Chemistry:McN5652
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| IUPAC name
rel-(6R,10bS)-6-[4-(Methylsulfanyl)phenyl]-1,2,3,5,6,10b-hexahydropyrrolo[2,1-a]isoquinoline
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| Other names
trans-McN-5652
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3D model (JSmol)
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PubChem CID
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| Properties | |
| 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). | |
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| 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
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)
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 et al. (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. PMID 25050161.
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