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| Chemical and physical data | |
| Formula | C12H12BrN3 |
| Molar mass | 278.153 g·mol−1 |
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VU6067416 is an indazole derivative which acts as an agonist for the 5-HT2 family of serotonin receptors. It is a potent full agonist at 5-HT2B, and has slightly lower affinity and partial agonist effects at 5-HT2A and 5-HT2C, [1] though some related compounds have improved selectivity for 5-HT2A. [2]
2C-B-FLY is a psychedelic phenethylamine and designer drug of the 2C family. It was first synthesized in 1996 by Aaron Monte, Professor of Chemistry at UW-La Crosse.
The 5-HT2A receptor is a subtype of the 5-HT2 receptor that belongs to the serotonin receptor family and is a G protein-coupled receptor (GPCR). The 5-HT2A receptor is a cell surface receptor, but has several intracellular locations.
A serotonin receptor agonist is an agonist of one or more serotonin receptors. They activate serotonin receptors in a manner similar to that of serotonin, a neurotransmitter and hormone and the endogenous ligand of the serotonin receptors.
AL-34662 is an indazole derivative drug that is being developed for the treatment of glaucoma. It acts as a selective 5-HT2A receptor agonist, the same target as that of psychedelic drugs like psilocin, but unlike these drugs, AL-34662 was designed specifically as a peripherally selective drug, which does not cross the blood–brain barrier. This means that AL-34662 can exploit a useful side effect of the hallucinogenic 5-HT2A agonists, namely reduction in intra-ocular pressure and hence relief from the symptoms of glaucoma, but without causing the hallucinogenic effects that make centrally active 5-HT2A agonists unsuitable for clinical use. In animal studies, AL-34662 has been shown to be potent and effective in the treatment of symptoms of glaucoma, with minimal side effects.
YM-348 is an indazole derivative drug which acts as a potent and selective 5-HT2C receptor agonist, with an EC50 of 1nM and 15x selectivity over 5-HT2A, although it only has moderate selectivity of 3x over the closely related 5-HT2B receptor. It has thermogenic and anorectic effects in animal studies, making it potentially useful for the treatment of obesity.
AMDA (9-Aminomethyl-9,10-dihydroanthracene) is an organic compound which acts as a potent and selective antagonist for the 5-HT2A receptor. It has been used to help study the shape of the 5-HT2A protein, and develop a large family of related derivatives with even higher potency and selectivity.
TFMFly is a compound related to psychedelic phenethylamines such as 2C-B-FLY and 2C-TFM. It was first reported in 2005 by a team at Purdue University led by David Nichols. It acts as a potent agonist at the 5HT2A serotonin receptor subtype, and is a chiral compound with the more active (R) enantiomer having a Ki of 0.12 nM at the human 5-HT2A receptor. While the fully aromatic benzodifurans such as Bromo-DragonFLY generally have higher binding affinity than saturated compounds like 2C-B-FLY, the saturated compounds have higher efficacy as agonists.
5-Methoxy-7,N,N-trimethyltryptamine (5-MeO-7,N,N-TMT, 5-MeO-7-TMT), is a tryptamine derivative which acts as a partial agonist at the 5-HT2 serotonin receptors, with an EC50 of 63.9 nM and an efficacy of 66.2% at 5-HT2A (vs 5-HT), and weaker activity at 5-HT2B and 5-HT2C. In animal tests, both 7,N,N-TMT and 5-MeO-7,N,N-TMT produced behavioural responses similar to those of psychedelic drugs such as DMT and 5-MeO-DMT, but compounds with larger 7-position substituents such as 7-ethyl-DMT and 7-bromo-DMT did not produce psychedelic-appropriate responding despite high 5-HT2 receptor binding affinity, suggesting these may be antagonists or weak partial agonists for the 5-HT2 receptors. The related compound 7-MeO-MiPT (cf. 5-MeO-MiPT) was also found to be inactive, suggesting that the 7-position has poor tolerance for bulky groups at this position, at least if agonist activity is desired.
4-Fluoro-5-Methoxy-N,N-dimethyltryptamine (4-F-5-MeO-DMT) was first described by David E. Nichols team in 2000. It is a potent 5-HT1A agonist. Substitution with the 4-fluorine markedly increased 5-HT1A selectivity over 5-HT2A/2C receptors with potency greater than that of the 5-HT1A agonist 8-OH-DPAT.
1-(2-Dimethylaminoethyl)dihydropyrano(3,2-e)indole (4,5-DHP-DMT) is a tricyclic tryptamine derivative which acts as a potent and reasonably selective partial agonist for the serotonin receptor 5-HT2A, with a Ki of 17.0 nM, and moderate selectivity over related serotonin receptors. It has lower 5-HT2 affinity and efficacy than the related compound AL-37350A, but higher lipophilicity.
Substituted tryptamines, or serotonin analogues, are organic compounds which may be thought of as being derived from tryptamine itself. The molecular structures of all tryptamines contain an indole ring, joined to an amino (NH2) group via an ethyl (−CH2–CH2−) sidechain. In substituted tryptamines, the indole ring, sidechain, and/or amino group are modified by substituting another group for one of the hydrogen (H) atoms.
5-MeO-NBpBrT is a N-substituted member of the methoxytryptamine family of compounds. Like other such compounds it acts as an antagonist for the 5-HT2A receptor, with a claimed 100x selectivity over the closely related 5-HT2C receptor. While N-benzyl substitution of psychedelic phenethylamines often results in potent 5-HT2A agonists, it had been thought that N-benzyl tryptamines show much lower efficacy and are either very weak partial agonists or antagonists at 5-HT2A, though more recent research has shown stronger agonist activity for 3-substituted benzyl derivatives. Extending the benzyl group to a substituted phenethyl can also recover agonist activity in certain cases.
25CN-NBOH is a compound indirectly derived from the phenethylamine series of hallucinogens, which was discovered in 2014 at the University of Copenhagen. This compound is notable as one of the most selective agonist ligands for the 5-HT2A receptor yet discovered, with a pKi of 8.88 at the human 5-HT2A receptor and with 100x selectivity for 5-HT2A over 5-HT2C, and 46x selectivity for 5-HT2A over 5-HT2B. A tritiated version of 25CN-NBOH has also been accessed and used for more detailed investigations of the binding to 5-HT2 receptors and autoradiography.
DMBMPP, or 2-(2,5-dimethoxy-4-bromobenzyl)-6-(2-methoxyphenyl)piperidine, is a 2-benzylpiperidine analog of the hallucinogenic N-benzylphenethylamine 25B-NBOMe and was discovered in 2011 by Jose Juncosa in the group of David E. Nichols at Purdue University. DMBMPP differs from 25B-NBOMe by incorporating the amine within a piperidine ring, making for a more rigid molecular structure than that of the open-chain 25B-NBOMe. The presence of the piperidine ring introduces two stereocenters, thus, four stereoisomers of this compound can be made.
CP-132,484 is a tryptamine derivative which acts as a potent and selective agonist for the 5-HT2 family of serotonin receptors. It has reasonable selectivity for 5-HT2A and 5-HT2C subtypes over 5-HT2B, but is only slightly selective for 5-HT2A over 5-HT2C. This compound and several related analogues have been shown to have ocular hypotensive activity in animal models, suggesting they may be useful for the treatment of glaucoma.
Substituted phenylmorpholines, or substituted phenmetrazines alternatively, are chemical derivatives of phenylmorpholine or of the psychostimulant drug phenmetrazine. Most such compounds act as releasers of monoamine neurotransmitters, and have stimulant effects. Some also act as agonists at serotonin receptors, and compounds with an N-propyl substitution act as dopamine receptor agonists. A number of derivatives from this class have been investigated for medical applications, such as for use as anorectics or medications for the treatment of ADHD. Some compounds have also become subject to illicit use as designer drugs.
The 25-NB (25x-NBx) series, sometimes alternatively referred to as the NBOMe compounds, is a family of serotonergic psychedelics. They are substituted phenethylamines and were derived from the 2C family. They act as selective agonists of the serotonin 5-HT2A receptor. The 25-NB family is unique relative to other classes of psychedelics in that they are, generally speaking, extremely potent and relatively selective for the 5-HT2A receptor. Use of NBOMe series drugs has caused many deaths and hospitalisations since the drugs popularisation in the 2010s. This is primarily due to their high potency, unpredictable pharmacokinetics, and sellers passing off the compounds in the series as LSD.
Perlapine, sold under the brand names Hypnodine and Pipnodine, is a hypnotic and sedative of the tricyclic group which is marketed in Japan. It acts primarily as a potent antihistamine, and also has anticholinergic, antiserotonergic, antiadrenergic, and some antidopaminergic activity. The drug has relatively weak affinity for the dopamine D2 receptor (IC50Tooltip Half-maximal inhibitory concentration = 1,803 nM) and, in accordance, is said to be ineffective as an antipsychotic. However, it retains higher affinity for the dopamine D1 receptor (IC50 = 198 nM). Its IC50 values are 19 nM for the α1-adrenergic receptor, 4,945 nM for the α2-adrenergic receptor, and 70 nM for the serotonin 5-HT2A receptor. Perlapine is closely related to clotiapine, clozapine, fluperlapine, loxapine, and tilozepine.
RS134-49 is a tetrahydropyridine derivative related to psychedelic tryptamines which acts as a 5-HT2A receptor agonist, with a 5-HT2A Ki of 11.5nM and an EC50 of 22nM. It is a biased agonist selective for activation of the Gq coupled signalling pathway with weaker activation of the β-arrestin 2 coupled pathway, but shows a more balanced profile than related compounds such as (R)-69.
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