Levomilnacipran | CAS#96847-54-0 | Antidepressant

MedKoo Cat#: 598732 | Name: Levomilnacipran

Description:

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

Levomilnacipran is an antidepressant.

Chemical Structure

Levomilnacipran

CAS#96847-54-0 (free base 1S2R)

Theoretical Analysis

MedKoo Cat#: 598732

Name: Levomilnacipran

CAS#: 96847-54-0 (free base 1S2R)

Chemical Formula: C15H22N2O

Exact Mass: 246.1732

Molecular Weight: 246.35

Elemental Analysis: C, 73.13; H, 9.00; N, 11.37; O, 6.49

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

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Related CAS #

175131-60-9 (HCl) 96847-55-1 (free base 1R2S) 96847-54-0 (free base 1S2R)

Synonym

Levomilnacipran; F2695; F 2695; F-2695

IUPAC/Chemical Name

(1S,2R)-2-(aminomethyl)-N,N-diethyl-1-phenylcyclopropane-1-carboxamide

InChi Key

GJJFMKBJSRMPLA-DZGCQCFKSA-N

InChi Code

InChI=1S/C15H22N2O/c1-3-17(4-2)14(18)15(10-13(15)11-16)12-8-6-5-7-9-12/h5-9,13H,3-4,10-11,16H2,1-2H3/t13-,15+/m0/s1

SMILES Code

O=C([C@]1(C2=CC=CC=C2)[C@H](CN)C1)N(CC)CC

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

Soluble in DMSO

Shelf Life

>3 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

2934.99.03.00

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Levomilnacipran is an antidepressant.

In vitro activity:

LVM (levomilnacipran) exhibited high affinity for human NE (Ki = 92.2 nM) and 5-HT (11.2 nM) transporters, and potently inhibited NE (IC50 = 10.5 nM) and 5-HT (19.0 nM) reuptake (human transporter) in vitro. LVM had 2-fold greater potency for norepinephrine relative to serotonin reuptake inhibition (i.e. NE/5-HT potency ratio: 0.6) and 17 and 27 times higher selectivity for NE reuptake inhibition compared with venlafaxine and duloxetine, respectively. Reference: Neuropharmacology. 2013 Jul;70:338-47. https://pubmed.ncbi.nlm.nih.gov/23499664/

In vivo activity:

In anti-depressive/anti-stress models, i.p. LVM (levomilnacipran) diminished immobility time in the mouse forced swim (MED = 20 mg/kg) and tail suspension (MED = 2.5 mg/kg) tests, and reduced shock-induced ultrasonic vocalizations in rats (MED = 5 mg/kg). Reference: Neuropharmacology. 2013 Jul;70:338-47. https://pubmed.ncbi.nlm.nih.gov/23499664/

Preparing Stock Solutions

The following data is based on the product molecular weight 246.35 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. Auclair AL, Martel JC, Assié MB, Bardin L, Heusler P, Cussac D, Marien M, Newman-Tancredi A, O'Connor JA, Depoortère R. Levomilnacipran (F2695), a norepinephrine-preferring SNRI: profile in vitro and in models of depression and anxiety. Neuropharmacology. 2013 Jul;70:338-47. doi: 10.1016/j.neuropharm.2013.02.024. Epub 2013 Mar 13. PMID: 23499664.

In vitro protocol:

In vivo protocol:

1: Chen L, Boinpally R, Gad N, Greenberg WM, Wangsa J, Periclou A, Ghahramani P. Evaluation of Cytochrome P450 (CYP) 3A4-Based Interactions of Levomilnacipran with Ketoconazole, Carbamazepine or Alprazolam in Healthy Subjects. Clin Drug Investig. 2015 Oct;35(10):601-12. doi: 10.1007/s40261-015-0318-2. PubMed PMID: 26315684. 2: Scott LJ. Levomilnacipran extended-release: a review of its use in adult patients with major depressive disorder. CNS Drugs. 2014 Nov;28(11):1071-82. doi: 10.1007/s40263-014-0203-1. Review. PubMed PMID: 25270036. 3: Brunner V, Maynadier B, Chen L, Roques L, Hude I, Séguier S, Barthe L, Hermann P. Disposition and metabolism of [14C]-levomilnacipran, a serotonin and norepinephrine reuptake inhibitor, in humans, monkeys, and rats. Drug Des Devel Ther. 2015 Jun 23;9:3199-215. doi: 10.2147/DDDT.S80886. eCollection 2015. PubMed PMID: 26150694; PubMed Central PMCID: PMC4484650. 4: Bakish D, Bose A, Gommoll C, Chen C, Nunez R, Greenberg WM, Liebowitz M, Khan A. Levomilnacipran ER 40 mg and 80 mg in patients with major depressive disorder: a phase III, randomized, double-blind, fixed-dose, placebo-controlled study. J Psychiatry Neurosci. 2014 Jan;39(1):40-9. doi: 10.1503/jpn.130040. PubMed PMID: 24144196; PubMed Central PMCID: PMC3868664. 5: Hair P, Cameron F, Garnock-Jones KP. Levomilnacipran extended release: first global approval. Drugs. 2013 Sep;73(14):1639-45. doi: 10.1007/s40265-013-0116-1. Review. PubMed PMID: 24000002. 6: Mago R, Mahajan R, Thase ME. Levomilnacipran: a newly approved drug for treatment of major depressive disorder. Expert Rev Clin Pharmacol. 2014 Mar;7(2):137-45. doi: 10.1586/17512433.2014.889563. Review. PubMed PMID: 24524592. 7: Chen L, Greenberg WM, Gommoll C, O'Connor J, Zukin SR, Periclou A, Ghahramani P. Levomilnacipran Pharmacokinetics in Healthy Volunteers Versus Patients with Major Depressive Disorder and Implications for Norepinephrine and Serotonin Reuptake Inhibition. Clin Ther. 2015 Sep;37(9):2059-70. doi: 10.1016/j.clinthera.2015.07.005. Epub 2015 Aug 20. PubMed PMID: 26256429. 8: Saraceni MM, Venci JV, Gandhi MA. Levomilnacipran (Fetzima): A New Serotonin-Norepinephrine Reuptake Inhibitor for the Treatment of Major Depressive Disorder. J Pharm Pract. 2014 Aug;27(4):389-95. doi: 10.1177/0897190013516504. Epub 2013 Dec 31. Review. PubMed PMID: 24381243. 9: Palmer EC, Binns LN, Carey H. Levomilnacipran: A New Serotonin-Norepinephrine Reuptake Inhibitor for the Treatment of Major Depressive Disorder. Ann Pharmacother. 2014 Aug;48(8):1030-1039. Epub 2014 May 8. Review. PubMed PMID: 24811398. 10: Zaman S, McLaughlin MR. Levomilnacipran (Fetzima) for Major Depressive Disorder. Am Fam Physician. 2015 Oct 15;92(8):727-31. PubMed PMID: 26554414. 11: Blum SI, Tourkodimitris S, Ruth A. Evaluation of functional health and well-being in patients receiving levomilnacipran ER for the treatment of major depressive disorder. J Affect Disord. 2015 Jan 1;170:230-6. doi: 10.1016/j.jad.2014.09.005. Epub 2014 Sep 10. PubMed PMID: 25259674. 12: Asnis GM, Henderson MA. Levomilnacipran for the treatment of major depressive disorder: a review. Neuropsychiatr Dis Treat. 2015 Jan 9;11:125-35. doi: 10.2147/NDT.S54710. eCollection 2015. Review. PubMed PMID: 25657584; PubMed Central PMCID: PMC4295915. 13: Montgomery SA, Gommoll CP, Chen C, Greenberg WM. Efficacy of levomilnacipran extended-release in major depressive disorder: pooled analysis of 5 double-blind, placebo-controlled trials. CNS Spectr. 2015 Apr;20(2):148-56. doi: 10.1017/S1092852914000273. Epub 2014 Jun 5. PubMed PMID: 24902007; PubMed Central PMCID: PMC4411644. 14: Bruno A, Morabito P, Spina E, Muscatello MR. The Role of Levomilnacipran in the Management of Major Depressive Disorder: A Comprehensive Review. Curr Neuropharmacol. 2016;14(2):191-9. Review. PubMed PMID: 26572745; PubMed Central PMCID: PMC4825949. 15: Rizvi SM, Shaikh S, Khan M, Biswas D, Hameed N, Shakil S. Fetzima (levomilnacipran), a drug for major depressive disorder as a dual inhibitor for human serotonin transporters and beta-site amyloid precursor protein cleaving enzyme-1. CNS Neurol Disord Drug Targets. 2014;13(8):1427-31. PubMed PMID: 25345508. 16: Citrome L. Levomilnacipran for major depressive disorder: a systematic review of the efficacy and safety profile for this newly approved antidepressant--what is the number needed to treat, number needed to harm and likelihood to be helped or harmed? Int J Clin Pract. 2013 Nov;67(11):1089-104. doi: 10.1111/ijcp.12298. Epub 2013 Sep 8. Review. PubMed PMID: 24016209. 17: Sambunaris A, Gommoll C, Chen C, Greenberg WM. Efficacy of levomilnacipran extended-release in improving functional impairment associated with major depressive disorder: pooled analyses of five double-blind, placebo-controlled trials. Int Clin Psychopharmacol. 2014 Jul;29(4):197-205. doi: 10.1097/YIC.0000000000000033. PubMed PMID: 24667487; PubMed Central PMCID: PMC4047314. 18: Sambunaris A, Bose A, Gommoll CP, Chen C, Greenberg WM, Sheehan DV. A phase III, double-blind, placebo-controlled, flexible-dose study of levomilnacipran extended-release in patients with major depressive disorder. J Clin Psychopharmacol. 2014 Feb;34(1):47-56. doi: 10.1097/JCP.0000000000000060. PubMed PMID: 24172209; PubMed Central PMCID: PMC4047313. 19: Montgomery SA, Mansuy L, Ruth AC, Li D, Gommoll C. The efficacy of extended-release levomilnacipran in moderate to severe major depressive disorder: secondary and post-hoc analyses from a randomized, double-blind, placebo-controlled study. Int Clin Psychopharmacol. 2014 Jan;29(1):26-35. doi: 10.1097/YIC.0000000000000009. PubMed PMID: 24172160; PubMed Central PMCID: PMC4235391. 20: Scarff JR. Levomilnacipran and Vortioxetine for Adults with Major Depressive Disorder. J S C Med Assoc. 2015 Dec-2016 Jan;111(4):131-3. Review. PubMed PMID: 27141705.