DOV-216303 free base | CAS# 66504-40-3 (free base) | serotonin, norepinephrine, and dopamine reuptake inhibitor

MedKoo Cat#: 413910 | Name: DOV-216303 free base

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

DOV-216303 free base is a potent triple serotonin, norepinephrine, and dopamine reuptake inhibitor, with IC50 values of 14 nM, 20 nM and 78 nM for hSERT, hNET and hDAT, respectively. Has antidepressant-like effects and increases monoamine release in the prefrontal cortex of olfactory bulbectomized (OBX) rats.

Chemical Structure

DOV-216303 free base

CAS#66504-40-3 (free base)

Theoretical Analysis

MedKoo Cat#: 413910

Name: DOV-216303 free base

CAS#: 66504-40-3 (free base)

Chemical Formula: C11H11Cl2N

Exact Mass: 227.0269

Molecular Weight: 228.12

Elemental Analysis: C, 57.92; H, 4.86; Cl, 31.08; N, 6.14

Price and Availability

Size	Price	Availability	Quantity
5mg	USD 350.00	2 Weeks
10mg	USD 550.00	2 Weeks

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Related CAS #

86215-36-3 (HCl) 66504-40-3 (free base)

Synonym

DOV-216303 free base; DOV 216,303 free base; DOV216,303 free base; DOV-216303; DOV216303; DOV 216303;

IUPAC/Chemical Name

1-(3,4-Dichlorophenyl)-3-azabicyclo(3.1.0)hexane

InChi Key

BSMNRYCSBFHEMQ-UHFFFAOYSA-N

InChi Code

InChI=1S/C11H11Cl2N/c12-9-2-1-7(3-10(9)13)11-4-8(11)5-14-6-11/h1-3,8,14H,4-6H2

SMILES Code

ClC1=CC=C(C23CNCC2C3)C=C1Cl

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

To be determined

Shelf Life

>2 years if stored properly

Drug Formulation

To be determined

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

DOV-216,303 (Free Base) is a potent triple serotonin, norepinephrine, and dopamine reuptake inhibitor, with IC50 values of 14 nM, 20 nM and 78 nM for hSERT, hNET and hDAT, respectively.

In vitro activity:

In vitro, neither duloxetine nor DOV 216,303 altered intracellular BDNF levels in murine HT22 neuronal cells. In contrast, BDNF release was more effectively decreased following treatment with DOV 216,303 in these cells. Reference: J Mol Neurosci. 2012 Sep;48(1):167-75. https://pubmed.ncbi.nlm.nih.gov/22581450/

In vivo activity:

Results showed that DOV 216,303-treated mice recovered significantly better than vehicle treated mice starting at 14 days post injury until the end of the survival period. Lesion size of the DOV 216,303 treated mice was also smaller compared to that of vehicle treated mice. This study suggests DOV 216,303 as a potential therapeutic after spinal cord injury warrants further investigation. Reference: Neurosci Lett. 2018 May 14;675:1-6. https://pubmed.ncbi.nlm.nih.gov/29578004/

	Solvent	mg/mL	mM
Solubility
	DMSO	125.0	547.97
	Ethanol	100.0	438.37

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 228.12 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Prickaerts J, De Vry J, Boere J, Kenis G, Quinton MS, Engel S, Melnick L, Schreiber R. Differential BDNF responses of triple versus dual reuptake inhibition in neuronal and astrocytoma cells as well as in rat hippocampus and prefrontal cortex. J Mol Neurosci. 2012 Sep;48(1):167-75. doi: 10.1007/s12031-012-9802-9. Epub 2012 May 13. PMID: 22581450; PMCID: PMC3413810. 2. Caldarone BJ, Paterson NE, Zhou J, Brunner D, Kozikowski AP, Westphal KG, Korte-Bouws GA, Prins J, Korte SM, Olivier B, Ghavami A. The novel triple reuptake inhibitor JZAD-IV-22 exhibits an antidepressant pharmacological profile without locomotor stimulant or sensitization properties. J Pharmacol Exp Ther. 2010 Dec;335(3):762-70. doi: 10.1124/jpet.110.174011. Epub 2010 Sep 23. PMID: 20864506; PMCID: PMC2993553. 3. Chu TH, Cummins K, Stys PK. The triple monoamine re-uptake inhibitor DOV 216,303 promotes functional recovery after spinal cord contusion injury in mice. Neurosci Lett. 2018 May 14;675:1-6. doi: 10.1016/j.neulet.2018.03.050. Epub 2018 Mar 22. PMID: 29578004. 4. Sørensen G, Husum H, Brennum LT, Bundgaard C, Montezinho LC, Mørk A, Wörtwein G, Woldbye DP. Addiction-related effects of DOV 216,303 and cocaine: A comparative study in the mouse. Basic Clin Pharmacol Toxicol. 2014 Jun;114(6):451-9. doi: 10.1111/bcpt.12182. Epub 2014 Jan 16. PMID: 24314270.

In vitro protocol:

In vivo protocol:

1. Chu TH, Cummins K, Stys PK. The triple monoamine re-uptake inhibitor DOV 216,303 promotes functional recovery after spinal cord contusion injury in mice. Neurosci Lett. 2018 May 14;675:1-6. doi: 10.1016/j.neulet.2018.03.050. Epub 2018 Mar 22. PMID: 29578004. 2. Sørensen G, Husum H, Brennum LT, Bundgaard C, Montezinho LC, Mørk A, Wörtwein G, Woldbye DP. Addiction-related effects of DOV 216,303 and cocaine: A comparative study in the mouse. Basic Clin Pharmacol Toxicol. 2014 Jun;114(6):451-9. doi: 10.1111/bcpt.12182. Epub 2014 Jan 16. PMID: 24314270.

1: Sørensen G, Husum H, Brennum LT, Bundgaard C, Montezinho LC, Mørk A, Wörtwein G, Woldbye DP. Addiction-related effects of DOV 216,303 and cocaine: A comparative study in the mouse. Basic Clin Pharmacol Toxicol. 2014 Jun;114(6):451-9. doi: 10.1111/bcpt.12182. Epub 2014 Jan 16. PMID: 24314270. 2: Skolnick P, Krieter P, Tizzano J, Basile A, Popik P, Czobor P, Lippa A. Preclinical and clinical pharmacology of DOV 216,303, a "triple" reuptake inhibitor. CNS Drug Rev. 2006 Summer;12(2):123-34. doi: 10.1111/j.1527-3458.2006.00123.x. PMID: 16958986; PMCID: PMC6494125. 3: Beer B, Stark J, Krieter P, Czobor P, Beer G, Lippa A, Skolnick P. DOV 216,303, a "triple" reuptake inhibitor: safety, tolerability, and pharmacokinetic profile. J Clin Pharmacol. 2004 Dec;44(12):1360-7. doi: 10.1177/0091270004269560. PMID: 15545306. 4: Chu TH, Cummins K, Stys PK. The triple monoamine re-uptake inhibitor DOV 216,303 promotes functional recovery after spinal cord contusion injury in mice. Neurosci Lett. 2018 May 14;675:1-6. doi: 10.1016/j.neulet.2018.03.050. Epub 2018 Mar 22. PMID: 29578004. 5: Skolnick P, Popik P, Janowsky A, Beer B, Lippa AS. Antidepressant-like actions of DOV 21,947: a "triple" reuptake inhibitor. Eur J Pharmacol. 2003 Feb 14;461(2-3):99-104. doi: 10.1016/s0014-2999(03)01310-4. PMID: 12586204. 6: Tizzano JP, Stribling DS, Perez-Tilve D, Strack A, Frassetto A, Chen RZ, Fong TM, Shearman L, Krieter PA, Tschöp MH, Skolnick P, Basile AS. The triple uptake inhibitor (1R,5S)-(+)-1-(3,4-dichlorophenyl)-3-azabicyclo[3.1.0] hexane hydrochloride (DOV 21947) reduces body weight and plasma triglycerides in rodent models of diet-induced obesity. J Pharmacol Exp Ther. 2008 Mar;324(3):1111-26. doi: 10.1124/jpet.107.133132. Epub 2007 Dec 18. PMID: 18089843. 7: Breuer ME, Chan JS, Oosting RS, Groenink L, Korte SM, Campbell U, Schreiber R, Hanania T, Snoeren EM, Waldinger M, Olivier B. The triple monoaminergic reuptake inhibitor DOV 216,303 has antidepressant effects in the rat olfactory bulbectomy model and lacks sexual side effects. Eur Neuropsychopharmacol. 2008 Dec;18(12):908-16. doi: 10.1016/j.euroneuro.2008.07.011. Epub 2008 Sep 11. PMID: 18789657. 8: Prins J, Westphal KG, Korte-Bouws GA, Quinton MS, Schreiber R, Olivier B, Korte SM. The potential and limitations of DOV 216,303 as a triple reuptake inhibitor for the treatment of major depression: a microdialysis study in olfactory bulbectomized rats. Pharmacol Biochem Behav. 2011 Jan;97(3):444-52. doi: 10.1016/j.pbb.2010.10.001. Epub 2010 Oct 8. PMID: 20934452. 9: Prins J, Denys DA, Westphal KG, Korte-Bouws GA, Quinton MS, Schreiber R, Groenink L, Olivier B, Korte SM. The putative antidepressant DOV 216,303, a triple reuptake inhibitor, increases monoamine release in the prefrontal cortex of olfactory bulbectomized rats. Eur J Pharmacol. 2010 May 10;633(1-3):55-61. doi: 10.1016/j.ejphar.2010.02.009. Epub 2010 Feb 12. PMID: 20153745. 10: Prins J, Kenny PJ, Doomernik I, Schreiber R, Olivier B, Mechiel Korte S. The triple reuptake inhibitor DOV 216,303 induces long-lasting enhancement of brain reward activity as measured by intracranial self-stimulation in rats. Eur J Pharmacol. 2012 Oct 15;693(1-3):51-6. doi: 10.1016/j.ejphar.2012.07.047. Epub 2012 Aug 21. PMID: 23010469.

View History

MS-4077

MedKoo CAT#: 464913

CAS#: unknown