McN 5707

Mcn 5707

Clinical data
Other names	McN-5707
Identifiers
IUPAC name (6R,10bR)-6-(2-chlorophenyl)-1,2,3,5,6,10b-hexahydropyrrolo[2,1-a]isoquinoline
CAS Number	96795-88-9 hydrobromide:  109214-56-4
PubChem CID	126059
ChemSpider	112085
ChEMBL	ChEMBL1743803
CompTox Dashboard (EPA)	DTXSID20914317
Chemical and physical data
Formula	C18H18ClN
Molar mass	283.80 g·mol−1
3D model (JSmol)	Interactive image
SMILES C1C[C@@H]2C3=CC=CC=C3[C@@H](CN2C1)C4=CC=CC=C4Cl
InChI InChI=1S/C18H18ClN/c19-17-9-4-3-7-14(17)16-12-20-11-5-10-18(20)15-8-2-1-6-13(15)16/h1-4,6-9,16,18H,5,10-12H2/t16-,18-/m1/s1 Key:KWMNBUDYCCTHHL-SJLPKXTDSA-N

Mcn 5707 is a SNDRI agent designated for the treatment of depression. It was developed by Bruce Maryanoff of McNeil (now Johnson & Johnson) in the 1980s. ^{[1] [2]}

Ki digits

These are the Ki digits:

Compound 24b	DA	NE	SER
racemic	35.9	1.9	8.5
(+)	17.5	1.1	5.5
(-)	775	261	537

As can be seen most of the Ki activity resides in a single optical antipode (or enantiomer). Hence, there is a good eudysmic ratio

SAR

For related agents, see: JNJ-7925476, McN-4612, McN-5292, McN-5558, McN5652 & McN-5908.

Other examples of ortho-chloro-phenyl rings include:

1. Ketamine
2. Clofedanol
3. Clortermine
4. Tulobuterol
5. Disobutamide
6. Bidisomide

References

1. Maryanoff BE, Shank RP, Gardocki JF (1986). "McN-5707 and McN-5652-Z". Drugs of the Future. 11 (1): 18. doi:10.1358/dof.1986.011.01.51629.
2. Maryanoff BE, McComsey DF, Castanzo MJ, Setler PE, Gardocki JF, Shank RP, et al. (August 1984). "Pyrroloisoquinoline antidepressants. Potent, enantioselective inhibition of tetrabenazine-induced ptosis and neuronal uptake of norepinephrine, dopamine, and serotonin". Journal of Medicinal Chemistry. 27 (8): 943–6. doi:10.1021/jm00374a001. PMID   6747993.