5-(Nonyloxy)tryptamine

5-(Nonyloxy)tryptamine
Clinical data
Other names5-NOT; 5-(Nonyloxy)-1H-indole-3-ethanamine
Identifiers
  • 2-(5-Nonyloxy-1H-indol-3-yl)ethanamine
CAS Number
PubChem CID
IUPHAR/BPS
ChemSpider
ChEBI
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC19H30N2O
Molar mass302.462 g·mol−1
3D model (JSmol)
  • CCCCCCCCCOC1=CC2=C(C=C1)NC=C2CCN
  • InChI=1S/C19H30N2O/c1-2-3-4-5-6-7-8-13-22-17-9-10-19-18(14-17)16(11-12-20)15-21-19/h9-10,14-15,21H,2-8,11-13,20H2,1H3 ☒N
  • Key:YHSMSRREJYOGQJ-UHFFFAOYSA-N ☒N
 ☒NcheckY (what is this?)  (verify)

5-(Nonyloxy)tryptamine (5-NOT) is a tryptamine derivative which acts as a selective agonist at the 5-HT1B receptor. Increasing the O-alkoxy chain length in this series gives generally increasing potency and selectivity for 5-HT1B, with highest activity found for the nonyloxy derivative, having a 5-HT1B binding affinity of 1.0 nM, and around 300-fold selectivity over the related 5-HT1A receptor.[1][2]

See also

References

  1. ^ Glennon RA, Hong SS, Dukat M, Teitler M, Davis K (September 1994). "5-(Nonyloxy)tryptamine: a novel high-affinity 5-HT1D beta serotonin receptor agonist". Journal of Medicinal Chemistry. 37 (18): 2828–30. doi:10.1021/jm00044a001. PMID 8071931.
  2. ^ Glennon RA, Hong SS, Bondarev M, Law H, Dukat M, Rakhi S, Power P, Fan E, Kinneau D, Kamboj R, Teitler M, Herrick-Davis K, Smith C (January 1996). "Binding of O-alkyl derivatives of serotonin at human 5-HT1D beta receptors". Journal of Medicinal Chemistry. 39 (1): 314–22. doi:10.1021/jm950498t. PMID 8568822.
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