5-(Nonyloxy)tryptamine

5-(Nonyloxy)tryptamine is a tryptamine derivative which acts as a selective agonist at the 5-HT_1B receptor. Increasing the O-alkoxy chain length in this series gives generally increasing potency and selectivity for 5-HT_1B, with highest activity found for the nonyloxy derivative, having a 5-HT_1B binding affinity of 1.0 nM, and around 300-fold selectivity over the related 5-HT_1A receptor.[1][2]

5-(Nonyloxy)tryptamine

Identifiers
IUPAC name 2-(5-Nonyloxy-1H-indol-3-yl)ethanamine
CAS Number	157798-12-4
PubChem CID	1797
IUPHAR/BPS	106
ChemSpider	1731
CompTox Dashboard (EPA)	DTXSID4058653
Chemical and physical data
Formula	C19H30N2O
Molar mass	302.462 g·mol^−1
3D model (JSmol)	Interactive image
SMILES CCCCCCCCCOC1=CC2=C(C=C1)NC=C2CCN
InChI 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 Key:YHSMSRREJYOGQJ-UHFFFAOYSA-N
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See also

• 5-Benzyloxytryptamine
• 5-Carboxamidotryptamine
• 5-Ethoxy-DMT
• Sumatriptan

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.