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MedKoo Cat#: 597945 | Name: Thermopsine
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Description:

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

Thermopsine is a quinolizidine alkaloid isolated from the fruits and pods and stem bark of Sophora velutina subsp. Thermopsine has antibacterial activity.

Chemical Structure

Thermopsine
Thermopsine
CAS#486-90-8

Theoretical Analysis

MedKoo Cat#: 597945

Name: Thermopsine

CAS#: 486-90-8

Chemical Formula: C15H20N2O

Exact Mass: 244.1576

Molecular Weight: 244.33

Elemental Analysis: C, 73.74; H, 8.25; N, 11.47; O, 6.55

Price and Availability

Size Price Availability Quantity
1mg USD 350.00 2 Weeks
5mg USD 950.00 2 Weeks
10mg USD 1,450.00 2 Weeks
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Related CAS #
No Data
Synonym
(-)-Thermopsine; l-Thermopsine; NSC 21725; NSC-21725; NSC21725;
IUPAC/Chemical Name
(7R,14R,14aS)-1,3,4,6,7,13,14,14a-octahydro-2H,11H-7,14-methanodipyrido[1,2-a:1',2'-e][1,5]diazocin-11-one
InChi Key
FQEQMASDZFXSJI-UPJWGTAASA-N
InChi Code
InChI=1S/C15H20N2O/c18-15-6-3-5-14-11-8-12(10-17(14)15)13-4-1-2-7-16(13)9-11/h3,5-6,11-13H,1-2,4,7-10H2/t11-,12-,13+/m1/s1
SMILES Code
O=C1C=CC=C2N1C[C@]3([H])[C@@](CCCC4)([H])N4C[C@@]2([H])C3
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 244.33 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: Chen Y, Hour MJ, Lin CS, Chang YS, Chen ZY, Koval'skaya AV, Su WC, Tsypysheva IP, Lin CW. Assessing the inhibitory effects of some secondary amines, thioureas and 1,3-dimethyluracil conjugates of (-)-cytisine and thermopsine on the RNA- dependent RNA polymerase of SARS-CoV-1 and SARS-CoV-2. Bioorg Med Chem Lett. 2024 Nov 15;113:129950. doi: 10.1016/j.bmcl.2024.129950. Epub 2024 Sep 7. PMID: 39251111. 2: Ning F, Zhu H, Yan H, Liu J, Aziz S, Hussain H, Song X, Xie L, Meng Z, Cao G, Wang D. Separation and purification of quinolyridine alkaloids from seeds of Thermopsis lanceolata R. Br. by conventional and pH-zone-refining counter- current chromatography. J Sep Sci. 2023 Aug;46(16):e2300053. doi: 10.1002/jssc.202300053. Epub 2023 Jun 27. PMID: 37376800. 3: Zhang P, An Q, Yi P, Cui Y, Zou JB, Yuan CM, Zhang Y, Gu W, Huang LJ, Zhao LH, Hu ZX, Hao XJ. Thermlanseedlines A-G, seven thermopsine-based alkaloids with antiviral and insecticidal activities from the seeds of Thermopsis lanceolata R. Br. Fitoterapia. 2022 Apr;158:105140. doi: 10.1016/j.fitote.2022.105140. Epub 2022 Feb 2. PMID: 35122885. 4: Koval'skaya AV, Petrova PR, Tsypyshev DO, Lobov AN, Tsypysheva IP. Thionation of quinolizidine alkaloids and their derivatives via Lawesson's reagent. Nat Prod Res. 2022 Jul;36(14):3538-3543. doi: 10.1080/14786419.2020.1868460. Epub 2021 Jan 4. PMID: 33397149. 5: Brimioulle R, Bach T. Enantioselective Lewis acid catalysis of intramolecular enone [2+2] photocycloaddition reactions. Science. 2013 Nov 15;342(6160):840-3. doi: 10.1126/science.1244809. PMID: 24233720. 6: Korir E, Kiplimo JJ, Crouch NR, Moodley N, Koorbanally NA. Quinolizidine alkaloids from Sophora velutina subsp. zimbabweensis (Fabaceae: Sophoreae). Nat Prod Commun. 2012 Aug;7(8):999-1003. PMID: 22978215. 7: Gray D, Gallagher T. A flexible strategy for the synthesis of tri- and tetracyclic lupin alkaloids: synthesis of (+)-cytisine, (+/-)-anagyrine, and (+/-)-thermopsine. Angew Chem Int Ed Engl. 2006 Apr 3;45(15):2419-23. doi: 10.1002/anie.200504015. PMID: 16521145. 8: Martins A, Wink M, Tei A, Brum-Bousquet M, Tillequin F, Rauter AP. A phytochemical study of the quinolizidine alkaloids from Genista tenera by gas chromatography-mass spectrometry. Phytochem Anal. 2005 Jul-Aug;16(4):264-6. doi: 10.1002/pca.832. PMID: 16042152. 9: Sagen AL, Gertsch J, Becker R, Heilmann J, Sticher O. Quinolizidine alkaloids from the curare adjuvant Clathrotropis glaucophylla. Phytochemistry. 2002 Dec;61(8):975-8. doi: 10.1016/s0031-9422(02)00394-1. PMID: 12453529. 10: Adler LS, Wink M. Transfer of quinolizidine alkaloids from hosts to hemiparasites in two Castilleja-Lupinus associations: analysis of floral and vegetative tissues. Biochem Syst Ecol. 2001 Jun;29(6):551-561. doi: 10.1016/s0305-1978(00)00090-9. PMID: 11336806. 11: Yu R, Li X, Song L, Zhang R, Zhu T, Yang G, Li Z, Yang B. [Toxic principles of Oxytropis glabra DC]. Zhongguo Zhong Yao Za Zhi. 1991 Mar;16(3):160-3, 191. Chinese. PMID: 1883498. 12: Keeler RF, Baker DC. Myopathy in cattle induced by alkaloid extracts from Thermopsis montanta, Laburnum anagyroides and a Lupinus sp. J Comp Pathol. 1990 Aug;103(2):169-82. doi: 10.1016/s0021-9975(08)80173-9. PMID: 2246392. 13: Keeler RF, Johnson AE, Chase RL. Toxicity of Thermopsis montana in cattle. Cornell Vet. 1986 Apr;76(2):115-27. PMID: 3698596. 14: Keller WJ, Zelenski SG. Alkaloids from Lupinus argenteus var. stenophyllus. J Pharm Sci. 1978 Mar;67(3):430-1. doi: 10.1002/jps.2600670348. PMID: 641742.