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MedKoo Cat#: 471012 | Name: Pimprinine
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Description:

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

Pimprinine is an alkaloid. It is a potent inhibitor of MAO (monoamine oxidase). More recently, pimprinine showed promising anticonvulsant activity in electric seizure threshold. Pimprinine is an indole alkaloids derived from marine or soil microorganisms.

Chemical Structure

Pimprinine
Pimprinine
CAS#13640-26-1

Theoretical Analysis

MedKoo Cat#: 471012

Name: Pimprinine

CAS#: 13640-26-1

Chemical Formula: C12H10N2O

Exact Mass: 198.0793

Molecular Weight: 198.23

Elemental Analysis: C, 72.71; H, 5.09; N, 14.13; O, 8.07

Price and Availability

Size Price Availability Quantity
5mg USD 600.00
10mg USD 850.00
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Related CAS #
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Synonym
NSC 80793, NSC80793, NSC-80793, Pimprinine, WS 30581C, APHE 3
IUPAC/Chemical Name
3-(2-Methyl-5-oxazolyl)-1H-indole
InChi Key
WZJPGCHCOHYLMB-UHFFFAOYSA-N
InChi Code
InChI=1S/C12H10N2O/c1-8-13-7-12(15-8)10-6-14-11-5-3-2-4-9(10)11/h2-7,14H,1H3
SMILES Code
CC1=NC=C(C2=CNC3=C2C=CC=C3)O1
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Wet ice in continental US; may vary elsewhere.
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 (20mg/mL)
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:
Pimprinine is an alkaloid. It is a potent inhibitor of MAO (monoamine oxidase).
In vitro activity:
A series of pimprinine alkaloids and their derivatives were prepared and identified by nuclear magnetic resonance (NMR) spectroscopy and high-resolution mass spectrometry (HR-MS). The antiviral activities of these alkaloids against tobacco mosaic virus (TMV) were systematically investigated for the first time. Most of the compounds exhibited higher antiviral activities than ribavirin. Compounds 5l, 9h, and 10h, which had similar or higher antiviral activities than ningnanmycin (perhaps the most widely used antiviral agent at present), emerged as new antiviral pilot compounds. This systematic structure-activity-relationship research lays the foundation for simplifying the structure of these alkaloids. The ring-open products, acylhydrazones 9a-9u, were also found to possess good antiviral activities. Moreover, all the synthesized compounds displayed broad-spectrum fungicidal activities. This study provides important information for the research and development of pimprinine alkaloids as novel antiviral agents. Reference: J Agric Food Chem. 2019 Feb 20;67(7):1795-1806. https://pubmed.ncbi.nlm.nih.gov/30681853/
In vivo activity:
Pimprinine, an extracellular alkaloid has been isolated from the culture filtrate of Streptomyces CDRIL-312. Pimprinine showed promising anticonvulsant activity in both minimum and maximum electric seizure threshold test in mice. Its anticonvulsant activity is very much comparable to that of phenyl hydantion sodium. Pimprinine also inhibited effectively tremorine-induced tremors and analgesia in mice. Reference: J Biotechnol. 2001 Jun 1;88(1):1-10. https://pubmed.ncbi.nlm.nih.gov/11377760/

Preparing Stock Solutions

The following data is based on the product molecular weight 198.23 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. Liu B, Li R, Li Y, Li S, Yu J, Zhao B, Liao A, Wang Y, Wang Z, Lu A, Liu Y, Wang Q. Discovery of Pimprinine Alkaloids as Novel Agents against a Plant Virus. J Agric Food Chem. 2019 Feb 20;67(7):1795-1806. doi: 10.1021/acs.jafc.8b06175. Epub 2019 Feb 6. PMID: 30681853. 2. Naik SR, Harindran J, Varde AB. Pimprinine, an extracellular alkaloid produced by Streptomyces CDRIL-312: fermentation, isolation and pharmacological activity. J Biotechnol. 2001 Jun 1;88(1):1-10. doi: 10.1016/s0168-1656(01)00244-9. PMID: 11377760.
In vitro protocol:
1. Liu B, Li R, Li Y, Li S, Yu J, Zhao B, Liao A, Wang Y, Wang Z, Lu A, Liu Y, Wang Q. Discovery of Pimprinine Alkaloids as Novel Agents against a Plant Virus. J Agric Food Chem. 2019 Feb 20;67(7):1795-1806. doi: 10.1021/acs.jafc.8b06175. Epub 2019 Feb 6. PMID: 30681853.
In vivo protocol:
1. Naik SR, Harindran J, Varde AB. Pimprinine, an extracellular alkaloid produced by Streptomyces CDRIL-312: fermentation, isolation and pharmacological activity. J Biotechnol. 2001 Jun 1;88(1):1-10. doi: 10.1016/s0168-1656(01)00244-9. PMID: 11377760.
1: Saha A, Sen C, Guin S, Das C, Maiti D, Sen S, Maiti D. Photoinduced [3+2] Cycloaddition of Carbenes and Nitriles: A Versatile Approach to Oxazole Synthesis. Angew Chem Int Ed Engl. 2023 Nov 27;62(48):e202308916. doi: 10.1002/anie.202308916. Epub 2023 Oct 26. PMID: 37843822. 2: Liu JR, Gao Y, Jin B, Guo D, Deng F, Bian Q, Zhang HF, Han XY, Ali AS, Zhang MZ, Zhang WH, Gu YC. Design, Synthesis, Antifungal Activity, and Molecular Docking of Streptochlorin Derivatives Containing the Nitrile Group. Mar Drugs. 2023 Jan 31;21(2):103. doi: 10.3390/md21020103. PMID: 36827144; PMCID: PMC9958711. 3: Cheng L, Liu JR, Liu JM, Guo D, Deng F, Bian Q, Zhang H, Han X, Ali AS, Zhang WH, Zhang MZ, Gu YC. Design, synthesis, antifungal activity and molecular docking of ring-opened pimprinine derivative containing (thio)amide structure. Pest Manag Sci. 2023 Jun;79(6):2220-2229. doi: 10.1002/ps.7400. Epub 2023 Feb 21. PMID: 36750400. 4: Liu JR, Liu JM, Gao Y, Shi Z, Nie KR, Guo D, Deng F, Zhang HF, Ali AS, Zhang MZ, Zhang WH, Gu YC. Discovery of Novel Pimprinine and Streptochlorin Derivatives as Potential Antifungal Agents. Mar Drugs. 2022 Nov 25;20(12):740. doi: 10.3390/md20120740. PMID: 36547887; PMCID: PMC9787289. 5: Liu M, Wan Z, Yang S, Liu F, Yang X, Wu Z, Zhang Y, Wang K, Fang W. Two new dipimprinine alkaloids from soil-derived Streptomyces sp. 44414B. J Antibiot (Tokyo). 2021 Jul;74(7):474-476. doi: 10.1038/s41429-021-00424-3. Epub 2021 May 21. PMID: 34021266. 6: Zhang S, Zhang L, Zhu J, Chen H, Chen Z, Si T, Liu T. Genomic and Metabolomic Investigation of a Rhizosphere Isolate Streptomyces netropsis WLXQSS-4 Associated with a Traditional Chinese Medicine. Molecules. 2021 Apr 8;26(8):2147. doi: 10.3390/molecules26082147. PMID: 33917975; PMCID: PMC8068340. 7: Lopez JAV, Nogawa T, Futamura Y, Aono H, Hashizume D, Osada H. N-Acetyl-α- hydroxy-β-oxotryptamine, a racemic natural product isolated from Streptomyces sp. 80H647. J Antibiot (Tokyo). 2021 Jul;74(7):477-479. doi: 10.1038/s41429-021-00420-7. Epub 2021 Apr 20. PMID: 33879862. 8: Gao Y, Huang DC, Liu C, Song ZL, Liu JR, Guo SK, Tan JY, Qiu RL, Jin B, Zhang H, Mulholland N, Han X, Xia Q, Ali AS, Guo D, Deng Y, Gu YC, Zhang MZ. Streptochlorin analogues as potential antifungal agents: Design, synthesis, antifungal activity and molecular docking study. Bioorg Med Chem. 2021 Apr 1;35:116073. doi: 10.1016/j.bmc.2021.116073. Epub 2021 Feb 14. PMID: 33610010. 9: Kretsch AM, Morgan GL, Acken KA, Barr SA, Li B. Pseudomonas Virulence Factor Pathway Synthesizes Autoinducers That Regulate the Secretome of a Pathogen. ACS Chem Biol. 2021 Mar 19;16(3):501-509. doi: 10.1021/acschembio.0c00901. Epub 2021 Feb 17. Erratum in: ACS Chem Biol. 2021 Sep 17;16(9):1791. doi: 10.1021/acschembio.1c00485. PMID: 33595276; PMCID: PMC8164881. 10: Yu Z, Jiang H, Wang L, Yang FX, Huang JP, Liu C, Guo X, Xiang W, Huang SX. Corrigendum: Dimeric Pimprinine Alkaloids From Soil-Derived Streptomyces sp. NEAU-C99. Front Chem. 2020 Aug 19;8:717. doi: 10.3389/fchem.2020.00717. Erratum for: Front Chem. 2020 Feb 18;8:95. doi: 10.3389/fchem.2020.00095. PMID: 32974281; PMCID: PMC7466438. 11: Yu Z, Jiang H, Wang L, Yang FX, Huang JP, Liu C, Guo X, Xiang W, Huang SX. Dimeric Pimprinine Alkaloids From Soil-Derived Streptomyces sp. NEAU-C99. Front Chem. 2020 Feb 18;8:95. doi: 10.3389/fchem.2020.00095. Erratum in: Front Chem. 2020 Aug 19;8:717. doi: 10.3389/fchem.2020.00717. PMID: 32133345; PMCID: PMC7040024. 12: Song ZL, Zhu Y, Liu JR, Guo SK, Gu YC, Han X, Dong HQ, Sun Q, Zhang WH, Zhang MZ. Diversity-oriented synthesis and antifungal activities of novel pimprinine derivative bearing a 1,3,4-oxadiazole-5-thioether moiety. Mol Divers. 2021 Feb;25(1):205-221. doi: 10.1007/s11030-020-10048-8. Epub 2020 Feb 13. PMID: 32056130. 13: Ohta T, Fukumoto A, Iizaka Y, Kato F, Koyama Y, Anzai Y. Quorum Sensing Inhibitors against Chromobacterium violaceum CV026 Derived from an Actinomycete Metabolite Library. Biol Pharm Bull. 2020;43(1):179-183. doi: 10.1248/bpb.b19-00564. PMID: 31902923. 14: Liu B, Li R, Li Y, Li S, Yu J, Zhao B, Liao A, Wang Y, Wang Z, Lu A, Liu Y, Wang Q. Discovery of Pimprinine Alkaloids as Novel Agents against a Plant Virus. J Agric Food Chem. 2019 Feb 20;67(7):1795-1806. doi: 10.1021/acs.jafc.8b06175. Epub 2019 Feb 6. PMID: 30681853. 15: Zhang MZ, Chen Q, Xie CH, Mulholland N, Turner S, Irwin D, Gu YC, Yang GF, Clough J. Synthesis and antifungal activity of novel streptochlorin analogues. Eur J Med Chem. 2015 Mar 6;92:776-83. doi: 10.1016/j.ejmech.2015.01.043. Epub 2015 Jan 22. PMID: 25633493. 16: Zhou H, Gai K, Lin A, Xu J, Wu X, Yao H. Palladium-catalyzed oxidative cross-coupling of azole-4-carboxylates with indoles: an approach to the synthesis of pimprinine. Org Biomol Chem. 2015 Jan 28;13(4):1243-8. doi: 10.1039/c4ob01844c. Epub 2014 Dec 1. PMID: 25434639. 17: Wei Y, Fang W, Wan Z, Wang K, Yang Q, Cai X, Shi L, Yang Z. Antiviral effects against EV71 of pimprinine and its derivatives isolated from Streptomyces sp. Virol J. 2014 Nov 20;11:195. doi: 10.1186/s12985-014-0195-y. PMID: 25410379; PMCID: PMC4253628. 18: Zhang MZ, Mulholland N, Beattie D, Irwin D, Gu YC, Chen Q, Yang GF, Clough J. Synthesis and antifungal activity of 3-(1,3,4-oxadiazol-5-yl)-indoles and 3-(1,3,4-oxadiazol-5-yl)methyl-indoles. Eur J Med Chem. 2013 May;63:22-32. doi: 10.1016/j.ejmech.2013.01.038. Epub 2013 Feb 9. PMID: 23454531. 19: Zhang MZ, Chen Q, Mulholland N, Beattie D, Irwin D, Gu YC, Yang GF, Clough J. Synthesis and fungicidal activity of novel pimprinine analogues. Eur J Med Chem. 2012 Jul;53:283-91. doi: 10.1016/j.ejmech.2012.04.012. Epub 2012 Apr 19. PMID: 22560632. 20: Pu X, Li G, Yang T, Li G, Yi J, Zhang G, Luo Y. A new cyclododeca[d]oxazole derivative from Streptomyces spp. CIBYL1. Nat Prod Res. 2013 Apr;27(7):603-8. doi: 10.1080/14786419.2012.682997. Epub 2012 May 1. PMID: 22548364.

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Arctic acid

Arctic acid