Chemistry: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
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 serotonin–norepinephrine–dopamine reuptake inhibitor (SNDRI) designated for the treatment of depression. It was developed by Bruce Maryanoff of McNeil (now Johnson & Johnson) in the 1980s.

Binding affinities

Binding affinities (K_i) are:

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 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, and McN-5908.

Other examples of drugs with ortho-chlorophenyl rings include:

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