Vortioxetine HBr
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MedKoo CAT#: 314242

CAS#: 960203-27-4 (HBr)

Description: Vortioxetine, also known as Lu AA21004, is an atypical antidepressant, and was approved in 2013 by the U.S. FDA for the treatment of major depressive disorder (MDD) in adults. Vortioxetine is a so-called "serotonin modulator and stimulator." It has been shown to possess the following pharmacological actions: Serotonin transporter (SERT) blocker (i.e. serotonin reuptake inhibitor (SRI)) — Ki (binding affinity) = 1.6 nM, IC50 = 5.4 nM; Norepinephrine transporter (NET) blocker — Ki = 113 nM; 5-HT1A receptor high-efficacy partial agonist/near-full agonist — Ki = 15 nM, IA = 80%; 5-HT1B receptor partial agonist — Ki = 33 nM; 5-HT1D receptor antagonist — Ki = 54 nM; 5-HT3A receptor antagonist — Ki = 3.7 nM; 5-HT7 receptor antagonist — Ki = 19 nM.


Chemical Structure

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Vortioxetine HBr
CAS# 960203-27-4 (HBr)

Theoretical Analysis

MedKoo Cat#: 314242
Name: Vortioxetine HBr
CAS#: 960203-27-4 (HBr)
Chemical Formula: C18H23BrN2S
Exact Mass: 378.07653
Molecular Weight: 379.36
Elemental Analysis: C, 56.99; H, 6.11; Br, 21.06; N, 7.38; S, 8.45

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100.0mg USD 150.0 Ready to ship
200.0mg USD 250.0 Ready to ship
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2.0g USD 950.0 Ready to ship
5.0g USD 1650.0 Ready to ship
10.0g USD 2450.0 Ready to ship
20.0g USD 3250.0 Ready to ship
50.0g USD 4650.0 Ready to ship
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Related CAS #: 960203-27-4 (HBr)   508233-74-7 (free base)   1253056-29-9 (lactate)  

Synonym: LuAA21004; LuAA 21004; LuAA-21004; Lu-AA21004; Lu AA21004; LuAA21004; AA21004; AA-21004; AA 21004; Vortioxetine, Vortioxetine Hydrobromide, Brintellix

IUPAC/Chemical Name: 1-[2-(2,4-dimethylphenyl)sulfanylphenyl]piperazine hydrobromide

InChi Key: InChI=1S/C18H22N2S.BrH/c1-14-7-8-17(15(2)13-14)21-18-6-4-3-5-16(18)20-11-9-19-10-12-20;/h3-8,13,19H,9-12H2,1-2H3;1H

InChi Code: InChI=1S/C18H22N2S.BrH/c1-14-7-8-17(15(2)13-14)21-18-6-4-3-5-16(18)20-11-9-19-10-12-20;/h3-8,13,19H,9-12H2,1-2H3;1H

SMILES Code: CC1=CC=C(SC2=CC=CC=C2N3CCNCC3)C(C)=C1.[H]Br

Appearance: White to off-white 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: Soluble in DMSO.

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

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

Biological target: Vortioxetine hydrobromide is a multimodal serotonergic agent, inhibits 5-HT1A, 5-HT1B, 5-HT3A, 5-HT7 receptor and SERT with Ki values of 15 nM, 33 nM, 3.7 nM, 19 nM and 1.6 nM, respectively.
In vitro activity: Relative to vehicle-treated neurons, vortioxetine promoted an increase in total spine area (1.30 ± 0.05 μm2; ****, p < 0.0001), spine width (1.16 ± 0.04 μm; ****, p < 0.0001), spine breadth (1.10 ± 0.03 μm; ***, p = 0.0003), which is comparable to spine head width in MetaMorph software, and spine length (1.16 ± 0.03 μm; ****, p < 0.0001) (Fig. 2A,B, Table 1). There was an increased proportion of large, mushroom-like spines with an area greater than 2.0 μm2 with vortioxetine treatment in comparison to vehicle (Fig. 6A). In contrast to the increase in spine density following subchronic and chronic vortioxetine treatment reported in vivo, there were no changes in the density of spines per 10 μm dendritic segment (7.50 ± 0.41 (VOR) vs. 7.07 ± 0.30 (VEH)) (Fig. 2A,C, Table 1). Interestingly, the proportion of spines that were closely apposed to or co-localized with the presynaptic vesicle marker synapsin I was greater with vortioxetine than in vehicle-treated neurons (45.44 ± 3.09% (VOR) vs. 34.47 ± 2.65% (VEH); *, p = 0.0145) (Fig. 2A,C, Table 1). Reference: Neuropharmacology. 2016 Apr;103:143-54. https://pubmed.ncbi.nlm.nih.gov/21486038/
In vivo activity: The analgesic activity of vortioxetine was evaluated by the tail-clip, tail-immersion and hot-plate tests. In the tail-clip tests, animals administered vortioxetine at 10 and 20 mg/kg had significantly longer reaction time than saline-administered control mice. Moreover, MPE% and AUC values were also significantly higher with respect to the control groups. 5 mg/kg dose of this drug was only effective at 60th minute (Figure 2). In the tail-clip method, the clamp-biting reaction of animals is known to be associated with spinal transmission of nociception. Therefore, these findings suggest that the analgesic activity of vortioxetine is related to its effect on spinal nociceptive pathways that carry painful mechanical stimuli. Reference: Molecules. 2021 May 28;26(11):3242. https://www.mdpi.com/1420-3049/26/11/3242/htm

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 52.0 137.07
DMSO:PBS (pH 7.2) (1:3) 0.25 0.66
DMF 30.0 79.08
Ethanol 22.0 57.99

Preparing Stock Solutions

The following data is based on the product molecular weight 379.36 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.

Recalculate based on batch purity %
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. Waller JA, Chen F, Sánchez C. Vortioxetine promotes maturation of dendritic spines in vitro: A comparative study in hippocampal cultures. Neuropharmacology. 2016 Apr;103:143-54. doi: 10.1016/j.neuropharm.2015.12.012. Epub 2015 Dec 15. PMID: 26702943. 2. Bang-Andersen B, Ruhland T, Jørgensen M, Smith G, Frederiksen K, Jensen KG, Zhong H, Nielsen SM, Hogg S, Mørk A, Stensbøl TB. Discovery of 1-[2-(2,4-dimethylphenylsulfanyl)phenyl]piperazine (Lu AA21004): a novel multimodal compound for the treatment of major depressive disorder. J Med Chem. 2011 May 12;54(9):3206-21. doi: 10.1021/jm101459g. Epub 2011 Apr 12. PMID: 21486038. 3. Turan Yücel N, Kandemir Ü, Demir Özkay Ü, Can ÖD. 5-HT1A Serotonergic, α-Adrenergic and Opioidergic Receptors Mediate the Analgesic Efficacy of Vortioxetine in Mice. Molecules. 2021 May 28;26(11):3242. doi: 10.3390/molecules26113242. PMID: 34071269. 4. Martis LS, Højgaard K, Holmes MC, Elfving B, Wiborg O. Vortioxetine ameliorates anhedonic-like behaviour and promotes strategic cognitive performance in a rodent touchscreen task. Sci Rep. 2021 Apr 27;11(1):9113. doi: 10.1038/s41598-021-88462-7. PMID: 33907240; PMCID: PMC8079376.
In vitro protocol: 1. Waller JA, Chen F, Sánchez C. Vortioxetine promotes maturation of dendritic spines in vitro: A comparative study in hippocampal cultures. Neuropharmacology. 2016 Apr;103:143-54. doi: 10.1016/j.neuropharm.2015.12.012. Epub 2015 Dec 15. PMID: 26702943. 2. Bang-Andersen B, Ruhland T, Jørgensen M, Smith G, Frederiksen K, Jensen KG, Zhong H, Nielsen SM, Hogg S, Mørk A, Stensbøl TB. Discovery of 1-[2-(2,4-dimethylphenylsulfanyl)phenyl]piperazine (Lu AA21004): a novel multimodal compound for the treatment of major depressive disorder. J Med Chem. 2011 May 12;54(9):3206-21. doi: 10.1021/jm101459g. Epub 2011 Apr 12. PMID: 21486038.
In vivo protocol: 1. Turan Yücel N, Kandemir Ü, Demir Özkay Ü, Can ÖD. 5-HT1A Serotonergic, α-Adrenergic and Opioidergic Receptors Mediate the Analgesic Efficacy of Vortioxetine in Mice. Molecules. 2021 May 28;26(11):3242. doi: 10.3390/molecules26113242. PMID: 34071269. 2. Martis LS, Højgaard K, Holmes MC, Elfving B, Wiborg O. Vortioxetine ameliorates anhedonic-like behaviour and promotes strategic cognitive performance in a rodent touchscreen task. Sci Rep. 2021 Apr 27;11(1):9113. doi: 10.1038/s41598-021-88462-7. PMID: 33907240; PMCID: PMC8079376.

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 1: Baune BT, Renger L. Pharmacological and non-pharmacological interventions to improve cognitive dysfunction and functional ability in clinical depression - A systematic review. Psychiatry Res. 2014 Sep 30;219(1):25-50. doi: 10.1016/j.psychres.2014.05.013. Epub 2014 May 14. Review. PubMed PMID: 24863864.

2: Katona CL, Katona CP. New generation multi-modal antidepressants: focus on vortioxetine for major depressive disorder. Neuropsychiatr Dis Treat. 2014 Feb 19;10:349-54. doi: 10.2147/NDT.S39544. eCollection 2014. Review. PubMed PMID: 24570588; PubMed Central PMCID: PMC3933721.

3: Pehrson AL, Sanchez C. Serotonergic modulation of glutamate neurotransmission as a strategy for treating depression and cognitive dysfunction. CNS Spectr. 2014 Apr;19(2):121-33. doi: 10.1017/S1092852913000540. Epub 2013 Aug 1. Review. PubMed PMID: 23903233; PubMed Central PMCID: PMC3968911.

4: Celada P, Bortolozzi A, Artigas F. Serotonin 5-HT1A receptors as targets for agents to treat psychiatric disorders: rationale and current status of research. CNS Drugs. 2013 Sep;27(9):703-16. doi: 10.1007/s40263-013-0071-0. Review. PubMed PMID: 23757185.

5: Stahl SM, Lee-Zimmerman C, Cartwright S, Morrissette DA. Serotonergic drugs for depression and beyond. Curr Drug Targets. 2013 May 1;14(5):578-85. Review. PubMed PMID: 23531115.

6: Adell A. Lu-AA21004, a multimodal serotonergic agent, for the potential treatment of depression and anxiety. IDrugs. 2010 Dec;13(12):900-10. Review. PubMed PMID: 21154150.