DASB

DASB

DASB (above) and [C-11]DASB
Radioactive carbon atom marked in cyan
Identifiers
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?)

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. In this context it is regarded as one of the superior radioligands for PET study of the serotonin transporter in the brain, since it has high selectivity for the serotonin transporter.

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.

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.

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. With single-photon emission computed tomography (SPECT) using the radioisotope iodine-123 there are further radioligands available: [¹²³I]ODAM, [¹²³I]IDAM, [¹²³I]ADAM, and [¹²³I]β-CIT. A few studies have examined the difference in binding between the radioligands in nonhuman primates, as well as in pigs.