Chemistry: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 ;
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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Short description: Chemical compound

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]

↑ "Indolealkylamine analogs share 5-HT2 binding characteristics with phenylalkylamine hallucinogens". European Journal of Pharmacology 145 (3): 291–297. January 1988. doi:10.1016/0014-2999(88)90432-3. PMID 3350047.
↑ "5-benzyloxytryptamine: a relatively selective 5-hydroxytryptamine 1D/1B agent". Life Sciences 49 (6): 409–418. 1991. doi:10.1016/0024-3205(91)90582-V. PMID 1650872.
↑ "Sumatriptan and 5-benzyloxytryptamine: contractility of two 5-HT1D receptor ligands in canine saphenous veins". European Journal of Pharmacology 211 (1): 43–46. January 1992. doi:10.1016/0014-2999(92)90260-B. PMID 1319907.
↑ "Functional and radioligand binding characterization of rat 5-HT6 receptors stably expressed in HEK293 cells". Neuropharmacology 36 (4–5): 713–720. 1997. doi:10.1016/S0028-3908(97)00019-1. PMID 9225298.
↑ "5-benzyloxytryptamine as an antagonist of TRPM8". Bioorganic & Medicinal Chemistry Letters 20 (23): 7076–7079. December 2010. doi:10.1016/j.bmcl.2010.09.099. PMID 20965726.
↑ "Misuse of Drugs Act - Singapore Statutes Online". https://sso.agc.gov.sg/Act/MDA1973.

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Legal status

Legal status	Illegal in Singapore
Identifiers
IUPAC name 2-(5-phenylmethoxy-1H-indol-3-yl)ethanamine
CAS Number	20776-45-8^N
PubChem CID	89576
IUPHAR/BPS	265
ChemSpider	80845^Y
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^Y Key:WKPDXBXNJWWWGQ-UHFFFAOYSA-N^Y
^NY (what is this?) (verify)