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MedKoo Cat#: 462643 | Name: Anagyrine
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Description:

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

Anagyrine is an alkaloid that has been found in L. albus and has nematocidal and anticancer activities. It binds to muscarinic and nicotinic acetylcholine receptors with IC50 values of 132 and 2,096 µM, respectively, in radioligand binding assays using pig brain membranes that endogenously express high levels of the receptors. Anagyrine decreases survival of B. xylophilus worms. It inhibits proliferation of TE-671 and SH-SY5Y cancer cells. Maternal ingestion of anagyrine during gestation is associated with the teratogenic condition crooked calf disease in cattle.

Chemical Structure

Anagyrine
Anagyrine
CAS#486-89-5

Theoretical Analysis

MedKoo Cat#: 462643

Name: Anagyrine

CAS#: 486-89-5

Chemical Formula: C15H20N2O

Exact Mass: 244.1576

Molecular Weight: 244.34

Elemental Analysis: C, 73.74; H, 8.25; N, 11.47; O, 6.55

Price and Availability

Size Price Availability Quantity
1mg USD 575.00 2 Weeks
5mg USD 1,250.00 2 Weeks
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Related CAS #
No Data
Synonym
Monolupine
IUPAC/Chemical Name
(7R,14R,14aR)-1,3,4,6,7,13,14,14a-octahydro-2H,11H-7,14-methanodipyrido[1,2-a:1',2'-e][1,5]diazocin-11-one
InChi Key
FQEQMASDZFXSJI-JHJVBQTASA-N
InChi Code
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
SMILES Code
O=C1N(C2)C([C@]3([H])C[C@@]2([H])[C@@]4([H])CCCCN4C3)=CC=C1
Appearance
Solid powder
Purity
>95% (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
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 244.34 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: Green BT, Lee ST, Welch KD, Cook D. Anagyrine desensitization of peripheral nicotinic acetylcholine receptors. A potential biomarker of quinolizidine alkaloid teratogenesis in cattle. Res Vet Sci. 2017 Dec;115:195-200. doi: 10.1016/j.rvsc.2017.04.019. Epub 2017 May 2. PMID: 28494312. 2: Lee ST, Panter KE, Pfister JA, Gardner DR, Welch KD. The effect of body condition on serum concentrations of two teratogenic alkaloids (anagyrine and ammodendrine) from lupines (Lupinus species) that cause crooked calf disease. J Anim Sci. 2008 Oct;86(10):2771-8. doi: 10.2527/jas.2007-0610. Epub 2008 Jun 6. PMID: 18539842. 3: Finnell RH, Chernoff GF. Anagyrine-induced congenital defects. J Pediatr. 1988 Feb;112(2):331. doi: 10.1016/s0022-3476(88)80099-4. PMID: 3339518. 4: Turgunov KK, Rakhimov SB, Vinogradova VI, Tashkhodjaev B. Crystal structure of anagyrine perchlorate. Acta Crystallogr E Crystallogr Commun. 2015 Apr 25;71(Pt 5):o343-4. doi: 10.1107/S2056989015007781. PMID: 25995939; PMCID: PMC4420039. 5: Gray D, Gallagher T. A flexible strategy for the synthesis of tri- and tetracyclic lupin alkaloids: synthesis of (+)-cytisine, (+/-)-anagyrine, and (+/-)-thermopsine. Angew Chem Int Ed Engl. 2006 Apr 3;45(15):2419-23. doi: 10.1002/anie.200504015. PMID: 16521145. 6: Keeler RF, Gross R. The total alkaloid and anagyrine contents of some bitter and sweet selections of lupin species used as food. J Environ Pathol Toxicol. 1980 Jun-Jul;3(5-6):333-40. PMID: 7441088. 7: Ortega JA, Lazerson J. Anagyrine-induced red cell aplasia, vascular anomaly, and skeletal dysplasia. J Pediatr. 1987 Jul;111(1):87-9. doi: 10.1016/s0022-3476(87)80349-9. PMID: 3110390. 8: Keeler RF, Cronin EH, Shupe JL. Lupin alkaloids from teratogenic and nonteratogenic lupins. IV. Concentration of total alkaloids, individual major alkaloids, and the teratogen anagyrine as a function of plant part and stage of growth and their relationship to crooked calf disease. J Toxicol Environ Health. 1976 Jul;1(6):899-908. doi: 10.1080/15287397609529392. PMID: 966319. 9: Green BT, Lee ST, Panter KE, Welch KD, Cook D, Pfister JA, Kem WR. Actions of piperidine alkaloid teratogens at fetal nicotinic acetylcholine receptors. Neurotoxicol Teratol. 2010 May-Jun;32(3):383-90. doi: 10.1016/j.ntt.2010.01.011. Epub 2010 Jan 29. PMID: 20116429. 10: He LJ, Liu JS, Luo D, Zheng YR, Zhang YB, Wang GC, Li YL. Quinolizidine alkaloids from Sophora tonkinensis and their anti-inflammatory activities. Fitoterapia. 2019 Nov;139:104391. doi: 10.1016/j.fitote.2019.104391. Epub 2019 Nov 1. PMID: 31682871. 11: Keeler RF. Lupin alkaloids from teratogenic and nonteratogenic lupins. III. Identification of anagyrine as the probable teratogen by feeding trials. J Toxicol Environ Health. 1976 Jul;1(6):887-98. doi: 10.1080/15287397609529391. PMID: 966318. 12: MARION L, OUELLET J. The papilionaceous alkaloids; identity of rhombinine and monolupine with anagyrine. J Am Chem Soc. 1948 Sep;70(9):3076-8. doi: 10.1021/ja01189a071. PMID: 18882541. 13: Rader JI, Pawar RS. Primary constituents of blue cohosh: quantification in dietary supplements and potential for toxicity. Anal Bioanal Chem. 2013 May;405(13):4409-17. doi: 10.1007/s00216-013-6783-7. Epub 2013 Feb 19. PMID: 23420136. 14: FAUGERAS G, PARIS R, MEYRUEY MH. SUR LES ALCALOUIDES DU RETAMA RAETAM WEBB ET BERTH. (GENISTA RAETAM FORSK.). II. ISOLEMENT DE L'ANAGYRINE 'A PARTIR DES FLEURS [ON THE ALKALOIDS OF RETAMA RAETAM WEBB AND BERTH. (GENISTA RAETAM FORSK.). II. ISOLATION OF ANAGYRINE FROM FLOWERS]. Ann Pharm Fr. 1963 Sep- Oct;21:675-9. French. PMID: 14091315. 15: Green BT, Lee ST, Welch KD, Gardner DR, Stegelmeier BL, Davis TZ. The serum concentrations of lupine alkaloids in orally-dosed Holstein cattle. Res Vet Sci. 2015 Jun;100:239-44. doi: 10.1016/j.rvsc.2015.04.001. Epub 2015 Apr 13. PMID: 25912242. 16: Gay CC, Panter KE, Mealey KL, Gay JM, Hjartarson SW, Tibary A, Motteram ES, Wierenga T, James LF. Comparison of plasma disposition of alkaloids after lupine challenge in cattle that had given birth to calves with lupine-induced arthrogryposis or clinically normal calves. Am J Vet Res. 2004 Nov;65(11):1580-3. doi: 10.2460/ajvr.2004.65.1580. PMID: 15566098. 17: Lopez-Ortiz S, Panter KE, Pfister JA, Launchbaugh KL. The effect of body condition on disposition of alkaloids from silvery lupine (Lupinus argenteus pursh) in sheep. J Anim Sci. 2004 Sep;82(9):2798-805. doi: 10.2527/2004.8292798x. PMID: 15446497. 18: Lee ST, Stonecipher CA, Dos Santos FC, Pfister JA, Welch KD, Cook D, Green BT, Gardner DR, Panter KE. An Evaluation of Hair, Oral Fluid, Earwax, and Nasal Mucus as Noninvasive Specimens to Determine Livestock Exposure to Teratogenic Lupine Species. J Agric Food Chem. 2019 Jan 9;67(1):43-49. doi: 10.1021/acs.jafc.8b05673. Epub 2018 Dec 18. PMID: 30525551. 19: Innocenti G, Dall'Acqua S, Viola G, Loi MC. Cytotoxic constituents from Anagyris foetida leaves. Fitoterapia. 2006 Dec;77(7-8):595-7. doi: 10.1016/j.fitote.2006.06.012. Epub 2006 Jul 7. PMID: 16887297. 20: Martins A, Wink M, Tei A, Brum-Bousquet M, Tillequin F, Rauter AP. A phytochemical study of the quinolizidine alkaloids from Genista tenera by gas chromatography-mass spectrometry. Phytochem Anal. 2005 Jul-Aug;16(4):264-6. doi: 10.1002/pca.832. PMID: 16042152.