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MedKoo Cat#: 592627 | Name: Allocryptopine
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Description:

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

Allocryptopine induces muscle contraction and relaxation in urinary bladder and ileum, respectively.

Chemical Structure

Allocryptopine
CAS#485-91-6

Theoretical Analysis

MedKoo Cat#: 592627

Name: Allocryptopine

CAS#: 485-91-6

Chemical Formula: C21H23NO5

Exact Mass: 369.1576

Molecular Weight: 369.42

Elemental Analysis: C, 68.28; H, 6.28; N, 3.79; O, 21.65

Price and Availability

Size Price Availability Quantity
5mg USD 250.00 2 Weeks
10mg USD 400.00 2 Weeks
25mg USD 750.00 2 Weeks
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Related CAS #
No Data
Synonym
Allocryptopine; α-Allocryptopine; α-Fagarine; β-Homochelidonine; Thalictrimine
IUPAC/Chemical Name
5,7,8,15-Tetrahydro-3,4-dimethoxy-6-methyl(1,3)benzodioxolo(5,6-e)(2)benzazecin-14(6H)-one
InChi Key
HYBRYAPKQCZIAE-UHFFFAOYSA-N
InChi Code
InChI=1S/C21H23NO5/c1-22-7-6-14-9-19-20(27-12-26-19)10-15(14)17(23)8-13-4-5-18(24-2)21(25-3)16(13)11-22/h4-5,9-10H,6-8,11-12H2,1-3H3
SMILES Code
O=C1C2=C(C=C3OCOC3=C2)CCN(C)CC4=C(OC)C(OC)=CC=C4C1
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 369.42 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: Zhang J, Chen Y, Yang J, Xu B, Wen Y, Xiang G, Wei G, Zhu C, Xing Y, Li Y. Electrophysiological and trafficking defects of the SCN5A T353I mutation in Brugada syndrome are rescued by alpha-allocryptopine. Eur J Pharmacol. 2015 Jan 5;746:333-43. doi: 10.1016/j.ejphar.2014.09.028. Epub 2014 Sep 23. PubMed PMID: 25261036. 2: Xu B, Fu Y, Liu L, Lin K, Zhao X, Zhang Y, Chen X, Cai Z, Huang Y, Li Y. Effect of α-Allocryptopine on Delayed Afterdepolarizations and Triggered Activities in Mice Cardiomyocytes Treated with Isoproterenol. Evid Based Complement Alternat Med. 2015;2015:634172. doi: 10.1155/2015/634172. Epub 2015 Oct 19. PubMed PMID: 26557861; PubMed Central PMCID: PMC4629026. 3: Lin K, Liu YQ, Xu B, Gao JL, Fu YC, Chen Y, Xue Q, Li Y. Allocryptopine and benzyltetrahydropalmatine block hERG potassium channels expressed in HEK293 cells. Acta Pharmacol Sin. 2013 Jun;34(6):847-58. doi: 10.1038/aps.2012.176. Epub 2013 Mar 25. PubMed PMID: 23524574; PubMed Central PMCID: PMC4002887. 4: Huang YJ, Xiao S, Sun ZL, Zeng JG, Liu YS, Liu ZY. Identification of allocryptopine and protopine metabolites in rat liver S9 by high-performance liquid chromatography/quadrupole-time-of-flight mass spectrometry. Rapid Commun Mass Spectrom. 2016 Jul 15;30(13):1549-59. doi: 10.1002/rcm.7586. PubMed PMID: 27321842. 5: Vrba J, Vrublova E, Modriansky M, Ulrichova J. Protopine and allocryptopine increase mRNA levels of cytochromes P450 1A in human hepatocytes and HepG2 cells independently of AhR. Toxicol Lett. 2011 Jun 10;203(2):135-41. doi: 10.1016/j.toxlet.2011.03.015. Epub 2011 Mar 23. PubMed PMID: 21419197. 6: Fu YC, Zhang Y, Tian LY, Li N, Chen X, Cai ZQ, Zhu C, Li Y. Effects of allocryptopine on outward potassium current and slow delayed rectifier potassium current in rabbit myocardium. J Geriatr Cardiol. 2016 May;13(4):316-25. doi: 10.11909/j.issn.1671-5411.2016.04.008. PubMed PMID: 27403141; PubMed Central PMCID: PMC4921544. 7: Abu-Ghalyun Y, Masalmeh A, al-Khalil S. Effects of allocryptopine, an alkaloid isolated from Glaucium arabicum on rat isolated ileum and urinary bladder. Gen Pharmacol. 1997 Oct;29(4):621-3. PubMed PMID: 9352312. 8: Sun W, Qin Y, Hou Z, Yao Y, Zhou L. Dihydro-allocryptopine. Acta Crystallogr Sect E Struct Rep Online. 2012 Jan;68(Pt 1):o69. doi: 10.1107/S1600536811052172. Epub 2011 Dec 10. PubMed PMID: 22259569; PubMed Central PMCID: PMC3254424. 9: Li Y, Wang S, Liu Y, Li Z, Yang X, Wang H, Wen Y, Chen Y. Effect of alpha-allocryptopine on transient outward potassium current in rabbit ventricular myocytes. Cardiology. 2008;111(4):229-36. doi: 10.1159/000127443. Epub 2008 Apr 23. PubMed PMID: 18434730. 10: Zhong M, Huang KL, Zeng JG, Li S, She JM, Li G, Zhang L. Optimization of microwave-assisted extraction of protopine and allocryptopine from stems of Macleaya cordata (Willd) R. Br. using response surface methodology. J Sep Sci. 2010 Jul;33(14):2160-7. doi: 10.1002/jssc.201000085. PubMed PMID: 20533346. 11: Wei Y, Wei X, Wang Y, Liu X, Chu T, Hu S, Wang X. Iodination and radiolabeling of alpha-allocryptopine with iodine-125. Appl Radiat Isot. 2005 Jan;62(1):55-62. PubMed PMID: 15498685. 12: Luo XB, Chen B, Yao SZ. Rapid determination of protopine, allocryptopine, sanguinarine and chelerythrine in fruits of Macleaya cordata by microwave-assisted solvent extraction and HPLC-ESI/MS. Phytochem Anal. 2006 Nov-Dec;17(6):431-8. PubMed PMID: 17144252. 13: Manda VK, Ibrahim MA, Dale OR, Kumarihamy M, Cutler SJ, Khan IA, Walker LA, Muhammad I, Khan SI. Modulation of CYPs, P-gp, and PXR by Eschscholzia californica (California Poppy) and Its Alkaloids. Planta Med. 2016 Apr;82(6):551-8. doi: 10.1055/s-0042-103689. Epub 2016 Apr 7. PubMed PMID: 27054913. 14: Stermitz FR, Muralidharan VP. Alkaloids of the Papaveraceae. VI. Protopine and allocryptopine from Arctomecon alifornica. J Pharm Sci. 1967 Jun;56(6):762. PubMed PMID: 6034815. 15: SOINE TO, WILLETTE RE. The isolation of beta-allocryptopine from Argemone squarrosa subsp. squarrosa. J Am Pharm Assoc Am Pharm Assoc. 1960 Jun;49:368-70. PubMed PMID: 13854891. 16: Zhang X, Zhang S, Yang Q, Cao W, Xie Y, Qiu P, Wang S. Simultaneous Quantitative Determination of 12 Active Components in Yuanhu Zhitong Prescription by RP-HPLC Coupled with Photodiode Array Detection. Pharmacogn Mag. 2015 Jan-Mar;11(41):61-8. doi: 10.4103/0973-1296.149705. PubMed PMID: 25709212; PubMed Central PMCID: PMC4329634. 17: Brochmann-Hanssen E, Nielsen B. Opium alkaloids. 3. Isolation of alpha-allocryptopine. J Pharm Sci. 1966 Jul;55(7):743-4. PubMed PMID: 5967757. 18: Hou Y, Wu T, Liu Y, Wang H, Chen Y, Chen B, Sun W. Direct analysis of quaternary alkaloids by in situ reactive desorption corona beam ionization MS. Analyst. 2014 Oct 21;139(20):5185-91. doi: 10.1039/c4an00704b. Epub 2014 Aug 13. PubMed PMID: 25118336. 19: Simoes-Pires C, Hostettmann K, Haouala A, Cuendet M, Falquet J, Graz B, Christen P. Reverse pharmacology for developing an anti-malarial phytomedicine. The example of Argemone mexicana. Int J Parasitol Drugs Drug Resist. 2014 Jul 30;4(3):338-46. doi: 10.1016/j.ijpddr.2014.07.001. eCollection 2014 Dec. PubMed PMID: 25516845; PubMed Central PMCID: PMC4266807. 20: Xiaowen L, Ling T, Yunfei L, Guoxiang S, Dailin Y, Herry S. Simultaneous determination of seven alkaloids in rat plasma by UFLC-MS/MS and its application to a pharmacokinetic study after oral administration of Cerebralcare Granule. J Chromatogr B Analyt Technol Biomed Life Sci. 2016 Apr 1;1017-1018:28-35. doi: 10.1016/j.jchromb.2016.01.062. Epub 2016 Feb 26. PubMed PMID: 26943262.