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MedKoo Cat#: 146131 | Name: Atisine

Description:

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

Atisine is a naturally occurring alkaloid found in several plant species, particularly in the Atis genus, known for its potent anticancer, anti-inflammatory, and analgesic properties. It has been studied for its potential to treat cancer by inhibiting tumor cell growth and metastasis. Atisine works by modulating various signaling pathways, including those involved in apoptosis and cell cycle regulation, leading to the death of cancer cells.

Chemical Structure

Atisine
Atisine
CAS#466-43-3

Theoretical Analysis

MedKoo Cat#: 146131

Name: Atisine

CAS#: 466-43-3

Chemical Formula: C22H33NO2

Exact Mass: 343.2511

Molecular Weight: 343.51

Elemental Analysis: C, 76.92; H, 9.68; N, 4.08; O, 9.31

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
Atisine; Anthorine;
IUPAC/Chemical Name
(6R,6aR,8aS,9R,11S,12aR,12bS,12cS)-6-methyl-10-methylenedecahydro-5H,9H,12cH-8a,11-ethano-6,12b-propanobenzo[h]oxazolo[2,3-a]isoquinolin-9-ol
InChi Key
KWVIBDAKHDJCNY-PTRUQLRHSA-N
InChi Code
1S/C22H33NO2/c1-14-15-4-8-21(18(14)24)9-5-16-20(2)6-3-7-22(16,17(21)12-15)19-23(13-20)10-11-25-19/h15-19,24H,1,3-13H2,2H3/t15-,16+,17+,18+,19-,20-,21-,22-/m0/s1
SMILES Code
[H][C@@]12OCCN1C[C@]3(C)CCC[C@@]24[C@]3([H])CC[C@@]56CC[C@@H](C[C@@]45[H])C(=C)[C@H]6O
Appearance
To be determined
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
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
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 343.51 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: Zheng J, Jiang H, Yan Y, Yin T. Overview of the chemistry and biological activities of natural atisine-type diterpenoid alkaloids. RSC Adv. 2024 Jul 22;14(32):22882-22893. doi: 10.1039/d4ra03305a. PMID: 39040692; PMCID: PMC11261430. 2: Atisine. Ind Med Gaz. 1874 Apr 1;9(4):103. PMID: 28994910; PMCID: PMC5128030. 3: Chen L, Tian M, Jin B, Yin B, Chen T, Guo J, Tang J, Cui G, Huang L. Integrating Metabolomics and Transcriptomics to Unveil Atisine Biosynthesis in Aconitum gymnandrum Maxim. Int J Mol Sci. 2022 Nov 3;23(21):13463. doi: 10.3390/ijms232113463. PMID: 36362268; PMCID: PMC9655601. 4: Li XH, Zhu M, Wang ZX, Liu XY, Song H, Zhang D, Wang FP, Qin Y. Synthesis of Atisine, Ajaconine, Denudatine, and Hetidine Diterpenoid Alkaloids by a Bioinspired Approach. Angew Chem Int Ed Engl. 2016 Dec 12;55(50):15667-15671. doi: 10.1002/anie.201609882. Epub 2016 Nov 17. PMID: 27860043. 5: IRELAND RE. A REVIEW OF RECENT ADVANCES IN THE CHEMISTRY OF THE DITERPENOID ALKALOID ATISINE. Rec Chem Prog. 1963 Dec;24:225-35. PMID: 14085629. 6: Kumar V, Malhotra N, Pal T, Chauhan RS. Molecular dissection of pathway components unravel atisine biosynthesis in a non-toxic Aconitum species, A. heterophyllum Wall. 3 Biotech. 2016 Jun;6(1):106. doi: 10.1007/s13205-016-0417-7. Epub 2016 Apr 18. PMID: 28330176; PMCID: PMC4835424. 7: Zhao PJ, Gao S, Fan LM, Nie JL, He HP, Zeng Y, Shen YM, Hao XJ. Approach to the biosynthesis of atisine-type diterpenoid alkaloids. J Nat Prod. 2009 Apr;72(4):645-9. doi: 10.1021/np800657j. PMID: 19275222. 8: Liu XY, Cheng H, Li XH, Chen QH, Xu L, Wang FP. Oxidative dearomatization/intramolecular Diels-Alder cycloaddition cascade for the syntheses of (±)-atisine and (±)-isoazitine. Org Biomol Chem. 2012 Feb 21;10(7):1411-7. doi: 10.1039/c1ob06704d. Epub 2011 Dec 23. PMID: 22193953. 9: Cheng H, Zeng FH, Yang X, Meng YJ, Xu L, Wang FP. Collective Total Syntheses of Atisane-Type Diterpenes and Atisine-Type Diterpenoid Alkaloids: (±)-Spiramilactone B, (±)-Spiraminol, (±)-Dihydroajaconine, and (±)-Spiramines C and D. Angew Chem Int Ed Engl. 2016 Jan 4;55(1):392-6. doi: 10.1002/anie.201508996. Epub 2015 Nov 6. PMID: 26545636. 10: Hamlin AM, Lapointe D, Owens K, Sarpong R. Studies on C20-diterpenoid alkaloids: synthesis of the hetidine framework and its application to the synthesis of dihydronavirine and the atisine skeleton. J Org Chem. 2014 Aug 1;79(15):6783-800. doi: 10.1021/jo501214b. Epub 2014 Jul 11. PMID: 25004408; PMCID: PMC4120980. 11: Liu J, Ma D. A Unified Approach for the Assembly of Atisine- and Hetidine- type Diterpenoid Alkaloids: Total Syntheses of Azitine and the Proposed Structure of Navirine C. Angew Chem Int Ed Engl. 2018 May 28;57(22):6676-6680. doi: 10.1002/anie.201803018. Epub 2018 Apr 26. PMID: 29611891. 12: Yin T, Zhang H, Zhang W, Jiang Z. Chemistry and biological activities of hetisine-type diterpenoid alkaloids. RSC Adv. 2021 Nov 8;11(57):36023-36033. doi: 10.1039/d1ra07173d. PMID: 35492752; PMCID: PMC9043348. 13: Tang DH, Ma D, Cheng H, Li YL, Xu L. A bio-inspired synthetic route to the core ring systems of Spiraea atisine-type diterpenoid alkaloids and related diterpenes. Org Biomol Chem. 2016 Mar 7;14(9):2716-22. doi: 10.1039/c6ob00053c. PMID: 26837236. 14: Ye X, Wang Y, Chen Q, Feng Q, Liu T, Feng W, Liang Y, Liu X, Li C, Wang Z. Anti-inflammatory diterpenoid alkaloids from Aconitum tanguticum (Maxim.) Stapf. Phytochemistry. 2023 Feb;206:113524. doi: 10.1016/j.phytochem.2022.113524. Epub 2022 Dec 1. PMID: 36464099. 15: He JR, Zhang LM, Lou HB, Lv D, Zuo AX, Shen Y. Two new bis-diterpenoid alkaloids from Aconitum weixiense. J Asian Nat Prod Res. 2023 Sep;25(9):842-848. doi: 10.1080/10286020.2022.2158819. Epub 2022 Dec 22. PMID: 36562123. 16: HUEBNER CF, JACOBS WA. The aconite alkaloids; further oxidation studies with atisine and isoatisine. J Biol Chem. 1948 Jul;174(3):1001-12. PMID: 18871258. 17: Li Q, Wang ZW, Wang MX, Yu HL, Chen L, Cai Z, Zhang Y, Gu MM, Shao YL, Han HP, Liao ZX. Brunonianines A-C, C20-diterpenoid alkaloids with cyano group from Delphinium brunonianum Royle. Phytochemistry. 2024 Mar;219:113987. doi: 10.1016/j.phytochem.2024.113987. Epub 2024 Jan 11. PMID: 38218306. 18: Hao X, Shen Y, Li L, He H. The chemistry and biochemistry of Spiraea japonica complex. Curr Med Chem. 2003 Nov;10(21):2253-63. doi: 10.2174/0929867033456684. PMID: 14529341. 19: Malhotra N, Kumar V, Sood H, Singh TR, Chauhan RS. Multiple genes of mevalonate and non-mevalonate pathways contribute to high aconites content in an endangered medicinal herb, Aconitum heterophyllum Wall. Phytochemistry. 2014 Dec;108:26-34. doi: 10.1016/j.phytochem.2014.08.025. Epub 2014 Sep 16. PMID: 25239552. 20: Nagarajan M, Kuruvilla GR, Kumar KS, Venkatasubramanian P. Abhava pratinidhi dravya: A comparative phytochemistry of Ativisha, Musta and related species. J Ayurveda Integr Med. 2015 Jan-Mar;6(1):53-63. doi: 10.4103/0975-9476.146550. PMID: 25878466; PMCID: PMC4395931.