McN5652 Names IUPAC name rel -(6R ,10bS )-6-[4-(Methylsulfanyl)phenyl]-1,2,3,5,6,10b-hexahydropyrrolo[2,1-a ]isoquinoline
Other namestrans-McN-5652
Identifiers ChEMBL ChemSpider UNII 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
Properties C 19 H 21 N S Molar mass −1 Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
Chemical compound
McN5652 [ 1] radioligand inpositron emission tomography (PET) studies. The [11 C]-(+)-McN5652enantiomer binds to theserotonin transporter .[ 2] neuroimaging and for imaging of the lungs.[ 3]
It was developed byJohnson & Johnson 'sMcNeil 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.
McN5652 and related structures have been analyzed forQSAR in terms of binding to the MAT receptor binding site.[ 4]
^ US 4595688 Certain Hexahydro-6-Arylprylpyrrolo [2,1-A]Isoquinoline ^ M. Suehiro; U. Scheffel; H. T. Ravert; R. F. Dannals; H. N. Jr Wagner (1993)."[11 C](+)McN5652 as a radiotracer for imaging serotonin uptake sites with PET" .Life Sciences .53 (11):883– 92.doi :10.1016/0024-3205(93)90440-E PMID 8366755 . ^ Akihiro Takano; Hiroshi Ito; Yasuhiko Sudo; Makoto Inoue; Tetsuya Ichimiya; Fumihiko Yasuno; Kazutoshi Suzuki; Tetsuya Suhara (August 2007). "Effects of smoking on the lung accumulation of [11 C]McN5652".Annals of Nuclear Medicine .21 (6):349– 54.doi :10.1007/s12149-007-0031-1 .PMID 17705015 .S2CID 43751275 . ^ Liu, Shuang; Zha, Congxiang; Nacro, Kassoum; Hu, Min; Cui, Wenge; Yang, Yuh-Lin; Bhatt, Ulhas; Sambandam, Aruna; Isherwood, Matthew; Yet, Larry; Herr, Michael T.; Ebeltoft, Sarah; Hassler, Carla; Fleming, Linda; Pechulis, Anthony D.; Payen-Fornicola, Anne; Holman, Nicholas; Milanowski, Dennis; Cotterill, Ian; Mozhaev, Vadim; Khmelnitsky, Yuri; Guzzo, Peter R.; Sargent, Bruce J.; Molino, Bruce F.; Olson, Richard; King, Dalton; Lelas, Snjezana; Li, Yu-Wen; Johnson, Kim; Molski, Thaddeus; Orie, Anitra; Ng, Alicia; Haskell, Roy; Clarke, Wendy; Bertekap, Robert; O’Connell, Jonathan; Lodge, Nicholas; Sinz, Michael; Adams, Stephen; Zaczek, Robert; Macor, John E. (2014)."Design and Synthesis of 4-Heteroaryl 1,2,3,4-Tetrahydroisoquinolines as Triple Reuptake Inhibitors" .ACS Medicinal Chemistry Letters .5 (7):760– 765.doi :10.1021/ml500053b .ISSN 1948-5875 .PMC 4094255 PMID 25050161 .
