MedKoo Biosciences, Inc.
Tel:   +1-919-636-5577    Fax:   +1-919-980-4831    Email:   sales@medkoo.com
Search
Login Register
Search
MedKoo Cat#: 563732 | Name: Oxalamine Citrate
Featured

Description:

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

Oxalamine Citrate is a cough suppressant.

Chemical Structure

Oxalamine Citrate
Oxalamine Citrate
CAS#1949-20-8

Theoretical Analysis

MedKoo Cat#: 563732

Name: Oxalamine Citrate

CAS#: 1949-20-8

Chemical Formula: C20H27N3O8

Exact Mass: 437.1798

Molecular Weight: 437.45

Elemental Analysis: C, 54.91; H, 6.22; N, 9.61; O, 29.26

Price and Availability

Size Price Availability Quantity
Bulk Inquiry
Buy Now
Add to Cart
Related CAS #
No Data
Synonym
Oxalamine Citrate; Oxalamine Citrate salt;
IUPAC/Chemical Name
N,N-Diethyl-2-(3-phenyl-1,2,4-oxadiazol-5-yl)ethanamine citrate
InChi Key
RBZIGQJSMCOHSS-UHFFFAOYSA-N
InChi Code
InChI=1S/C14H19N3O.C6H8O7/c1-3-17(4-2)11-10-13-15-14(16-18-13)12-8-6-5-7-9-12;7-3(8)1-6(13,5(11)12)2-4(9)10/h5-9H,3-4,10-11H2,1-2H3;13H,1-2H2,(H,7,8)(H,9,10)(H,11,12)
SMILES Code
CCN(CC)CCC1=NC(C2=CC=CC=C2)=NO1.OC(C(O)=O)(CC(O)=O)CC(O)=O
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:
Oxolamine citrate (SKF-9976 citrate) is a cough suppressant.
In vitro activity:
TBD
In vivo activity:
After oral administration of warfarin at a dose of 2 mg/kg to male rats with oxolamine at doses of 10 and 50 mg/kg, the AUC values of warfarin were significantly greater than the controls (254 and 330 versus 180 microg h/ml). However, the AUC values of warfarin were not affected by oxolamine in female rats. This could be due to inhibition of CYP2B1, 2C11 and 3A2 by oxolamine in male rats, since warfarin was metabolized via CYP1A1, 2B1, 2C6, 2C11 and 3A2 in rats and CYP2B1 is male dominant, and CYP2C11 and 3A2 are male specific. Reference: Biopharm Drug Dispos. 2007 Apr;28(3):125-33. https://pubmed.ncbi.nlm.nih.gov/17295362/
Solvent mg/mL mM
Solubility
DMSO 93.5 213.74
Water 28.7 65.48
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 437.45 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. Zhu X, Lee DY, Shin WG. Gender difference in the pharmacokinetic interaction between oral warfarin and oxolamine in rats: inhibition of CYP2B1 by oxolamine in male rats. Biopharm Drug Dispos. 2007 Apr;28(3):125-33. doi: 10.1002/bdd.538. PMID: 17295362. 2. Silvestrini B, Pozzatti C. Pharmacological properties of 3-phenyl-5beta diethylaminoethyl-1,2,4-oxadiazole. Br J Pharmacol Chemother. 1961 Jun;16(3):209-17. doi: 10.1111/j.1476-5381.1961.tb01080.x. PMID: 19108149; PMCID: PMC1482017.
In vitro protocol:
TBD
In vivo protocol:
1. Zhu X, Lee DY, Shin WG. Gender difference in the pharmacokinetic interaction between oral warfarin and oxolamine in rats: inhibition of CYP2B1 by oxolamine in male rats. Biopharm Drug Dispos. 2007 Apr;28(3):125-33. doi: 10.1002/bdd.538. PMID: 17295362. 2. Silvestrini B, Pozzatti C. Pharmacological properties of 3-phenyl-5beta diethylaminoethyl-1,2,4-oxadiazole. Br J Pharmacol Chemother. 1961 Jun;16(3):209-17. doi: 10.1111/j.1476-5381.1961.tb01080.x. PMID: 19108149; PMCID: PMC1482017.
1: Hadni H, Mazigh M, Charif E, Bouayad A, Elhallaoui M. Molecular Modeling of Antimalarial Agents by 3D-QSAR Study and Molecular Docking of Two Hybrids 4-Aminoquinoline-1,3,5-triazine and 4-Aminoquinoline-oxalamide Derivatives with the Receptor Protein in Its Both Wild and Mutant Types. Biochem Res Int. 2018 Jun 24;2018:8639173. doi: 10.1155/2018/8639173. eCollection 2018. PubMed PMID: 30034881; PubMed Central PMCID: PMC6035821. 2: Wilsens CHRM, Hawke LGD, Troisi EM, Hermida-Merino D, de Kort G, Leoné N, Saralidze K, Peters GWM, Rastogi S. Effect of Self-Assembly of Oxalamide Based Organic Compounds on Melt Behavior, Nucleation, and Crystallization of Isotactic Polypropylene. Macromolecules. 2018 Jul 10;51(13):4882-4895. doi: 10.1021/acs.macromol.8b00489. Epub 2018 Jun 21. PubMed PMID: 30018462; PubMed Central PMCID: PMC6041772. 3: Ndoye C, Diallo W, Diouf O, Barry AH, Gaye M, Gautier R. Crystal structure of (μ-trans-1,2-bis-{2-[(2-oxido-phen-yl)methyl-idene]hydrazin-1-yl-idene}ethane-1,2 -diolato-κ(3)O,O',N)bis-[di-tert-butyl-tin(IV)]. Acta Crystallogr E Crystallogr Commun. 2018 May 15;74(Pt 6):799-802. doi: 10.1107/S2056989018007077. eCollection 2018 Jun 1. PubMed PMID: 29951233; PubMed Central PMCID: PMC6002830. 4: Li XY, Ma LN, Liu Y, Hou L, Wang YY, Zhu Z. Honeycomb Metal-Organic Framework with Lewis Acidic and Basic Bifunctional Sites: Selective Adsorption and CO(2) Catalytic Fixation. ACS Appl Mater Interfaces. 2018 Apr 4;10(13):10965-10973. doi: 10.1021/acsami.8b01291. Epub 2018 Mar 22. PubMed PMID: 29565563. 5: Dhanishta P, Mishra SK, Suryaprakash N. Intramolecular HB Interactions Evidenced in Dibenzoyl Oxalamide Derivatives: NMR, QTAIM, and NCI Studies. J Phys Chem A. 2018 Jan 11;122(1):199-208. doi: 10.1021/acs.jpca.7b10598. Epub 2017 Dec 21. PubMed PMID: 29220174. 6: Džolić Z, Beyeh NK, Cetina M, Turunen L, Rissanen K. Self-Complementary Dimers of Oxalamide-Functionalized Resorcinarene Tetrabenzoxazines. Chem Asian J. 2018 Jan 18;13(2):164-169. doi: 10.1002/asia.201701426. Epub 2017 Dec 18. PubMed PMID: 29205943. 7: Harig T, Schlawis C, Ziesche L, Pohlner M, Engelen B, Schulz S. Nitrogen-Containing Volatiles from Marine Salinispora pacifica and Roseobacter-Group Bacteria. J Nat Prod. 2017 Dec 22;80(12):3289-3295. doi: 10.1021/acs.jnatprod.7b00789. Epub 2017 Dec 1. PubMed PMID: 29192774. 8: Li XY, Li YZ, Yang Y, Hou L, Wang YY, Zhu Z. Efficient light hydrocarbon separation and CO(2) capture and conversion in a stable MOF with oxalamide-decorated polar tubes. Chem Commun (Camb). 2017 Nov 30;53(96):12970-12973. doi: 10.1039/c7cc08298c. PubMed PMID: 29160877. 9: Bhunia S, Kumar SV, Ma D. N,N'-Bisoxalamides Enhance the Catalytic Activity in Cu-Catalyzed Coupling of (Hetero)Aryl Bromides with Anilines and Secondary Amines. J Org Chem. 2017 Dec 1;82(23):12603-12612. doi: 10.1021/acs.joc.7b02363. Epub 2017 Nov 16. PubMed PMID: 29117476. 10: Park J, Jean A, Chen DY. Organocatalytic and Late-Stage CH-Functionalization Enabled Asymmetric Synthesis of Communesin F and Putative Communesins. J Org Chem. 2018 Jul 6;83(13):6936-6957. doi: 10.1021/acs.joc.7b02426. Epub 2017 Nov 9. PubMed PMID: 29090575. 11: Dabić D, Brkljačić L, Tandarić T, Žinić M, Vianello R, Frkanec L, Kobetić R. The Metal Effect on Self-Assembling of Oxalamide Gelators Explored by Mass Spectrometry and DFT Calculations. J Am Soc Mass Spectrom. 2018 Jan;29(1):103-113. doi: 10.1007/s13361-017-1834-5. Epub 2017 Oct 30. PubMed PMID: 29086338. 12: De S, Yin J, Ma D. Copper-Catalyzed Coupling Reaction of (Hetero)Aryl Chlorides and Amides. Org Lett. 2017 Sep 15;19(18):4864-4867. doi: 10.1021/acs.orglett.7b02326. Epub 2017 Aug 31. PubMed PMID: 28858514. 13: Bigdeli F, Hosseini-Monfared H, Morsali A, Mayer P. Synthesis of a new Hg(II) coordination polymer: Ultrasonic-assisted synthesis and mechanical preparation of nanostructure. Ultrason Sonochem. 2017 Nov;39:669-675. doi: 10.1016/j.ultsonch.2017.03.055. Epub 2017 Apr 1. PubMed PMID: 28732993. 14: Žilić D, Maity D, Cetina M, Molčanov K, Džolić Z, Herak M. Magnetostructural Characterization of Oxalamide Dihalo-Bridged Copper Dimers: Intra- and Interdimer Interactions Studied by Single-Crystal Electron Spin Resonance Spectroscopy. Chemphyschem. 2017 Sep 6;18(17):2397-2408. doi: 10.1002/cphc.201700433. Epub 2017 Aug 1. PubMed PMID: 28636148. 15: Xu P, Feng Y, Ma P, Chen Y, Dong W, Chen M. Crystallization behaviours of bacterially synthesized poly(hydroxyalkanoate)s in the presence of oxalamide compounds with different configurations. Int J Biol Macromol. 2017 Nov;104(Pt A):624-630. doi: 10.1016/j.ijbiomac.2017.06.001. Epub 2017 Jun 2. PubMed PMID: 28583870. 16: Gao J, Bhunia S, Wang K, Gan L, Xia S, Ma D. Discovery of N-(Naphthalen-1-yl)-N'-alkyl Oxalamide Ligands Enables Cu-Catalyzed Aryl Amination with High Turnovers. Org Lett. 2017 Jun 2;19(11):2809-2812. doi: 10.1021/acs.orglett.7b00901. Epub 2017 May 22. PubMed PMID: 28530100. 17: Zhai Y, Chen X, Zhou W, Fan M, Lai Y, Ma D. Copper-Catalyzed Diaryl Ether Formation from (Hetero)aryl Halides at Low Catalytic Loadings. J Org Chem. 2017 May 5;82(9):4964-4969. doi: 10.1021/acs.joc.7b00493. Epub 2017 Apr 26. PubMed PMID: 28427259. 18: Krátký M, Stolaříková J, Vinšová J. Novel Sulfamethoxazole Ureas and Oxalamide as Potential Antimycobacterial Agents. Molecules. 2017 Mar 28;22(4). pii: E535. doi: 10.3390/molecules22040535. PubMed PMID: 28350331. 19: Yu F, Guo X, Tian X, Jia L. A Ratiomeric Fluorescent Sensor for Zn(2+) Based on N,N'-Di(quinolin-8-yl)oxalamide. J Fluoresc. 2017 Mar;27(2):723-728. doi: 10.1007/s10895-016-2003-0. Epub 2016 Dec 21. PubMed PMID: 28004345. 20: Xia S, Gan L, Wang K, Li Z, Ma D. Copper-Catalyzed Hydroxylation of (Hetero)aryl Halides under Mild Conditions. J Am Chem Soc. 2016 Oct 5. [Epub ahead of print] PubMed PMID: 27682010.