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{{short description|Chemical compound}} |
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{{Drugbox |
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{{Drugbox |
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| Verifiedfields = changed |
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| verifiedrevid = 449579899 |
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| verifiedrevid = 477224082 |
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| IUPAC_name = 2-(5-phenylmethoxy-1''H''-indol-3-yl)ethanamine |
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| IUPAC_name = 2-(5-phenylmethoxy-1''H''-indol-3-yl)ethanamine |
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| image = 5-benzyloxytryptamine.png |
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| image = 5-benzyloxytryptamine.png |
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<!--Clinical data--> |
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<!--Clinical data--> |
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| tradename = |
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| tradename = |
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<!--Identifiers--> |
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<!--Identifiers--> |
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| CASNo_Ref = {{cascite|??|??}} |
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| CAS_number_Ref = {{cascite|changed|??}} |
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| CAS_number = 20776-45-8 |
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| CAS_number = 20776-45-8 |
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| PubChem = 89576 |
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| PubChem = 89576 |
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| IUPHAR_ligand = |
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| IUPHAR_ligand = 265 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 80845 |
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| ChemSpiderID = 80845 |
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| legal_status = Illegal in Singapore |
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<!--Chemical data--> |
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<!--Chemical data--> |
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| C=17 | H=18 | N=2 | O=1 |
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| C=17 | H=18 | N=2 | O=1 |
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| molecular_weight = 266.34 g/mol |
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| smiles = NCCC1=CNC2=CC=C(OCC3=CC=CC=C3)C=C21 |
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| smiles = NCCC1=CNC2=CC=C(OCC3=CC=CC=C3)C=C21 |
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| InChI = 1/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 |
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| InChIKey = |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 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 |
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| StdInChI = 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 |
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'''5-Benzyloxytryptamine''' ('''5-BT'''), is a ] ] which acts as an ] at the ], ] and ] ] ].<ref name="pmid3350047">{{cite journal |author=Lyon RA, Titeler M, Seggel MR, Glennon RA |title=Indolealkylamine analogs share 5-HT2 binding characteristics with phenylalkylamine hallucinogens |journal=European Journal of Pharmacology |volume=145 |issue=3 |pages=291–7 |year=1988 |month=January |pmid=3350047 |doi= 10.1016/0014-2999(88)90432-3|url=}}</ref><ref name="pmid1650872">{{cite journal |author=Peroutka SJ, McCarthy BG, Guan XM |title=5-benzyloxytryptamine: a relatively selective 5-hydroxytryptamine 1D/1B agent |journal=Life Sciences |volume=49 |issue=6 |pages=409–18 |year=1991 |pmid=1650872 |doi= 10.1016/0024-3205(91)90582-V|url=}}</ref><ref name="pmid1319907">{{cite journal |author=Cohen ML, Schenck K, Nelson D, Robertson DW |title=Sumatriptan and 5-benzyloxytryptamine: contractility of two 5-HT1D receptor ligands in canine saphenous veins |journal=European Journal of Pharmacology |volume=211 |issue=1 |pages=43–6 |year=1992 |month=January |pmid=1319907 |doi= 10.1016/0014-2999(92)90260-B|url=}}</ref><ref name="pmid9225298">{{cite journal |author=Boess FG, Monsma FJ, Carolo C, Meyer V, Rudler A, Zwingelstein C, Sleight AJ |title=Functional and radioligand binding characterization of rat 5-HT6 receptors stably expressed in HEK293 cells |journal=Neuropharmacology |volume=36 |issue=4-5 |pages=713–20 |year=1997 |pmid=9225298 |doi= 10.1016/S0028-3908(97)00019-1|url=}}</ref> |
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'''5-Benzyloxytryptamine''' ('''5-BT'''), is a ] ] which acts as an ] at the ], ] and ] ] ],<ref name="pmid3350047">{{cite journal | vauthors = Lyon RA, Titeler M, Seggel MR, Glennon RA | title = Indolealkylamine analogs share 5-HT2 binding characteristics with phenylalkylamine hallucinogens | journal = European Journal of Pharmacology | volume = 145 | issue = 3 | pages = 291–297 | date = January 1988 | pmid = 3350047 | doi = 10.1016/0014-2999(88)90432-3 }}</ref><ref name="pmid1650872">{{cite journal | vauthors = Peroutka SJ, McCarthy BG, Guan XM | title = 5-benzyloxytryptamine: a relatively selective 5-hydroxytryptamine 1D/1B agent | journal = Life Sciences | volume = 49 | issue = 6 | pages = 409–418 | year = 1991 | pmid = 1650872 | doi = 10.1016/0024-3205(91)90582-V | doi-access = free }}</ref><ref name="pmid1319907">{{cite journal | vauthors = Cohen ML, Schenck K, Nelson D, Robertson DW | title = Sumatriptan and 5-benzyloxytryptamine: contractility of two 5-HT1D receptor ligands in canine saphenous veins | journal = European Journal of Pharmacology | volume = 211 | issue = 1 | pages = 43–46 | date = January 1992 | pmid = 1319907 | doi = 10.1016/0014-2999(92)90260-B }}</ref><ref name="pmid9225298">{{cite journal | vauthors = Boess FG, Monsma FJ, Carolo C, Meyer V, Rudler A, Zwingelstein C, Sleight AJ | title = Functional and radioligand binding characterization of rat 5-HT6 receptors stably expressed in HEK293 cells | journal = Neuropharmacology | volume = 36 | issue = 4–5 | pages = 713–720 | year = 1997 | pmid = 9225298 | doi = 10.1016/S0028-3908(97)00019-1 | s2cid = 41813873 }}</ref> and an antagonist of ].<ref>{{cite journal | vauthors = DeFalco J, Steiger D, Dourado M, Emerling D, Duncton MA | title = 5-benzyloxytryptamine as an antagonist of TRPM8 | journal = Bioorganic & Medicinal Chemistry Letters | volume = 20 | issue = 23 | pages = 7076–7079 | date = December 2010 | pmid = 20965726 | doi = 10.1016/j.bmcl.2010.09.099 }}</ref> |
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==Legality== |
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5-Benzyloxytryptamine is illegal in Singapore.<ref>{{cite web|title=Misuse of Drugs Act - Singapore Statutes Online|url=https://sso.agc.gov.sg/Act/MDA1973|website=sso.agc.gov.sg}}</ref> |
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== See also == |
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== See also == |
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{{Reflist}} |
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{{Reflist}} |
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{{Serotonin receptor modulators}} |
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{{Serotonergics}} |
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{{Tryptamines}} |
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{{Tryptamines}} |
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{{DEFAULTSORT:Benzyloxytryptamine, 5-}} |
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{{DEFAULTSORT:Benzyloxytryptamine, 5-}} |
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{{nervous-system-drug-stub}} |
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