Lupinine

• CAT Number: I011947
• CAS Number: 486-70-4
• Molecular Formula: C10H19NO
• Molecular Weight: 169.26
• Purity: ≥95%
• Synonyms: NSC 21723; NSC21723; NSC-21723; Lupinine;((1R,9aR)-octahydro-2H-quinolizin-1-yl)methanol
• Target: BChE inhibitor
• Solubility: Soluble in DMSO
• Storage: Room Temperature
• IUPAC Name: [(1R,9aR)-2,3,4,6,7,8,9,9a-octahydro-1H-quinolizin-1-yl]methanol
• InChI: InChI=1S/C10H19NO/c12-8-9-4-3-7-11-6-2-1-5-10(9)11/h9-10,12H,1-8H2/t9-,10+/m0/s1
• InChIKey: HDVAWXXJVMJBAR-VHSXEESVSA-N
• SMILES: C1CCN2CCCC(C2C1)CO

Lupine (Cat No.: I011947) is a lupine alkaloid with applications in the preparation of chemical pesticides and insecticides. This compound plays a crucial role in the formulation of pest control solutions, contributing to agricultural practices aimed at protecting crops from harmful insects and pests. Researchers and professionals in the agricultural and chemical industries seeking to utilize Lupine for these purposes or requiring more information can contact us for prompt assistance.

Reference

1: Davies SG, Fletcher AM, Foster EM, Houlsby IT, Roberts PM, Schofield TM, Thomson JE. An efficient asymmetric synthesis of (-)-lupinine. Chem Commun (Camb). 2014 Aug 7;50(61):8309-11. doi: 10.1039/c4cc02135e. PubMed PMID: 24938152.2: Basova NE, Kormilitsyn BN, Perchenok AIu, Rosengart EV, Saakov VS, Suvorov AA. [Isomeric derivatives of lupinine and epilupinine–organophosphorus inhibitors of cholinesterases]. Ukr Biokhim Zh (1999). 2012 Jan-Feb;84(1):26-33. Russian. PubMed PMID: 22679755.3: Jahn MK, Dewald D, Vallejo-López M, Cocinero EJ, Lesarri A, Grabow JU. Rotational spectra of bicyclic decanes: the trans conformation of (-)-lupinine. J Phys Chem A. 2013 Dec 19;117(50):13673-9. doi: 10.1021/jp407671m. Epub 2013 Sep 27. PubMed PMID: 24028578.4: WINTERFELD K, KNIEPS R. [The synthesis of 1-carbethoxy- and 3-carbethoxyquinolizidine-2-one, of 1-lupinine and of 1-epilupinine]. Arch Pharm Ber Dtsch Pharm Ges. 1960 Mar;293/65:325-33. German. PubMed PMID: 13845336.5: Airiau E, Spangenberg T, Girard N, Breit B, Mann A. Short access to (+)-lupinine and (+)-epiquinamide via double hydroformylation. Org Lett. 2010 Feb 5;12(3):528-31. doi: 10.1021/ol902718q. PubMed PMID: 20038131.6: WINTERFELD K, JAP TB. [On the knowledge of the rearrangement of lupinine and epilupinine with metallic sodium]. Arch Pharm Ber Dtsch Pharm Ges. 1962 Jan;295/67:14-5. German. PubMed PMID: 14007612.7: Tlegenov RT, Aĭtmambetov A. [Synthesis of lupinine derivatives of flavonoids]. Bioorg Khim. 2005 Sep-Oct;31(5):549-52. Russian. PubMed PMID: 16245698.8: Sparatore A, Sparatore F. 2-(4-R-phenoxy/phenylthio)alkanoic esters of l-lupinine. Farmaco. 2001 Mar;56(3):169-74. PubMed PMID: 11409323.9: Mirzaev S. [Inhibiting effect of anabasine, anabasamine and lupinine alkaloids on ethanol action in mice]. Farmakol Toksikol. 1978 Jan-Feb;41(1):52-5. Russian. PubMed PMID: 624390.10: Iusupov NU, Kim ON, Abdurakhmanov IuD, Iunusov GSh, Karimov A. [Synthesis and pharmacokinetic characteristics of 14CH3-polymethacryloyl lupinine–a heparin antagonist]. Farmakol Toksikol. 1985 Nov-Dec;48(6):71-3. Russian. PubMed PMID: 4085634.11: Usmanova DM, Musaev UN, Efimov VS. [Antiheparin activity of polymers based on the alkaloid, lupinine]. Farmakol Toksikol. 1979 Nov-Dec;42(6):628-32. Russian. PubMed PMID: 499471.12: SCHUETTE HR, HINDORF H. [ON THE BIOSYNTHESIS OF LUPININE]. Z Naturforsch B. 1964 Sep;19:855. German. PubMed PMID: 14317278.13: Basova NE, Rozengart EV, Suvorov AA. Cholinesterase hydrolysis of substituted lupinine benzoates. Dokl Biochem Biophys. 2008 Mar-Apr;419:69-71. PubMed PMID: 18505160.14: Rusconi C, Vaiana N, Casagrande M, Basilico N, Parapini S, Taramelli D, Romeo S, Sparatore A. Synthesis and comparison of antiplasmodial activity of (+), (-) and racemic 7-chloro-4-(N-lupinyl)aminoquinoline. Bioorg Med Chem. 2012 Oct 1;20(19):5980-5. doi: 10.1016/j.bmc.2012.07.041. Epub 2012 Jul 31. PubMed PMID: 22901673.15: Balashova EK, Kugusheva LI, Rozengart VI, Sheretobitov OE, Vasil/’eva TI. [Effect of organophosphorus inhibitors, lupinine and epilupinine derivatives, on mammalian and arthropod cholinesterases]. Zh Evol Biokhim Fiziol. 1980 May-Jun;16(3):244-50. Russian. PubMed PMID: 7405439.16: Usmanova DM. [Experimental effect of a lupinine-based homopolymer on blood coagulation in animals]. Farmakol Toksikol. 1980 May-Jun;43(3):327-30. Russian. PubMed PMID: 7449971.17: OHKI S, YAMAKAWA K. Synthesis of quinolizine derivatives. III. Syntheses of 3-aminomethyl- and 3-dimethylaminomethyl-quinolizidine and di-3-lupinine. Pharm Bull. 1953 Sep;1(3):260-5. PubMed PMID: 13166535.18: Abduvakhabov AA, Kasymov SK, Rozengart EV, Soboleva IN, Aslanov KA. [Cholinesterase substrates based on lupinine and epilupinine]. Dokl Akad Nauk SSSR. 1975;220(4):961-4. Russian. PubMed PMID: 1112186.19: Rozengart EV, Basova NE. [Application of bisalkaloid derivatives of dicarboxylic acids based on lupinine, anabasine and cytisine as cholinesterase inhibitors of various origin]. Zh Evol Biokhim Fiziol. 2004 Jul-Aug;40(4):305-10. Russian. PubMed PMID: 15481367.20: Ma S, Ni B. Double ring-closing metathesis reaction of nitrogen-containing tetraenes: efficient construction of bicyclic alkaloid skeletons and synthetic application to four stereoisomers of lupinine and their derivatives. Chemistry. 2004 Jul 5;10(13):3286-300. PubMed PMID: 15224338.