Lycoramine HBr

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MedKoo CAT#: 330151

CAS#: 89505-76-0 (HBr)

Description: Lycoramine is a natural alkaloid isolated from Lycoris chinensis.


Price and Availability

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Pricing updated 2020-10-29. Prices are subject to change without notice.

Lycoramine HBr is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 330151
Name: Lycoramine HBr
CAS#: 89505-76-0 (HBr)
Chemical Formula: C17H24BrNO3
Exact Mass:
Molecular Weight: 370.287
Elemental Analysis: C, 55.14; H, 6.53; Br, 21.58; N, 3.78; O, 12.96


Related CAS #: 21133-52-8 (free base)   89505-76-0 (HBr)    

Synonym: Lycoramine HBr; Lycoramine hydrobromide

IUPAC/Chemical Name: (4aS,6S,8aR)-3-methoxy-11-methyl-4a,5,7,8,9,10,11,12-octahydro-6H-benzo[2,3]benzofuro[4,3-cd]azepin-6-ol hydrobromide

InChi Key: ICGKMCUNORDOLD-XPSHAMGMSA-N

InChi Code: InChI=1S/C17H23NO3.BrH/c1-18-8-7-17-6-5-12(19)9-14(17)21-16-13(20-2)4-3-11(10-18)15(16)17;/h3-4,12,14,19H,5-10H2,1-2H3;1H/t12-,14-,17-;/m0./s1

SMILES Code: O[C@H]1CC[C@@]23C(C(CN(C)CC3)=CC=C4OC)=C4O[C@@]2([H])C1.[H]Br


Technical Data

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


References

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2: Li L, Yang Q, Wang Y, Jia Y. Catalytic asymmetric total synthesis of (-)-galanthamine and (-)-lycoramine. Angew Chem Int Ed Engl. 2015 May 18;54(21):6255-9. doi: 10.1002/anie.201411338. Epub 2015 Apr 2. PubMed PMID: 25847447.

3: Feng Y, Yu ZX. Formal synthesis of (±)-galanthamine and (±)-lycoramine using Rh(I)-catalyzed [(3 + 2) + 1] cycloaddition of 1-ene-vinylcyclopropane and CO. J Org Chem. 2015 Feb 6;80(3):1952-6. doi: 10.1021/jo502604p. Epub 2015 Jan 16. PubMed PMID: 25558884.

4: Cortes N, Alvarez R, Osorio EH, Alzate F, Berkov S, Osorio E. Alkaloid metabolite profiles by GC/MS and acetylcholinesterase inhibitory activities with binding-mode predictions of five Amaryllidaceae plants. J Pharm Biomed Anal. 2015 Jan;102:222-8. doi: 10.1016/j.jpba.2014.09.022. Epub 2014 Sep 28. PubMed PMID: 25305596.

5: Zhang Y, Li Y, Zhou J, Chen N, Wang M, Dong Z, Gao C, Zhong Y. [Effect of precursor on growth and accumulation of alkaloids of Lycoris radiata suspension cells]. Sheng Wu Gong Cheng Xue Bao. 2014 Feb;30(2):247-54. Chinese. PubMed PMID: 24945053.

6: Jin A, Li X, Zhu YY, Yu HY, Pi HF, Zhang P, Ruan HL. Four new compounds from the bulbs of Lycoris aurea with neuroprotective effects against CoCl₂ and H₂O₂-induced SH-SY5Y cell injuries. Arch Pharm Res. 2014 Mar;37(3):315-23. doi: 10.1007/s12272-013-0188-1. Epub 2013 Jun 18. PubMed PMID: 23775477.

7: Katoch D, Kumar D, Sharma U, Kumar N, Padwad YS, Lal B, Singh B. Zephgrabetaine: a new betaine-type amaryllidaceae alkaloid from Zephyranthes grandiflora. Nat Prod Commun. 2013 Feb;8(2):161-4. PubMed PMID: 23513717.

8: Zhang Y, Chen Z. Nonaqueous CE ESI-IT-MS analysis of Amaryllidaceae alkaloids. J Sep Sci. 2013 Mar;36(6):1078-84. doi: 10.1002/jssc.201201083. Epub 2013 Feb 25. PubMed PMID: 23436771.

9: Katoch D, Kumar S, Kumar N, Singh B. Simultaneous quantification of Amaryllidaceae alkaloids from Zephyranthes grandiflora by UPLC-DAD/ESI-MS/MS. J Pharm Biomed Anal. 2012 Dec;71:187-92. doi: 10.1016/j.jpba.2012.08.001. Epub 2012 Aug 16. PubMed PMID: 22939505.

10: Chen JQ, Xie JH, Bao DH, Liu S, Zhou QL. Total synthesis of (-)-galanthamine and (-)-lycoramine via catalytic asymmetric hydrogenation and intramolecular reductive Heck cyclization. Org Lett. 2012 Jun 1;14(11):2714-7. doi: 10.1021/ol300913g. Epub 2012 May 21. PubMed PMID: 22612349.

11: Chen P, Bao X, Zhang LF, Ding M, Han XJ, Li J, Zhang GB, Tu YQ, Fan CA. Asymmetric synthesis of bioactive hydrodibenzofuran alkaloids: (-)-lycoramine, (-)-galanthamine, and (+)-lunarine. Angew Chem Int Ed Engl. 2011 Aug 22;50(35):8161-6. doi: 10.1002/anie.201103198. Epub 2011 Jul 11. PubMed PMID: 21748835.

12: Mu HM, Wang R, Li XD, Jiang YM, Peng F, Xia B. Alkaloid accumulation in different parts and ages of Lycoris chinensis. Z Naturforsch C. 2010 Jul-Aug;65(7-8):458-62. PubMed PMID: 20737914.

13: Ishikawa T, Kudo K, Kuroyabu K, Uchida S, Kudoh T, Saito S. Domino double Michael-Claisen cyclizations: a powerful general tool for introducing quaternary stereocenters at C4 of cyclohexane-1,3-diones and total synthesis of diverse families of sterically congested alkaloids. J Org Chem. 2008 Oct 3;73(19):7498-508. doi: 10.1021/jo801316s. Epub 2008 Sep 10. PubMed PMID: 18781800.

14: Malachowski WP, Paul T, Phounsavath S. The enantioselective synthesis of (-)-lycoramine with the Birch-Cope sequence. J Org Chem. 2007 Aug 31;72(18):6792-6. Epub 2007 Aug 4. PubMed PMID: 17676911.

15: Youssef DT, Frahm AW. Alkaloids of the flowers of Pancratium maritimum. Planta Med. 1998 Oct;64(7):669-70. PubMed PMID: 17253308.

16: Fan CA, Tu YQ, Song ZL, Zhang E, Shi L, Wang M, Wang B, Zhang SY. An efficient total synthesis of (+/-)-lycoramine. Org Lett. 2004 Dec 9;6(25):4691-4. PubMed PMID: 15575662.

17: Arisawa M, Tohma H, Kita Y. [Development of intramolecular oxidative phenolic coupling reactions using hypervalent iodine (III) reagents and their application to the synthesis of Amaryllidaceae alkaloids]. Yakugaku Zasshi. 2000 Oct;120(10):1061-73. Review. Japanese. PubMed PMID: 11082716.

18: Li HY, Ma GE, Xu Y, Hong SH. Alkaloids of Lycoris guangxiensis1. Planta Med. 1987 Jun;53(3):259-61. PubMed PMID: 17269013.

19: Misaka Y, Mizutani T, Sekido M, Uyeo S. The total synthesis of (+-)-lycoramine. II. J Chem Soc Perkin 1. 1968;23:2954-9. PubMed PMID: 5749970.

20: Hazama N, Irie H, Mizutani T, Shingu T, Takada M, Uyeo S, Yoshitake A. The total synthesis of (plus or minus)-lycoramine. I. J Chem Soc Perkin 1. 1968;23:2947-53. PubMed PMID: 5749969.