(±)-McN 5652

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Cat.No. 2148 - (±)-McN 5652 | C19H21NS | CAS No. 96795-89-0
Description: Potent, orally active 5-HT uptake inhibitor. Also inhibits noradrenalin and dopamine uptake in vitro
Alternative Names: McN 5652-Z
Chemical Name: (6R,10bS)-rel-1,2,3,5,6,10b-Hexahydro-6-[4-(methylthio)phenyl]-pyrrolo[2,1-a]isoquinoline
Purity: ≥98% (HPLC)
Datasheet
Citations
Literature

Biological Activity

Potent, high affinity serotonin re-uptake inhibitor; selective in vivo. Displays moderate selectivity over noradrenalin and dopamine re-uptake in vitro (Ki values are 0.68, 2.9 and 36.8 nM for inhibition of serotonin, noradrenalin and dopamine uptake respectively in rat brain synaptosomes). Potently potentiates 5-HT-induced effects in vivo following oral administration. Biological activity resides predominantly in the (+)-enantiomer.

Technical Data

M. Wt 295.44
Formula C19H21NS
Storage Store at -20°C
Purity ≥98% (HPLC)
CAS Number 96795-89-0
PubChem ID 6336338
InChI Key YVKDUIAAPBKHMJ-MOPGFXCFSA-N
Smiles [H][C@]23C1=CC=CC=C1[C@@H]([C@]4=CC=C(SC)C=C4)CN2CCC3

The technical data provided above is for guidance only. For batch specific data refer to the Certificate of Analysis.

All Tocris products are intended for laboratory research use only.

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
1eq. HCl 14.77 50
DMSO 22.16 75

Preparing Stock Solutions

The following data is based on the product molecular weight 295.44. Batch specific molecular weights may vary from batch to batch due to solvent of hydration, which will affect the solvent volumes required to prepare stock solutions.

Select a batch to recalculate based on the batch molecular weight:
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 3.38 mL 16.92 mL 33.85 mL
5 mM 0.68 mL 3.38 mL 6.77 mL
10 mM 0.34 mL 1.69 mL 3.38 mL
50 mM 0.07 mL 0.34 mL 0.68 mL

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Product Datasheets

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References

References are publications that support the products' biological activity.

Shank et al (1988) McN-5652: a highly potent inhibitor of serotonin uptake. J.Pharmacol.Exp.Ther. 247 1032 PMID: 2905001

Maryanoff et al (1990) Pyrroloisoquinoline antidepressants. 3. A focus on serotonin. J.Med.Chem. 33 2793 PMID: 2213832

Smith et al (1991) Effects of pyrroloisoquinoline enantiomers ((+)- and (-)-McN-5652-Z) on behavioral and pharmacological serotonergic mechanisms in rats. Eur.J.Pharmacol. 196 85 PMID: 1831423


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5-HT Receptors Scientific Review

Written by Nicholas M. Barnes and John F. Neumaier, this review summarizes the various serotonin receptor subtypes and their importance in mediating the role of serotonin in numerous physiological and pharmacological processes. Compounds available from Tocris are listed.

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