Synonym
Tetrahydroalstonine
IUPAC/Chemical Name
Alstonine, 3,4,5,6-tetrahydro- (8CI)
InChi Key
GRTOGORTSDXSFK-DLLGKBFGSA-N
InChi Code
InChI=1S/C21H24N2O3/c1-12-16-10-23-8-7-14-13-5-3-4-6-18(13)22-20(14)19(23)9-15(16)17(11-26-12)21(24)25-2/h3-6,11-12,15-16,19,22H,7-10H2,1-2H3/t12-,15-,16-,19-/m0/s1
SMILES Code
[H][C@]12C(NC3=C4C=CC=C3)=C4CCN1C[C@]5([C@H](C)OC=C(C(OC)=O)[C@]5(C2)[H])[H]
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
352.43
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: Cachet X, Porée FH, Michel S, Lemoine P. Tetra-hydro-alstonine. Acta Crystallogr Sect E Struct Rep Online. 2013 Aug 7;69(Pt 9):o1389-90. doi: 10.1107/S1600536813021168. eCollection 2013. PubMed PMID: 24427031; PubMed Central PMCID: PMC3884471.
2: Malik S. Tetrahydroalstonine from Fruits of Rhazya stricta. Planta Med. 1984 Jun;50(3):283. PubMed PMID: 17340319.
3: Arbain D, Putra DP, Sargent MV. Tetrahydroalstonine from Ophiorrhiza discolor. Planta Med. 1991 Aug;57(4):396. PubMed PMID: 17226176.
4: Lynch VM, Corbett JW, Martin SF, Davis BE. Structure of a key intermediate in the synthesis of (-)-5-carboxytetrahydroalstonine and (-)-tetrahydroalstonine. Acta Crystallogr C. 1991 Feb 15;47 ( Pt 2):464-6. PubMed PMID: 2025406.
5: Pomahacová B, Dusek J, Dusková J, Yazaki K, Roytrakul S, Verpoorte R. Improved accumulation of ajmalicine and tetrahydroalstonine in Catharanthus cells expressing an ABC transporter. J Plant Physiol. 2009 Sep 1;166(13):1405-12. doi: 10.1016/j.jplph.2009.02.015. Epub 2009 Apr 29. PubMed PMID: 19403195.
6: Maloney EM, Farnsworth NR, Blomster RN, Abraham DJ, Sharkey AG Jr. Catharanthus lanceus VII. Isolation of tetrahydroalstonine, lochnerinine, and periformyline. J Pharm Sci. 1965 Aug;54(8):1166-8. PubMed PMID: 5882223.
7: Segelman AB, Farnsworth NR. Catharanthus alkaloids XXXI: isolation of ajmalicine, pericalline, tetrahydroalstonine, vindolinine, and ursolic acid from Catharanthus trichophyllus roots. J Pharm Sci. 1974 Sep;63(9):1419-22. PubMed PMID: 4473533.
8: Roquebert J, Demichel P. Inhibition of the alpha 1 and alpha 2-adrenoceptor-mediated pressor response in pithed rats by raubasine, tetrahydroalstonine and akuammigine. Eur J Pharmacol. 1984 Oct 30;106(1):203-5. PubMed PMID: 6099269.
9: Hemscheidt T, Zenk MH. Partial purification and characterization of a NADPH dependent tetrahydroalstonine synthase from Catharanthus roseus cell suspension cultures. Plant Cell Rep. 1985 Aug;4(4):216-9. doi: 10.1007/BF00269293. PubMed PMID: 24253886.
10: Roquebert J, Demichel P, Dufour P. [Differential inhibition of raubasine and tetrahydroalstonine on the vasopressor response to sympathetic nervous stimulation and intravenous noradrenaline in the pithed rat]. J Pharmacol. 1985 Oct-Dec;16(4):412-20. French. PubMed PMID: 2869187.
11: Kocialski AB, Marozzi FJ Jr, Malone MH. Effects of certain nonsteroid anti-inflammatory drugs, tolbutamide, and tetrahydroalstonine on blood glucose and carrageen in-induced pedal edema in rats. J Pharm Sci. 1972 Aug;61(8):1202-5. PubMed PMID: 5050366.
