Amitifadine free base

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

MedKoo CAT#: 319726

CAS#: 410074-73-6 (free base)

Description: Amitifadine, also known as DOV-21,947 or EB-1010, is an antidepressant drug candidate. It is a so-called triple reuptake inhibitor (TRI) or serotonin-norepinephrine-dopamine reuptake inhibitor (SNDRI). Amitifadine reduces nicotine self-administration in female rats. Amitifadine reduces binge drinking and negative affect in an animal model of co-occurring alcoholism and depression symptomatology.


Chemical Structure

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Amitifadine free base
CAS# 410074-73-6 (free base)

Theoretical Analysis

MedKoo Cat#: 319726
Name: Amitifadine free base
CAS#: 410074-73-6 (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

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Related CAS #: 410074-74-7 (HCl)   410074-73-6 (free base)    

Synonym: DOV-21,947; DOV21,947; DOV 21,947; DOV-21947; DOV21947; DOV 21947; EB-1010; EB 1010; EB1010; Amitifadine

IUPAC/Chemical Name: (1R,5S)-1-(3,4-dichlorophenyl)-3-azabicyclo[3.1.0]hexane

InChi Key: BSMNRYCSBFHEMQ-KCJUWKMLSA-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/t8-,11+/m1/s1

SMILES Code: ClC1=CC=C([C@]23CNC[C@@]2([H])C3)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: Soluble in DMSO, not in water

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: Related CAS# 410074-73-6 (Amitifadine) 410074-74-7 (Amitifadine Hydrochloride)

Biological target:
In vitro activity:
In vivo activity:

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.

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:
In vitro protocol:
In vivo protocol:

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1: 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.

2: Miller LL, Leitl MD, Banks ML, Blough BE, Negus SS. Effects of the triple monoamine uptake inhibitor amitifadine on pain-related depression of behavior and mesolimbic dopamine release in rats. Pain. 2015 Jan;156(1):175-84. doi: 10.1016/j.pain.0000000000000018. PubMed PMID: 25599313; PubMed Central PMCID: PMC4351716.

3: 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.

4: 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.

5: Marks DM, Abramowitz JS, Spielmans GI. Concerns about data reporting and interpretation in "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 May;46(5):692-3; author reply 694-5. doi: 10.1016/j.jpsychires.2012.02.002. PubMed PMID: 22520251.

6: 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.

7: 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. 1: 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.

2: Miller LL, Leitl MD, Banks ML, Blough BE, Negus SS. Effects of the triple monoamine uptake inhibitor amitifadine on pain-related depression of behavior and mesolimbic dopamine release in rats. Pain. 2015 Jan;156(1):175-84. doi: 10.1016/j.pain.0000000000000018. PubMed PMID: 25599313; PubMed Central PMCID: PMC4351716.

3: 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.

4: 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.

5: Marks DM, Abramowitz JS, Spielmans GI. Concerns about data reporting and interpretation in "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 May;46(5):692-3; author reply 694-5. doi: 10.1016/j.jpsychires.2012.02.002. PubMed PMID: 22520251.

6: 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.

7: 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.