MedKoo Cat#: 540278 | Name: Lupinine
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Description:

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

Lupinine is an AChE and BChE inhibitor and potential CD69 activator found in species of Loranthus, Calia, and Lupinus. It may also inhibit heparin.

Chemical Structure

 Lupinine
Lupinine
CAS#486-70-4

Theoretical Analysis

MedKoo Cat#: 540278

Name: Lupinine

CAS#: 486-70-4

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

Size Price Availability Quantity
100mg USD 350.00 2 weeks
500mg USD 650.00 2 weeks
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Related CAS #
No Data
Synonym
NSC 21723; NSC21723; NSC-21723; Lupinine
IUPAC/Chemical Name
((1R,9aR)-octahydro-2H-quinolizin-1-yl)methanol
InChi Key
HDVAWXXJVMJBAR-VHSXEESVSA-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+/m0/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
>2 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
2934.99.9001
More Info
Product Data
Biological target:
Lupinine is an AChE and BChE inhibitor.
In vitro activity:
TBD
In vivo activity:
TBD
Solvent mg/mL mM
Solubility
PBS (pH 7.2) 10.0 59.08
DMSO 30.0 177.23
Ethanol 30.0 177.23
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 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
Formulation protocol:
TBD
In vitro protocol:
TBD
In vivo protocol:
TBD
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.