Anagyrine

Formula: C₁₅H₂₀N₂O
Molecular weight: 244.3321
IUPAC Standard InChI: InChI=1S/C15H20N2O/c18-15-6-3-5-14-11-8-12(10-17(14)15)13-4-1-2-7-16(13)9-11/h3,5-6,11-13H,1-2,4,7-10H2/t11-,12+,13-/m1/s1
IUPAC Standard InChIKey: FQEQMASDZFXSJI-FRRDWIJNSA-N
CAS Registry Number: 486-89-5
Chemical structure:
This structure is also available as a 2d Mol file or as a computed 3d SD file
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Stereoisomers:
- 7,14-Methano-4H,6H-dipyrido[1,2-a:1',2'-E][1,5]diazocin-4-one, 7,7a,8,9,10,11,13,14-octahydro-, [7R-(7α,7aα,14α)]-
- Camoensidine
Other names: 7,14-Methano-4H,6H-dipyrido[1,2-a:1',2'-e][1,5]diazocin-4-one, 7,7a,8,9,10,11,13,14-octahydro-, [7R-(7α,7aβ,14α)]-; Rhombinine; Anagyrin; Monolupin; Monolupine; Rhombinin
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Mass spectrum (electron ionization)

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

Spectrum

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Additional Data

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Owner	NIST Mass Spectrometry Data Center Collection (C) 2014 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved.
NIST MS number	11810

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Gas Chromatography

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

Normal alkane RI, non-polar column, temperature ramp

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Column type	Active phase	I	Reference	Comment
Capillary	OV-1	2390.	Martins, Wink, et al., 2005	He, 120. C @ 3. min, 8. K/min; Column length: 30. m; Column diameter: 0.25 mm; T_end: 300. C
Capillary	DB-1	2406.	Kite and Pennington, 2003	30. m/0.25 mm/0.25 μm, 6. K/min; T_start: 120. C; T_end: 320. C
Capillary	OV-1	2408.	Woldemichael and Wink, 2002	30. m/0.32 mm/0.25 μm, He, 70. C @ 3. min, 6. K/min; T_end: 300. C
Capillary	DB-1	2380.	Greinwald, Bachmann, et al., 1995	He, 6. K/min; Column length: 30. m; Column diameter: 0.32 mm; T_start: 150. C; T_end: 300. C
Capillary	DB-1	2390.	Greinwald, Henrichs, et al., 1995	He, 6. K/min; Column length: 30. m; Column diameter: 0.32 mm; T_start: 150. C; T_end: 300. C
Capillary	DB-1	2390.	Kirch, Veit, et al., 1995	He, 6. K/min; Column length: 30. m; Column diameter: 0.32 mm; T_start: 150. C; T_end: 300. C
Capillary	DB-1	2387.	van Wyk, Greinwald, et al., 1995	6. K/min; Column length: 30. m; Column diameter: 0.32 mm; T_start: 150. C; T_end: 300. C
Capillary	DB-1	2375.	Greinwald, Canto, et al., 1992	He, 6. K/min; Column length: 30. m; Column diameter: 0.32 mm; T_start: 150. C; T_end: 300. C
Capillary	DB-1	2375.	Greinwald, Canto, et al., 1992	He, 6. K/min; Column length: 30. m; Column diameter: 0.32 mm; T_start: 150. C; T_end: 300. C
Capillary	DB-1	2390.	Wink and Witte, 1991	30. m/0.32 mm/1.0 μm, Helium, 150. C @ 1. min, 10. K/min; T_end: 300. C
Capillary	SE-30	2380.	Wink, Witte, et al., 1983	He, 6. K/min; Column length: 15. m; Column diameter: 0.26 mm; T_start: 150. C; T_end: 270. C
Capillary	SE-30	2375.	Wink, Witte, et al., 1981	He, 6. K/min; Column length: 15. m; Column diameter: 0.26 mm; T_start: 150. C; T_end: 270. C

Normal alkane RI, non-polar column, custom temperature program

View large format table.

Column type	Active phase	I	Reference	Comment
Capillary	DB-5 MS	2390.	Cook, Lee, et al., 2009	Column length: 30. m; Column diameter: 0.25 mm; Program: 100 0C (1 min) 40 0C/min -> 200 0C 5 0C/min -> 275 0C (15 min)
Capillary	OV-1	2390.	Asres, Tei, et al., 1997	He; Column length: 15. m; Column diameter: 0.25 mm; Program: 120C (2min) => 10C/min => 250C => 15C/min => 300C
Capillary	DB-1	2380.	Greinwald, Ross, et al., 1996	He; Column length: 15. m; Column diameter: 0.25 mm; Program: 150C(2min) => 10C/min => 250C => 20C/min => 300C (10min)
Capillary	DB-1	2382.	Greinwald, van Rensen, et al., 1995	He; Column length: 30. m; Column diameter: 0.32 mm; Program: 150C (2min) => 10C/min => 250C => 20C/min => 300C (5min)
Capillary	DB-1	2375.	Greinwald, Ross, et al., 1995	He; Column length: 30. m; Column diameter: 0.32 mm; Program: 150C (2min) => 10C/min => 250C => 20C/min => 300C (5min)
Capillary	DB-1	2390.	Wink, Meissner, et al., 1995	Column length: 30. m; Column diameter: 0.3 mm; Program: not specified

References

Go To: Top, Mass spectrum (electron ionization), Gas Chromatography, 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]

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]

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]

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]

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]

Cook, Lee, et al., 2009
Cook, D.; Lee, S.T.; GArdner, D.R.; Pfister, J.A.; Welch, K.D.; Green, B.T.; Davis, T.Z.; Panter, K.E., The alkaloids profiles of lupinus sulphureus, J. Agric. Food Chem., 2009, 57, 4, 1646-1653, https://doi.org/10.1021/jf803468q . [all data]

Asres, Tei, et al., 1997
Asres, K.; Tei, A.; Wink, M., Quinolizidine alkaloids from the East-African legume Dicraeopetalum stipulare harms, Biochem. Syst. Ecol., 1997, 25, 4, 305-308, https://doi.org/10.1016/S0305-1978(97)00004-5 . [all data]

Greinwald, Ross, et al., 1996
Greinwald, R.; Ross, J.H.; Witte, L.; Czygan, F.-C., Alkaloids of Templetonia incana, Biochem. Syst. Ecol., 1996, 24, 5, 423-426, https://doi.org/10.1016/0305-1978(96)00024-5 . [all data]

Greinwald, van Rensen, et al., 1995
Greinwald, R.; van Rensen, I.; Veit, M.; Canto, P.; Witte, L., A chemical dichotomy in quinolizidine alkaloid accumulation within the section Spartioides of the genus Genista (Fabaceae: Genisteae), Biochem. Syst. Ecol., 1995, 23, 1, 89-97, https://doi.org/10.1016/0305-1978(95)93662-M . [all data]

Greinwald, Ross, et al., 1995
Greinwald, R.; Ross, J.H.; Witte, L.; Czygan, F.-C., The alkaloid pattern of Plagiocarpus axillaris (Fabaceae: Brongniartieae), Biochem. Syst. Ecol., 1995, 23, 6, 645-648, https://doi.org/10.1016/0305-1978(95)00059-3 . [all data]

Wink, Meissner, et al., 1995
Wink, M.; Meissner, C.; Witte, L., Patterns of quinolizidine alkaloids in 56 species of the genus Lupinus, Phytochemistry, 1995, 38, 1, 139-153, https://doi.org/10.1016/0031-9422(95)91890-D . [all data]

Notes

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Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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