7-Methyltryptamine
Pharmaceutical compound
From Wikipedia, the free encyclopedia
7-Methyltryptamine (7-Me-T or 7-methyl-T; developmental code name PAL-286) is a serotonin receptor modulator and monoamine releasing agent of the tryptamine family.[1] It is the 7-methyl derivative of tryptamine.[1]
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| Other names | 7-Methyl-T; 7-MT; 7-Me-T; PAL-286; PAL286 |
| Drug class | Serotonin receptor modulator; Serotonin 5-HT2A receptor agonist; Serotonin releasing agent |
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| ECHA InfoCard | 100.034.983 |
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| Formula | C11H14N2 |
| Molar mass | 174.247 g·mol−1 |
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The drug acts as a potent full agonist of the serotonin 5-HT2A receptor, with an EC50 of 44.7 nM and an Emax of 103%.[1] It shows 6-fold lower potency as a serotonin 5-HT2A receptor agonist compared to tryptamine itself.[1] 7-Methyltryptamine also shows affinity for the serotonin 5-HT1D receptor, but has greatly reduced affinity compared to tryptamine (IC50 = 1,900 nM and 57 nM, respectively; 33-fold lower).[2] It shows extremely weak affinity for the dizocilpine (MK-801) site of the NMDA receptor (IC50 = ~650,000 nM).[3][4] In addition to its serotonin 5-HT2A receptor agonism, 7-methyltryptamine is a serotonin releasing agent (SRA), with EC50 values for induction of monoamine release of 23.7 nM for serotonin, 3,380 nM for dopamine, and >10,000 nM for norepinephrine in rat brain synaptosomes.[1][5][6][7][8]
Tryptamines without substitutions at the amine or alpha carbon, such as tryptamine, serotonin (5-hydroxytryptamine; 5-HT), and 5-methoxytryptamine (5-MeO-T), are known to be very rapidly metabolized and thereby inactivated by monoamine oxidase A (MAO-A) in vivo and to have very short elimination half-lives.[9][10][11][12][13][14][15] However, given intravenously at sufficiently high doses, tryptamine is still known to be able to produce weak and short-lived psychoactive effects in humans.[16][10][1][15]
The chemical synthesis of 7-methyltryptamine has been described.[1][17] The chemical identification of 7-methyltryptamine has been described as well.[18][19]
7-Methyltryptamine was first described in the scientific literature by 1956.[17] Its pharmacology was subsequently assessed in greater detail in 2014.[1]