MedKoo Cat#: 413346 | Name: Crinamine

Description:

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

Crinamine is a biochemical

Chemical Structure

Crinamine
Crinamine
CAS#639-41-8

Theoretical Analysis

MedKoo Cat#: 413346

Name: Crinamine

CAS#: 639-41-8

Chemical Formula: C17H19NO4

Exact Mass: 301.1314

Molecular Weight: 301.34

Elemental Analysis: C, 67.76; H, 6.36; N, 4.65; O, 21.24

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
Crinamine; NSC88421; NSC-88421; NSC 88421
IUPAC/Chemical Name
(3R,4aS,11bS,12R)-3-methoxy-4,4a-dihydro-3H,6H-11b,5-ethano[1,3]dioxolo[4,5-j]phenanthridin-12-ol
InChi Key
YGPRSGKVLATIHT-SPOWBLRKSA-N
InChi Code
InChI=1S/C17H19NO4/c1-20-11-2-3-17-12-6-14-13(21-9-22-14)4-10(12)7-18(8-16(17)19)15(17)5-11/h2-4,6,11,15-16,19H,5,7-9H2,1H3/t11-,15-,16-,17-/m0/s1
SMILES Code
CO[C@@H]1C[C@@H]2N3C[C@@H]([C@]2(c4c(C3)cc5c(OCO5)c4)C=C1)O
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
>2 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
Solvent mg/mL mM
Solubility
Soluble in DMSO 0.0 100.00
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 301.34 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: Khumkhrong P, Piboonprai K, Chaichompoo W, Pimtong W, Khongkow M, Namdee K, Jantimaporn A, Japrung D, Asawapirom U, Suksamrarn A, Iempridee T. Crinamine Induces Apoptosis and Inhibits Proliferation, Migration, and Angiogenesis in Cervical Cancer SiHa Cells. Biomolecules. 2019 Sep 16;9(9):494. doi: 10.3390/biom9090494. PMID: 31527550; PMCID: PMC6770758. 2: Naidoo D, Roy A, Slavětínská LP, Chukwujekwu JC, Gupta S, Van Staden J. New role for crinamine as a potent, safe and selective inhibitor of human monoamine oxidase B: In vitro and in silico pharmacology and modeling. J Ethnopharmacol. 2020 Feb 10;248:112305. doi: 10.1016/j.jep.2019.112305. Epub 2019 Oct 19. PMID: 31639490. 3: Kim YH, Park EJ, Park MH, Badarch U, Woldemichael GM, Beutler JA. Crinamine from Crinum asiaticum var. japonicum inhibits hypoxia inducible factor-1 activity but not activity of hypoxia inducible factor-2. Biol Pharm Bull. 2006 Oct;29(10):2140-2. doi: 10.1248/bpb.29.2140. PMID: 17015967. 4: Nguyen TT, Chang J, Jung EJ, Cho CG. Total syntheses of (+/-)-crinine, (+/-)-crinamine, and (+/-)-6a-epi-crinamine via the regioselective synthesis and Diels-Alder reaction of 3-aryl-5-bromo-2-pyrone. J Org Chem. 2008 Aug 15;73(16):6258-64. doi: 10.1021/jo8008353. Epub 2008 Jul 16. PMID: 18630885. 5: Endo Y, Sugiura Y, Funasaki M, Kagechika H, Ishibashi M, Ohsaki A. Two new alkaloids from Crinum asiaticum var. japonicum. J Nat Med. 2019 Jun;73(3):648-652. doi: 10.1007/s11418-019-01304-9. Epub 2019 Apr 8. PMID: 30963375. 6: Campbell WE, Nair JJ, Gammon DW, Codina C, Bastida J, Viladomat F, Smith PJ, Albrecht CF. Bioactive alkaloids from Brunsvigia radulosa. Phytochemistry. 2000 Mar;53(5):587-91. doi: 10.1016/s0031-9422(99)00575-0. PMID: 10724185. 7: Liu ZM, Huang XY, Cui MR, Zhang XD, Chen Z, Yang BS, Zhao XK. Amaryllidaceae alkaloids from the bulbs of Lycoris radiata with cytotoxic and anti-inflammatory activities. Fitoterapia. 2015 Mar;101:188-93. doi: 10.1016/j.fitote.2015.01.003. Epub 2015 Jan 14. PMID: 25596094. 8: Nishimata T, Sato Y, Mori M. Palladium-catalyzed asymmetric allylic substitution of 2-arylcyclohexenol derivatives: asymmetric total syntheses of (+)-crinamine, (-)-haemanthidine, and (+)-pretazettine. J Org Chem. 2004 Mar 19;69(6):1837-43. doi: 10.1021/jo030309b. PMID: 15058926. 9: Mori M. Development of a novel synthetic method for ring construction using organometallic complexes and its application to the total syntheses of natural products. Chem Pharm Bull (Tokyo). 2005 May;53(5):457-70. doi: 10.1248/cpb.53.457. PMID: 15863913. 10: Houghton PJ, Agbedahunsi JM, Adegbulugbe A. Choline esterase inhibitory properties of alkaloids from two Nigerian Crinum species. Phytochemistry. 2004 Nov;65(21):2893-6. doi: 10.1016/j.phytochem.2004.08.052. PMID: 15501257.