McN5652

McN5652^[1] is a molecule that can be radiolabeled and then used as a radioligand in positron emission tomography (PET) studies. The [¹¹C]-(+)-McN5652 enantiomer binds to the serotonin transporter.^[2] The radioligand is used for molecular neuroimaging and for imaging of the lungs.^[3]

McN5652

Names
IUPAC name rel-(6R,10bS)-6-[4-(Methylsulfanyl)phenyl]-1,2,3,5,6,10b-hexahydropyrrolo[2,1-a]isoquinoline
Other names trans-McN-5652
Identifiers
CAS Number	96795-89-0 (±)-trans Y
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL361259 Y
ChemSpider	4891622 Y
PubChem CID	6336338
UNII	21MT8QF2LI Y
CompTox Dashboard (EPA)	DTXSID001128845
InChI InChI=1S/C19H21NS/c1-21-15-10-8-14(9-11-15)18-13-20-12-4-7-19(20)17-6-3-2-5-16(17)18/h2-3,5-6,8-11,18-19H,4,7,12-13H2,1H3/t18-,19+/m1/s1 Y Key: YVKDUIAAPBKHMJ-MOPGFXCFSA-N Y InChI=1/C19H21NS/c1-21-15-10-8-14(9-11-15)18-13-20-12-4-7-19(20)17-6-3-2-5-16(17)18/h2-3,5-6,8-11,18-19H,4,7,12-13H2,1H3/t18-,19+/m1/s1 Key: YVKDUIAAPBKHMJ-MOPGFXCFBW
SMILES CSC1=CC=C([C@H]2CN3[C@](CCC3)([H])C4=C2C=CC=C4)C=C1
Properties
Chemical formula	C19H21NS
Molar mass	295.44 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is YN ?) Infobox references

It was developed by Johnson & Johnson's McNeil Laboratories. According to McNeil, McN5652 was among the strongest SRI ever reported at the time of its discovery (sub nM Ki). However, it is not completely 5-HT selective: the racemate has 5-HT=0.68, NA=2.9, and D=36.8nM, whereas (+)-enantiomer has 5-HT=0.39, NA=1.8, and D=23.5 nM. Paroxetine was listed as 5-HT=0.44 nM, NA=20, and DA=460nM in the same paper by the same authors.

Derivatives

McN5652 and related structures have been analyzed for QSAR in terms of binding to the MAT receptor binding site.^[4]

See also

• DASB
• JNJ-7925476 (p-ethynyl)