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| Formula | C18H21NO2 |
| Molar mass | 283.371 g·mol−1 |
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SCHEMBL5334361 is a drug which acts as an agonist at the 5-HT2 family of serotonin receptors, and was developed for the treatment of glaucoma. It is a benzazepine derivative structurally related to the anorectic drug lorcaserin. It is selective for 5-HT2A, with an EC50 of 0.4nM at 5-HT2A vs 3.9nM at 5-HT2C and a much lower affinity of 417nM at 5-HT2B. [1]
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.
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.
2CBCB-NBOMe (NBOMe-TCB-2) is a compound indirectly derived from the phenethylamine series of hallucinogens, which was discovered in 2007 at Purdue University as part of the ongoing research program of the team led by David Nichols focusing on the mapping of the specific amino acid residues responsible for ligand binding to the 5HT2A receptor. 2CBCB-NBOMe acts as a potent and selective agonist for the 5-HT2A and 5-HT2C receptors, with a Ki of 0.27 nM at the human 5-HT2A receptor, a similar potency to other agonists such as TCB-2, NBOMe-2C-I and Bromo-DragonFLY.
Jimscaline (C-(4,5,6-trimethoxyindan-1-yl)methanamine) is a conformationally-restricted derivative of the cactus-derived hallucinogen mescaline, which was reported in 2006 by a team at Purdue University led by David E. Nichols. It acts as a potent agonist for the 5-HT2A and 5-HT2C receptors with the more active (R)-enantiomer having a Ki of 69 nM at the human 5-HT2A receptor, and around three times the potency of mescaline in drug-substitution experiments in animals. This discovery that the side chain of the phenethylamine hallucinogens could be constrained to give chiral ligands with increased activity then led to the later development of the super-potent benzocyclobutene derivative TCB-2.
2CBFly-NBOMe is a compound indirectly derived from the phenethylamine hallucinogen 2C-B, and related to benzodifurans like 2C-B-FLY and N-benzylphenethylamines like 25I-NBOMe. It was discovered in 2002, and further researched by Ralf Heim at the Free University of Berlin, and subsequently investigated in more detail by a team at Purdue University led by David E. Nichols. It acts as a potent partial agonist for the 5-HT2A serotonin receptor subtype.
25I-NBMD is a derivative of the phenethylamine hallucinogen 2C-I, discovered in 2006 by a team at Purdue University led by David Nichols. It acts as a potent partial agonist for the 5HT2A receptor with a Ki of 0.049 nM at the human 5HT2A receptor. The corresponding 4-bromo analogue 25B-NBMD has been used for molecular dynamics studies on the shape of the 5-HT2A receptor.
AL-37350A (4,5-DHP-AMT) is a tricyclic tryptamine derivative which acts as a potent and selective agonist for the serotonin receptor 5-HT2A, with a Ki of 2.0 nM, and moderate selectivity over the related 5-HT2B and 5-HT2C receptors. It has been shown to have ocular hypotensive activity in animal models, suggesting it may be useful for the treatment of glaucoma.
4-Substituted-2,5-dimethoxyamphetamines (DOx) is a chemical class of substituted amphetamine derivatives featuring methoxy groups at the 2- and 5- positions of the phenyl ring, and a substituent such as alkyl or halogen at the 4- position of the phenyl ring. Most compounds of this class are potent and long-lasting psychedelic drugs, and act as highly selective 5-HT2A, 5-HT2B, and 5-HT2C receptor partial agonists. A few bulkier derivatives such as DOAM have similarly high binding affinity for 5-HT2 receptors but instead act as antagonists, and so do not produce psychedelic effects though they retain amphetamine-like stimulant effects.
2CB-Ind is a conformationally-restricted derivative of the phenethylamine hallucinogen 2C-B, discovered in 1974 by Alexander Shulgin. It acts as a moderately potent and selective agonist for the 5-HT2A and 5-HT2C receptors, but unlike the corresponding benzocyclobutene derivative TCB-2 which is considerably more potent than the parent compound 2C-B, 2CB-Ind is several times weaker, with racemic 2CB-Ind having a Ki of 47nM at the human 5-HT2A receptor, only slightly more potent than the mescaline analogue (R)-jimscaline.
25TFM-NBOMe is a derivative of the phenethylamine hallucinogen 2C-TFM, discovered in 2004 by Ralf Heim at the Free University of Berlin. It acts as a potent partial agonist for the 5-HT2A receptor, though its relative potency is disputed, with some studies finding it to be of lower potency than 25I-NBOMe, while others show it to be of similar or higher potency, possibly because of differences in the assay used. 2C-TFM-NB2OMe can be taken to produce psychedelic effects similar to 2C-I-NB2OMe and 2C-D-NB2OMe.
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.
1-Methylpsilocin (developmental code names CMY, CMY-16) is a tryptamine derivative developed by Sandoz which acts as a selective agonist of the serotonin 5-HT2C receptor (IC50Tooltip half-maximal inhibitory concentration of 12 nM, vs. 633 nM at 5-HT2A), and an inverse agonist at 5-HT2B (Ki of 38 nM). While 1-methylpsilocin does have higher affinity for 5-HT2C than 5-HT2A, it does produce a head-twitch response in mice that is dependent on 5-HT2A, so it is not entirely free of effects on 5-HT2Ain vivo. In contrast to psilocin, 1-methylpsilocin did not activate 5-HT1A receptors in mice.
25B-NBOH is a derivative of the phenethylamine derived hallucinogen 2C-B which has been sold as a designer drug. It acts as a potent serotonin receptor agonist with similar affinity to the better-known compound 25B-NBOMe at 5-HT2A and 5-HT2C receptors with pKis values of 8.3 and 9.4, respectively.
NBOMe-mescaline or mescaline-NBOMe is a synthetic substituted phenethylamine. It is a partial agonist of serotonin receptors with a 5-HT2A pKi originally reported as 7.3, though more modern techniques assayed it as 140nM at 5-HT2A and 640nM at 5-HT2C, making it one of the least potent compounds among the N-benzyl phenethylamines.
2C-B-BUTTERFLY is a conformationally-restricted derivative of the phenethylamine hallucinogen 2C-B, which was discovered in 1999 by Michael S. Whiteside and Aaron Monte. It is a ring-expanded homologue of the better known compound 2C-B-FLY, and has similar properties as an agonist for serotonin receptors, but with more selectivity for 5-HT2C over 5-HT2A.
25B-NBF is a derivative of the phenethylamine hallucinogen 2C-B, which acts as a highly potent partial agonist for the human 5-HT2A receptor.
25I-NB4OMe is a derivative of the phenethylamine hallucinogen 2C-I, which acts as a partial agonist for the human 5-HT2A receptor.
25C-NB4OMe is a derivative of the phenethylamine hallucinogen 2C-C, which acts as a partial agonist for the human 5-HT2A receptor.
25I-NB3OMe is a phenethylamine hallucinogen which acts as a partial agonist for the human 5-HT2A receptor. It is a derivative of 2C-I.
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