McN5652

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 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL361259 ;
ChemSpider	4891622 ;
PubChem CID	6336338;
UNII	21MT8QF2LI ;
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 Key: YVKDUIAAPBKHMJ-MOPGFXCFSA-N ; 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). verify (what is ?) Infobox references

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]

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

See for example: U.S. patent 20,120,321,559 cited in PC44438935. In terms of to get to the highest philosopher, either the para-3-thiophen or para-3-furan could be tested in a QSAR, c.f. Tamagnan. Alternatively, the thioindole by Bruce Molino of AMRI/BMS could also be compatible with the QSAR modelled on the MAT receptor binding site.

Hybrid between McN5652 & Molino, i.e. U.S. patent 9,085,531 & ^[4] .

References

^ 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). "[¹¹C](+)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 [¹¹C]McN5652". Annals of Nuclear Medicine. 21 (6): 349–54. doi:10.1007/s12149-007-0031-1. PMID 17705015.
^ 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.

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[1] US 4595688 Certain Hexahydro-6-Arylprylpyrrolo [2,1-A]Isoquinoline

[2] M. Suehiro; U. Scheffel; H. T. Ravert; R. F. Dannals; H. N. Jr Wagner (1993). "[¹¹C](+)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.

[3] 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 [¹¹C]McN5652". Annals of Nuclear Medicine. 21 (6): 349–54. doi:10.1007/s12149-007-0031-1. PMID 17705015.

[LiuZha2014-4] 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.

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[2]

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Derivatives

See also

References