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MedKoo Cat#: 461394 | Name: Antioquine

Description:

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

Antioquine is a bisbenzyltetrahydroisoquinoline alkaloid isolated from Pseudoxandra sclerocarpa.

Chemical Structure

Antioquine
Antioquine
CAS#93767-27-2

Theoretical Analysis

MedKoo Cat#: 461394

Name: Antioquine

CAS#: 93767-27-2

Chemical Formula: C37H40N2O6

Exact Mass: 608.2886

Molecular Weight: 608.73

Elemental Analysis: C, 73.01; H, 6.62; N, 4.60; O, 15.77

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
Antioquine;
IUPAC/Chemical Name
(41R,61R)-16,47,66-trimethoxy-42,62-dimethyl-41,42,43,44,61,62,63,64-octahydro-5-oxa-4(1,6),6(8,1)-diisoquinolina-1,2(1,3)-dibenzenacycloheptaphane-26,67-diol
InChi Key
MCVHJNNOOCVDLO-FQLXRVMXSA-N
InChi Code
InChI=1S/C37H40N2O6/c1-38-12-10-23-18-33-32(43-4)20-25(23)28(38)16-21-6-8-30(40)26(14-21)27-15-22(7-9-31(27)42-3)17-29-35-24(11-13-39(29)2)19-34(44-5)36(41)37(35)45-33/h6-9,14-15,18-20,28-29,40-41H,10-13,16-17H2,1-5H3/t28-,29-/m1/s1
SMILES Code
CN(CCc1cc(OC)c(O)c(Oc2cc(CCN(C)[C@@H]3Cc4ccc(O)c5C4)c3cc2OC)c16)[C@@H]6Cc7cc5c(OC)cc7
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 608.73 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: Ivorra MD, Lugnier C, Catret M, Anselmi E, Cortes D, D'Ocon P. Investigations of the dual contractile/relaxant properties showed by antioquine in rat aorta. Br J Pharmacol. 1993 Jun;109(2):502-9. PubMed PMID: 8358549; PubMed Central PMCID: PMC2175685. 2: D'Ocon MP, Candenas ML, Anselmi E, Zafra-Polo MC, Cortes D. Antioquine: a new bisbenzylisoquinoleine alkaloid with calcium antagonist activity. Arch Int Pharmacodyn Ther. 1989 Jan-Feb;297:205-16. PubMed PMID: 2730236. 3: Catret M, Ivorra MD, D'Ocón MP, Anselmi E. The 5-HT and alpha-adrenoceptor antagonist effect of four benzylisoquinoline alkaloids on rat aorta. J Pharm Pharmacol. 1998 Mar;50(3):317-22. PubMed PMID: 9600725. 4: Mahiou V, Roblot F, Fournet A, Hocquemiller R. Bisbenzylisoquinoline alkaloids from Guatteria boliviana (Annonaceae). Phytochemistry. 2000 Aug;54(7):709-16. PubMed PMID: 10975506. 5: Correché ER, Andujar SA, Kurdelas RR, Gómez Lechón MJ, Freile ML, Enriz RD. Antioxidant and cytotoxic activities of canadine: biological effects and structural aspects. Bioorg Med Chem. 2008 Apr 1;16(7):3641-51. doi: 10.1016/j.bmc.2008.02.015. Epub 2008 Feb 8. PubMed PMID: 18295494. 6: Schleifer KJ, Tot E. Pharmacophore modelling of structurally unusual diltiazem mimics at L-type calcium channels. J Comput Aided Mol Des. 2000 Jul;14(5):427-33. PubMed PMID: 10896315. 7: Ivorra MD, Cercós A, Zafra-Polo MC, Perez-Prieto J, Sáez J, Cortes D, D'Ocon P. Selective chiral inhibition of Ca2+ entry promoted by bisbenzyltetrahydroisoquinolines in rat uterus. Eur J Pharmacol. 1992 Aug 25;219(2):303-9. PubMed PMID: 1425956. 8: Protais P, Arbaoui J, Bakkali EH, Bermejo A, Cortes D. Effects of various isoquinoline alkaloids on in vitro 3H-dopamine uptake by rat striatal synaptosomes. J Nat Prod. 1995 Oct;58(10):1475-84. PubMed PMID: 8676127. 9: Granell S, Andreu I, Martí D, Cavé A, Aragón R, Estornell E, Cortes D, Zafra-Polo MC. Bisbenzyltetrahydroisoquinolines, a new class of inhibitors of the mitochondrial respiratory chain complex I. Planta Med. 2004 Mar;70(3):266-8. PubMed PMID: 15114508. 10: Martinez JL, Benites J, Gomez H, Vargas-Rueda S, Vinet R, Jaimes L, Laurido C. Effects of two bisbenzylisoquinoline alkaloids, Antioquine and Tetrandrine, compared to Verapamil in Rat Thoracic Aorta. An Acad Bras Cienc. 2018 Apr-Jun;90(2):1459-1463. doi: 10.1590/0001-3765201820170608. PubMed PMID: 29898104. 11: Fournet A, Inchausti A, Yaluff G, Rojas De Arias A, Guinaudeau H, Bruneton J, Breidenbach MA, Karplus PA, Faerman CH. Trypanocidal bisbenzylisoquinoline alkaloids are inhibitors of trypanothione reductase. J Enzyme Inhib. 1998 Feb;13(1):1-9. PubMed PMID: 9879510. 12: Cortes D, Figadere B, Saez J, Protais P. Displacement activity of bisbenzylisoquinoline alkaloids at striatal 3H-SCH 23390 and 3H-raclopride binding sites. J Nat Prod. 1992 Sep;55(9):1281-6. PubMed PMID: 1431946. 13: Candenas ML, Naline E, D'Ocón MP, Cortes D, Advenier C. Effects of cularine and other isoquinoline alkaloids on guinea-pig trachea and human bronchus. J Pharm Pharmacol. 1990 Feb;42(2):102-7. PubMed PMID: 1972394.