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MedKoo Cat#: 584376 | Name: Amitifadine HCl

Description:

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

Amitifadine the only drug ever clinically tested in Phase 3 for treating depression, is a triple reuptake inhibitor (TRI) that simultaneously interacts with human monoamine transporters (MATs) including hSERT, hNET and hDAT. This novel multi-target strategy improves drug efficacy and reduces the toxic side effects of drugs. However, the binding modes accounting for amitifadine's polypharmacological mode of action are still elusive, and extensive exploration of the amitifadine-target interactions between amitifadine and MATs is urgently needed.

Chemical Structure

Amitifadine HCl
Amitifadine HCl
CAS#410074-74-7 (HCl)

Theoretical Analysis

MedKoo Cat#: 584376

Name: Amitifadine HCl

CAS#: 410074-74-7 (HCl)

Chemical Formula: C11H12Cl3N

Exact Mass: 227.0269

Molecular Weight: 264.57

Elemental Analysis: C, 49.94; H, 4.57; Cl, 40.20; N, 5.29

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 #
410074-74-7 (HCl) 410074-73-6 (free base)
Synonym
Amitifadine; DOV 21,947; EB 1010; Amitifadine HCl; Amitifadine hydrochloride
IUPAC/Chemical Name
3-Azabicyclo(3.1.0)hexane, 1-(3,4-dichlorophenyl)-, (1R,5S)- hydrochloride
InChi Key
KAGBHVBIOJBGBD-NINOIYOQSA-N
InChi Code
InChI=1S/C11H11Cl2N.ClH/c12-9-2-1-7(3-10(9)13)11-4-8(11)5-14-6-11;/h1-3,8,14H,4-6H2;1H/t8-,11+;/m1./s1
SMILES Code
ClC1=CC=C([C@]23CNC[C@@]2([H])C3)C=C1Cl.[H]Cl
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
>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
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 264.57 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
1: Golembiowska K, Kowalska M, Bymaster FP. Effects of the triple reuptake inhibitor amitifadine on extracellular levels of monoamines in rat brain regions and on locomotor activity. Synapse. 2012 May;66(5):435-44. doi: 10.1002/syn.21531. Epub 2012 Feb 15. PubMed PMID: 22213370. 2: 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. PubMed PMID: 23010469. 3: van Heesch F, Prins J, Konsman JP, Korte-Bouws GA, Westphal KG, Rybka J, Olivier B, Kraneveld AD, Korte SM. Lipopolysaccharide increases degradation of central monoamines: an in vivo microdialysis study in the nucleus accumbens and medial prefrontal cortex of mice. Eur J Pharmacol. 2014 Feb 15;725:55-63. doi: 10.1016/j.ejphar.2014.01.014. Epub 2014 Jan 17. PubMed PMID: 24444442. 4: 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. PubMed PMID: 12586204. 5: 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. PubMed PMID: 20934452. 6: Levin ED, Wells C, Johnson JE, Rezvani AH, Bymaster FP, Rose JE. Amitifadine, a triple monoamine re-uptake inhibitor, reduces nicotine self-administration in female rats. Eur J Pharmacol. 2015 Oct 5;764:30-7. doi: 10.1016/j.ejphar.2015.06.041. Epub 2015 Jun 20. PubMed PMID: 26101069; PubMed Central PMCID: PMC4941618. 7: 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. PubMed PMID: 20153745. 8: 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. PubMed PMID: 22581450; PubMed Central PMCID: PMC3413810. 9: 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. PubMed PMID: 15545306. 10: O'Tousa DS, Warnock KT, Matson LM, Namjoshi OA, Linn MV, Tiruveedhula VV, Halcomb ME, Cook J, Grahame NJ, June HL. Triple monoamine uptake inhibitors demonstrate a pharmacologic association between excessive drinking and impulsivity in high-alcohol-preferring (HAP) mice. Addict Biol. 2015 Mar;20(2):236-47. doi: 10.1111/adb.12100. Epub 2013 Oct 13. PubMed PMID: 24118509; PubMed Central PMCID: PMC3984927. 11: 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. Epub 2007 Dec 18. PubMed PMID: 18089843. 12: Tran P, Skolnick P, Czobor P, Huang NY, Bradshaw M, McKinney A, Fava M. Efficacy and tolerability of the novel triple reuptake inhibitor amitifadine in the treatment of patients with major depressive disorder: a randomized, double-blind, placebo-controlled trial. J Psychiatr Res. 2012 Jan;46(1):64-71. doi: 10.1016/j.jpsychires.2011.09.003. Epub 2011 Sep 16. PubMed PMID: 21925682. 13: 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. Review. PubMed PMID: 16958986. 14: 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. PubMed PMID: 24314270. 15: 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. PubMed PMID: 18789657. 16: 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. PubMed PMID: 20864506; PubMed Central PMCID: PMC2993553. 17: Warnock KT, Yang AR, Yi HS, June HL Jr, Kelly T, Basile AS, Skolnick P, June HL. Amitifadine, a triple monoamine uptake inhibitor, reduces binge drinking and negative affect in an animal model of co-occurring alcoholism and depression symptomatology. Pharmacol Biochem Behav. 2012 Nov;103(1):111-8. PubMed PMID: 22884707; PubMed Central PMCID: PMC3537915. 18: Bijlsma EY, Chan JS, Olivier B, Veening JG, Millan MJ, Waldinger MD, Oosting RS. Sexual side effects of serotonergic antidepressants: mediated by inhibition of serotonin on central dopamine release? Pharmacol Biochem Behav. 2014 Jun;121:88-101. doi: 10.1016/j.pbb.2013.10.004. Epub 2013 Oct 12. Review. PubMed PMID: 24128918. 19: Bymaster FP, Chao P, Schulze H, Tran PV, Marshall RD. Biopharmaceutical characterization, metabolism, and brain penetration of the triple reuptake inhibitor amitifadine. Drug Metab Lett. 2013 Mar;7(1):23-33. PubMed PMID: 23826879. 20: Korte SM, Prins J, Krajnc AM, Hendriksen H, Oosting RS, Westphal KG, Korte-Bouws GA, Olivier B. The many different faces of major depression: it is time for personalized medicine. Eur J Pharmacol. 2015 Apr 15;753:88-104. doi: 10.1016/j.ejphar.2014.11.045. Epub 2015 Jan 12. Review. PubMed PMID: 25592320.