Login
Login

DASB

{{short description|Chemical compound}}

{{About|the chemical compound|the Swedish automaker commonly known as DASB (Den Andra Svenska Bilen)|Volvo Cars}}

{{Infobox drug

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 429877266

| IUPAC_name = 3-amino-4-[2-[(di(methyl)amino)methyl]phenyl]sulfanylbenzonitrile

| image = DASB and (C-11)DASB formulas skeletal.svg

| caption = DASB (above) and [C-11]DASB

| alt = Structural formulas

| image2 = (C-11)DASB molecule spacefill.png

| width = 250

| caption2 = Radioactive carbon atom marked in cyan

| alt2 = Space-filling model

| width2 = 220

| tradename =

| pregnancy_AU =

| pregnancy_US =

| pregnancy_category =

| legal_AU =

| legal_CA =

| legal_UK =

| legal_US =

| legal_status =

| routes_of_administration =

| bioavailability =

| protein_bound =

| metabolism =

| elimination_half-life =

| excretion =

| index_label =

| index2_label =11C-labelled

| CAS_number_Ref = {{cascite|correct|CAS}}

| CAS_number = 627490-01-1

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = PP549Z0645

| ATC_prefix =

| ATC_suffix =

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| DrugBank =

| PubChem = 10446567

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID = 8621986

| smiles = N#Cc2ccc(Sc1c(cccc1)CN(C)C)c(c2)N

| CAS_number2_Ref = {{cascite|correct|CAS}}

| CAS_number2 = 296774-13-5

| UNII2_Ref = {{fdacite|correct|FDA}}

| UNII2 = FJU46Q2BPU

| PubChem2 = 656408

| ChemSpiderID2_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID2 = 570800

| smiles2 = [11CH3]N(C)Cc1ccccc1Sc2ccc(cc2N)C#N

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| StdInChI = 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

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = UVWLEPXXYOYDGR-UHFFFAOYSA-N

| StdInChI2_Ref = {{stdinchicite|changed|chemspider}}

| StdInChI2 = 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

| StdInChIKey2_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey2 = UVWLEPXXYOYDGR-BJUDXGSMSA-N

| C=16 | H=17 | N=3 | S=1

}}

DASB, also known as 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.{{cite journal | vauthors = Houle S, Ginovart N, Hussey D, Meyer JH, Wilson AA | title = Imaging the serotonin transporter with positron emission tomography: initial human studies with [11C]DAPP and [11C]DASB | journal = European Journal of Nuclear Medicine | volume = 27 | issue = 11 | pages = 1719–1722 | date = November 2000 | pmid = 11105830 | doi = 10.1007/s002590000365 | s2cid = 18932686 }}

In this context it is regarded as one of the superior radioligands for PET study of the serotonin transporter in the brain,{{Cite journal | vauthors = Brust P, Hesse S, Muller U, Szabo Z | title = Neuroimaging of the Serotonin Transporter — Possibilities and Pitfalls | journal = Current Psychiatry Reviews | date = February 2006 | volume = 2 | issue = 1 | pages = 111–149 | url = http://www-bmu.psychiatry.cam.ac.uk/publications/brust06neu.pdf | doi = 10.2174/157340006775101508 | access-date = 2008-01-23 | archive-url = https://web.archive.org/web/20110723033800/http://www-bmu.psychiatry.cam.ac.uk/publications/brust06neu.pdf | archive-date = 2011-07-23 | url-status = dead }}

since it has high selectivity for the serotonin transporter.{{cite journal | vauthors = Wilson AA, Ginovart N, Hussey D, Meyer J, Houle S | title = In vitro and in vivo characterisation of [11C]-DASB: a probe for in vivo measurements of the serotonin transporter by positron emission tomography | journal = Nuclear Medicine and Biology | volume = 29 | issue = 5 | pages = 509–515 | date = July 2002 | pmid = 12088720 | doi = 10.1016/S0969-8051(02)00316-5 }}

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.{{cite journal | vauthors = Frankle WG, Slifstein M, Gunn RN, Huang Y, Hwang DR, Darr EA, Narendran R, Abi-Dargham A, Laruelle M | display-authors = 6 | title = Estimation of serotonin transporter parameters with 11C-DASB in healthy humans: reproducibility and comparison of methods | journal = Journal of Nuclear Medicine | volume = 47 | issue = 5 | pages = 815–826 | date = May 2006 | pmid = 16644752 | url = http://jnm.snmjournals.org/cgi/content/abstract/47/5/815 | author-link8 = Marc Laruelle | author-link1 = W. Gordon Frankle }}

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.{{cite journal | vauthors = Meyer JH | title = Imaging the serotonin transporter during major depressive disorder and antidepressant treatment | journal = Journal of Psychiatry & Neuroscience | volume = 32 | issue = 2 | pages = 86–102 | date = March 2007 | pmid = 17353938 | pmc = 1810585 | author-link = Jeffrey H. Meyer }}

There are a number of alternative PET radioligands for imaging the serotonin transporter: [11C]ADAM, [11C]MADAM, [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.{{cite journal | vauthors = Garg S, Thopate SR, Minton RC, Black KW, Lynch AJ, Garg PK | title = 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 | journal = Bioconjugate Chemistry | volume = 18 | issue = 5 | pages = 1612–1618 | date = September–October 2007 | pmid = 17705553 | doi = 10.1021/bc070112g }}

With single-photon emission computed tomography (SPECT) using the radioisotope iodine-123 there are further radioligands available: [123I]ODAM, [123I]IDAM, [123I]ADAM,{{cite journal | vauthors = Oya S, Choi SR, Hou C, Mu M, Kung MP, Acton PD, Siciliano M, Kung HF | display-authors = 6 | title = 2-((2-((dimethylamino)methyl)phenyl)thio)-5-iodophenylamine (ADAM): an improved serotonin transporter ligand | journal = Nuclear Medicine and Biology | volume = 27 | issue = 3 | pages = 249–254 | date = April 2000 | pmid = 10832081 | doi = 10.1016/s0969-8051(00)00084-6 | doi-access = free }} and [123I]β-CIT.

A few studies have examined the difference in binding between the radioligands in nonhuman primates,{{cite journal | vauthors = Szabo Z, McCann UD, Wilson AA, Scheffel U, Owonikoko T, Mathews WB, Ravert HT, Hilton J, Dannals RF, Ricaurte GA | display-authors = 6 | title = Comparison of (+)-(11)C-McN5652 and (11)C-DASB as serotonin transporter radioligands under various experimental conditions | journal = Journal of Nuclear Medicine | volume = 43 | issue = 5 | pages = 678–692 | date = May 2002 | pmid = 11994534 | pmc = 2078607 | url = http://jnm.snmjournals.org/cgi/content/abstract/43/5/678 | author-link5 = Taofeek Owonikoko }}{{cite journal | vauthors = Huang Y, Hwang DR, Narendran R, Sudo Y, Chatterjee R, Bae SA, Mawlawi O, Kegeles LS, Wilson AA, Kung HF, Laruelle M | display-authors = 6 | title = 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 = Journal of Cerebral Blood Flow and Metabolism | volume = 22 | issue = 11 | pages = 1377–1398 | date = November 2002 | pmid = 12439295 | doi = 10.1097/00004647-200211000-00011 }}

as well as in pigs.{{cite journal | vauthors = Jensen SB, Smith DF, Bender D, Jakobsen S, Peters D, Nielsen EØ, Olsen GM, Scheel-Krüger J, Wilson A, Cumming P | display-authors = 6 | title = [11C]-NS 4194 versus [11C]-DASB for PET imaging of serotonin transporters in living porcine brain | journal = Synapse | volume = 49 | issue = 3 | pages = 170–177 | date = September 2003 | pmid = 12774301 | doi = 10.1002/syn.10222 | author-link10 = Paul Cumming | s2cid = 35777731 }}

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.{{cite journal | vauthors = Ginovart N, Wilson AA, Meyer JH, Hussey D, Houle S | title = Positron emission tomography quantification of [(11)C]-DASB binding to the human serotonin transporter: modeling strategies | journal = Journal of Cerebral Blood Flow and Metabolism | volume = 21 | issue = 11 | pages = 1342–1353 | date = November 2001 | pmid = 11702049 | doi = 10.1097/00004647-200111000-00010 | doi-access = free }}

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.

When the DASB neuroimages are analyzed the kinetic models suggested by Ichise and coworkers{{cite journal | vauthors = Ichise M, Liow JS, Lu JQ, Takano A, Model K, Toyama H, Suhara T, Suzuki K, Innis RB, Carson RE | display-authors = 6 | title = Linearized reference tissue parametric imaging methods: application to [11C]DASB positron emission tomography studies of the serotonin transporter in human brain | journal = Journal of Cerebral Blood Flow and Metabolism | volume = 23 | issue = 9 | pages = 1096–1112 | date = September 2003 | pmid = 12973026 | doi = 10.1097/01.WCB.0000085441.37552.CA | doi-access = free }} can be employed to estimate the binding potential.

A test-retest reproducibility experiment has been performed to evaluate this approach.{{cite journal | vauthors = Kim JS, Ichise M, Sangare J, Innis RB | title = PET imaging of serotonin transporters with [11C]DASB: test-retest reproducibility using a multilinear reference tissue parametric imaging method | journal = Journal of Nuclear Medicine | volume = 47 | issue = 2 | pages = 208–214 | date = February 2006 | pmid = 16455625 }}

Studies

Besides the studies listed below a few occupancy studies have been reported.

class="wikitable"

|+ DASB binding neuroimaging studies (patients compared to healthy control subjects).

WhatResultSubjectsRef.
5-HTTLPR LALA serotonin transporter genotype

| Increase in putamen

| 43/30

| {{cite journal | vauthors = Praschak-Rieder N, Kennedy J, Wilson AA, Hussey D, Boovariwala A, Willeit M, Ginovart N, Tharmalingam S, Masellis M, Houle S, Meyer JH | display-authors = 6 | title = Novel 5-HTTLPR allele associates with higher serotonin transporter binding in putamen: a [(11)C] DASB positron emission tomography study | journal = Biological Psychiatry | volume = 62 | issue = 4 | pages = 327–331 | date = August 2007 | pmid = 17210141 | doi = 10.1016/j.biopsych.2006.09.022 | s2cid = 46096787 }}

5-HTTLPR LALA serotonin transporter genotype

| Increase in midbrain

| 19

| {{cite journal | vauthors = Reimold M, Smolka MN, Schumann G, Zimmer A, Wrase J, Mann K, Hu XZ, Goldman D, Reischl G, Solbach C, Machulla HJ, Bares R, Heinz A | display-authors = 6 | title = Midbrain serotonin transporter binding potential measured with [11C]DASB is affected by serotonin transporter genotype | journal = Journal of Neural Transmission | volume = 114 | issue = 5 | pages = 635–639 | date = May 2007 | pmid = 17225932 | doi = 10.1007/s00702-006-0609-0 | s2cid = 9369923 }}

5-HTTLPR LALA serotonin transporter genotype

| No difference

| 63

| {{cite journal | vauthors = Murthy NV, Selvaraj S, Cowen PJ, Bhagwagar Z, Riedel WJ, Peers P, Kennedy JL, Sahakian BJ, Laruelle MA, Rabiner EA, Grasby PM | display-authors = 6 | title = 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 | journal = NeuroImage | volume = 52 | issue = 1 | pages = 50–54 | date = August 2010 | pmid = 20406689 | doi = 10.1016/j.neuroimage.2010.04.032 | s2cid = 2690593 }}

Age

| No effect found

|

| {{cite journal | vauthors = Meyer JH, Houle S, Sagrati S, Carella A, Hussey DF, Ginovart N, Goulding V, Kennedy J, Wilson AA | display-authors = 6 | title = Brain serotonin transporter binding potential measured with carbon 11-labeled DASB positron emission tomography: effects of major depressive episodes and severity of dysfunctional attitudes | journal = Archives of General Psychiatry | volume = 61 | issue = 12 | pages = 1271–1279 | date = December 2004 | pmid = 15583118 | doi = 10.1001/archpsyc.61.12.1271 | author-link2 = Sylvain Houle | doi-access = | s2cid = 6769025 | author-link9 = Alan A. Wilson | author-link1 = Jeffrey H. Meyer }} ()

Body mass index

| Inverse correlation (?)

| ?

| {{Cite journal | vauthors = Matsumoto R, Ito H, Takahashi H, Takano H, Suhara T | title = Inverse correlation between body mass index and serotonin transporter binding in human brain: A [11C]DASB PET study | journal = NeuroImage | doi = 10.1016/j.neuroimage.2008.04.128 | volume = 2, supplement 2 | year = 2008 | pages = T161 | s2cid = 53257175 }} Neuroreceptor Mapping 2008, The Seventh International Symposium on Functional Neuroreceptor Mapping of Living Brain

Seasonality

| Higher in winter in putamen and caudate

| 54

| {{cite journal | vauthors = Kalbitzer J, Erritzoe D, Holst KK, Nielsen FA, Marner L, Lehel S, Arentzen T, Jernigan TL, Knudsen GM | display-authors = 6 | title = Seasonal changes in brain serotonin transporter binding in short serotonin transporter linked polymorphic region-allele carriers but not in long-allele homozygotes | journal = Biological Psychiatry | volume = 67 | issue = 11 | pages = 1033–1039 | date = June 2010 | pmid = 20110086 | doi = 10.1016/j.biopsych.2009.11.027 | s2cid = 22393782 | author-link1 = Jan Kalbitzer }}

Seasonality

| Higher in fall and winter

| 88

| {{cite journal | vauthors = Praschak-Rieder N, Willeit M, Wilson AA, Houle S, Meyer JH | title = Seasonal variation in human brain serotonin transporter binding | journal = Archives of General Psychiatry | volume = 65 | issue = 9 | pages = 1072–1078 | date = September 2008 | pmid = 18762593 | doi = 10.1001/archpsyc.65.9.1072 | author-link2 = Matthaeus Willeit | author-link3 = Alan A. Wilson | author-link4 = Sylvain Houle | doi-access = | author-link1 = Nicole Praschak-Rieder }}

NEO PI-R Neuroticism

| Positive correlation in thalamus

| 31 males

| {{cite journal | vauthors = Takano A, Arakawa R, Hayashi M, Takahashi H, Ito H, Suhara T | title = Relationship between neuroticism personality trait and serotonin transporter binding | journal = Biological Psychiatry | volume = 62 | issue = 6 | pages = 588–592 | date = September 2007 | pmid = 17336939 | doi = 10.1016/j.biopsych.2006.11.007 | s2cid = 41664835 | author-link5 = Tetsuya Suhara | author-link1 = Akihiro Takano }}

Disease
Depressed during major depressive episodes

| No difference found

| 20+20

|

Depressed with highly negativistic "dysfunctional attitudes" during major depressive episodes

| Increase in prefrontal cortex, anterior cingulate, thalamus, bilateral caudate, and bilateral putamen

| 20(?)+20

|

Recovered depressed patients

| No difference found

| 24+20 males

| {{cite journal | vauthors = Bhagwagar Z, Murthy N, Selvaraj S, Hinz R, Taylor M, Fancy S, Grasby P, Cowen P | display-authors = 6 | title = 5-HTT binding in recovered depressed patients and healthy volunteers: a positron emission tomography study with [11C]DASB | journal = The American Journal of Psychiatry | volume = 164 | issue = 12 | pages = 1858–1865 | date = December 2007 | pmid = 18056241 | doi = 10.1176/appi.ajp.2007.06111933 | author-link8 = Philip Cowen | author-link7 = Paul Grasby | author-link1 = Zubin Bhagwagar }}

Unipolar depression

| Increase in thalamus, insula and striatum

| 18+34

| {{cite journal | vauthors = Cannon DM, Ichise M, Rollis D, Klaver JM, Gandhi SK, Charney DS, Manji HK, Drevets WC | display-authors = 6 | title = Elevated serotonin transporter binding in major depressive disorder assessed using positron emission tomography and [11C]DASB; comparison with bipolar disorder | journal = Biological Psychiatry | volume = 62 | issue = 8 | pages = 870–877 | date = October 2007 | pmid = 17678634 | doi = 10.1016/j.biopsych.2007.03.016 | s2cid = 19689483 }}

Unmedicated unipolar major depression

| Reduced 5-HTT availability in the thalamus

|

| {{cite journal | vauthors = Reimold M, Batra A, Knobel A, Smolka MN, Zimmer A, Mann K, Solbach C, Reischl G, Schwärzler F, Gründer G, Machulla HJ, Bares R, Heinz A | display-authors = 6 | title = Anxiety is associated with reduced central serotonin transporter availability in unmedicated patients with unipolar major depression: a [11C]DASB PET study | journal = Molecular Psychiatry | volume = 13 | issue = 6 | pages = 606–13, 557 | date = June 2008 | pmid = 18268503 | doi = 10.1038/sj.mp.4002149 | doi-access = free | author-link1 = Matthias Reimold }}. Electronic publication

TCI anxiety in unmedicated unipolar major depression

| Reduced 5-HTT availability in the thalamus, midbrain and amygdala

|

|

Bipolar depression

| Increase in thalamus, insula and striatum

| 18+34

|

Bipolar depression

| Decrease in midbrain, amygdala, hippocampus, thalamus, putamen, and anterior cingulate cortex

| 18+41

| {{cite journal | vauthors = Oquendo MA, Hastings RS, Huang YY, Simpson N, Ogden RT, Hu XZ, Goldman D, Arango V, Van Heertum RL, Mann JJ, Parsey RV | display-authors = 6 | title = Brain serotonin transporter binding in depressed patients with bipolar disorder using positron emission tomography | journal = Archives of General Psychiatry | volume = 64 | issue = 2 | pages = 201–208 | date = February 2007 | pmid = 17283287 | pmc = 3767993 | doi = 10.1001/archpsyc.64.2.201 }}

Obsessive compulsive disorder

| Reduction and correlation with severity in thalamus and midbrain

| 9+19

| {{cite journal | vauthors = Reimold M, Smolka MN, Zimmer A, Batra A, Knobel A, Solbach C, Mundt A, Smoltczyk HU, Goldman D, Mann K, Reischl G, Machulla HJ, Bares R, Heinz A | display-authors = 6 | title = Reduced availability of serotonin transporters in obsessive-compulsive disorder correlates with symptom severity - a [11C]DASB PET study | journal = Journal of Neural Transmission | volume = 114 | issue = 12 | pages = 1603–1609 | date = December 2007 | pmid = 17713719 | doi = 10.1007/s00702-007-0785-6 | s2cid = 33872765 }}

Alcoholism

| No significant alteration

| 30 + 18

| {{cite journal | vauthors = Brown AK, George DT, Fujita M, Liow JS, Ichise M, Hibbeln J, Ghose S, Sangare J, Hommer D, Innis RB | display-authors = 6 | title = PET [11C]DASB imaging of serotonin transporters in patients with alcoholism | journal = Alcoholism: Clinical and Experimental Research | volume = 31 | issue = 1 | pages = 28–32 | date = January 2007 | pmid = 17207098 | doi = 10.1111/j.1530-0277.2006.00261.x }}

Parkinson's disease

| Reduction in forebrain

| 5+8

| {{cite journal | vauthors = Albin RL, Koeppe RA, Bohnen NI, Wernette K, Kilbourn MA, Frey KA | title = Spared caudal brainstem SERT binding in early Parkinson's disease | journal = Journal of Cerebral Blood Flow and Metabolism | volume = 28 | issue = 3 | pages = 441–444 | date = March 2008 | pmid = 18073772 | doi = 10.1038/sj.jcbfm.9600599 | doi-access = free }}

Non-depressed Parkinson's disease

| Decreased binding in caudate, midbrain, putamen, orbitofrontal cortex and (non-significantly) dorsolateral prefrontal cortex

|

| {{cite journal | vauthors = Guttman M, Boileau I, Warsh J, Saint-Cyr JA, Ginovart N, McCluskey T, Houle S, Wilson A, Mundo E, Rusjan P, Meyer J, Kish SJ | display-authors = 6 | title = Brain serotonin transporter binding in non-depressed patients with Parkinson's disease | journal = European Journal of Neurology | volume = 14 | issue = 5 | pages = 523–528 | date = May 2007 | pmid = 17437611 | doi = 10.1111/j.1468-1331.2007.01727.x | author-link10 = P. Rusjan | author-link11 = J. Meyer | author-link2 = I. Boileau | s2cid = 30077418 | author-link3 = J. Warsh | author-link6 = T. McCluskey | author-link4 = J. A. Saint-Cyr | author-link8 = A. Wilson | author-link9 = E. Mundo | author-link7 = S. Houle | author-link5 = N. Ginovart | author-link1 = M. Guttman }}

Depressed Parkinson's disease patients

| Increase in prefrontal and dorsolateral cortices

| 7+7

| {{cite journal | vauthors = Boileau I, Warsh JJ, Guttman M, Saint-Cyr JA, McCluskey T, Rusjan P, Houle S, Wilson AA, Meyer JH, Kish SJ | display-authors = 6 | title = Elevated serotonin transporter binding in depressed patients with Parkinson's disease: a preliminary PET study with [11C]DASB | journal = Movement Disorders | volume = 23 | issue = 12 | pages = 1776–1780 | date = September 2008 | pmid = 18661545 | doi = 10.1002/mds.22212 | s2cid = 33907854 | author-link9 = Jeffrey H. Meyer | author-link7 = Sylvain Houle }}

Drug/intervention
Abstinent MDMA ('Ecstasy') users

| Global reduction

| 23+19

| {{cite journal | vauthors = McCann UD, Szabo Z, Seckin E, Rosenblatt P, Mathews WB, Ravert HT, Dannals RF, Ricaurte GA | display-authors = 6 | title = Quantitative PET studies of the serotonin transporter in MDMA users and controls using [11C]McN5652 and [11C]DASB | journal = Neuropsychopharmacology | volume = 30 | issue = 9 | pages = 1741–1750 | date = September 2005 | pmid = 15841106 | pmc = 2034411 | doi = 10.1038/sj.npp.1300736 | author-link = Una D. McCann }}

Former MDMA users and polydrug users

| No significant difference in brain regions examined

| 12+9+19

| {{cite journal | vauthors = Selvaraj S, Hoshi R, Bhagwagar Z, Murthy NV, Hinz R, Cowen P, Curran HV, Grasby P | display-authors = 6 | title = Brain serotonin transporter binding in former users of MDMA ('ecstasy') | journal = The British Journal of Psychiatry | volume = 194 | issue = 4 | pages = 355–359 | date = April 2009 | pmid = 19336788 | doi = 10.1192/bjp.bp.108.050344 | doi-access = free | author-link8 = Paul Grasby }}

Reduced synaptic serotonin (by rapid tryptophan depletion)

| (small reduction in binding potential)

| 8

| {{cite journal | vauthors = Talbot PS, Frankle WG, Hwang DR, Huang Y, Suckow RF, Slifstein M, Abi-Dargham A, Laruelle M | display-authors = 6 | title = Effects of reduced endogenous 5-HT on the in vivo binding of the serotonin transporter radioligand 11C-DASB in healthy humans | journal = Synapse | volume = 55 | issue = 3 | pages = 164–175 | date = March 2005 | pmid = 15605360 | doi = 10.1002/syn.20105 | s2cid = 16602728 }}

Lowering of brain serotonin (by acute tryptophan depletion)

| No change observed

| 25 (14)

| {{cite journal | vauthors = Praschak-Rieder N, Wilson AA, Hussey D, Carella A, Wei C, Ginovart N, Schwarz MJ, Zach J, Houle S, Meyer JH | display-authors = 6 | title = Effects of tryptophan depletion on the serotonin transporter in healthy humans | journal = Biological Psychiatry | volume = 58 | issue = 10 | pages = 825–830 | date = November 2005 | pmid = 16026765 | doi = 10.1016/j.biopsych.2005.04.038 | s2cid = 19327582 | author-link9 = Sylvain Houle }}

References

{{Reflist}}

{{Serotonergics}}

Category:Treatment of bipolar disorder

Category:Nitriles

Category:Thioethers

Category:PET radiotracers