IUPAC/Chemical Name
3,5-Ethanoquinolin-10-one, decahydro-1,7-dimethyl-, (3R,4aS,5S,7S,8aR)-
InChi Key
PISGDLOMGNKHKP-HHHUOAJASA-N
InChi Code
InChI=1S/C13H21NO/c1-8-3-9-6-13(15)10-5-11(9)12(4-8)14(2)7-10/h8-12H,3-7H2,1-2H3/t8-,9-,10+,11-,12+/m0/s1
SMILES Code
O=C1C[C@@]2([H])[C@]3([H])C[C@]1([H])CN(C)[C@]3([H])C[C@@H](C)C2
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
Preparing Stock Solutions
The following data is based on the
product
molecular weight
207.32
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.
| 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: Pinto A, Piccichè M, Griera R, Molins E, Bosch J, Amat M. Studies on the Synthesis of Phlegmarine-Type Lycopodium Alkaloids: Enantioselective Synthesis of (-)-Cermizine B, (+)-Serratezomine E, and (+)-Luciduline. J Org Chem. 2018 Aug 3;83(15):8364-8375. doi: 10.1021/acs.joc.8b00983. Epub 2018 Jul 10. PubMed PMID: 29947225.
2: Cheng X, Waters SP. Pyridone annulation via tandem Curtius rearrangement/6π-electrocyclization: total synthesis of (-)-lyconadin C. Org Lett. 2013 Aug 16;15(16):4226-9. doi: 10.1021/ol401954f. Epub 2013 Aug 2. PubMed PMID: 23909645; PubMed Central PMCID: PMC3788595.
3: Barbe G, Fiset D, Charette AB. Asymmetric total synthesis of (+)-luciduline: toward a general approach to related Lycopodium alkaloids. J Org Chem. 2011 Jul 1;76(13):5354-62. doi: 10.1021/jo200745n. Epub 2011 Jun 1. PubMed PMID: 21598990.
4: Cheng X, Waters SP. Concise total syntheses of the Lycopodium alkaloids (+/-)-nankakurines A and B via luciduline. Org Lett. 2010 Jan 15;12(2):205-7. doi: 10.1021/ol902455y. PubMed PMID: 20014779; PubMed Central PMCID: PMC2804776.
5: Comins DL, Brooks CA, al-awar RS, Goehring RR. IMDA/retro-Mannich approach to cis-perhydroquinoline Lycopodium alkaloids: asymmetric synthesis of (+)-luciduline. Org Lett. 1999 Jul 29;1(2):229-31. PubMed PMID: 10822560.
6: Tori M, Shimoji T, Shimura SE, Takaoka S, Nakashima K, Sono M, Ayer WA. Four alkaloids, lucidine B, oxolucidine A, lucidine A, and lucidulinone from Lycopodium lucidulum. Phytochemistry. 2000 Feb;53(4):503-9. PubMed PMID: 10731030.
7: Scott WL, Evans DA. The total synthesis of ( )-luciduline. J Am Chem Soc. 1972 Jun 28;94(13):4779-80. PubMed PMID: 5036174.
