5-Benzyloxytryptamine

5-Benzyloxytryptamine
Legal status
Legal status	Illegal in Singapore;
Identifiers
	IUPAC name 2-(5-phenylmethoxy-1H-indol-3-yl)ethanamine;
CAS Number	20776-45-8 ;
PubChem CID	89576;
IUPHAR/BPS	265;
ChemSpider	80845 ;
CompTox Dashboard (EPA)	DTXSID60942992 ;
ECHA InfoCard	100.040.007
Chemical and physical data
Formula	C17H18N2O
Molar mass	266.344 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES NCCC1=CNC2=CC=C(OCC3=CC=CC=C3)C=C21;
	InChI InChI=1S/C17H18N2O/c18-9-8-14-11-19-17-7-6-15(10-16(14)17)20-12-13-4-2-1-3-5-13/h1-7,10-11,19H,8-9,12,18H2 ; Key:WKPDXBXNJWWWGQ-UHFFFAOYSA-N ;
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5-Benzyloxytryptamine (5-BT), is a tryptamine derivative which acts as an agonist at the 5-HT_1D, 5-HT₂ and 5-HT₆ serotonin receptors,[1][2][3][4] and an antagonist of TRPM8.[5]

Legality

5-Benzyloxytryptamine is illegal in Singapore.[6]

Lyon RA, Titeler M, Seggel MR, Glennon RA (January 1988). "Indolealkylamine analogs share 5-HT2 binding characteristics with phenylalkylamine hallucinogens". European Journal of Pharmacology. 145 (3): 291–7. doi:10.1016/0014-2999(88)90432-3. PMID 3350047.
Peroutka SJ, McCarthy BG, Guan XM (1991). "5-benzyloxytryptamine: a relatively selective 5-hydroxytryptamine 1D/1B agent". Life Sciences. 49 (6): 409–18. doi:10.1016/0024-3205(91)90582-V. PMID 1650872.
Cohen ML, Schenck K, Nelson D, Robertson DW (January 1992). "Sumatriptan and 5-benzyloxytryptamine: contractility of two 5-HT1D receptor ligands in canine saphenous veins". European Journal of Pharmacology. 211 (1): 43–6. doi:10.1016/0014-2999(92)90260-B. PMID 1319907.
Boess FG, Monsma FJ, Carolo C, Meyer V, Rudler A, Zwingelstein C, Sleight AJ (1997). "Functional and radioligand binding characterization of rat 5-HT6 receptors stably expressed in HEK293 cells". Neuropharmacology. 36 (4–5): 713–20. doi:10.1016/S0028-3908(97)00019-1. PMID 9225298. S2CID 41813873.
DeFalco, Jeff; Steiger, Daniel; Dourado, Michelle; Emerling, Daniel; Duncton, Matthew A.J. (December 2010). "5-Benzyloxytryptamine as an antagonist of TRPM8". Bioorganic & Medicinal Chemistry Letters. 20 (23): 7076–7079. doi:10.1016/j.bmcl.2010.09.099. PMID 20965726.
"Misuse of Drugs Act - Singapore Statutes Online". sso.agc.gov.sg.

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