DASB

DASB
Identifiers
DASB (above) and [C-11]DASB
Radioactive carbon atom marked in cyan
IUPAC name 3-amino-4-[2-[(di(methyl)amino)methyl]phenyl]sulfanylbenzonitrile
CAS Number	627490-01-1^N 11C-labelled: 296774-13-5
PubChem (CID)	10446567 11C-labelled: CID 656408
ChemSpider	8621986^N 11C-labelled: 570800
UNII	PP549Z0645^N 11C-labelled: FJU46Q2BPU
Chemical and physical data
Formula	C₁₆H₁₇N₃S
Molar mass	282.392014 g/mol
3D model (Jmol)	Interactive image
SMILES N#Cc2ccc(Sc1c(cccc1)CN(C)C)c(c2)N 11C-labelled: [11CH3]N(C)Cc1ccccc1Sc2ccc(cc2N)C#N
InChI InChI=1S/C16H17N3S/c1-19(2)11-13-5-3-4-6-15(13)20-16-8-7-12(10-17)9-14(16)18/h3-9H,11,18H2,1-2H3^N Key:UVWLEPXXYOYDGR-UHFFFAOYSA-N^N 11C-labelled: InChI=1S/C16H17N3S/c1-19(2)11-13-5-3-4-6-15(13)20-16-8-7-12(10-17)9-14(16)18/h3-9H,11,18H2,1-2H3/i1-1^N Key:UVWLEPXXYOYDGR-BJUDXGSMSA-N^N
^NY (what is this?) (verify)

DASB, 3-amino-4-(2-dimethylaminomethylphenylsulfanyl)-benzonitrile, is a compound that binds to the serotonin transporter. Labeled with carbon-11 — a radioactive isotope — it has been used as a radioligand in neuroimaging with positron emission tomography (PET) since around year 2000.^[1] In this context it is regarded as one of the superior radioligands for PET study of the serotonin transporter in the brain,^[2] since it has high selectivity for the serotonin transporter.^[3]

The DASB image from a human PET scan shows high binding in the midbrain, thalamus and striatum, moderate binding in the medial temporal lobe and anterior cingulate, and low binding in neocortex. The cerebellum is often regarded as a region with no specific serotonin transporter binding and the brain region is used as a reference in some studies.^[4]

Since the serotonin transporter is the target of SSRIs used in the treatment of major depression it has been natural to examine DASB binding in depressed patients. Several such research studies have been performed.^[5]

There are a number of alternative PET radioligands for imaging the serotonin transporter: [¹¹C]ADAM, [¹¹C]AFM, [¹¹C]DAPA, [¹¹C]McN5652, and [¹¹C]-NS 4194. A related molecule to DASB, that can be labeled with fluorine-18, has also been suggested as a PET radioligand.^[6] With single-photon emission computed tomography (SPECT) using the radioisotope iodine-123 there are further radioligands available: [¹²³I]ODAM, [¹²³I]IDAM, [¹²³I]ADAM,^[7] and [¹²³I]β-CIT.^[2] A few studies have examined the difference in binding between the radioligands in nonhuman primates,^[8]^[9] as well as in pigs.^[10]

Other compounds that can be labeled to work as PET radioligands for the study of the serotonin system are, e.g., altanserin and WAY-100635.

Methodological issues

The binding potential of DASB can be estimated with kinetic modeling on a series of brain scans.^[11]

A test-retest reproducibility PET study indicates that [¹¹C]DASB can be used to measure the serotonin transporter parameters with high reliability in receptor-rich brain regions.^[4]

When the DASB neuroimages are analyzed the kinetic models suggested by Ichise and coworkers^[12] can be employed to estimate the binding potential. A test-retest reproducibility experiment has been performed to evaluate this approach.^[13]

Studies

Besides the studies listed below a few occupancy studies have been reported.^[5]

DASB binding neuroimaging studies (patients compared to healthy control subjects).
What	Result	Subjects	Ref.
5-HTTLPR L_AL_A serotonin transporter genotype	Increase in putamen	43/30	^[14]
5-HTTLPR L_AL_A serotonin transporter genotype	Increase in midbrain	19	^[15]
5-HTTLPR L_AL_A serotonin transporter genotype	No difference	63	^[16]
Age	No effect found		^[17] (^[2])
Body mass index	Inverse correlation (?)	?	^[18]
Seasonality	Higher in winter in putamen and caudate	54	^[19]
Seasonality	Higher in fall and winter	88	^[20]
NEO PI-R Neuroticism	Positive correlation in thalamus	31 males	^[21]
Disease
Depressed during major depressive episodes	No difference found	20+20	^[17]
Depressed with highly negativistic "dysfunctional attitudes" during major depressive episodes	Increase in prefrontal cortex, anterior cingulate, thalamus, bilateral caudate, and bilateral putamen	20(?)+20	^[17]
Recovered depressed patients	No difference found	24+20 males	^[22]
Unipolar depression	Increase in thalamus, insula and striatum	18+34	^[23]
Unmedicated unipolar major depression	Reduced 5-HTT availability in the thalamus		^[24]
TCI anxiety in unmedicated unipolar major depression	Reduced 5-HTT availability in the thalamus, midbrain and amygdala		^[24]
Bipolar depression	Increase in thalamus, insula and striatum	18+34	^[23]
Bipolar depression	Decrease in midbrain, amygdala, hippocampus, thalamus, putamen, and anterior cingulate cortex	18+41	^[25]
Obsessive compulsive disorder	Reduction and correlation with severity in thalamus and midbrain	9+19	^[26]
Alcoholism	No significant alteration	30 + 18	^[27]
Parkinson's disease	Reduction in forebrain	5+8	^[28]
Non-depressed Parkinson's disease	Decreased binding in caudate, midbrain, putamen, orbitofrontal cortex and (non-significantly) dorsolateral prefrontal cortex		^[29]
Depressed Parkinson's disease patients	Increase in prefrontal and dorsolateral cortices	7+7	^[30]
Drug/intervention
Abstinent MDMA ('Ecstasy') users	Global reduction	23+19	^[31]
Former MDMA users and polydrug users	No significant difference in brain regions examined	12+9+19	^[32]
Reduced synaptic serotonin (by rapid tryptophan depletion)	(small reduction in binding potential)	8	^[33]
Lowering of brain serotonin (by acute tryptophan depletion)	No change observed	25 (14)	^[34]

References

↑ S. Houle; N. Ginovart; D. Hussey; J.H. Meyer; A.A. Wilson (October 2000). "Imaging the serotonin transporter with positron emission tomography: initial human studies with [¹¹C]DAPP and [¹¹C]DASB". European Journal of Nuclear Medicine and Molecular Imaging. 27 (11): 1719–22. doi:10.1007/s002590000365. PMID 11105830.
1 2 3 Peter Brust; Swen Hess; Ulrich Müller; Zsolt Szabo (February 2006). "Neuroimaging of the Serotonin Transporter — Possibilities and Pitfalls" (PDF). Current Psychiatry Reviews. 2 (1): 111–149. doi:10.2174/157340006775101508.
↑ Alan A. Wilson; Nathalie Ginovart; Doug Hussey; Jeff Meyer; Sylvain Houle (July 2002). "In vitro and in vivo characterisation of [¹¹C]-DASB: a probe for in vivo measurements of the serotonin transporter by positron emission tomography". Nuclear Medicine and Biology. 29 (5): 509–515. doi:10.1016/S0969-8051(02)00316-5. PMID 12088720.
1 2 W. Gordon Frankle; Mark Slifstein; Roger N. Gunn; Yiyun Huang; Dah-Ren Hwang; E. Ashlie Darr; Rajesh Narendran; Marc Laruelle (May 1, 2006). "Estimation of Serotonin Transporter Parameters with ¹¹C-DASB in Healthy Humans: Reproducibility and Comparison of Methods". Journal of Nuclear Medicine. 47 (5): 815–826. PMID 16644752.
1 2 Jeffrey H. Meyer (March 2007). "Imaging the serotonin transporter during major depressive disorder and antidepressant treatment". Journal of Psychiatry & Neuroscience. 32 (2): 86–82. PMC 1810585. PMID 17353938.
↑ Sudha Garg; Shankar R. Thopate; Richard C. Minton; Kimberly W. Black; Andrew J. H. Lynch; Pradeep K. Garg (September–October 2007). "3-Amino-4-(2-((4-[18F]fluorobenzyl)methylamino)methylphenylsulfanyl)benzonitrile, an F-18 fluorobenzyl analogue of DASB: synthesis, in vitro binding, and in vivo biodistribution studies". Bioconjug Chem. 18 (5): 1612–1618. doi:10.1021/bc070112g. PMID 17705553.
↑ Oya S, Choi SR, Hou C, et al. (April 2000). "2-((2-((dimethylamino)methyl)phenyl)thio)-5-iodophenylamine (ADAM): an improved serotonin transporter ligand". Nucl. Med. Biol. 27 (3): 249–54. doi:10.1016/s0969-8051(00)00084-6. PMID 10832081.
↑ Zsolt Szabo; Una D. McCann; Alan A. Wilson; Ursula Scheffel; Taofeek Owonikoko; William B. Mathews; Hayden T. Ravert; John Hilton; Robert F. Dannals; George A. Ricaurte (May 1, 2002). "Comparison of (+)-¹¹C-McN5652 and ¹¹C-DASB as Serotonin Transporter Radioligands Under Various Experimental Conditions". Journal of Nuclear Medicine. 43 (5): 678–692. PMC 2078607. PMID 11994534.
↑ Yiyun Huang, Dah-Ren Hwang, Raj Narendran, Yasuhiko Sudo, Rano Chatterjee, Sung-A Bae, Osama Mawlawi, Lawrence S. Kegeles, Alan A. Wilson, Hank F. Kung and Marc Laruelle (2002). "Comparative Evaluation in Nonhuman Primates of Five PET Radiotracers for Imaging the Serotonin Transporters: [¹¹C]McN 5652, [¹¹C]ADAM, [¹¹C]DASB, [¹¹C]DAPA, and [¹¹C]AFM". Journal of Cerebral Blood Flow & Metabolism. 22 (11): 1377–1398. doi:10.1097/00004647-200211000-00011. PMID 12439295.
↑ Svend B. Jensen; Donald F. Smith; Dirk Bender; Steen Jakobsen; Dan Peters; Elsebet Ø. Nielsen; Gunnar M. Olsen; Jørgen Scheel-Krüger; Alan Wilson; Paul Cumming (May 2003). "[¹¹C]-NS 4194 versus [¹¹C]-DASB for PET imaging of serotonin transporters in living porcine brain". Synapse. 49 (3): 170–177. doi:10.1002/syn.10222. PMID 12774301.
↑ Nathalie Ginovart, Alan A. Wilson, Jeffrey H. Meyer, Doug Hussey and Sylvain Houle (2001). "Positron Emission Tomography Quantification of [¹¹C]-DASB Binding to the Human Serotonin Transporter: Modeling Strategies". Journal of Cerebral Blood Flow & Metabolism. 21: 1342–1353. doi:10.1097/00004647-200111000-00010.
↑ Masanori Ichise; Jeih-San Liow; Jian-Qiang Lu; Akihiro Takano; Kendra Model; Hiroshi Toyama; Tetsuya Suhara; Kazutoshi Suzuki; Robert B Innis; Richard E Carson (2003). "Linearized Reference Tissue Parametric Imaging Methods: Application to [¹¹C]DASB Positron Emission Tomography Studies of the Serotonin Transporter in Human Brain". Journal of Cerebral Blood Flow & Metabolism. 23 (9): 1096–1112. doi:10.1097/01.WCB.0000085441.37552.CA. PMID 12973026.
↑ Jae Seung Kim; Masanori Ichise; Janet Sangare; Robert B. Innis (2006 China). "PET Imaging of Serotonin Transporters with [¹¹C]DASB: Test–Retest Reproducibility Using a Multilinear Reference Tissue Parametric Imaging Method". Journal of Nuclear Medicine. 47 (2): 208–214. Check date values in: |date= (help)
↑ Nicole Praschak-Rieder; J. Kennedy; A. Wilson; D. Hussey; A. Boovariwala; M. Willeit; N. Ginovart; S. Tharmalingam; M. Masellis; S. Houle; Jeffrey H. Meyer (August 2007). "Novel 5-HTTLPR allele associates with higher serotonin transporter binding in putamen: a [¹¹C] DASB positron emission tomography study". Biological Psychiatry. 62 (4): 327–331. doi:10.1016/j.biopsych.2006.09.022. PMID 17210141.
↑ M. Reimold, M. N. Smolka, G. Schumann, A. Zimmer, J. Wrase, K. Mann, X.-Z. Hu, D. Goldman, G. Reischl, C. Solbach, H.-J. Machulla, R. Bares1 and A. Heinz (May 2007). "Midbrain serotonin transporter binding potential measured with [¹¹C]DASB is affected by serotonin transporter genotype". Journal of Neural Transmission. 114 (5): 635–9. doi:10.1007/s00702-006-0609-0. PMID 17225932.
↑ Murthy, NV; Selvaraj, S; Cowen, PJ; Bhagwagar, Z; Riedel, WJ; Peers, P; Kennedy, JL; Sahakian, BJ; et al. (August 2010). "Serotonin transporter polymorphisms (SLC6A4 insertion/deletion and rs25531) do not affect the availability of 5-HTT to [11C] DASB binding in the living human brain". NeuroImage. 52 (1): 50–54. doi:10.1016/j.neuroimage.2010.04.032. PMID 20406689.
1 2 3 Jeffrey H. Meyer; Sylvain Houle; Sandra Sagrati; Anna Carella; Doug F. Hussey; Nathalie Ginovart; Verdell Goulding; James Kennedy; Alan A. Wilson (December 2004). "Brain Serotonin Transporter Binding Potential Measured With Carbon 11–Labeled DASB Positron Emission Tomography. Effects of Major Depressive Episodes and Severity of Dysfunctional Attitudes". Archives of General Psychiatry. 61 (12): 1271–9. doi:10.1001/archpsyc.61.12.1271. PMID 15583118.
↑ Ryohei Matsumoto; H. Ito; H. Takahashi; H. Takano; T. Suhara (2008). "Inverse correlation between body mass index and serotonin transporter binding in human brain: A [¹¹C]DASB PET study". NeuroImage. 2, supplement 2: T161. doi:10.1016/j.neuroimage.2008.04.128. Neuroreceptor Mapping 2008, The Seventh International Symposium on Functional Neuroreceptor Mapping of Living Brain
↑ Jan Kalbitzer; David Erritzoe; Klaus K. Holst; Finn Å. Nielsen; Lisbeth Marner; Szabolcs Lehel; Tine Arentzen; Terry L. Jernigan; & Gitte M. Knudsen (28 January 2010). "Seasonal changes in brain serotonin transporter binding in short 5-HTTLPR-allele carriers but not in long-allele homozygotes". Biological Psychiatry. 67 (11): 1033–1039. doi:10.1016/j.biopsych.2009.11.027. PMID 20110086.
↑ Nicole Praschak-Rieder; Matthaeus Willeit; Alan A. Wilson; Sylvain Houle (September 2008). "Seasonal variation in human brain serotonin transporter binding". Archives of General Psychiatry. 65 (9): 1072–1078. doi:10.1001/archpsyc.65.9.1072. PMID 18762593.
↑ Akihiro Takano; Ryosuke Arakawaa; Mika Hayashia; Hidehiko Takahashia; Tetsuya Suhara (September 2007). "Relationship between neuroticism personality trait and serotonin transporter binding". Biological Psychiatry. 62 (6): 588–592. doi:10.1016/j.biopsych.2006.11.007. PMID 17336939.
↑ Zubin Bhagwagar; Naga Murthy; Sudhakar Selvaraj; Rainer Hinz; Matthew Taylor; Sabrina Fancy; Paul Grasby; Philip Cowen (December 2007). "5-HTT Binding in Recovered Depressed Patients and Healthy Volunteers: A Positron Emission Tomography Study With [11C]DASB". The American Journal of Psychiatry. 164 (12): 1858–1865. doi:10.1176/appi.ajp.2007.06111933. PMID 18056241.
1 2 Dara M. Cannon, Masanori Ichise, Denise Rollis, Jacqueline M. Klaver, Shilpa K. Gandhi, Dennis S. Charney, Husseini K. Manji and Wayne C. Drevets (October 2007). "Elevated serotonin transporter binding in major depressive disorder assessed using positron emission tomography and [¹¹C]DASB; comparison with bipolar disorder". Biological Psychiatry. 62 (8): 870–877. doi:10.1016/j.biopsych.2007.03.016. PMID 17678634.
1 2 Matthias Reimold; Batra A; Knobel A; Smolka MN; Zimmer A; Mann K; Solbach C; Reischl G; Schwärzler F; Gründer G; Machulla HJ; Bares R; A. Heinz (2008). "Anxiety is associated with reduced central serotonin transporter availability in unmedicated patients with unipolar major depression: a [¹¹C]DASB PET study". Molecular Psychiatry. 13 (6): 606–13, 557. doi:10.1038/sj.mp.4002149. PMID 18268503. . Electronic publication
↑ Maria A. Oquendo; Ramin S. Hastings; Yung-yu Huang; Norman Simpson; R. Todd Ogden; Xian-zhang Hu; David Goldman; Victoria Arango; Ronald L. Van Heertum; J. John Mann; Ramin V. Parsey (February 2007). "Brain Serotonin Transporter Binding in Depressed Patients With Bipolar Disorder Using Positron Emission Tomography". Archives of General Psychiatry. 64 (2): 201–208. doi:10.1001/archpsyc.64.2.201. PMID 17283287.
↑ M. Reimold; M. N. Smolka; A. Zimmer; A. Batra; A. Knobel; C. Solbach; A. Mundt; H. U. Smoltczyk; D. Goldman; K. Mann; G. Reischl; H.-J. Machulla; R. Bares; A. Heinz (December 2007). "Reduced availability of serotonin transporters in obsessive-compulsive disorder correlates with symptom severity - a [¹¹C]DASB PET study". Journal of Neural Transmission. 114 (12): 1603–1609. doi:10.1007/s00702-007-0785-6. PMID 17713719.
↑ Amira K. Brown; David T. George; Masahiro Fujita; Jeih-San Liow; Masanori Ichise; Joseph Hibbeln; Subroto Ghose; Janet Sangare; Daniel Hommer; Robert B. Innis (January 2007). "PET [¹¹C]DASB imaging of serotonin transporters in patients with alcoholism". Alcohol Clin Exp Res. 31 (1): 28–32. doi:10.1111/j.1530-0277.2006.00261.x. PMID 17207098.
↑ Roger L Albin; Robert A. Koeppe; Nicolaas I. Bohnen; Kristine Wernette; Michael A. Kilbourn; Kirk A. Frey (2008). "Spared caudal brainstem SERT binding in early Parkinson's disease". Journal of Cerebral Blood Flow & Metabolism. 28 (3): 441–444. doi:10.1038/sj.jcbfm.9600599. PMID 18073772.
↑ M. Guttman; I. Boileau; J. Warsh; J. A. Saint-Cyr; N. Ginovart; T. McCluskey; S. Houle; A. Wilson; E. Mundo; P. Rusjan; J. Meyer (May 2007). "Brain serotonin transporter binding in non-depressed patients with Parkinson's disease". European Journal of Neurology. 14 (5): 523–528. doi:10.1111/j.1468-1331.2007.01727.x. PMID 17437611.
↑ Isabelle Boileau; Jerry J. Warsh; Mark Guttman; Jean A. Saint-Cyr; Tina McCluskey; Pablo Rusjan; Sylvain Houle; Alan A. Wilson; Jeffrey H. Meyer; Stephen J. Kish (July 2008). "Elevated serotonin transporter binding in depressed patients with Parkinson's disease: A preliminary PET study with [(11)C]DASB". Movement Disorders. 23 (12): 1776–80. doi:10.1002/mds.22212. PMID 18661545.
↑ Una D McCann; Zsolt Szabo; Esen Seckin; Peter Rosenblatt; William B Mathews; Hayden T Ravert; Robert F Dannals; George A Ricaurte (2005). "Quantitative PET Studies of the Serotonin Transporter in MDMA Users and Controls Using [¹¹C]McN5652 and [¹¹C]DASB". Neuropsychopharmacology. 30 (9): 1741–1750. doi:10.1038/sj.npp.1300736. PMC 2034411. PMID 15841106.
↑ Sudhakar Selvaraj; Rosa Hoshi; Zubin Bhagwagar; Naga Venkatesha Murthy; Rainer Hinz; Philip Cowen; H. Valerie Curran; Paul Grasby (2009). "Brain serotonin transporter binding in former users of MDMA ('ecstasy')". The British Journal of Psychiatry. 194 (4): 355–359. doi:10.1192/bjp.bp.108.050344. PMID 19336788.
↑ Peter S. Talbot, W. Gordon Frankle, Dah-Ren Hwang, Yiyun Huang, Raymond F. Suckow, Mark Slifstein, Anissa Abi-Dargham & Marc Laruelle (2004). "Effects of reduced endogenous 5-HT on the in vivo binding of the serotonin transporter radioligand ¹¹C-DASB in healthy humans". Synapse. 55 (3): 164–175. doi:10.1002/syn.20105. PMID 15605360.
↑ Nicole Praschak-Riedera; Alan A. Wilson; Douglas Hussey; Anna Carella; Corie Wei; Nathalie Ginovart; Markus J. Schwarz; Johanna Zach; et al. (November 2005). "Effects of Tryptophan Depletion on the Serotonin Transporter in Healthy Humans". Biological Psychiatry. 58 (10): 825–830. doi:10.1016/j.biopsych.2005.04.038. PMID 16026765.

Serotonin receptor modulators

5-HT₁ receptors

5-HT_1A

Agonists: 8-OH-DPAT Adatanserin Amphetamine Antidepressants (e.g., etoperidone, nefazodone, trazodone, vilazodone, vortioxetine) Atypical antipsychotics (e.g., aripiprazole, asenapine, clozapine, lurasidone, quetiapine, ziprasidone) Azapirones (e.g., buspirone, eptapirone, gepirone, perospirone, tandospirone) Bay R 1531 Befiradol BMY-14802 Cannabidiol Dimemebfe Dopamine Ebalzotan Eltoprazine Ergolines (e.g., bromocriptine, cabergoline, dihydroergotamine, ergotamine, lisuride, LSD, methylergometrine (methylergonovine), methysergide, pergolide) F-11461 F-12826 F-13714 F-14679 F-15063 F-15599 Flesinoxan Flibanserin Flumexadol Lesopitron LY-293284 LY-301317 mCPP MKC-242 Naluzotan NBUMP Osemozotan Oxaflozane Pardoprunox Piclozotan Rauwolscine Repinotan Roxindole RU-24969 S-14506 S-14671 S-15535 Sarizotan Serotonin (5-HT) SSR-181507 Sunepitron Tryptamines (e.g., 5-CT, 5-MeO-DMT, 5-MT, bufotenin, DMT, indorenate, N-Me-5-HT, psilocin, psilocybin) TGBA01AD U-92016A Urapidil Vilazodone Xaliproden Yohimbine

Antagonists: Atypical antipsychotics (e.g., iloperidone, risperidone, sertindole) AV965 Beta blockers (e.g., alprenolol, cyanopindolol, iodocyanopindolol, oxprenolol, pindobind, pindolol, propranolol, tertatolol) BMY-7378 CSP-2503 Dotarizine Ergolines (e.g., metergoline) Flopropione GR-46611 Isamoltane Lecozotan Mefway Metitepine (methiothepin) MIN-117 (WF-516) MPPF NAN-190 Robalzotan S-15535 SB-649915 SDZ 216-525 Spiperone Spiramide Spiroxatrine UH-301 WAY-100135 WAY-100635 Xylamidine

Unknown/unsorted: Ergolines (e.g., ergometrine (ergonovine))

5-HT_1B

Agonists: CGS-12066A CP-93129 CP-94253 CP-122,288 CP-135807 Eltoprazine Ergolines (e.g., bromocriptine, dihydroergotamine, ergotamine, methylergometrine (methylergonovine), methysergide, pergolide) mCPP RU-24969 Serotonin (5-HT) Triptans (e.g., avitriptan, donitriptan, eletriptan, sumatriptan, zolmitriptan) TFMPP Tryptamines (e.g., 5-BT, 5-CT, 5-MT, DMT) Vortioxetine

Antagonists: AR-A000002 Elzasonan Ergolines (e.g., metergoline) GR-127935 Isamoltane LY-393558 Metitepine (methiothepin) SB-216641 SB-224289 SB-236057 Yohimbine

Unknown/unsorted: Ergolines (e.g., cabergoline, ergometrine (ergonovine), lisuride)

5-HT_1D

Agonists: CP-122,288 CP-135807 CP-286601 Ergolines (e.g., bromocriptine, cabergoline, dihydroergotamine, ergotamine, LSD, methysergide) GR-46611 L-694247 L-772405 mCPP PNU-109291 PNU-142633 Serotonin (5-HT) TGBA01AD Triptans (e.g., almotriptan, avitriptan, donitriptan, eletriptan, frovatriptan, naratriptan, rizatriptan, sumatriptan, zolmitriptan) Tryptamines (e.g., 5-BT, 5-CT, 5-Et-DMT, 5-MT, 5-(nonyloxy)tryptamine, DMT)

Antagonists: Alniditan BRL-15572 Elzasonan Ergolines (e.g., metergoline) GR-127935 Ketanserin LY-310762 LY-367642 LY-393558 LY-456219 LY-456220 Metitepine (methiothepin) Mianserin Ritanserin Yohimbine Ziprasidone

Unknown/unsorted: Ergolines (e.g., lisuride, lysergol, pergolide)

5-HT_1E

Agonists: BRL-54443 Ergolines (e.g., methysergide) Serotonin (5-HT) Triptans (e.g., eletriptan) Tryptamines (e.g., tryptamine)

Antagonists: Metitepine (methiothepin)

Unknown/unsorted: Ergolines (e.g., ergometrine (ergonovine), lysergol, methylergometrine (methylergonovine)

5-HT_1F

Agonists: BRL-54443 CP-122,288 Ergolines (e.g., bromocriptine, lysergol, methylergometrine (methylergonovine) methysergide) Lasmiditan LY-334370 Serotonin (5-HT) Triptans (e.g., eletriptan, naratriptan, sumatriptan) Tryptamines (e.g., 5-MT)

Antagonists: Mianserin Metitepine (methiothepin)

5-HT₂ receptors

5-HT_2A

Agonists: 25H/NB series (e.g., 25I-NBF, 25I-NBMD, 25I-NBOH, 25I-NBOMe, 25B-NBOMe, 25C-NBOMe, 25TFM-NBOMe, 2CBCB-NBOMe, 25CN-NBOH, 2CBFly-NBOMe) 2Cs (e.g., 2C-B, 2C-E, 2C-I, 2C-T-2, 2C-T-7, 2C-T-21) 2C-B-FLY 2CB-Ind 5-Methoxytryptamines (5-MeO-DET, 5-MeO-DiPT, 5-MeO-DMT, 5-MeO-DPT, 5-MT) α-Alkyltryptamines (e.g., 5-Cl-αMT, 5-Fl-αMT, 5-MeO-αET, 5-MeO-αMT, α-Me-5-HT, αET, αMT) AL-34662 AL-37350A Bromo-DragonFLY Dimemebfe DMBMPP DOx (e.g., DOB, DOC, DOI, DOM) Efavirenz Ergolines (e.g., 1P-LSD, ALD-52, bromocriptine, cabergoline, ergine (LSA), ergotamine, lisuride, LA-SS-Az, LSB, LSD, LSD-Pip, LSH, LSP, methylergometrine (methylergonovine), pergolide) Flumexadol Jimscaline Lorcaserin MDxx (e.g., MDA, MDMA, MDOH, MMDA) O-4310 Oxaflozane PHA-57378 PNU-22394 PNU-181731 RH-34 Phenethylamines (e.g., lophophine, mescaline) Piperazines (e.g., BZP, mCPP, quipazine, TFMPP) Serotonin (5-HT) TCB-2 TFMFly Tryptamines (e.g., 5-BT, 5-CT, bufotenin, DET, DiPT, DMT, DPT, psilocin, psilocybin, tryptamine)

Antagonists: 5-I-R91150 5-MeO-NBpBrT AC-90179 Adatanserin Altanserin AMDA APD-215 Atypical antipsychotics (e.g., amperozide, aripiprazole, asenapine, blonanserin, carpipramine, clocapramine, clorotepine, clozapine, fluperlapine, gevotroline, iloperidone, melperone, mosapramine, ocaperidone, olanzapine, paliperidone, quetiapine, risperidone, sertindole, zicronapine, ziprasidone, zotepine) Cinanserin CSP-2503 Cyproheptadine Deramciclane Dotarizine Eplivanserin Ergolines (e.g., amesergide, LY-53857, LY-215840, mesulergine, metergoline, methysergide, sergolexole) Etoperidone Fananserin Flibanserin Glemanserin Irindalone Ketanserin KML-010 Lubazodone LY-393558 Medifoxamine Mepiprazole Metitepine (methiothepin) MIN-101 Naftidrofuryl Nantenine Nefazodone Pelanserin Phenoxybenzamine Pimavanserin Pirenperone Pizotifen Pruvanserin Rauwolscine Ritanserin S-14671 Sarpogrelate Setoperone Spiperone Spiramide SR-46349B TGBA01AD Teniloxazine Temanogrel Tetracyclic antidepressants (e.g., amoxapine, aptazapine, esmirtazapine, maprotiline, mianserin, mirtazapine) Trazodone Tricyclic antidepressants (e.g., amitriptyline) Typical antipsychotics (e.g., chlorpromazine, fluphenazine, haloperidol, loxapine, perphenazine, pimozide, pipamperone, prochlorperazine, thioridazine, thiothixene, trifluoperazine) Volinanserin Xylamidine Yohimbine

Unknown/unsorted: Ergolines (e.g., dihydroergotamine, ergometrine (ergonovine), nicergoline) MIN-117 (WF-516)

5-HT_2B

Agonists: 4-Methylaminorex Aminorex Amphetamines (eg., chlorphentermine, cloforex, dexfenfluramine, fenfluramine, levofenfluramine, norfenfluramine) BW-723C86 DOx (e.g., DOB, DOC, DOI, DOM) Ergolines (e.g., cabergoline, dihydroergocryptine, dihydroergotamine, ergotamine, methylergometrine (methylergonovine), methysergide, pergolide) MDxx (e.g., MDA, MDMA, MDOH, MMDA) Piperazines (e.g., mCPP) PNU-22394 Ro60-0175 Serotonin (5-HT) Tryptamines (e.g., 5-BT, 5-CT, 5-MT, α-Me-5-HT, bufotenin, DET, DiPT, DMT, DPT, psilocin, psilocybin, tryptamine)

Antagonists: Agomelatine Asenapine Cyproheptadine EGIS-7625 Ergolines (e.g., amesergide, bromocriptine, lisuride, LY-53857, LY-272015, mesulergine) Ketanserin LY-393558 Metadoxine Metitepine (methiothepin) Pirenperone Propranolol PRX-08066 Rauwolscine Ritanserin RS-127445 Sarpogrelate SB-200646 SB-204741 SB-206553 SB-215505 SB-221284 SB-228357 SDZ SER-082 Tegaserod Tetracyclic antidepressants (e.g., amoxapine, mianserin) TIK-301 Yohimbine

Unknown/unsorted: Ergolines (e.g., ergometrine (ergonovine))

5-HT_2C

Agonists: 2Cs (e.g., 2C-B, 2C-E, 2C-I, 2C-T-2, 2C-T-7, 2C-T-21) 5-Methoxytryptamines (5-MeO-DET, 5-MeO-DiPT, 5-MeO-DMT, 5-MeO-DPT, 5-MT) α-Alkyltryptamines (e.g., 5-Cl-αMT, 5-Fl-αMT, 5-MeO-αET, 5-MeO-αMT, α-Me-5-HT, αET, αMT) A-372159 AL-38022A Alstonine CP-809101 Dimemebfe DOx (e.g., DOB, DOC, DOI, DOM) Ergolines (e.g., ALD-52, cabergoline, dihydroergotamine, ergine (LSA), ergotamine, lisuride, LA-SS-Az, LSB, LSD, LSD-Pip, LSH, LSP, pergolide) Flumexadol Lorcaserin MDxx (e.g., MDA, MDMA, MDOH, MMDA) MK-212 Org 12962 Org 37684 Oxaflozane PHA-57378 Phenethylamines (e.g., lophophine, mescaline) Piperazines (e.g., aripiprazole, BZP, mCPP, quipazine, TFMPP) PNU-22394 PNU-181731 Ro60-0175 Ro60-0213 Serotonin (5-HT) Tryptamines (e.g., 5-BT, 5-CT, bufotenin, DET, DiPT, DMT, DPT, psilocin, psilocybin, tryptamine) Vabicaserin WAY-629 WAY-161503 YM-348

Antagonists: Adatanserin Agomelatine Atypical antipsychotics (e.g., asenapine, clorotepine, clozapine, fluperlapine, iloperidone, melperone, olanzapine, paliperidone, quetiapine, risperidone, sertindole, ziprasidone, zotepine) Captodiame CEPC Cinanserin Cyproheptadine Deramciclane Dotarizine Eltoprazine Ergolines (e.g., amesergide, bromocriptine, LY-53857, LY-215840, mesulergine, metergoline, methysergide, sergolexole) Etoperidone Fluoxetine FR-260010 Irindalone Ketanserin Ketotifen Latrepirdine (dimebolin) Medifoxamine Metitepine (methiothepin) Nefazodone Pirenperone Pizotifen Propranolol Ritanserin RS-102221 S-14671 SB-200646 SB-206553 SB-221284 SB-228357 SB-242084 SB-243213 SDZ SER-082 Tedatioxetine Tetracyclic antidepressants (e.g., amoxapine, aptazapine, esmirtazapine, maprotiline, mianserin, mirtazapine) TIK-301 Trazodone Tricyclic antidepressants (e.g., amitriptyline, nortriptyline) Typical antipsychotics (e.g., chlorpromazine, loxapine, pimozide, pipamperone, thioridazine) Xylamidine

Unknown/unsorted: Efavirenz Ergolines (e.g., ergometrine (ergonovine), methylergometrine (methylergonovine))

5-HT₃ – 5-HT₇ receptors

5-HT₃

Agonists: Alcohols (e.g., butanol, ethanol, trichloroethanol) m-CPBG Phenylbiguanide Piperazines (e.g., BZP, mCPP, quipazine) RS-56812 Serotonin (5-HT) SR-57227 SR-57227A Tryptamines (e.g., 2-Me-5-HT, 5-CT, bufotenidine (5-HTQ)) Volatiles/gases (e.g., halothane, isoflurane, toluene, trichloroethane) YM-31636

Antagonists: Alosetron AS-8112 Atypical antipsychotics (e.g., clozapine, olanzapine, quetiapine) Azasetron Batanopride Bemesetron (MDL-72222) Cilansetron CSP-2503 Dazopride Dolasetron Galanolactone Granisetron ICS-205930 Lerisetron Memantine Ondansetron Palonosetron Ramosetron Renzapride Ricasetron Tedatioxetine Tetracyclic antidepressants (e.g., amoxapine, mianserin, mirtazapine) Thujone Tropanserin Tropisetron Typical antipsychotics (e.g., loxapine) Volatiles/gases (e.g., nitrous oxide, sevoflurane, xenon) Vortioxetine Zacopride Zatosetron

Unknown/unsorted: LY-53857 Piperazines (e.g., naphthylpiperazine)

5-HT₄

Agonists: 5-MT BIMU8 Capeserod Cinitapride Cisapride CJ-033466 Dazopride Metoclopramide Mosapride Prucalopride PRX-03140 Renzapride RS-67333 RS-67506 Serotonin (5-HT) Tegaserod Velusetrag Zacopride

Antagonists: GR-113808 GR-125487 L-Lysine Piboserod RS-39604 RS-67532 SB-203186 SB-204070

5-HT_5A

Agonists: Ergolines (e.g., 2-Br-LSD (BOL-148), ergotamine, LSD) Serotonin (5-HT) Tryptamines (e.g., 5-CT) Valerenic Acid

Antagonists: Asenapine Latrepirdine (dimebolin) Metitepine (methiothepin) Ritanserin SB-699551 Unknown/unsorted: Ergolines (e.g., metergoline, methysergide) Piperazines (e.g., naphthylpiperazine)

5-HT₆

Agonists: Ergolines (e.g., dihydroergocryptine, dihydroergotamine, ergotamine, lisuride, LSD, mesulergine, metergoline, methysergide) Serotonin (5-HT) Tryptamines (e.g., 2-Me-5-HT, 5-BT, 5-CT, 5-MT, Bufotenin, E-6801, E-6837, EMD-386088, EMDT, LY-586713, N-Me-5-HT, tryptamine) WAY-181187 WAY-208466

Antagonists: ABT-354 Atypical antipsychotics (e.g., aripiprazole, asenapine, clorotepine, clozapine, fluperlapine, iloperidone, olanzapine, tiospirone) AVN-101 AVN-211 AVN-322 AVN-397 BGC20-760 BVT-5182 BVT-74316 Cerlapirdine EGIS-12233 GW-742457 Idalopirdine Ketanserin Latrepirdine (dimebolin) Metitepine (methiothepin) MS-245 PRX-07034 Ritanserin Ro04-6790 Ro 63-0563 SB-258585 SB-271046 SB-357134 SB-399885 SB-742457 Tetracyclic antidepressants (e.g., amoxapine, mianserin) Tricyclic antidepressants (e.g., amitriptyline, clomipramine, doxepin, nortriptyline) Typical antipsychotics (e.g., chlorpromazine, loxapine)

Unknown/unsorted: Ergolines (e.g., 2-Br-LSD (BOL-148), bromocriptine, lergotrile, pergolide) Piperazines (e.g., naphthylpiperazine)

5-HT₇

Agonists: 8-OH-DPAT AS-19 Bifeprunox E-55888 Ergolines (e.g., LSD) LP-12 LP-44 RU-24969 Sarizotan Serotonin (5-HT) Triptans (e.g., frovatriptan) Tryptamines (e.g., 5-CT, 5-MT, bufotenin, N-Me-5-HT)

Antagonists: Atypical antipsychotics (e.g., amisulpride, aripiprazole, asenapine, clorotepine, clozapine, fluperlapine, olanzapine, risperidone, sertindole, tiospirone, ziprasidone, zotepine) Butaclamol DR-4485 EGIS-12233 Ergolines (e.g., 2-Br-LSD (BOL-148), amesergide, bromocriptine, cabergoline, dihydroergotamine, ergotamine, LY-53857, LY-215840, mesulergine, metergoline, methysergide, sergolexole) JNJ-18038683 Ketanserin LY-215840 Metitepine (methiothepin) Ritanserin SB-258719 SB-258741 SB-269970 SB-656104 SB-656104A SB-691673 SLV-313 SLV-314 Spiperone SSR-181507 Tetracyclic antidepressants (e.g., amoxapine, maprotiline, mianserin, mirtazapine) Tricyclic antidepressants (e.g., amitriptyline, clomipramine, imipramine) Typical antipsychotics (e.g., acetophenazine, chlorpromazine, chlorprothixene, fluphenazine, loxapine, pimozide) Vortioxetine

Unknown/unsorted: Ergolines (e.g., lisuride, pergolide) Piperazines (e.g., naphthylpiperazine)

See also: Adrenergics

Dopaminergics

Melatonergics

Monoamine reuptake and release modulators

Monoamine metabolism modulators

Monoamine neurotoxins

This article is issued from Wikipedia - version of the 10/23/2016. The text is available under the Creative Commons Attribution/Share Alike but additional terms may apply for the media files.