5-甲氧基-7,N,N-三甲基色胺

化合物

5-甲氧基-7,N,N-三甲基色胺英語5-Methoxy-7,N,N-trimethyltryptamine,簡稱5-MeO-7,N,N-TMT),是一種色胺衍生物,可作為5-HT2血清素受體激動劑[1][2]在動物試驗中,7,N,N-TMT和5-MeO-7,N,N-TMT產生的行為反應類似於DMT5-MeO-DMT等迷幻藥的行為反應,但是具有較大7位取代基的化合物(如7-乙基-DMT7-溴-DMT)不會產生適合迷幻的反應,儘管它們具有高5-HT2受體結合親和力,這表明它們可能是5-HT2受體的拮抗劑或弱部分激動劑。[3]相關化合物7-MeO-MiPT(參見5-MeO-MiPT)也被發現無活性,表明7位對該位置的大基團耐受性差,至少在需要激動劑活性時如此。[4]

5-甲氧基-7,N,N-三甲基色胺
識別資訊
  • 2-(5-Methoxy-7-methyl-1H-indol-3-yl)-N,N-dimethylethanamine
CAS號61018-77-7(游離鹼)  checkY
74798-76-8(草酸鹽)
PubChem CID
ChemSpider
ChEMBL
CompTox Dashboard英語CompTox Chemicals Dashboard (EPA)
化學資訊
化學式C14H20N2O
摩爾質量232.33 g·mol−1
3D模型(JSmol英語JSmol
  • CC1=C(NC=C2CCN(C)C)C2=CC(OC)=C1
  • InChI=1S/C14H20N2O/c1-10-7-12(17-4)8-13-11(5-6-16(2)3)9-15-14(10)13/h7-9,15H,5-6H2,1-4H3 checkY
  • Key:YGAOMGVUIWNFMD-UHFFFAOYSA-N checkY

參見

參考資料

  1. ^ Benington F, Morin RD, Bradley RJ. 7-(N,N-Trimethyl)-5-methoxytryptamine.. Journal of Heterocyclic Chemistry. 1976, 13 (4): 749–751. doi:10.1002/jhet.5570130412. 
  2. ^ Lyon RA, Titeler M, Seggel MR, Glennon RA. Indolealkylamine analogs share 5-HT2 binding characteristics with phenylalkylamine hallucinogens. European Journal of Pharmacology. January 1988, 145 (3): 291–7. PMID 3350047. doi:10.1016/0014-2999(88)90432-3. 
  3. ^ Glennon RA, Schubert E, Jacyno JM, Rosecrans JA. Studies on several 7-substituted N,N-dimethyltryptamines. Journal of Medicinal Chemistry. November 1980, 23 (11): 1222–6. PMID 6779006. doi:10.1021/jm00185a014. 
  4. ^ Repke DB, Grotjahn DB, Shulgin AT. Psychotomimetic N-methyl-N-isopropyltryptamines. Effects of variation of aromatic oxygen substituents. Journal of Medicinal Chemistry. July 1985, 28 (7): 892–6. PMID 4009612. doi:10.1021/jm00145a007.