Cannabaceae

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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
3D model (JSmol)
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 checkY
    Key: YVKDUIAAPBKHMJ-MOPGFXCFSA-N checkY
  • 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
  • CSC1=CC=C([C@H]2CN3[C@](CCC3)([H])C4=C2C=CC=C4)C=C1
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).
☒N verify (what is checkY☒N ?)

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[edit]

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

See also[edit]

References[edit]

  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. S2CID 43751275.
  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. PMID 25050161.


source: https://en.wikipedia.org/wiki/McN5652

One thought on “Cannabaceae”

  1. Well, that’s interesting to know that Psilotum nudum are known as whisk ferns. Psilotum nudum is the commoner species of the two. While the P. flaccidum is a rare species and is found in the tropical islands. Both the species are usually epiphytic in habit and grow upon tree ferns. These species may also be terrestrial and grow in humus or in the crevices of the rocks.
    View the detailed Guide of Psilotum nudum: Detailed Study Of Psilotum Nudum (Whisk Fern), Classification, Anatomy, Reproduction

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