Benmoxin

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

MedKoo CAT#: 558388

CAS#: 7654-03-7

Description: Benmoxin is an irreversible and nonselective monoamine oxidase inhibitor (MAOI).


Price and Availability

Size
Price

Size
Price

Size
Price

Benmoxin is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

img

Theoretical Analysis

MedKoo Cat#: 558388
Name: Benmoxin
CAS#: 7654-03-7
Chemical Formula: C15H16N2O
Exact Mass: 240.13
Molecular Weight: 240.31
Elemental Analysis: C, 74.97; H, 6.71; N, 11.66; O, 6.66


Synonym: Benmoxin; Neuralex; Nerusil;

IUPAC/Chemical Name: N'-(1-Phenylethyl)benzohydrazide

InChi Key: BEWNZPMDJIGBED-UHFFFAOYSA-N

InChi Code: InChI=1S/C15H16N2O/c1-12(13-8-4-2-5-9-13)16-17-15(18)14-10-6-3-7-11-14/h2-12,16H,1H3,(H,17,18)

SMILES Code: O=C(NNC(C1=CC=CC=C1)C)C2=CC=CC=C2


Technical Data

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).

Harmonized System Code:
2934.99.03.00


References

1: Śmist M, Kwiecień H, Krawczyk M. Synthesis and antifungal activity of 2H-1,4-benzoxazin-3(4H)-one derivatives. J Environ Sci Health B. 2016;51(6):393-401. doi: 10.1080/03601234.2016.1142744. Epub 2016 Mar 10. PubMed PMID: 26963527.

2: Li C, Lu Z, Zhao C, Yang L, Fu Y, Shi K, He X, Li Z, Zu Y. Ionic-liquid-based ultrasound/microwave-assisted extraction of 2,4-dihydroxy-7-methoxy-1,4-benzoxazin-3-one and 6-methoxy-benzoxazolin-2-one from maize (Zea mays L.) seedlings. J Sep Sci. 2015 Jan;38(2):291-300. doi: 10.1002/jssc.201401081. Epub 2014 Dec 11. PubMed PMID: 25413336.

3: Tiekink ER, Wardell JL. 2-(2-Amino-4-nitro-phen-yl)-7-nitro-4H-3,1-benzoxazin-4-one. Acta Crystallogr Sect E Struct Rep Online. 2014 Jan 18;70(Pt 2):o158-9. doi: 10.1107/S1600536814000609. eCollection 2014 Feb 1. PubMed PMID: 24764879; PubMed Central PMCID: PMC3998318.

4: Etzerodt T, Maeda K, Nakajima Y, Laursen B, Fomsgaard IS, Kimura M. 2,4-dihydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one (DIMBOA) inhibits trichothecene production by Fusarium graminearum through suppression of Tri6 expression. Int J Food Microbiol. 2015 Dec 2;214:123-128. doi: 10.1016/j.ijfoodmicro.2015.07.014. Epub 2015 Jul 15. PubMed PMID: 26276561.

5: Köhler A, Maag D, Veyrat N, Glauser G, Wolfender JL, Turlings TC, Erb M. Within-plant distribution of 1,4-benzoxazin-3-ones contributes to herbivore niche differentiation in maize. Plant Cell Environ. 2015 Jun;38(6):1081-93. doi: 10.1111/pce.12464. Epub 2014 Nov 28. PubMed PMID: 25293400.

6: Rao RM, Luther BJ, Rani CS, Suresh N, Kapavarapu R, Parsa KV, Rao MV, Pal M. Synthesis of 2H-1,3-benzoxazin-4(3H)-one derivatives containing indole moiety: their in vitro evaluation against PDE4B. Bioorg Med Chem Lett. 2014 Feb 15;24(4):1166-71. doi: 10.1016/j.bmcl.2013.12.117. Epub 2014 Jan 7. PubMed PMID: 24440301.

7: Huo C, Dong J, Su Y, Tang J, Chen F. Iron-catalyzed oxidative sp(3) carbon-hydrogen bond functionalization of 3,4-dihydro-1,4-benzoxazin-2-ones. Chem Commun (Camb). 2016 Nov 8;52(91):13341-13344. PubMed PMID: 27709206.

8: Gleńsk M, Gajda B, Franiczek R, Krzyżanowska B, Biskup I, Włodarczyk M. In vitro evaluation of the antioxidant and antimicrobial activity of DIMBOA [2,4-dihydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one]. Nat Prod Res. 2016 Jun;30(11):1305-8. doi: 10.1080/14786419.2015.1054284. Epub 2015 Jul 13. PubMed PMID: 26166773.

9: Maag D, Dalvit C, Thevenet D, Köhler A, Wouters FC, Vassão DG, Gershenzon J, Wolfender JL, Turlings TC, Erb M, Glauser G. 3-β-D-Glucopyranosyl-6-methoxy-2-benzoxazolinone (MBOA-N-Glc) is an insect detoxification product of maize 1,4-benzoxazin-3-ones. Phytochemistry. 2014 Jun;102:97-105. doi: 10.1016/j.phytochem.2014.03.018. Epub 2014 Apr 5. PubMed PMID: 24713572.

10: Proisl K, Kafka S, Urankar D, Gazvoda M, Kimmel R, Košmrlj J. Fischer indolisation of N-(α-ketoacyl)anthranilic acids into 2-(indol-2-carboxamido)benzoic acids and 2-indolyl-3,1-benzoxazin-4-ones and their NMR study. Org Biomol Chem. 2014 Dec 21;12(47):9650-64. doi: 10.1039/c4ob01714e. Epub 2014 Oct 27. PubMed PMID: 25347568.

11: Shariat M, Samsudin MW, Zakaria Z. One-pot synthesis of 2-substituted 4H-3,1-benzoxazin-4-one derivatives under mild conditions using iminium cation from cyanuric chloride/dimethylformamide as a cyclizing agent. Chem Cent J. 2013 Mar 27;7(1):58. doi: 10.1186/1752-153X-7-58. PubMed PMID: 23537478; PubMed Central PMCID: PMC3662593.

12: Hasui T, Ohyabu N, Ohra T, Fuji K, Sugimoto T, Fujimoto J, Asano K, Oosawa M, Shiotani S, Nishigaki N, Kusumoto K, Matsui H, Mizukami A, Habuka N, Sogabe S, Endo S, Ono M, Siedem CS, Tang TP, Gauthier C, De Meese LA, Boyd SA, Fukumoto S. Discovery of 6-[5-(4-fluorophenyl)-3-methyl-pyrazol-4-yl]-benzoxazin-3-one derivatives as novel selective nonsteroidal mineralocorticoid receptor antagonists. Bioorg Med Chem. 2014 Oct 1;22(19):5428-45. doi: 10.1016/j.bmc.2014.07.038. Epub 2014 Aug 12. PubMed PMID: 25187277.

13: Barlaam B, Cosulich S, Degorce S, Fitzek M, Green S, Hancox U, Lambert-van der Brempt C, Lohmann JJ, Maudet M, Morgentin R, Péru A, Plé P, Saleh T, Ward L, Warin N. Discovery of a series of 8-(2,3-dihydro-1,4-benzoxazin-4-ylmethyl)-2-morpholino-4-oxo-chromene-6-carboxami des as PI3Kβ/δ inhibitors for the treatment of PTEN-deficient tumours. Bioorg Med Chem Lett. 2016 May 1;26(9):2318-23. doi: 10.1016/j.bmcl.2016.03.034. Epub 2016 Mar 11. PubMed PMID: 26996374.

14: Ge ZY, Xu QM, Fei XD, Tang T, Zhu YM, Ji SJ. Copper-catalyzed C-N bond formation/rearrangement sequence: synthesis of 4H-3,1-benzoxazin-4-ones. J Org Chem. 2013 May 3;78(9):4524-9. doi: 10.1021/jo400515y. Epub 2013 Apr 22. PubMed PMID: 23581844.

15: Glauser G, Marti G, Villard N, Doyen GA, Wolfender JL, Turlings TC, Erb M. Induction and detoxification of maize 1,4-benzoxazin-3-ones by insect herbivores. Plant J. 2011 Dec;68(5):901-11. doi: 10.1111/j.1365-313X.2011.04740.x. Epub 2011 Oct 4. PubMed PMID: 21838747.

16: Chouguiat L, Boulcina R, Bouacida S, Merazig H, Debache A. 4-(2-Nitro-benz-yl)-3-phenyl-3,4-di-hydro-2H-1,4-benzoxazin-2-ol. Acta Crystallogr Sect E Struct Rep Online. 2014 Jul 11;70(Pt 8):o863-4. doi: 10.1107/S1600536814015645. eCollection 2014 Aug 1. PubMed PMID: 25249912; PubMed Central PMCID: PMC4158540.

17: Meihls LN, Handrick V, Glauser G, Barbier H, Kaur H, Haribal MM, Lipka AE, Gershenzon J, Buckler ES, Erb M, Köllner TG, Jander G. Natural variation in maize aphid resistance is associated with 2,4-dihydroxy-7-methoxy-1,4-benzoxazin-3-one glucoside methyltransferase activity. Plant Cell. 2013 Jun;25(6):2341-55. doi: 10.1105/tpc.113.112409. Epub 2013 Jun 28. PubMed PMID: 23898034; PubMed Central PMCID: PMC3723630.

18: Guo S, Liu X, Shen B, Lin L, Feng X. Organocatalytic Asymmetric Cascade Reaction of 2-Hydroxyphenyl-Substituted Enones and Isocyanates To Construct 1,3-Benzoxazin-2-ones. Org Lett. 2016 Oct 7;18(19):5070-5073. Epub 2016 Sep 13. PubMed PMID: 27623021.

19: Hasui T, Matsunaga N, Ora T, Ohyabu N, Nishigaki N, Imura Y, Igata Y, Matsui H, Motoyaji T, Tanaka T, Habuka N, Sogabe S, Ono M, Siedem CS, Tang TP, Gauthier C, De Meese LA, Boyd SA, Fukumoto S. Identification of benzoxazin-3-one derivatives as novel, potent, and selective nonsteroidal mineralocorticoid receptor antagonists. J Med Chem. 2011 Dec 22;54(24):8616-31. doi: 10.1021/jm2011645. Epub 2011 Nov 29. PubMed PMID: 22074142.

20: Huang C, Wang X, Wang R, Xue K, Yan F, Xu C. Distribution and variations of three 1,4-benzoxazin-3-ones in maize induced by the Asian corn borer, Ostrinia furnacalis (Guenée). Z Naturforsch C. 2006 Mar-Apr;61(3-4):257-62. PubMed PMID: 16729586.