Nantenine

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MedKoo CAT#: 413884

CAS#: 2565-01-7

Description: Nantenine is an alkaloid found in the plant Nandina domestica as well as some Corydalis species. It is an antagonist at both the α1 adrenergic receptor and the 5-HT2A serotonin receptor, and blocks both the behavioural and physiological effects of MDMA in animals.


Chemical Structure

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Nantenine
CAS# 2565-01-7

Theoretical Analysis

MedKoo Cat#: 413884
Name: Nantenine
CAS#: 2565-01-7
Chemical Formula: C20H21NO4
Exact Mass: 339.15
Molecular Weight: 339.390
Elemental Analysis: C, 70.78; H, 6.24; N, 4.13; O, 18.86

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

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Synonym: Nantenine; CCRIS3807; CCRIS-3807; CCRIS 3807; 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]

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: 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

More Info:

Biological target:
In vitro activity:
In vivo activity:

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.

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
Formulation protocol:
In vitro protocol:
In vivo protocol:

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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.