Lupanine

Formula: C₁₅H₂₄N₂O
Molecular weight: 248.3639
IUPAC Standard InChI: InChI=1S/C15H24N2O/c18-15-6-3-5-14-11-8-12(10-17(14)15)13-4-1-2-7-16(13)9-11/h11-14H,1-10H2/t11-,12+,13-,14+/m1/s1
IUPAC Standard InChIKey: JYIJIIVLEOETIQ-RQJABVFESA-N
CAS Registry Number: 550-90-3
Chemical structure:
This structure is also available as a 2d Mol file
Stereoisomers:
- α-Isolupanine
Other names: 7,14-Methano-4H,6H-dipyrido[1,2-a:1',2'-e][1,5]diazocin-4-one, dodecahydro-, [7S-(7α,7aβ,14α,14aα)]-; (+)-Lupanine; 2-Oxosparteine; Lupanin; d-Lupanine
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Information on this page:
Other data available:
- Mass spectrum (electron ionization)
- Gas Chromatography
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Normal alkane RI, non-polar column, temperature ramp

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	OV-1	DB-5	DB-1	DB-1	OV-1
Column length (m)	30.	30.	30.	30.	30.
Carrier gas	He	He		He	He
Substrate
Column diameter (mm)	0.25	0.25	0.25	0.25	0.32
Phase thickness (μm)			0.25	0.25	0.25
T_start (C)	120.	180.	120.	120.	70.
T_end (C)	300.	300.	320.	260.	300.
Heat rate (K/min)	8.	5.	6.	10.	6.
Initial hold (min)	3.	2.		3.	3.
Final hold (min)		10.		10.
I	2165.	2165.	2178.	2185.	2193.
Reference	Martins, Wink, et al., 2005	Przybylak, Ciesiolka, et al., 2005	Kite and Pennington, 2003	Torres, Quintos, et al., 2002	Woldemichael and Wink, 2002
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	DB-1	DB-1	DB-1	DB-1	DB-1
Column length (m)	30.	30.	30.	30.	30.
Carrier gas	He	He	He	He
Substrate
Column diameter (mm)	0.25	0.32	0.32	0.32	0.32
Phase thickness (μm)	0.25
T_start (C)	150.	150.	150.	150.	150.
T_end (C)	280.	300.	300.	300.	300.
Heat rate (K/min)	2.	6.	6.	6.	6.
Initial hold (min)
Final hold (min)	15.
I	2170.	2160.	2165.	2165.	2160.
Reference	Martínez-Herrera, Robledo-Quintos, et al., 2001	Greinwald, Bachmann, et al., 1995	Greinwald, Henrichs, et al., 1995	Kirch, Veit, et al., 1995	van Wyk, Greinwald, et al., 1995
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	DB-1	DB-1	DB-1	SE-30	SE-30
Column length (m)	30.	30.	30.	15.	15.
Carrier gas		He	Helium	He	He
Substrate
Column diameter (mm)	0.3	0.32	0.32	0.26	0.26
Phase thickness (μm)			1.0
T_start (C)	150.	150.	150.	150.	150.
T_end (C)	270.	300.	300.	270.	270.
Heat rate (K/min)	6.	6.	10.	6.	6.
Initial hold (min)			1.
Final hold (min)
I	2165.	2160.	2165.	2170.	2165.
Reference	Planchuelo-Ravelo and Wink, 1993	Greinwald, Canto, et al., 1992	Wink and Witte, 1991	Wink, Witte, et al., 1983	Wink, Witte, et al., 1981
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

References

Go To: Top, Normal alkane RI, non-polar column, temperature ramp, Notes

Martins, Wink, et al., 2005
Martins, A.; Wink, M.; Tei, A.; Brum-Bousquet, M.; Tillequin, F.; Rauter, A.-P., A phytochemical study of the quinolizidine alkaloids from Genista tenera by gas chromatography-mass spectrometry, Phytochem. Anal., 2005, 16, 4, 264-266, https://doi.org/10.1002/pca.832 . [all data]

Przybylak, Ciesiolka, et al., 2005
Przybylak, J.K.; Ciesiolka, D.; Wysocka, W.; García-López, P.M.; Ruiz-López, M.A.; Wysocki, W.; Gulewicz, K., Alkaloid profiles of Mexican wild lupin and an effect of alkaloid preparation from Lupinus exaltatus seeds on growth and yield of paprika (Capsicum annuum L.), Ind. Crops Prod., 2005, 21, 1, 1-7, https://doi.org/10.1016/j.indcrop.2003.12.001 . [all data]

Kite and Pennington, 2003
Kite, G.C.; Pennington, R.T., Quinolizidine alkaloid status of Styphnolobium and Cladrastis (Leguminosae), Biochem. Syst. Ecol., 2003, 31, 12, 1409-1416, https://doi.org/10.1016/S0305-1978(03)00118-2 . [all data]

Torres, Quintos, et al., 2002
Torres, K.B.; Quintos, N.R.; Necha, L.L.B.; Wink, M., Alkaloid profile of leaves and seeds of Lupinus hintonii C.P. Smith, Z. Naturforsch., 2002, 57c, 243-247. [all data]

Woldemichael and Wink, 2002
Woldemichael, G.M.; Wink, M., Concomitant occurrence of pyrrolizidine and quinolizidine alkaloids in hemiparasite Osyris alba L. (Santalaceae), Biochem. Syst. Ecol., 2002, 30, 2, 139-149, https://doi.org/10.1016/S0305-1978(01)00065-5 . [all data]

Martínez-Herrera, Robledo-Quintos, et al., 2001
Martínez-Herrera, J.; Robledo-Quintos, N.; Mora-Escobedo, R.; Dávila-Ortiz, G., Alkaloid composition of Lupinus campestris from Mexico, J. Food Biochem., 2001, 25, 2, 117-125, https://doi.org/10.1111/j.1745-4514.2001.tb00728.x . [all data]

Greinwald, Bachmann, et al., 1995
Greinwald, R.; Bachmann, P.; Lewis, G.; Witte, L.; Czygan, F.-C., Alkaloids of the genus Poecilanthe (Leguminosae: Papilionoideae), Biochem. Syst. Ecol., 1995, 23, 5, 547-553, https://doi.org/10.1016/0305-1978(95)00050-5 . [all data]

Greinwald, Henrichs, et al., 1995
Greinwald, R.; Henrichs, C.; Veen, G.; Ross, J.H.; Witte, L.; Czygan, F.-C., A survey of alkaloids in templetonia biloba (Benth.) Polhill (Fabaceae: Brongniartieae), Biochem. Syst. Ecol., 1995, 23, 6, 649-654, https://doi.org/10.1016/0305-1978(95)00035-6 . [all data]

Kirch, Veit, et al., 1995
Kirch, J.; Veit, M.; Wätzig, Greinwald; Czygan, F.-C., Alkaloidal variation in Genista Iobelii s.l. (Fabaceae), Biochem. Syst. Ecol., 1995, 23, 6, 635-643, https://doi.org/10.1016/0305-1978(95)00037-2 . [all data]

van Wyk, Greinwald, et al., 1995
van Wyk, B.-E.; Greinwald, R.; Witte, L., Alkaloid variation in the Lupinus pusillus group (Fabaceae: tribe Genisteae), Biochem. Syst. Ecol., 1995, 23, 5, 533-537, https://doi.org/10.1016/0305-1978(95)00036-T . [all data]

Planchuelo-Ravelo and Wink, 1993
Planchuelo-Ravelo, A.M.; Wink, M., Alkaloid composition of Lupinus-albescens (Fabaceae) from South America, Z. Naturforsch. C:, 1993, 48, 5-6, 414-416. [all data]

Greinwald, Canto, et al., 1992
Greinwald, R.; Canto, P.; Bachmann, P.; Witte, L.; Czygan, F.-C., Distribution and taxdonomic significance of alkaloids in the Genista cinerea agregat, Biochem. Syst. Ecol., 1992, 20, 1, 75-81, https://doi.org/10.1016/0305-1978(92)90074-N . [all data]

Wink and Witte, 1991
Wink, M.; Witte, L., Storage of quinolizidine alkaloids in Macrosiphum albifrons and Aphis genistae (Homoptera: Aphididae), Entomol. Gener., 1991, 15, 4, 237-254, https://doi.org/10.1127/entom.gen/15/1991/237 . [all data]

Wink, Witte, et al., 1983
Wink, M.; Witte, L.; Hartmann, T.; Theuring, C.; Volz. V., Accumulation of quinolizidine alkaloids in plants and cell suspension cultures: genera lupinus, cytisus, baptisia, genista, laburnum, and sophora, Planta Medica, 1983, 48, 4, 253-257, https://doi.org/10.1055/s-2007-969928 . [all data]

Wink, Witte, et al., 1981
Wink, M.; Witte, L.; Hartmann. T., Quinolizidine Alkaloid Composition of Plants and of Photomixotrophis Cell Suspension Cultures of Sarothamnus scoparius and Orobanche rapum-genistae, Planta Medica, 1981, 43, 12, 342-352, https://doi.org/10.1055/s-2007-971522 . [all data]

Notes

Go To: Top, Normal alkane RI, non-polar column, temperature ramp, References

Symbols used in this document:

T_end Final temperature

T_start Initial temperature
Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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