List of miscellaneous 5HT2A agonists

Last updated

This is a list of agonists of the serotonin receptor subtype 5-HT2A (and other 5-HT2 subtypes to a varying extent) which fall outside the common structural classes. Most agonists at this receptor are either substituted phenethylamine derivatives from the 2C, DOx and 25-NB groups, or substituted tryptamines and related compounds along with more complex derivatives of these such as lysergamides and iboga-type alkaloids. [1] There are however numerous 5-HT2A receptor agonists which do not fall within any of these groups, some representative examples of which are listed below. Ki and EC50 values vary depending on the assay conditions used and so may not be directly comparable between sources. Many of these compounds have been designed to be non-psychoactive derivatives for medical applications, and it should not be assumed that a compound which acts as a 5-HT2A agonist will necessarily be psychedelic in nature. [2]

StructureNameChemical nameh5-HT2A Ki (EC50) (nM)PubChemCAS numberReference
11a from Bioorg Med Chem Lett 2003, 13, 2369 structure.png Compound 11a11-chloro-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole6.5 20726100 599173-28-1 [3]
23 from Bioorg Med Chem Lett 2003, 13, 2369 structure.png Compound 239-Chloro-7-(2-ethoxy-phenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole32 44315398 599173-25-8 [3]
10d from Bioorg Med Chem Lett 2005, 15, 1467 structure.png Compound 10d7-Benzyloxy-8-bromo-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine22 10472780 616201-60-6 [4]
22.67 from WO 2009-079765 structure.png Example 22.674-(6,7,8,9-tetrahydro-5H-pyrido[2,3-d]azepin-2-yl)thiomorpholine21 44124494 [5]
3d from J Med Chem 2013, 56, 1211 structure.png Compound 3d (N-Bn-THAZ)2-benzyl-5,6,7,8-tetrahydro-4H-[1,2]oxazolo[4,5-d]azepin-3-one(549) 14515725 125115-66-4 [6]
11 from WO 2021-076572 structure.png Compound 11(3R)-N,N-diethyl-5-(1H-indol-4-yl)-1-methyl-3,6-dihydro-2H-pyridine-3-carboxamide(<10) 156278040 [7]
106 from ACS Med Chem Lett 2022, 13, 4, 648 structure.png Compound 1066-chloro-1-(2,4,5-trimethoxyphenyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole 4376990 528525-37-3 [8]
6c from J Med Chem 2023, 66, 11536 structure.png Compound 6c(6S)-2,3-dichloro-7,8,9,10-tetrahydro-6H-6,9-epiminocyclohepta[b]quinoxaline(400) [9]
WO2004-058722-ex70 structure.png Compound 703-(4-bromo-2-methylpyrazol-3-yl)-N-(4-chlorophenyl)-4-methoxyaniline1.77 9952456 [10]
22jmedchem2007-50-1367 structure.png Compound 227-(trifluoromethoxy)-2,3,4,10b-tetrahydro-1H-pyrazino[1,2-b]isoindol-6-one67 (87) 11448649 [10]
WO2021-0137908-1 structure.png Example 1 (ZC-B)3-(4-bromo-2,5-dimethoxyphenyl)azetidine(1.6) 156337249 2641630-65-9 [11]
2CB-AR structure.png 2C-B-aminorex 5-(4-bromo-2,5-dimethoxyphenyl)-4,5-dihydro-1,3-oxazol-2-amine 165360199 [12]
2CB-norphenmetrazine structure.png 2-(2,5-dimethoxy-4-bromophenyl)morpholine2-(2,5-dimethoxy-4-bromophenyl)morpholine20.6 11429275 [13]
LPH-5 structure.png LPH-5 (3S)-3-[2,5-dimethoxy-4-(trifluoromethyl)phenyl]piperidine(3.2) 156337168 2641630-97-7 [14]
2C-B-PP Structure.svg 2C-B-PP 1-(2,5-dimethoxy-4-bromophenyl)piperazine 4738744 100939-87-5 [15]
Cis-urocanic-acid structure.png cis-urocanic acid (cis-UCA)(Z)-3-(1H-imidazol-5-yl)prop-2-enoic acid4.6 1549103 7699-35-6 [16] [17] [18]
CPD-1 Structure.svg CPD-1 (3S)-3-Methyl-1-[4-(trifluoromethyl)-1-benzofuran-7-yl]piperazine 9925822 325145-37-7 [19]
Efavirenz.svg Efavirenz (4S)-6-Chloro-4-(2-cyclopropylethynyl)-4-(trifluoromethyl)-2,4-dihydro-1H-3,1-benzoxazin-2-one 64139 154598-52-4 [20]
IHCH-7079 structure.png IHCH-7079(6bR,10aS)-8-(2-Methoxyphenethyl)-3-methyl-2,3,6b,7,8,9,10,10a-octahydro-1H-pyrido[3',4':4,5]pyrrolo[1,2,3-de]quinoxaline 169488014 2957888-63-8 [21]
IHCH-7113.svg IHCH-7113 (6bR,10aS)-3-methyl-2,3,6b,7,8,9,10,10a-octahydro-1H-pyrido[3',4':4,5]pyrrolo[1,2,3-de]quinoxaline 21302499 313368-85-3 [21]
NDTDI structure.png NDTDI N,N-diethyl-3-[methyl(1,3,4,5-tetrahydrobenzo[cd]indol-4-yl)amino]propanamide 163192742 [22]
Mefloquine structure without stereochemistry.svg Mefloquine 2,8-bis(trifluoromethyl)quinolin-4-yl-(2-piperidyl)methanol 40692 53230-10-7 [23]
Org12962 structure.png ORG-12962 1-(5-trifluoromethyl-6-chloropyridin-2-yl)piperazine 9796408 210821-63-9 [24]
ORG-37684.svg ORG-37684 (3S)-3-[(2,3-dihydro-5-methoxy-1H-inden-4-yl)oxy]pyrrolidine 9794656 213007-95-5 [25]
OSU-6162.svg OSU-6162 (3S)-3-[3-(methylsulfonyl)phenyl]-1-propylpiperidine 9795741 156907-84-5 [26]
PHA-57378.svg PHA-57378 2,7,8,9,10,11-hexahydro-1H-azepino[4,5-b][1,4]oxazino[2,3,4-hi]indole4.1 10198481 303798-94-9 [3]
P-54 structure.png P-542-(5-methoxypyrazolo[1,5-a]pyridin-3-yl)-N,N-dimethylethanamine 168946740 [27]
R69 structure.png (R)-69 3-[(5R)-5-methyl-1,2,5,6-tetrahydropyridin-3-yl]-1H-pyrrolo[2,3-b]pyridine 164513426 [28]
RS134-49 structure.png RS134-49 4-methyl-3-(1,2,3,6-tetrahydropyridin-5-yl)-1H-indole 168941768 [29] [30]
RH-34 structure.png RH-34 3-[2-(2-methoxybenzylamino)ethyl]-1H-quinazoline-2,4-dione 10041987 1028307-48-3 [31]
SCHEMBL5334361.svg SCHEMBL5334361 7-[(3-methoxyphenoxy)methyl]-2,3,4,5-tetrahydro-1H-3-benzazepine(0.4) 59027940 959867-47-1 [32]
Tabernanthalog.svg Tabernanthalog 8-methoxy-3-methyl-2,4,5,6-tetrahydro-1H-azepino[4,5-b]indole 146026994 2483829-59-8 [33]
TKU-II-100 structure.png TKU-II-100[(1S,2S)-2-(2-fluorophenyl)cyclopropyl]methanamine0.62 44572747 [34]
WAY-470 structure.png WAY-470 1,16-diazatetracyclo[8.8.1.02,9.014,19]nonadeca-2(9),10,12,14(19)-tetraene36 10037962 [35]
WXVL BT0793LQ2118 structure.png WXVL_BT0793LQ21186-fluoro-4-(1-methyl-1,2,5,6-tetrahydropyridin-3-yl)-1H-indole [36]
Z2825713589 structure.png Z2825713589(4-amino-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrol-2-yl)-(6-methoxypyrazin-2-yl)methanone 167788805 [36]
Z2876442907 structure.png Z2876442907ethyl 2-[[2-(4-methyl-1H-indol-3-yl)ethylamino]methyl]-1,3-thiazole-5-carboxylate 167850865 [36]
Z3517967757 structure.png Z3517967757 4-[1-(1-pyrimidin-2-ylethyl)piperidin-3-yl]phenol 167949972 [36]
Z3881312504 structure.png Z38813125042-bromo-4-[2-[methyl-[2-(1,3-thiazol-2-yl)ethyl]amino]ethyl]phenol 167904469 [36]
Z4154032166 structure.png Z41540321662,2,2-trifluoro-1-[6-(1,2,3,6-tetrahydropyridin-5-yl)pyridin-2-yl]ethanol 167878716 [36]
Z5247692566 structure.png Z52476925664-[(3,3-dimethyloxolan-2-yl)methyl]-3-[(1H-indol-3-yl)methyl]morpholine [36]
Z5247692629 structure.png Z52476926291-(1-bicyclo[1.1.1]pentanyl)-4-[[5-(4-chlorophenyl)-1H-pyrazol-4-yl]methyl]piperazine 166358273 [36]

See also

Related Research Articles

<span class="mw-page-title-main">Psilocin</span> Chemical compound

Psilocin is a substituted tryptamine alkaloid and a serotonergic psychedelic substance. It is present in most psychedelic mushrooms together with its phosphorylated counterpart psilocybin. Psilocin is a Schedule I drug under the Convention on Psychotropic Substances. Acting on the 5-HT2A receptors, psilocin modulates the production and reuptake of serotonin. The mind-altering effects of psilocin are highly variable and subjective and resemble those of LSD and DMT.

<span class="mw-page-title-main">2C-B-FLY</span> Psychedelic designer drug

2C-BFLY 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.

5-HT<sub>2A</sub> receptor Subtype of serotonin receptor

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.

<span class="mw-page-title-main">Serotonin receptor agonist</span> Neurotransmission-modulating substance

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.

<span class="mw-page-title-main">TCB-2</span> Potent hallucinogenic drug discovered in 2006

TCB-2 is a hallucinogen discovered in 2006 by Thomas McLean working in the lab of David Nichols at Purdue University. It is a conformationally-restricted derivative of the phenethylamine 2C-B, also a hallucinogen, and acts as a potent agonist for the 5-HT2A and 5-HT2C receptors with a Ki of 0.26 nM at the human 5-HT2A receptor. In drug-substitution experiments in rats, TCB-2 was found to be of similar potency to both LSD and Bromo-DragonFLY, ranking it among the most potent phenethylamine hallucinogens yet discovered. This high potency and selectivity has made TCB-2 useful for distinguishing 5-HT2A mediated responses from those produced by other similar receptors. TCB-2 has similar but not identical effects in animals to related phenethylamine hallucinogens such as DOI, and has been used for studying how the function of the 5-HT2A receptor differs from that of other serotonin receptors in a number of animal models, such as studies of cocaine addiction and neuropathic pain.

<span class="mw-page-title-main">YM-348</span> Chemical compound

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.

<span class="mw-page-title-main">PNU-22394</span> Chemical compound

PNU-22394 is a drug which acts as an agonist at serotonin 5-HT2 receptors, with strongest binding affinity for 5-HT2A and 5-HT2C and slightly weaker at 5-HT2B, although it is only a full agonist at 5-HT2C, but partial agonist at 5-HT2A and 5-HT2B. It has anorectic effects in both animal studies and human trials, along with "Pro-Cognitive Properties", although it has never been developed for medical use.

<span class="mw-page-title-main">Adatanserin</span> Chemical compound

Adatanserin is a mixed 5-HT1A receptor partial agonist and 5-HT2A and 5-HT2C receptor antagonist. It was under development by Wyeth as an antidepressant but was ultimately not pursued.

<span class="mw-page-title-main">SB-206553</span> Chemical compound

SB-206553 is a drug which acts as a mixed antagonist for the 5-HT2B and 5-HT2C serotonin receptors. It has anxiolytic properties in animal studies and interacts with a range of other drugs. It has also been shown to act as a positive allosteric modulator of α7 nicotinic acetylcholine receptors. Modified derivatives of SB-206553 have been used to probe the structure of the 5-HT2B receptor.

<span class="mw-page-title-main">Substituted tryptamine</span> Class of indoles

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.

<span class="mw-page-title-main">5-MeO-NBpBrT</span> Chemical compound

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.

5-HT2C receptor agonists are a class of drugs that activate 5-HT2C receptors. They have been investigated for the treatment of a number of conditions including obesity, psychiatric disorders, sexual dysfunction and urinary incontinence.

<span class="mw-page-title-main">PNU-181731</span> Chemical compound

PNU-181731 is a drug which acts as an agonist at serotonin 5-HT2 receptors, with strongest binding affinity for the 5-HT2C subtype at 4.8nM, and weaker 5-HT2A affinity of 18nM. It has anxiolytic effects in animal studies with around one tenth the potency of alprazolam and no significant ataxia or other side effects noted.

<span class="mw-page-title-main">PHA-57378</span> Chemical compound

PHA-57378 is a drug which acts as an agonist at serotonin 5-HT2 receptors, having a binding affinity of 4.1 nM at the 5-HT2A subtype and 4.3 nM at 5-HT2C. It has anxiolytic effects in animal studies.

<span class="mw-page-title-main">25CN-NBOH</span> Chemical compound

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.

<span class="mw-page-title-main">1-Methylpsilocin</span> Chemical compound

1-Methylpsilocin is a tryptamine derivative which acts as a selective agonist for the 5-HT2C receptor (IC50 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 are dependent on 5-HT2A, so it is not entirely free of effects on 5-HT2A in vivo. In contrast to psilocin, 1-methylpsilocin did not activate 5-HT1A receptors in mice. 1-Methylpsilocin has been investigated for applications such as treatment of glaucoma, OCD, and cluster headaches, as these conditions are amenable to treatment with psychedelic drugs but are not generally treated with such agents due to the hallucinogenic side effects they produce, which are considered undesirable. 1-Methylpsilocin therefore represents a potential alternative treatment to psilocin that may be less likely to produce hallucinogenic effects.

<span class="mw-page-title-main">2C-B-BUTTERFLY</span> Chemical compound

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.

<span class="mw-page-title-main">25-NB</span> Family of serotonergic psychedelics

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.

<span class="mw-page-title-main">CPD-1</span> Drug

CPD-1 (LS-193743) is a drug with a benzofuranyl piperazine structure, which acts as a potent and selective agonist for the 5-HT2 receptor family, with highest affinity and full agonist efficacy at the 5-HT2C subtype, and lower affinity and partial agonist action at the 5-HT2A and 5-HT2B subtypes.

<span class="mw-page-title-main">CYB210010</span>

CYB210010 (2C-T-TFM) is a lesser-known psychedelic drug related to compounds such as 2C-T-21. Alexander Shulgin attempted to synthesise this compound in the 1990s, and mentions it in his book PiHKAL under the entry for 2C-T-21, but was unsuccessful in producing a key intermediate and never assigned it a 2C-T number. This compound was ultimately first synthesised by Geoffrey Varty and colleagues at Irish biopharmaceutical company Cybin in 2023. It has a Ki of 0.35 nM at 5-HT2A, and an EC50 of 4.1 nM at 5-HT2A and 7.3 nM at 5-HT2C, compared to 88 nM at 5-HT2B. It is a potent, selective, long acting and orally active agonist for the 5-HT2A and 5-HT2C receptors and produces psychedelic-like responding in several different animal species. It is not known to have been tested in humans.

References

  1. ↑ Nichols DE (2018). "Chemistry and Structure-Activity Relationships of Psychedelics". Current Topics in Behavioral Neurosciences. 36: 1–43. doi:10.1007/7854_2017_475. ISBN   978-3-662-55878-2. PMID   28401524.
  2. ↑ Duan W, Cao D, Wang S, Cheng J (January 2024). "Serotonin 2A Receptor (5-HT2AR) Agonists: Psychedelics and Non-Hallucinogenic Analogues as Emerging Antidepressants". Chemical Reviews. 124 (1): 124–163. doi:10.1021/acs.chemrev.3c00375. PMID   38033123. S2CID   265512698.
  3. 1 2 3 Ennis MD, Hoffman RL, Ghazal NB, Olson RM, Knauer CS, Chio CL, et al. (July 2003). "2,3,4,5-tetrahydro- and 2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indoles: new templates for 5-HT(2C) agonists". Bioorganic & Medicinal Chemistry Letters. 13 (14): 2369–2372. doi:10.1016/s0960-894x(03)00403-7. PMID   12824036.
  4. ↑ Smith BM, Smith JM, Tsai JH, Schultz JA, Gilson CA, Estrada SA, et al. (March 2005). "Discovery and SAR of new benzazepines as potent and selective 5-HT(2C) receptor agonists for the treatment of obesity". Bioorganic & Medicinal Chemistry Letters. 15 (5): 1467–1470. doi:10.1016/j.bmcl.2004.12.080. PMID   15713408.
  5. ↑ WO 2009/079765,Slassi A, Isaac M, Xin T, Higgins G, He Z, Sun G, Quach T,"Compounds with activity at the 5-ht2c receptor",published 2 July 2009, assigned to Cascade Therapeutics Inc.
  6. ↑ Jensen AA, Plath N, Pedersen MH, Isberg V, Krall J, Wellendorph P, et al. (February 2013). "Design, synthesis, and pharmacological characterization of N- and O-substituted 5,6,7,8-tetrahydro-4H-isoxazolo[4,5-d]azepin-3-ol analogues: novel 5-HT(2A)/5-HT(2C) receptor agonists with pro-cognitive properties". Journal of Medicinal Chemistry. 56 (3): 1211–1227. doi:10.1021/jm301656h. PMID   23301527.
  7. ↑ WO 2021/076572,Olson DE, Dunlap L, Wagner F, Chytil M, Powell NA,"Ergoline-like compounds for promoting neural plasticity",published 22 April 2021, assigned to The Regents Of The University Of Californiaand Delix Therapeutics, Inc.
  8. ↑ Orr MJ, Cao AB, Wang CT, Gaisin A, Csakai A, Friswold AP, et al. (April 2022). "Discovery of Highly Potent Serotonin 5-HT2 Receptor Agonists Inspired by Heteroyohimbine Natural Products". ACS Medicinal Chemistry Letters. 13 (4): 648–657. doi:10.1021/acsmedchemlett.1c00694. PMC   9014500 . PMID   35450369.
  9. ↑ Yao R, Jensen AA, Bryce-Rogers HP, Schultz-Knudsen K, Zhou L, Hovendal NP, et al. (August 2023). "Identification of 5-HT2 Serotonin Receptor Modulators through the Synthesis of a Diverse, Tropane- and Quinuclidine-alkaloid-Inspired Compound Library". Journal of Medicinal Chemistry. 66 (16): 11536–11554. doi:10.1021/acs.jmedchem.3c01059. PMID   37566000. S2CID   260806387.
  10. 1 2 WO 2004/058722,Teegarden B, Jayakumar H, Strah-Pleynet S,"Diarylamine and arylheteroarylamine pyrazole derivatives as modulators of 5ht2a.",published 15 July 2004, assigned to Arena Pharmaceuticals, Inc.
  11. ↑ US 2021/0137908,Kristensen JL, Jensen AA, Märcher-Rørsted E,"5-HT2A Agonists for Use in Treatment of Depression.",published 13 May 2021, assigned to Lophora ApS.
  12. ↑ Evans-Brown M, Gallegos A, Christie R, Jorge R, De Morais J, Almeida A, Sedefov R, et al. (European Monitoring Center for Drugs and Drug Addiction) (December 2020). New Psychoactive Substances: Global Markets, Glocal Threats and the COVID-19 Pandemic. An update from the EU Early Warning System (PDF). Luxembourg: Publications Office of the European Union. doi:10.2810/921262. ISBN   978-92-9497-557-7.
  13. ↑ Glennon RA, Bondarev ML, Khorana N, Young R, May JA, Hellberg MR, et al. (November 2004). "Beta-oxygenated analogues of the 5-HT2A serotonin receptor agonist 1-(4-bromo-2,5-dimethoxyphenyl)-2-aminopropane". Journal of Medicinal Chemistry. 47 (24): 6034–41. doi:10.1021/jm040082s. PMID   15537358.
  14. ↑ Rorsted EM, et al. Discovery and Structure–Activity Relationships of 2,5-Dimethoxyphenylpiperidines as Selective Serotonin 5-HT2A Receptor Agonists. J Med Chem 2024. doi : 10.1021/acs.jmedchem.4c00082
  15. ↑ Lyon RA, Titeler M, McKenney JD, Magee PS, Glennon RA (May 1986). "Synthesis and evaluation of phenyl- and benzoylpiperazines as potential serotonergic agents". Journal of Medicinal Chemistry. 29 (5): 630–634. doi:10.1021/jm00155a008. PMID   3701781.
  16. ↑ Walterscheid JP, Nghiem DX, Kazimi N, Nutt LK, McConkey DJ, Norval M, Ullrich SE (November 2006). "Cis-urocanic acid, a sunlight-induced immunosuppressive factor, activates immune suppression via the 5-HT2A receptor". Proceedings of the National Academy of Sciences of the United States of America. 103 (46): 17420–17425. doi: 10.1073/pnas.0603119103 . PMC   1859944 . PMID   17085585.
  17. ↑ Shen L, Ji HF (September 2009). "Molecular basis for cis-urocanic acid as a 5-HT(2A) receptor agonist". Bioorganic & Medicinal Chemistry Letters. 19 (18): 5307–5309. doi:10.1016/j.bmcl.2009.07.143. PMID   19683920.
  18. ↑ Menezes AC, Raposo S, Simões S, Ribeiro H, Oliveira H, Ascenso A (March 2016). "Prevention of Photocarcinogenesis by Agonists of 5-HT1A and Antagonists of 5-HT2A Receptors". Molecular Neurobiology. 53 (2): 1145–1164. doi:10.1007/s12035-014-9068-z. PMID   25589005. S2CID   14282500.
  19. ↑ Ahmed A, Choo H, Cho YS, Park WK, Pae AN (July 2009). "Identification of novel serotonin 2C receptor ligands by sequential virtual screening". Bioorganic & Medicinal Chemistry. 17 (13): 4559–4568. doi:10.1016/j.bmc.2009.05.003. PMID   19464901.
  20. ↑ Gatch MB, Kozlenkov A, Huang RQ, Yang W, Nguyen JD, González-Maeso J, et al. (November 2013). "The HIV antiretroviral drug efavirenz has LSD-like properties". Neuropsychopharmacology. 38 (12): 2373–2384. doi:10.1038/npp.2013.135. PMC   3799056 . PMID   23702798.
  21. 1 2 Cao D, Yu J, Wang H, Luo Z, Liu X, He L, et al. (January 2022). "Structure-based discovery of nonhallucinogenic psychedelic analogs". Science. 375 (6579): 403–411. Bibcode:2022Sci...375..403C. doi:10.1126/science.abl8615. PMID   35084960. S2CID   246360313.
  22. ↑ "Analytical Report NDTDI" (PDF). Nacionalni Forenzični Laboratorij. Slovenia. June 2017.
  23. ↑ Janowsky A, Eshleman AJ, Johnson RA, Wolfrum KM, Hinrichs DJ, Yang J, et al. (July 2014). "Mefloquine and psychotomimetics share neurotransmitter receptor and transporter interactions in vitro". Psychopharmacology. 231 (14): 2771–2783. doi:10.1007/s00213-014-3446-0. PMC   4097020 . PMID   24488404.
  24. ↑ Porter RH, Benwell KR, Lamb H, Malcolm CS, Allen NH, Revell DF, et al. (September 1999). "Functional characterization of agonists at recombinant human 5-HT2A, 5-HT2B and 5-HT2C receptors in CHO-K1 cells". British Journal of Pharmacology. 128 (1): 13–20. doi:10.1038/sj.bjp.0702751. PMC   1571597 . PMID   10498829.
  25. ↑ Knight AR, Misra A, Quirk K, Benwell K, Revell D, Kennett G, Bickerdike M (August 2004). "Pharmacological characterisation of the agonist radioligand binding site of 5-HT(2A), 5-HT(2B) and 5-HT(2C) receptors". Naunyn-Schmiedeberg's Archives of Pharmacology. 370 (2): 114–123. doi:10.1007/s00210-004-0951-4. PMID   15322733. S2CID   8938111.
  26. ↑ Carlsson ML, Burstein ES, Kloberg A, Hansson S, Schedwin A, Nilsson M, et al. (November 2011). "I. In vivo evidence for partial agonist effects of (-)-OSU6162 and (+)-OSU6162 on 5-HT2A serotonin receptors". Journal of Neural Transmission. 118 (11): 1511–1522. doi:10.1007/s00702-011-0704-8. PMID   21874578. S2CID   43580367.
  27. ↑ WO 2023115165,Banister S, Jorgensen W, Jinlong T,"Compounds",published 29 June 2023, assigned to Psylo Pty Ltd.
  28. ↑ Kaplan AL, Confair DN, Kim K, Barros-Álvarez X, Rodriguiz RM, Yang Y, et al. (October 2022). "Bespoke library docking for 5-HT2A receptor agonists with antidepressant activity". Nature. 610 (7932): 582–591. Bibcode:2022Natur.610..582K. doi:10.1038/s41586-022-05258-z. PMC   9996387 . PMID   36171289. S2CID   252598838.
  29. ↑ Kargbo RB (November 2023). "Small-Molecule Heterocyclic Compounds: Gq-Biased Agonists for the 5-HT2A Receptor in Neuropsychiatric Treatment". ACS Medicinal Chemistry Letters. 14 (11): 1498–1500. doi:10.1021/acsmedchemlett.3c00444. PMC  10641896. PMID   37974947.
  30. ↑ WO 2023114472,Manish J, Slocum S, Skiniotis G, Barros X, Jin J, Kaniskan HU, Sun N, Xiong Y, Shen Y, Xu Z, Qui X, Qian C, Song X, Deng Z, Roth B, Biberto J, Kuglae K, Suomivuori CM, Daemgen MA, Dror R, Shoichet B, Kaplan AL,published 22 June 2023 title = Heterocyclic compounds as 5ht2a biased agonists., assigned to Icahn School Of Medicine at Mount Sinai, The University Of North Carolina at Chapel Hill, The Board of Trustees of The Leland Stanford Junior University, The Regents Of The University Of California
  31. ↑ Silva ME, Heim R, Strasser A, Elz S, Dove S (January 2011). "Theoretical studies on the interaction of partial agonists with the 5-HT2A receptor". Journal of Computer-Aided Molecular Design. 25 (1): 51–66. Bibcode:2011JCAMD..25...51S. CiteSeerX   10.1.1.688.2670 . doi:10.1007/s10822-010-9400-2. PMID   21088982. S2CID   3103050.
  32. ↑ WO 2007149728,Mohapatra S, Hellberg MR, Feng Z,"Aryl and heteroaryl tetrahydrobenzazepine derivatives and their use for treating glaucoma", assigned to Alcon Manufacturing, Ltd.
  33. ↑ Cameron LP, Tombari RJ, Lu J, Pell AJ, Hurley ZQ, Ehinger Y, et al. (January 2021). "A non-hallucinogenic psychedelic analogue with therapeutic potential". Nature. 589 (7842): 474–479. Bibcode:2021Natur.589..474C. doi:10.1038/s41586-020-3008-z. PMC   7874389 . PMID   33299186.
  34. ↑ WO 2007/025144,Kozikowski A, Kurome T, Setola V, Roth B,"5-ht2c receptor agonists as anorectic agents",published 1 March 2007, assigned to University Of Illinois - Chicago
  35. ↑ Sabb AL, Vogel RL, Welmaker GS, Sabalski JE, Coupet J, Dunlop J, Rosenzweig-Lipson S, Harrison B (May 2004). "Cycloalkyl[b][1,4]benzodiazepinoindoles are agonists at the human 5-HT2C receptor". Bioorganic & Medicinal Chemistry Letters. 14 (10): 2603–7. doi:10.1016/j.bmcl.2004.02.100. PMID   15109661.
  36. 1 2 3 4 5 6 7 8 Lyu J, Kapolka N, Gumpper R, Alon A, Wang L, Jain MK, et al. (December 2023). "AlphaFold2 structures template ligand discovery". bioRxiv. doi:10.1101/2023.12.20.572662. PMC   10769324 . PMID   38187536.
This page is based on this Wikipedia article
Text is available under the CC BY-SA 4.0 license; additional terms may apply.
Images, videos and audio are available under their respective licenses.