,4,5-trimethoxyphenethylamine.svg
2C-O-4 -H - OCH (CH 3 ) 2 2,5-dimethoxy-4-isopropoxyphenethylamine.svg
2C-P -H - CH 2 CH 2 CH 3 2,5-dimethoxy-4-propylphenethylamine.svg
2C-SE -H - Se CH 3 2,5-dimethoxy-4-methylseleneophenethylamine.svg
2C-T -H - SCH 3 2,5-dimethoxy-4-methylthiophenethylamine.svg
2C-T-2 -H - SCH 2 CH 3 2C-T-2-Chemdraw.png
2C-T-4 -H - SCH (CH 3 ) 2 2C-T-4-Chemdraw.png
2C-T-7 -H -S (CH 2 ) 2 CH 3 2C-T-7-Chemdraw.png
2C-T-8 -H - SCH 2 CH (CH 2 ) 2 2C-T-8-Chemdraw.png
2C-T-9 -H -SC (CH 3 ) 3 2C-T-9-Chemdraw.png
2C-T-13 -H -S (CH 2 ) 2 OCH 3 2C-T-13-Chemdraw.png
2C-T-15 -H - SCH (CH 2 ) 2 2C-T-15-Chemdraw.png
2C-T-17 -H - SCH (CH 3 ) CH 2 CH 3 2C-T-17-Chemdraw.png
2C-T-21 -H -S (CH 2 ) 2 F 2C-T-21-Chemdraw.png
2C-TFM -H - CF 3 2,5-dimethoxy-4-trifluoromethylphenethylamine.svg
2C-YN -H - C≡CH 2C-YN skeletal.svg
2C-V -H - CH = CH 2 -
2C-CN -H - C≡N -
2C-CA -H - COOH -
2C-BI-1 -H - C 6 H 5 -
2C-IP -H - C 3 H 7 -
2C-HM -H - CH 2 -OH -
2C-NH -H - NH 2 -

literature

  • Trachsel D., Lehmann D., Enzensperger Ch .: Phenethylamine From Structure to Function , Nightshade Science Edition, Solothurn, Switzerland, 2013 ISBN 978-3-03788-700-4
  • Alexander T. Shulgin, Tania Manning, Paul F. Daley: The Shulgin Index: Psychedelic Phenethylamines and Related Compounds, Volume One . Transform Press, Berkeley 2011, ISBN 0-9630096-3-X .

Web links

Individual evidence

  1. ↑ Daniel Trachsel: Synthesis of new (phenylalkyl) amines for the investigation of structure-activity relationships. Communication 2. In: Helvetica Chimica Acta . 86, 2003, pp. 2610-2619, doi : 10.1002 / hlca.200390210 .
  2. ↑ Antoni R. Blaazer, Pieter Smid, Chris G. Kruse: Structure-Activity Relationships of Phenylalkylamines as agonist ligand for 5-HT Receptors. In: ChemMedChem . 3, 2008, pp. 1299-1309, doi : 10.1002 / cmdc.200800133 .
  3. ↑ Ahmet Altun, Kurtulus Golcuk, Mustafa Kumru, Abraham F. Jalbout: Electron-conformational study for the structure-hallucinogenic activity relationships of phenylalkylamines. In: Bioorganic & Medicinal Chemistry . 11, 2003, pp. 3861-3868, doi : 10.1016 / S0968-0896 (03) 00437-1 .
  4. ^ Thomas S. Ray, Olivier Jacques Manzoni: Psychedelics and the Human Receptorome. In: PLoS ONE . 5, 2010, p. E9019, doi : 10.1371 / journal.pone.0009019 .