5-Benzyloxytryptamine

5-Benzyloxytryptamine
Legal status
Legal status
  • Illegal in Singapore
Identifiers
IUPAC name
  • 2-(5-phenylmethoxy-1H-indol-3-yl)ethanamine
CAS Number
PubChem CID
IUPHAR/BPS
ChemSpider
CompTox Dashboard (EPA)
ECHA InfoCard100.040.007
Chemical and physical data
FormulaC17H18N2O
Molar mass266.344 g·mol−1
3D model (JSmol)
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 checkY
  • Key:WKPDXBXNJWWWGQ-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

5-Benzyloxytryptamine (5-BT), is a tryptamine derivative which acts as an agonist at the 5-HT1D, 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] may be considered illegal due to the U.S. Analog Act, citing similar looking chemicals that are analogic in nature

See also

References

  1. ↑ 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): 291–297. doi:10.1016/0014-2999(88)90432-3. PMID 3350047.
  2. ↑ Peroutka SJ, McCarthy BG, Guan XM (1991). "5-benzyloxytryptamine: a relatively selective 5-hydroxytryptamine 1D/1B agent". Life Sciences. 49 (6): 409–418. doi:10.1016/0024-3205(91)90582-V. PMID 1650872.
  3. ↑ 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): 43–46. doi:10.1016/0014-2999(92)90260-B. PMID 1319907.
  4. ↑ 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): 713–720. doi:10.1016/S0028-3908(97)00019-1. PMID 9225298. S2CID 41813873.
  5. ↑ DeFalco J, Steiger D, Dourado M, Emerling D, Duncton MA (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.
  6. ↑ "Misuse of Drugs Act - Singapore Statutes Online". sso.agc.gov.sg.
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