6-Fluoro-DMT: Difference between revisions
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{{Short description|Chemical compound}} |
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{{Orphan|date=April 2011}} |
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{{Drugbox |
{{Drugbox |
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| verifiedrevid = |
| verifiedrevid = 458134580 |
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| IUPAC_name = 2-(6-fluoro-1H-indol-3-yl)-''N'',''N''-dimethyl-ethanamine |
| IUPAC_name = 2-(6-fluoro-1H-indol-3-yl)-''N'',''N''-dimethyl-ethanamine |
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| image = 6-Fluoro-DMT skeletal.svg |
| image = 6-Fluoro-DMT skeletal.svg |
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<!--Identifiers--> |
<!--Identifiers--> |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 26286731 |
| ChemSpiderID = 26286731 |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| InChI = 1/C12H15FN2/c1-15(2)6-5-9-8-14-12-7-10(13)3-4-11(9)12/h3-4,7-8,14H,5-6H2,1-2H3 |
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| InChIKey = DZXZPVGWRZCXDH-UHFFFAOYAC |
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| StdInChI = 1S/C12H15FN2/c1-15(2)6-5-9-8-14-12-7-10(13)3-4-11(9)12/h3-4,7-8,14H,5-6H2,1-2H3 |
| StdInChI = 1S/C12H15FN2/c1-15(2)6-5-9-8-14-12-7-10(13)3-4-11(9)12/h3-4,7-8,14H,5-6H2,1-2H3 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = DZXZPVGWRZCXDH-UHFFFAOYSA-N |
| StdInChIKey = DZXZPVGWRZCXDH-UHFFFAOYSA-N |
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| CAS_number_Ref = {{cascite|correct|??}} |
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| CAS_number = |
| CAS_number = 1511-31-5 |
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| ATC_prefix = none |
| ATC_prefix = none |
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| ATC_suffix = |
| ATC_suffix = |
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| PubChem = |
| PubChem = |
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<!--Chemical data--> |
<!--Chemical data--> |
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| C=12 | H=15 | F=1 | N=2 |
| C=12 | H=15 | F=1 | N=2 |
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⚫ | |||
| molecular_weight = 206.26 g/mol |
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⚫ | |||
}} |
}} |
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== Pharmacology == |
== Pharmacology == |
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=== Binding profile === |
=== Binding profile === |
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6-Fluoro-DMT possess [[affinity (pharmacology)|affinity]] for the [[5-HT1A|5-HT<sub>1A</sub>]] (392.6 nM), [[5-HT1B|5-HT<sub>1B</sub>]] (217.7 nM), [[5-HT1D|5-HT<sub>1D</sub>]] (55.4 nM), [[5-HT1E|5-HT<sub>1E</sub>]] (460.8 nM), [[5-HT2A|5-HT<sub>2A</sub>]] (866 nM), [[5-HT2B|5-HT<sub>2B</sub>]] (29.8 nM), [[5-HT2C|5-HT<sub>2C</sub>]] (674.2 nM), [[5-HT5A|5-HT<sub>5A</sub>]] (960.5 nM), [[5-HT6|5-HT<sub>6</sub>]] (25.6 nM), [[5-HT7|5-HT<sub>7</sub>]] (40.8 nM), [[D1 receptor|D<sub>1</sub>]] (547.3 nM), [[D2 receptor|D<sub>2</sub>]] (610.4 nM), [[D3 receptor|D<sub>3</sub>]] (866.8 nM), [[D4 receptor|D<sub>4</sub>]] (1,454 nM), [[D5 receptor|D<sub>5</sub>]] (6,291 nM), [[α1A-adrenergic|α<sub>1A</sub>-adrenergic]] (173.3 nM), [[α2B-adrenergic|α<sub>2B</sub>-adrenergic]] (295.5 nM), [[α2C-adrenergic|α<sub>2C</sub>-adrenergic]] (148.8 nM), [[H1 receptor|H<sub>1</sub>]] (46.6 nM), [[H2 receptor|H<sub>2</sub>]] (925.4 nM), [[Imidazoline-1 receptor|I<sub>1</sub>]] (898.4 nM), [[Sigma-1 receptor|<sub>1</sub>]] (6,892 nM), and [[Sigma-2 receptor|<sub>2</sub>]] (7,128 nM) [[receptor (biochemistry)|receptor]]s, as well as the [[serotonin transporter|SERT]] (144.6 nM).<ref name="pmid20126400">{{cite journal | |
6-Fluoro-DMT possess [[affinity (pharmacology)|affinity]] for the [[5-HT1A|5-HT<sub>1A</sub>]] (392.6 nM), [[5-HT1B|5-HT<sub>1B</sub>]] (217.7 nM), [[5-HT1D|5-HT<sub>1D</sub>]] (55.4 nM), [[5-HT1E|5-HT<sub>1E</sub>]] (460.8 nM), [[5-HT2A|5-HT<sub>2A</sub>]] (866 nM), [[5-HT2B|5-HT<sub>2B</sub>]] (29.8 nM), [[5-HT2C|5-HT<sub>2C</sub>]] (674.2 nM), [[5-HT5A|5-HT<sub>5A</sub>]] (960.5 nM), [[5-HT6|5-HT<sub>6</sub>]] (25.6 nM), [[5-HT7|5-HT<sub>7</sub>]] (40.8 nM), [[D1 receptor|D<sub>1</sub>]] (547.3 nM), [[D2 receptor|D<sub>2</sub>]] (610.4 nM), [[D3 receptor|D<sub>3</sub>]] (866.8 nM), [[D4 receptor|D<sub>4</sub>]] (1,454 nM), [[D5 receptor|D<sub>5</sub>]] (6,291 nM), [[α1A-adrenergic|α<sub>1A</sub>-adrenergic]] (173.3 nM), [[α2B-adrenergic|α<sub>2B</sub>-adrenergic]] (295.5 nM), [[α2C-adrenergic|α<sub>2C</sub>-adrenergic]] (148.8 nM), [[H1 receptor|H<sub>1</sub>]] (46.6 nM), [[H2 receptor|H<sub>2</sub>]] (925.4 nM), [[Imidazoline-1 receptor|I<sub>1</sub>]] (898.4 nM), [[Sigma-1 receptor|<sub>1</sub>]] (6,892 nM), and [[Sigma-2 receptor|<sub>2</sub>]] (7,128 nM) [[receptor (biochemistry)|receptor]]s, as well as the [[serotonin transporter|SERT]] (144.6 nM).<ref name="pmid20126400">{{cite journal | vauthors = Ray TS | title = Psychedelics and the human receptorome | journal = PLOS ONE | volume = 5 | issue = 2 | pages = e9019 | date = February 2010 | pmid = 20126400 | pmc = 2814854 | doi = 10.1371/journal.pone.0009019 | bibcode = 2010PLoSO...5.9019R | doi-access = free }}</ref> It has low/negligible (> 10,000 nM) affinity for the [[5-HT3|5-HT<sub>3</sub>]], [[α1B-adrenergic|α<sub>1B</sub>-adrenergic]], [[α2A-adrenergic|α<sub>2A</sub>-adrenergic]], [[β1-adrenergic|β<sub>1</sub>-adrenergic]], [[β2-adrenergic|β<sub>2</sub>-adrenergic]], [[H3 receptor|H<sub>3</sub>]], [[H4 receptor|H<sub>4</sub>]], and [[Muscarinic acetylcholine receptor M1|M<sub>1</sub>]]-[[Muscarinic acetylcholine receptor M5|M<sub>5</sub>]] receptors, as well as the [[dopamine transporter|DAT]] and [[norepinephrine transporter|NET]].<ref name="pmid20126400"/> It has not been screened at [[5-HT1F|5-HT<sub>1F</sub>]], [[5-HT4|5-HT<sub>4</sub>]], [[α1D-adrenergic|α<sub>1D</sub>-adrenergic]], [[β3-adrenergic|β<sub>3</sub>-adrenergic]], or [[vesicular monoamine transporter 1|VMAT<sub>1</sub>]]/[[vesicular monoamine transporter 2|VMAT<sub>2</sub>]]. |
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== See also == |
== See also == |
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* [[5-Fluoro-αMT]] |
* [[5-Fluoro-αMT]] |
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* [[5-Bromo-DMT]] |
* [[5-Bromo-DMT]] |
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* [[6-Fluoro-AMT]] |
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* [[6-Fluoro-DET]] |
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== References == |
== References == |
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{{Tryptamines}} |
{{Tryptamines}} |
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[[Category:Tryptamines]] |
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[[Category:Psychedelic tryptamines]] |
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{{nervous-system-drug-stub}} |