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

DOV-216303 free base
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WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 413910

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

Description: 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)

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 413910
Name: DOV-216303 free base
CAS#: 66504-40-3 (free base)
Chemical Formula: C11H11Cl2N
Exact Mass: 227.03
Molecular Weight: 228.116
Elemental Analysis: C, 57.92; H, 4.86; Cl, 31.08; N, 6.14

Price and Availability

Size	Price	Availability
5mg	USD 323	2 Weeks
25mg	USD 920	2 Weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Related CAS #: 86215-36-3 (HCl) 66504-40-3 (free base)

Synonym: DOV-216303 free base; DOV 216,303 free base

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

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Product Data:

Product Data

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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/

Solubility Data

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

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:	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.
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.

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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.

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