南天竹啡鹼

化合物

南天竹啡鹼(英語:Nantenine)是一種在南天竹[1]和一些紫堇屬植物中發現的生物鹼[2]它是α1-腎上腺素能受體[3]血清素5-HT2A受體拮抗劑[4]可阻斷MDMA對動物的行為和生理作用。[5]

南天竹啡鹼
臨床資料
ATC碼
  • 未分配
識別資訊
  • (S)-1,2-Dimethoxy-6-methyl-5,6,6a,7-tetrahydro-4H-benzo[de][1,3]benzodioxolo[5,6-g]quinoline
CAS號2565-01-7  checkY
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard英語CompTox Chemicals Dashboard (EPA)
化學資訊
化學式C20H21NO4
摩爾質量339.39 g·mol−1
3D模型(JSmol英語JSmol
  • CN1CCC2=CC(=C(C3=C2[C@@H]1CC4=CC5=C(C=C43)OCO5)OC)OC
  • InChI=1S/C20H21NO4/c1-21-5-4-11-7-17(22-2)20(23-3)19-13-9-16-15(24-10-25-16)8-12(13)6-14(21)18(11)19/h7-9,14H,4-6,10H2,1-3H3/t14-/m0/s1 ☒N
  • Key:WSVWKHTVFGTTKJ-AWEZNQCLSA-N ☒N

參見

參考資料

  1. ^ Shoji N, Umeyama A, Takemoto T, Ohizumi Y. Serotonergic receptor antagonist from Nandina domestica Thunberg. Journal of Pharmaceutical Sciences. April 1984, 73 (4): 568–70. PMID 6726648. doi:10.1002/jps.2600730435. 
  2. ^ Kiryakov HG, Iskrenova E, Daskalova E, Kuzmanov B, Evstatieva L. Alkaloids of Corydalis slivenensis. Planta Medica. March 1982, 44 (3): 168–70. PMID 17402105. doi:10.1055/s-2007-971432. 
  3. ^ Indra B, Matsunaga K, Hoshino O, Suzuki M, Ogasawara H, Ohizumi Y. Structure-activity relationship studies with (+/-)-nantenine derivatives for alpha1-adrenoceptor antagonist activity. European Journal of Pharmacology. February 2002, 437 (3): 173–8. PMID 11890906. doi:10.1016/S0014-2999(02)01303-1. 
  4. ^ Chaudhary S, Pecic S, Legendre O, Navarro HA, Harding WW. (+/-)-Nantenine analogs as antagonists at human 5-HT(2A) receptors: C1 and flexible congeners. Bioorganic & Medicinal Chemistry Letters. May 2009, 19 (9): 2530–2. PMC 2677726 . PMID 19328689. doi:10.1016/j.bmcl.2009.03.048. 
  5. ^ Fantegrossi WE, Kiessel CL, Leach PT, Van Martin C, Karabenick RL, Chen X, Ohizumi Y, Ullrich T, Rice KC, Woods JH. Nantenine: an antagonist of the behavioral and physiological effects of MDMA in mice. Psychopharmacology. May 2004, 173 (3–4): 270–7. PMID 14740148. S2CID 8425621. doi:10.1007/s00213-003-1741-2. hdl:2027.42/46360 . 

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