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5-methoxy-2-phenyl-N,N-dimethyltryptamine as a nootropic

Migrated topic.
I have been researching medical use of dimethyltryptamine homologues and bioisosteres, and every day I find another compound with a dimethyltryptamine skeleton that has medical applications.

We all know about the obvious medical dimethyltryptamine compounds, such as the triptan compounds (zolmatriptan, sumatriptan, etc...) and most have probably read about the potential medical uses of brominated dimethyltryptamine compounds found in some sea invertabrates, but this compound stood out to me, specially in its purported claims to improve memory and brain function.

Anyone with information on this or other dimethyltryptamine homologues with potential medical uses would be helping me greatly by directing me towards it, any information sources on novel dimethyltryptamine's would be greatly appreciated!

-eg

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Neuropharmacology
Volume 50, Issue 4, March 2006, Pages 412-420
Ellen S. Mitchell, Blair J. Hoplight, Sean P. Lear and John F. Neumaier

Abstract
Inhibition of 5-HT6 receptors has been shown to improve memory consolidation, thus we tested whether a novel tryptamine analog with high affinity for 5-HT6 receptors, BGC20-761 (5-methoxy-2-phenyl-N,N-dimethyltryptamine, PMDT), can enhance long-term memory. BGC20-761 (10 mg/kg i.p.) alone had no effect on social recognition in young rats, however, at doses of 5 mg/kg and 10 mg/kg i.p, BGC20-761 dose-dependently reversed a deficit of social recognition induced by scopolamine (0.4 mg/kg i.p.), an anticholinergic drug that impairs memory. BGC20-761 (10 mg/kg i.p.), scopolamine (0.2 mg/kg i.p.) or BGC20-761 + scopolamine had no effects on novel object discrimination in young rats (2 months). In mature rats (6 months), recognition of the novel object was improved following administration of BGC20-761. Scopolamine had no effect in object recognition. However, the addition of scopolamine disrupted the memory-enhancing effect of BGC20-761. Based on the high affinity of BGC20-761 for 5-HT6 receptors, these cognitive enhancing effects are most likely mediated by 5-HT6 receptor inhibition. The difference in effects of BGC20-761 in young vs. mature rats may reflect the status of memory consolidation in these different age ranges.
 
2-Ethyl-5-methoxy-N,N-dimethyltryptamine (EMDT) is a tryptamine derivative which is used in scientific research. It acts as a selective 5-HT6 receptor agonist, with a Ki of 16 nM, and was one of the first selective agonists developed for this receptor.[1] EMDT inhibits both short- and long-term memory formation in animal studies, and this effect can be reversed by the selective 5-HT6 antagonist SB-399,885.[2] Additionally, it is active in the tail suspension test, suggesting that it could be an effective antidepressant.-wikipedia

This compound has an ethyl chain at position two rather than a benzene ring at two as with 5-MEO-2-phenyl-DMT, but shares agonism at the 5ht6 receptor site....fascinating!

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"ST-1936" 2-methyl-5-chloro-N,N-dimethyltryptamine is another 5ht6 agonist used medically....

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I know very little about these compounds at this point but am very eager to learn, any information or leads would be much appreciated.

-eg
 
5-methoxy-2-phenyl-N,N-dimethyltryptamine [Supplementary Concept]
a nootropic agent
Date introduced: July 6, 2006
MeSH Unique ID: C511537

5-methoxy-2-phenyl-N,N-dimethyltryptamine Summary

Description: a nootropic agent

Also Known As: BGC20-761; PMDT cpd
Networked: 1 relevant articles (0 outcomes, 0 trials/studies) for this Bio-Agent

Key Diseases for which 5-methoxy-2-phenyl-N,N-dimethyltryptamine is Relevant
Memory Disorders (Memory Loss) : 1 result

-eg
 
BGC20-761, a novel tryptamine analog, enhances memory consolidation and reverses scopolamine-induced memory deficit in social and visuospatial memory tasks through a 5-HT6 receptor-mediated mechanism.

Abstract
Inhibition of 5-HT(6) receptors has been shown to improve memory consolidation, thus we tested whether a novel tryptamine analog with high affinity for 5-HT(6) receptors, BGC20-761 (5-methoxy-2-phenyl-N,N-dimethyltryptamine, PMDT), can enhance long-term memory. BGC20-761 (10 mg/kg i.p.) alone had no effect on social recognition in young rats, however, at doses of 5 mg/kg and 10 mg/kg i.p, BGC20-761 dose-dependently reversed a deficit of social recognition induced by scopolamine (0.4 mg/kg i.p.), an anticholinergic drug that impairs memory. BGC20-761 (10 mg/kg i.p.), scopolamine (0.2 mg/kg i.p.) or BGC20-761 + scopolamine had no effects on novel object discrimination in young rats (2 months). In mature rats (6 months), recognition of the novel object was improved following administration of BGC20-761. Scopolamine had no effect in object recognition. However, the addition of scopolamine disrupted the memory-enhancing effect of BGC20-761. Based on the high affinity of BGC20-761 for 5-HT(6) receptors, these cognitive enhancing effects are most likely mediated by 5-HT(6) receptor inhibition. The difference in effects of BGC20-761 in young vs. mature rats may reflect the status of memory consolidation in these different age ranges

2-Substituted Tryptamines: Agents with Selectivity for 5-HT6 Serotonin Receptors, which specifically mentions 2-ethyl-5-methoxy-N, N-dimethyltryptamine

Abstract
Several 2-alkyl-5-methoxytryptamine analogues were designed and prepared as potential 5-HT(6) serotonin agonists. It was found that 5-HT(6) receptors accommodate small alkyl substituents at the indole 2-position and that the resulting compounds can bind with affinities comparable to that of serotonin. In particular, 2-ethyl-5-methoxy-N, N-dimethyltryptamine (Cool binds with high affinity at human 5-HT(6) receptors (K(i) = 16 nM) relative to 5-HT (K(i) = 75 nM) and was a full agonist, at least as potent (8: K(act) = 3.6 nM) as serotonin (K(act) = 5.0 nM), in activating adenylate cyclase. Compound 8 displays modest affinity for several other populations of 5-HT receptors, notably h5-HT(1A) (K(i) = 170 nM), h5-HT(1D) (K(i) = 290 nM), and h5-HT(7) (K(i) = 300 nM) receptors, but is otherwise quite selective. Compound 8 represents the first and most selective 5-HT(6) agonist reported to date. Replacing the 2-ethyl substituent with a phenyl group results in a compound that retains 5-HT(6) receptor affinity (i.e., 10: K(i) = 20 nM) but lacks agonist character.

-eg
 
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