MedKoo Cat#: 413011 | Name: Bicifadine free base

Description:

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

Bicifadine, also known as DOV-220075, CL 220,075, is a SNDR inhibitor potentially for the treatment of lower back pain. Bicifadine has a non-opioid, non-NSAID mechanism for the treatment of pain, which should have less abuse potential than opioid drugs and less propensity to cause gastric ulcers than NSAID drugs. While the drug is purported to be a serotonin (SERT) and noradrenaline transporter (NET) inhibitor, it also has effects at the dopamine transporter (DAT), effectively making it a broad-spectrum monoamine transporter inhibitor or "triple reuptake inhibitor."

Chemical Structure

Bicifadine free base
Bicifadine free base
CAS#71195-57-8 (free base)

Theoretical Analysis

MedKoo Cat#: 413011

Name: Bicifadine free base

CAS#: 71195-57-8 (free base)

Chemical Formula: C12H15N

Exact Mass: 173.1204

Molecular Weight: 173.26

Elemental Analysis: C, 83.19; H, 8.73; N, 8.08

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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Synonym
Bicifadine (free base); CL220075; CL-220075; CL 220075
IUPAC/Chemical Name
3-Azabicyclo(3.1.0)hexane, 1-(4-methylphenyl)-, (+-)-
InChi Key
OFYVIGTWSQPCLF-UHFFFAOYSA-N
InChi Code
InChI=1S/C12H15N/c1-9-2-4-10(5-3-9)12-6-11(12)7-13-8-12/h2-5,11,13H,6-8H2,1H3
SMILES Code
CC1=CC=C(C23CNCC2C3)C=C1
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 173.26 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: Di Cesare Mannelli L, Micheli L, Crocetti L, Giovannoni MP, Vergelli C, Ghelardini C. α2 Adrenoceptor: a Target for Neuropathic Pain Treatment. Mini Rev Med Chem. 2017;17(2):95-107. doi: 10.2174/1389557516666160609065535. PMID: 27292786. 2: Srinivas NR, Ahlawat P. Prediction of human pharmacokinetic parameters using animal data and principles of allometry. A case using bicifadine, a non-narcotic analgesic, as an example. Arzneimittelforschung. 2009;59(12):625-30. doi: 10.1055/s-0031-1296450. PMID: 20108647. 3: Nicholson KL, Balster RL, Golembiowska K, Kowalska M, Tizzano JP, Skolnick P, Basile AS. Preclinical evaluation of the abuse potential of the analgesic bicifadine. J Pharmacol Exp Ther. 2009 Jul;330(1):236-48. doi: 10.1124/jpet.109.150540. Epub 2009 Apr 8. PMID: 19357320; PMCID: PMC3202431. 4: Musick TJ, Gohdes M, Duffy A, Erickson DA, Krieter PA. Pharmacokinetics, disposition, and metabolism of bicifadine in the mouse, rat, and monkey. Drug Metab Dispos. 2008 Feb;36(2):241-51. doi: 10.1124/dmd.107.017863. Epub 2007 Nov 8. PMID: 17991767. 5: Krieter PA, Gohdes M, Musick TJ, Duncanson FP, Bridson WE. Pharmacokinetics, disposition, and metabolism of bicifadine in humans. Drug Metab Dispos. 2008 Feb;36(2):252-9. doi: 10.1124/dmd.107.017871. Epub 2007 Nov 8. PMID: 17991768. 6: Basile AS, Janowsky A, Golembiowska K, Kowalska M, Tam E, Benveniste M, Popik P, Nikiforuk A, Krawczyk M, Nowak G, Krieter PA, Lippa AS, Skolnick P, Koustova E. Characterization of the antinociceptive actions of bicifadine in models of acute, persistent, and chronic pain. J Pharmacol Exp Ther. 2007 Jun;321(3):1208-25. doi: 10.1124/jpet.106.116483. Epub 2007 Feb 26. PMID: 17325229. 7: Zhang M, Jovic F, Vickers T, Dyck B, Tamiya J, Grey J, Tran JA, Fleck BA, Pick R, Foster AC, Chen C. Studies on the structure-activity relationship of bicifadine analogs as monoamine transporter inhibitors. Bioorg Med Chem Lett. 2008 Jul 1;18(13):3682-6. doi: 10.1016/j.bmcl.2008.05.077. Epub 2008 May 23. PMID: 18539031. 8: Xu F, Murry JA, Simmons B, Corley E, Fitch K, Karady S, Tschaen D. Stereocontrolled synthesis of trisubstituted cyclopropanes: expedient, atom- economical, asymmetric syntheses of (+)-Bicifadine and DOV21947. Org Lett. 2006 Aug 17;8(17):3885-8. doi: 10.1021/ol061650w. PMID: 16898842.