Synonym
Nantenine; Thalictruberine
IUPAC/Chemical Name
6a-alpha-Aporphine, 1,2-dimethoxy-9,10-(methylenedioxy)-
InChi Key
WSVWKHTVFGTTKJ-AWEZNQCLSA-N
InChi Code
InChI=1S/C20H21NO4/c1-21-5-4-11-7-17(22-2)20(23-3)19-13-9-16-15(24-10-25-16)8-12(13)6-14(21)18(11)19/h7-9,14H,4-6,10H2,1-3H3/t14-/m0/s1
SMILES Code
CN1CCC2=CC(OC)=C(OC)C3=C2[C@@]1(CC4=CC(OCO5)=C5C=C43)[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
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
Preparing Stock Solutions
The following data is based on the
product
molecular weight
339.39
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: Pecic S, McAnuff MA, Harding WW. Nantenine as an acetylcholinesterase inhibitor: SAR, enzyme kinetics and molecular modeling investigations. J Enzyme Inhib Med Chem. 2011 Feb;26(1):46-55. doi: 10.3109/14756361003671078. Epub 2010 Jun 28. PMID: 20583856; PMCID: PMC4663080.
2: Fantegrossi WE, Kiessel CL, Leach PT, Van Martin C, Karabenick RL, Chen X, Ohizumi Y, Ullrich T, Rice KC, Woods JH. Nantenine: an antagonist of the behavioral and physiological effects of MDMA in mice. Psychopharmacology (Berl). 2004 May;173(3-4):270-7. doi: 10.1007/s00213-003-1741-2. Epub 2004 Jan 22. PMID: 14740148.
3: Chaudhary S, Pecic S, Legendre O, Navarro HA, Harding WW. (+/-)-Nantenine analogs as antagonists at human 5-HT(2A) receptors: C1 and flexible congeners. Bioorg Med Chem Lett. 2009 May 1;19(9):2530-2. doi: 10.1016/j.bmcl.2009.03.048. Epub 2009 Mar 16. PMID: 19328689; PMCID: PMC2677726.
4: Tsuchida H, Ohizumi Y. (+)-Nantenine isolated from Nandina domestica Thunb. inhibits adrenergic pressor responses in pithed rats. Eur J Pharmacol. 2003 Sep 5;477(1):53-8. doi: 10.1016/j.ejphar.2003.08.002. PMID: 14512098.
5: Ribeiro RA, Leite JR. Nantenine alkaloid presents anticonvulsant effect on two classical animal models. Phytomedicine. 2003;10(6-7):563-8. doi: 10.1078/094471103322331557. PMID: 13678244.
6: Legendre O, Pecic S, Chaudhary S, Zimmerman SM, Fantegrossi WE, Harding WW. Synthetic studies and pharmacological evaluations on the MDMA ('Ecstasy') antagonist nantenine. Bioorg Med Chem Lett. 2010 Jan 15;20(2):628-31. doi: 10.1016/j.bmcl.2009.11.053. Epub 2009 Nov 20. PMID: 19963380; PMCID: PMC2818532.
7: Orallo F. Pharmacological effects of (+)-nantenine, an alkaloid isolated from Platycapnos spicata, in several rat isolated tissues. Planta Med. 2003 Feb;69(2):135-42. doi: 10.1055/s-2003-37700. PMID: 12624818.
8: Ueki T, Akaishi T, Okumura H, Morioka T, Abe K. Biphasic tracheal relaxation induced by higenamine and nantenine from Nandina domestica Thunberg. J Pharmacol Sci. 2011;115(2):254-7. doi: 10.1254/jphs.10251sc. Epub 2011 Jan 26. PMID: 21282929.
9: Ueki T, Akaishi T, Okumura H, Morioka T, Abe K. Biphasic Tracheal Relaxation Induced by Higenamine and Nantenine From Nandina domestica THUNBERG. J Pharmacol Sci. 2011;115(2):254-257. doi: 10.1254/jphs.10251SC. Epub 2019 Jun 11. PMID: 32272546.
10: Orallo F, Alzueta AF. Preliminary study of the vasorelaxant effects of (+)-nantenine, an alkaloid isolated from Platycapnos spicata, in rat aorta. Planta Med. 2001 Dec;67(9):800-6. doi: 10.1055/s-2001-18848. PMID: 11745014.
