2,5-二甲氧基苯乙胺衍生物

2,5-二甲氧基苯乙胺衍生物,也称为2C类化合物(英語:2C-x)或2C家族(英語:2C family)是苯乙胺衍生物中的一类,苯基上2号位与5号位的氢被甲氧基取代,即以2,5-二甲氧基苯乙胺(也称为2C-H)为母结构,其中绝大多数的取代基位于4号位,少数位于3号位,6号位基本上没有取代基[1]。许多这一类化合物由亚历山大·舒尔金在1970年代到1980年代首次合成[2]

2,5-二甲氧基苯乙胺衍生物的结构骨架

衍生物

编辑
名称 R3基团 R4基团 R6基团 分子式 2D结构 CAS号
2C-B H Br H C
10
H
14
BrNO
2
  66142-81-2
2C-Bn H CH2C6H5 H C17H21NO2   2888537-43-5
2C-Bu H CH2CH2CH2CH3 H C14H23NO2   2888537-44-6
2C-C H Cl H C10H14ClNO2   88441-14-9
2C-C-3 [3] Cl Cl Cl C10H12Cl3NO2   1112937-89-9
2C-CN H C≡N H C11H14N2O2   88441-07-0
2C-cP H C3H5 H C13H19NO2   2888537-46-8
2C-D H CH3 H C11H17NO2   24333-19-5
2C-E H CH2CH3 H C12H19NO2   71539-34-9
2C-EF H CH2CH2F H C12H18FNO2   1222814-77-8
2C-F H F H C10H14FNO2   207740-15-6
2C-G CH3 CH3 H C12H19NO2   207740-18-9
2C-G-1 CH2 H C11H15NO2   2888537-47-9
2C-G-2 (CH2)2 H C12H17NO2   2888537-48-0
2C-G-3波兰语2C-G-3 (CH2)3 H C13H19NO2   207740-19-0
2C-G-4波兰语2C-G-4 (CH2)4 H C14H21NO2   952006-59-6
2C-G-5 (CH2)5 H C15H21NO2   207740-20-3
2C-G-6 (CH2)6 H C16H23NO2   2888537-49-1
2C-G-N (CH)4 H C14H17NO2   207740-21-4
2C-H H H H C10H15NO2   3600-86-0
2C-I H I H C10H14INO2   69587-11-7
2C-iP H CH(CH3)2 H C13H21NO2   1498978-47-4
2C-N H NO2 H C10H14N2O4   261789-00-8
2C-NH2 H NH2 H C10H16N2O2   168699-66-9
2C-PYR H 吡咯烷 H C14H22N2O2   910381-23-6
2C-PIP H 哌啶 H C15H24N2O2   1898118-63-2
2C-O H OCH3 H C11H17NO3   15394-83-9
2C-O-4 H OCH(CH3)2 H C13H21NO3   952006-65-4
2C-MOM [4] H CH2OCH3 H C12H19NO3   1898203-98-9
2C-P H CH2CH2CH3 H C13H21NO2   207740-22-5
2C-Ph H C6H5 H C16H19NO2   1217170-12-1
2C-Se H SeCH3 H C11H17NO2Se   1189246-68-1
2C-T H SCH3 H C11H17NO2S   61638-09-3
2C-DFM [5]:770 H CHF2 H C11H15F2NO2   1891474-10-4
2C-TFM H CF3 H C11H14F3NO2   159277-08-4
2C-TFE H CH2CF3 H C12H16F3NO2   2888537-56-0
2C-PFE H CF2CF3 H C12H14F5NO2   暂未注册
2C-PFS H SF5 H C10H14F5NO2S   暂未注册
2C-YN H C≡CH H C12H15NO2   752982-24-4
2C-V H CH=CH2 H C12H17NO2   2888537-57-1
2C-AL[6] H CH2CH=CH2 H C13H19NO2   2756686-02-7

含硫衍生物

编辑
2C-T衍生物
名称 R3基团 R4基团 R6基团 分子式 2D结构 CAS号
2C-T H SCH3 H C11H17NO2S   61638-09-3
2C-T-2 H SCH2CH3 H C12H19NO2S   207740-24-7
2C-T-3[7] H SCH2C(=CH2)CH3 H C14H19NO2S   648957-40-8
2C-T-4 H SCH(CH3)2 H C13H19NO2S   207740-25-8
2C-T-5[7] H H   1187859-38-6
2C-T-6[7] H H   2888537-50-4
2C-T-7 H S(CH2)2CH3 H C13H19NO2S   207740-26-9
2C-T-8 H SCH2CH(CH2)2 H C14H19NO2S   207740-27-0
2C-T-9[7] H H C14H21NO2S   207740-28-1
2C-T-10[7] H H   2888537-51-5
2C-T-11[7] H H   1798390-41-6
2C-T-12[7] H H   2888537-52-6
2C-T-13 H S(CH2)2OCH3 H   207740-30-5
2C-T-14[7] H H   暂未注册
2C-T-15 H SCH(CH2)2 H C13H17NO2S   952006-95-0
2C-T-16[8] H SCH2CH=CH2 H   648957-42-0
2C-T-17 H SCH(CH3)CH2CH3 H   207740-32-7
2C-T-18[7] H H   2888537-53-7
2C-T-19 H SCH2CH2CH2CH3 H C14H21NO2S   732244-33-6
2C-T-21 H S(CH2)2F H   207740-33-8
2C-T-21.5[7] H H   648957-46-4
2C-T-22[7] H H   648957-48-6
2C-T-23[7] H H   2888537-54-8
2C-T-24[7] H H   暂未注册
2C-T-25[7] H H C14H21NO2S   740797-11-9
2C-T-27[7] H H   648957-52-2
2C-T-28[7] H H   648957-54-4
2C-T-30[7] H H   775578-10-4
2C-T-31[7] H H   765269-48-5
2C-T-32[7] H H   737754-27-7
2C-T-33[7] H H   暂未注册

苯并杂环衍生物

编辑
苯并杂环衍生物
名称 R3基团 R4基团 R6基团 分子式 2D结构 CAS号
2C-B-FLY 苯并二氢呋喃 Br 苯并二氢呋喃 C12H14BrNO2   733720-95-1
2C-B-BFLY 苯并二氢吡喃 Br 苯并二氢吡喃 C14H18BrNO2   502659-24-7
2C-B-DFLY 苯并呋喃 Br 苯并呋喃 C12H10BrNO2   260809-98-1
2C-C-FLY 苯并二氢呋喃 Cl 苯并二氢呋喃 C12H14ClNO2   1354633-83-2
2C-D-FLY 苯并二氢呋喃 CH3 苯并二氢呋喃 C13H17NO2   1354634-07-3
2C-E-FLY 苯并二氢呋喃 CH2CH3 苯并二氢呋喃 C14H19NO2   2697190-39-7
2C-EF-FLY 苯并二氢呋喃 CH2CH2F 苯并二氢呋喃 C14H18FNO2  
2C-I-FLY 苯并二氢呋喃 I 苯并二氢呋喃 C12H14INO2   1354633-88-7
2C-T-7-FLY 苯并二氢呋喃 SCH2CH3 苯并二氢呋喃 C15H21NO2S   1354633-05-8

参考文献

编辑
  1. ^ Alexander Shulgin, Tania Manning and Paul F Daley. The Shulgin Index. Volume 1. Psychedelic Phenethylamines and Related Compounds. Transform Press, 2011. ISBN 978-0-9630096-3-0
  2. ^ Daniel Trachsel, David Lehmann and Christoph Enzensperger. Phenethylamine Von der Struktur zur Funktion, pp 762-810. Nachtschatten Verlag AG, 2013. ISBN 978-3-03788-700-4
  3. ^ Takahashi M, Nagashima M, Suzuki J, Seto T, Yasuda I, Yoshida T. Creation and application of psychoactive designer drugs data library using liquid chromatography with photodiode array spectrophotometry detector and gas chromatography–mass spectrometry. Talanta, 15 Feb 2009, 77(4): 1245–1272. doi:10.1016/j.talanta.2008.07.062
  4. ^ Leth-Petersen S, Petersen IN, Jensen AA, Bundgaard C, Bæk M, Kehler J, Kristensen JL. 5-HT2A/5-HT2C receptor pharmacology and intrinsic clearance of N-benzylphenethylamines modified at the primary site of metabolism. ACS Chem. Neurosci., 16 Nov 2016, 7 (11), 1614–1619. doi:10.1021/acschemneuro.6b00265
  5. ^ Daniel Trachsel; David Lehmann & Christoph Enzensperger. Phenethylamine: Von der Struktur zur Funktion. Nachtschatten Verlag AG. 2013. ISBN 978-3-03788-700-4. 
  6. ^ Kruegel AC. Phenalkylamines and Methods of Treating Mood Disorders. Patent WO 2022/006186 (PDF). [2023-11-19]. (原始内容存档 (PDF)于2022-12-20). 
  7. ^ 7.00 7.01 7.02 7.03 7.04 7.05 7.06 7.07 7.08 7.09 7.10 7.11 7.12 7.13 7.14 7.15 7.16 7.17 7.18 7.19 Shulgin's Sulfur Symphony – Part I. countyourculture. 15 January 2011 [22 October 2017]. (原始内容存档于19 September 2019). 
  8. ^ Daniel Trachsel. Synthesis of novel (phenylalkyl)amines for the investigation of structure-activity relationships. Part 2. 4-Thio-substituted [2-(2,5-dimethoxyphenyl)ethyl]amines (=2,5-dimethoxybenzeneethanamines). Helvetica Chimica Acta. 2003, 86 (7): 2610–2619. doi:10.1002/hlca.200390210.