MedKoo Cat#: 528070 | Name: Lupinine, (+)-

Description:

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

Lupinine, (+)- is a bioactive chemical.

Chemical Structure

Lupinine, (+)-
Lupinine, (+)-
CAS#7635-60-1

Theoretical Analysis

MedKoo Cat#: 528070

Name: Lupinine, (+)-

CAS#: 7635-60-1

Chemical Formula: C10H19NO

Exact Mass: 169.1467

Molecular Weight: 169.27

Elemental Analysis: C, 70.96; H, 11.31; N, 8.28; O, 9.45

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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Related CAS #
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Synonym
Lupinine, (+)-
IUPAC/Chemical Name
2H-Quinolizine-1-methanol, octahydro-, (1S-trans)-
InChi Key
HDVAWXXJVMJBAR-ZJUUUORDSA-N
InChi Code
InChI=1S/C10H19NO/c12-8-9-4-3-7-11-6-2-1-5-10(9)11/h9-10,12H,1-8H2/t9-,10+/m1/s1
SMILES Code
OC[C@H]1CCCN2CCCC[C@]21[H]
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

Preparing Stock Solutions

The following data is based on the product molecular weight 169.27 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: Lee JA, An J, Kang TM, De D, Kim KK. Discovery of natural compounds promoting cardiomyocyte differentiation. Stem Cells Dev. 2018 Oct 25. doi: 10.1089/scd.2018.0153. [Epub ahead of print] PubMed PMID: 30358491. 2: Basilico N, Parapini S, Sparatore A, Romeo S, Misiano P, Vivas L, Yardley V, Croft SL, Habluetzel A, Lucantoni L, Renia L, Russell B, Suwanarusk R, Nosten F, Dondio G, Bigogno C, Jabes D, Taramelli D. In Vivo and In Vitro Activities and ADME-Tox Profile of a Quinolizidine-Modified 4-Aminoquinoline: A Potent Anti-P. falciparum and Anti-P. vivax Blood-Stage Antimalarial. Molecules. 2017 Dec 1;22(12). pii: E2102. doi: 10.3390/molecules22122102. PubMed PMID: 29194347. 3: Davies SG, Fletcher AM, Foster EM, Houlsby IT, Roberts PM, Schofield TM, Thomson JE. The asymmetric syntheses of pyrrolizidines, indolizidines and quinolizidines via two sequential tandem ring-closure/N-debenzylation processes. Org Biomol Chem. 2014 Dec 7;12(45):9223-35. doi: 10.1039/c4ob01737d. PubMed PMID: 25300749. 4: Koley D, Krishna Y, Srinivas K, Khan AA, Kant R. Organocatalytic asymmetric Mannich cyclization of hydroxylactams with acetals: total syntheses of (-)-epilupinine, (-)-tashiromine, and (-)-trachelanthamidine. Angew Chem Int Ed Engl. 2014 Nov 24;53(48):13196-200. doi: 10.1002/anie.201407185. Epub 2014 Sep 26. PubMed PMID: 25264221. 5: 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. 6: Brimioulle R, Bach T. Enantioselective Lewis acid catalysis of intramolecular enone [2+2] photocycloaddition reactions. Science. 2013 Nov 15;342(6160):840-3. doi: 10.1126/science.1244809. PubMed PMID: 24233720. 7: 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. 8: 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. 9: Basova NE, Kormilitsyn BN, Perchenok AIu, Rozengart EV, Saakov VS, Suvorov AA. [Reversible lupininin inhibitors of cholinesterases of mammalian blood and of optical ganglia of individuals of the commander squid Berryteuthis magister from different zones of species areal]. Zh Evol Biokhim Fiziol. 2012 May-Jun;48(3):213-8. Russian. PubMed PMID: 22827020. 10: 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. 11: Basova NE, Kormilitsyn BN, Rozengart EV, Saakov VS, Suvorov AA. [Derivatives of lupinin and epilupinin as ligands of various cholinesterases]. Zh Evol Biokhim Fiziol. 2012 Jan-Feb;48(1):8-16. Review. Russian. PubMed PMID: 22567970. 12: Omeje EO, Osadebe PO, Nworu CS, Nwodo JN, Obonga WO, Kawamura A, Esimone CO, Proksch P. A novel sesquiterpene acid and an alkaloid from leaves of the Eastern Nigeria mistletoe, Loranthus micranthus with potent immunostimulatory activity on C57BL6 mice splenocytes and CD69 molecule. Pharm Biol. 2011 Dec;49(12):1271-6. doi: 10.3109/13880209.2011.621129. Epub 2011 Oct 12. PubMed PMID: 21988279. 13: Cutter AC, Miller IR, Keily JF, Bellingham RK, Light ME, Brown RC. Total syntheses of (-) epilupinine and (-)-tashiromine using imino-aldol reactions. Org Lett. 2011 Aug 5;13(15):3988-91. doi: 10.1021/ol2015048. Epub 2011 Jul 11. PubMed PMID: 21744783. 14: Su D, Wang X, Shao C, Xu J, Zhu R, Hu Y. Total synthesis of (+)-epilupinine via an intramolecular nitrile oxide-alkene cycloaddition. J Org Chem. 2011 Jan 7;76(1):188-94. doi: 10.1021/jo101910r. Epub 2010 Dec 1. PubMed PMID: 21121617. 15: 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. 16: Fitch RW, Sturgeon GD, Patel SR, Spande TF, Garraffo HM, Daly JW, Blaauw RH. Epiquinamide: a poison that wasn't from a frog that was. J Nat Prod. 2009 Feb 27;72(2):243-7. doi: 10.1021/np8005452. PubMed PMID: 19245264; PubMed Central PMCID: PMC3107123. 17: Pérez-Laínez D, García-Mateos R, San Miguel-Chávez R, Soto-Hernández M, Rodríguez-Pérez E, Kite G. Bactericidal and fungicidal activities of Calia secundiflora (Ort.) Yakovlev. Z Naturforsch C. 2008 Sep-Oct;63(9-10):653-7. PubMed PMID: 19040102. 18: Basova NE, Rozengart EV, Suvorov AA. Cholinesterase hydrolysis of substituted lupinine benzoates. Dokl Biochem Biophys. 2008 Mar-Apr;419:69-71. PubMed PMID: 18505160. 19: Ahari M, Perez A, Menant C, Vasse JL, Szymoniak J. A direct stereoselective approach to trans-2,3-disubstituted piperidines: application in the synthesis of 2-Epi-CP-99,994 and (+)-epilupinine. Org Lett. 2008 Jun 19;10(12):2473-6. doi: 10.1021/ol800722a. Epub 2008 May 14. PubMed PMID: 18476706. 20: Zavala-Chávez F, García-Mateos R, Soto-Hernández M, Kite G. Phytochemical differences between Calia secundiflora (Leguminosae) growing at two sites in Mexico. Z Naturforsch C. 2006 Mar-Apr;61(3-4):155-9. PubMed PMID: 16729569.