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MedKoo Cat#: 592398 | Name: Strictamine

Description:

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

Strictamine is a akuammiline alkaloid.

Chemical Structure

Strictamine
Strictamine
CAS#6475-05-4

Theoretical Analysis

MedKoo Cat#: 592398

Name: Strictamine

CAS#: 6475-05-4

Chemical Formula: C20H22N2O2

Exact Mass: 322.1681

Molecular Weight: 322.41

Elemental Analysis: C, 74.51; H, 6.88; N, 8.69; O, 9.92

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
Strictamine; NSC 180521; NSC-180521; NSC180521
IUPAC/Chemical Name
Akuammilan-17-oic acid, methyl ester
InChi Key
LITYYRLWHAQJQS-ZYJJEPLOSA-N
InChi Code
InChI=1S/C20H22N2O2/c1-3-12-11-22-9-8-20-14-6-4-5-7-15(14)21-18(20)16(22)10-13(12)17(20)19(23)24-2/h3-7,13,16-17H,8-11H2,1-2H3/b12-3-/t13-,16-,17?,20-/m0/s1
SMILES Code
C/C=C1CN2CC[C@@]34c5c(N=C3[C@@H]2C[C@@H]/1C4C(OC)=O)cccc5
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 322.41 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: Picazo E, Morrill LA, Susick RB, Moreno J, Smith JM, Garg NK. Enantioselective Total Syntheses of Methanoquinolizidine-Containing Akuammiline Alkaloids and Related Studies. J Am Chem Soc. 2018 May 23;140(20):6483-6492. doi: 10.1021/jacs.8b03404. Epub 2018 May 15. PubMed PMID: 29694031. 2: Xiao T, Chen ZT, Deng LF, Zhang D, Liu XY, Song H, Qin Y. Formal total synthesis of the akuammiline alkaloid (+)-strictamine. Chem Commun (Camb). 2017 Nov 23;53(94):12665-12667. doi: 10.1039/c7cc08153g. PubMed PMID: 29167841. 3: Abouzeid S, Beutling U, Surup F, Abdel Bar FM, Amer MM, Badria FA, Yahyazadeh M, Brönstrup M, Selmar D. Treatment of Vinca minor Leaves with Methyl Jasmonate Extensively Alters the Pattern and Composition of Indole Alkaloids. J Nat Prod. 2017 Nov 22;80(11):2905-2909. doi: 10.1021/acs.jnatprod.7b00424. Epub 2017 Nov 13. PubMed PMID: 29131648. 4: Xie X, Wei B, Li G, Zu L. Unified Total Syntheses of Structurally Diverse Akuammiline Alkaloids. Org Lett. 2017 Oct 6;19(19):5430-5433. doi: 10.1021/acs.orglett.7b02698. Epub 2017 Sep 27. PubMed PMID: 28952737. 5: Smith MW, Zhou Z, Gao AX, Shimbayashi T, Snyder SA. A 7-Step Formal Asymmetric Total Synthesis of Strictamine via an Asymmetric Propargylation and Metal-Mediated Cyclization. Org Lett. 2017 Mar 3;19(5):1004-1007. doi: 10.1021/acs.orglett.6b03839. Epub 2017 Feb 13. PubMed PMID: 28253628. 6: Eckermann R, Breunig M, Gaich T. Formal Total Synthesis of (±)-Strictamine by [2,3]-Sigmatropic Stevens Rearrangements. Chemistry. 2017 Mar 17;23(16):3938-3949. doi: 10.1002/chem.201605361. Epub 2017 Feb 22. PubMed PMID: 28071823. 7: Andreansky ES, Blakey SB. An Iminium Ion Cascade Annulation Strategy for the Synthesis of Akuammiline Alkaloid Pentacyclic Core Structures. Org Lett. 2016 Dec 16;18(24):6492-6495. Epub 2016 Dec 1. PubMed PMID: 27978638. 8: Eckermann R, Breunig M, Gaich T. Formal total synthesis of (±)-strictamine - the [2,3]-Stevens rearrangement for construction of octahydro-2H-2,8-methanoquinolizines. Chem Commun (Camb). 2016 Sep 15;52(76):11363-11365. PubMed PMID: 27711394. 9: Nishiyama D, Ohara A, Chiba H, Kumagai H, Oishi S, Fujii N, Ohno H. Formal Total Synthesis of (±)-Strictamine Based on a Gold-Catalyzed Cyclization. Org Lett. 2016 Apr 1;18(7):1670-3. doi: 10.1021/acs.orglett.6b00536. Epub 2016 Mar 24. PubMed PMID: 27011119. 10: Ren W, Wang Q, Zhu J. Total Synthesis of (±)-Strictamine. Angew Chem Int Ed Engl. 2016 Mar 1;55(10):3500-3. doi: 10.1002/anie.201511638. Epub 2016 Feb 4. PubMed PMID: 26845231. 11: Moreno J, Picazo E, Morrill LA, Smith JM, Garg NK. Enantioselective Total Syntheses of Akuammiline Alkaloids (+)-Strictamine, (-)-2(S)-Cathafoline, and (-)-Aspidophylline A. J Am Chem Soc. 2016 Feb 3;138(4):1162-5. doi: 10.1021/jacs.5b12880. Epub 2016 Jan 19. PubMed PMID: 26783944; PubMed Central PMCID: PMC5154302. 12: Smith JM, Moreno J, Boal BW, Garg NK. Total synthesis of the akuammiline alkaloid picrinine. J Am Chem Soc. 2014 Mar 26;136(12):4504-7. doi: 10.1021/ja501780w. Epub 2014 Mar 12. PubMed PMID: 24597784; PubMed Central PMCID: PMC3985766. 13: Edwankar RV, Edwankar CR, Namjoshi OA, Deschamps JR, Cook JM. Brønsted acid mediated cyclization of enaminones. Rapid and efficient access to the tetracyclic framework of the Strychnos alkaloids. J Nat Prod. 2012 Feb 24;75(2):181-8. doi: 10.1021/np200759h. Epub 2012 Jan 18. PubMed PMID: 22257244; PubMed Central PMCID: PMC3288251. 14: Jain L, Pandey MB, Singh S, Singh AK, Pandey VB. A new indole alkaloid from Alstonia scholaris. Nat Prod Res. 2009;23(17):1599-602. doi: 10.1080/14786410802547499. PubMed PMID: 19851925. 15: Jossang A, Fodor P, Bodo B. A New Structural Class of Bisindole Alkaloids from the Seeds of Catharanthus roseus: Vingramine and Methylvingramine. J Org Chem. 1998 Oct 16;63(21):7162-7167. PubMed PMID: 11672355. 16: Hugel G, Royer D, Le Men-Olivier L, Richard B, Jacquier MJ, Lévy J. Flow Thermolysis Rearrangements in the Indole Alkaloid Series: Strictamine and Akuammicine Derivatives. The Absolute Configurations of Ngouniensine and epi-Ngouniensine. J Org Chem. 1997 Feb 7;62(3):578-583. PubMed PMID: 11671452. 17: Liu HM, Wu B, Zheng QT, Feng XZ. New Indole Alkaloids from Amsonia sinensis. Planta Med. 1991 Dec;57(6):566-8. PubMed PMID: 17226203. 18: Nasser AM, Court WE. Stem bark alkaloids of Rauvolfia caffra. J Ethnopharmacol. 1984 Jun;11(1):99-117. PubMed PMID: 6471882. 19: Bhattacharya SK, Bose R, Dutta SC, Ray AB, Guha SR. Neuropharmacological studies on strictamine isolated from Alstonia scholaris. Indian J Exp Biol. 1979 Jun;17(6):598-600. PubMed PMID: 500142.