MedKoo Biosciences, Inc.
Tel:   +1-919-636-5577    Fax:   +1-919-980-4831    Email:   sales@medkoo.com
Search
Login Register
Search
MedKoo Cat#: 596441 | Name: (+)-Armepavine

Description:

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

(+)-Armepavine is a bioactive chemical.

Chemical Structure

(+)-Armepavine
(+)-Armepavine
CAS#14400-96-5

Theoretical Analysis

MedKoo Cat#: 596441

Name: (+)-Armepavine

CAS#: 14400-96-5

Chemical Formula: C19H23NO3

Exact Mass: 313.1678

Molecular Weight: 313.39

Elemental Analysis: C, 72.82; H, 7.40; N, 4.47; O, 15.32

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
Bulk Inquiry
Related CAS #
No Data
Synonym
(+)-Armepavine; (S)-Armepavine; L-(+)-Armepavine; S-(+)-Armepavine;
IUPAC/Chemical Name
(S)-4-((6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-1-yl)methyl)phenol
InChi Key
ZBKFZIUKXTWQTP-KRWDZBQOSA-N
InChi Code
InChI=1S/C19H23NO3/c1-20-9-8-14-11-18(22-2)19(23-3)12-16(14)17(20)10-13-4-6-15(21)7-5-13/h4-7,11-12,17,21H,8-10H2,1-3H3/t17-/m0/s1
SMILES Code
OC1=CC=C(C[C@@H]2N(C)CCC3=C2C=C(OC)C(OC)=C3)C=C1
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
>2 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
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 313.39 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
1: Geng P, Luo J, Weng Z, Fan Z, Zhang B, Ma J, Wang X, Zhang M. Determination of armepavine in mouse blood by UPLC-MS/MS and its application to pharmacokinetic study. Biomed Chromatogr. 2018 May 3:e4273. doi: 10.1002/bmc.4273. [Epub ahead of print] PubMed PMID: 29726027. 2: Morikawa T, Kitagawa N, Tanabe G, Ninomiya K, Okugawa S, Motai C, Kamei I, Yoshikawa M, Lee IJ, Muraoka O. Quantitative Determination of Alkaloids in Lotus Flower (Flower Buds of Nelumbo nucifera) and Their Melanogenesis Inhibitory Activity. Molecules. 2016 Jul 19;21(7). pii: E930. doi: 10.3390/molecules21070930. PubMed PMID: 27447599. 3: Kumarihamy M, León F, Pettaway S, Wilson L, Lambert JA, Wang M, Hill C, McCurdy CR, ElSohly MA, Cutler SJ, Muhammad I. In vitro opioid receptor affinity and in vivo behavioral studies of Nelumbo nucifera flower. J Ethnopharmacol. 2015 Nov 4;174:57-65. doi: 10.1016/j.jep.2015.08.006. Epub 2015 Aug 7. PubMed PMID: 26260436; PubMed Central PMCID: PMC4636954. 4: Ruiz-Olalla A, Würdemann MA, Wanner MJ, Ingemann S, van Maarseveen JH, Hiemstra H. Organocatalytic enantioselective Pictet-Spengler approach to biologically relevant 1-benzyl-1,2,3,4-tetrahydroisoquinoline alkaloids. J Org Chem. 2015 May 15;80(10):5125-32. doi: 10.1021/acs.joc.5b00509. Epub 2015 May 7. PubMed PMID: 25909585. 5: Duan XH, Pei L, Jiang JQ. [Cytotoxic alkaloids from stems of Nelumbo nucifera]. Zhongguo Zhong Yao Za Zhi. 2013 Dec;38(23):4104-8. Chinese. PubMed PMID: 24791498. 6: Do TC, Nguyen TD, Tran H, Stuppner H, Ganzera M. Analysis of alkaloids in Lotus (Nelumbo nucifera Gaertn.) leaves by non-aqueous capillary electrophoresis using ultraviolet and mass spectrometric detection. J Chromatogr A. 2013 Aug 9;1302:174-80. doi: 10.1016/j.chroma.2013.06.002. Epub 2013 Jun 12. PubMed PMID: 23838305. 7: Orejarena Pacheco JC, Lahm G, Opatz T. Synthesis of alkaloids by Stevens rearrangement of nitrile-stabilized ammonium ylides: (±)-laudanosine, (±)-laudanidine, (±)-armepavine, (±)-7-methoxycryptopleurine, and (±)-xylopinine. J Org Chem. 2013 May 17;78(10):4985-92. doi: 10.1021/jo400659n. Epub 2013 May 9. PubMed PMID: 23634947. 8: Vila-Nova NS, Morais SM, Falcão MJ, Machado LK, Beviláqua CM, Costa IR, Brasil NV, Andrade Júnior HF. Leishmanicidal activity and cytotoxicity of compounds from two Annonacea species cultivated in Northeastern Brazil. Rev Soc Bras Med Trop. 2011 Oct;44(5):567-71. PubMed PMID: 22031071. 9: Blank N, Opatz T. Enantioselective synthesis of tetrahydroprotoberberines and bisbenzylisoquinoline alkaloids from a deprotonated α-aminonitrile. J Org Chem. 2011 Dec 2;76(23):9777-84. doi: 10.1021/jo201871c. Epub 2011 Oct 26. PubMed PMID: 22004161. 10: Weng TC, Shen CC, Chiu YT, Lin YL, Huang YT. Effects of armepavine against hepatic fibrosis induced by thioacetamide in rats. Phytother Res. 2012 Mar;26(3):344-53. doi: 10.1002/ptr.3539. Epub 2011 Jun 30. PubMed PMID: 21717514. 11: Ropivia J, Derbré S, Rouger C, Pagniez F, Le Pape P, Richomme P. Isoquinolines from the roots of Thalictrum flavum L. and their evaluation as antiparasitic compounds. Molecules. 2010 Sep 16;15(9):6476-84. doi: 10.3390/molecules15096476. PubMed PMID: 20877237. 12: Ka SM, Kuo YC, Ho PJ, Tsai PY, Hsu YJ, Tsai WJ, Lin YL, Shen CC, Chen A. (S)-armepavine from Chinese medicine improves experimental autoimmune crescentic glomerulonephritis. Rheumatology (Oxford). 2010 Oct;49(10):1840-51. doi: 10.1093/rheumatology/keq164. Epub 2010 Jun 15. PubMed PMID: 20551296. 13: Weng TC, Shen CC, Chiu YT, Lin YL, Kuo CD, Huang YT. Inhibitory effects of armepavine against hepatic fibrosis in rats. J Biomed Sci. 2009 Sep 2;16:78. doi: 10.1186/1423-0127-16-78. PubMed PMID: 19723340; PubMed Central PMCID: PMC2741443. 14: Liu CP, Kuo YC, Shen CC, Wu MH, Liao JF, Lin YL, Chen CF, Tsai WJ. (S)-armepavine inhibits human peripheral blood mononuclear cell activation by regulating Itk and PLCgamma activation in a PI-3K-dependent manner. J Leukoc Biol. 2007 May;81(5):1276-86. Epub 2007 Feb 6. PubMed PMID: 17284681. 15: Liu CP, Tsai WJ, Shen CC, Lin YL, Liao JF, Chen CF, Kuo YC. Inhibition of (S)-armepavine from Nelumbo nucifera on autoimmune disease of MRL/MpJ-lpr/lpr mice. Eur J Pharmacol. 2006 Feb 15;531(1-3):270-9. Epub 2006 Jan 17. PubMed PMID: 16413531. 16: Exley R, Iturriaga-Vásquez P, Lukas RJ, Sher E, Cassels BK, Bermudez I. Evaluation of benzyltetrahydroisoquinolines as ligands for neuronal nicotinic acetylcholine receptors. Br J Pharmacol. 2005 Sep;146(1):15-24. PubMed PMID: 15980871; PubMed Central PMCID: PMC1576253. 17: Jow GM, Wu YC, Guh JH, Teng CM. Armepavine oxalate induces cell death on CCRF-CEM leukemia cell line through an apoptotic pathway. Life Sci. 2004 Jun 18;75(5):549-57. PubMed PMID: 15158365. 18: Philipov S, Ivanovska N, Istatkova R, Velikova M, Tuleva P. Phytochemical study and cytotoxic activity of alkaloids from Uvaria chamae P. Beauv. Pharmazie. 2000 Sep;55(9):688-9. PubMed PMID: 11031775. 19: Sekine Y, Brossi A. Expedient synthesis of (S)- and (R)-norcoclaurine from (S)- and (R)-norarmepavine [corrected] prepared by the 1-phenylethylurea method. J Nat Prod. 1990 Mar-Apr;53(2):533-5. Erratum in: J Nat Prod 1990 Nov-Dec;53(6):1630. PubMed PMID: 2380726. 20: Tsai IL, Liou YF, Lu ST. Screening of isoquinoline alkaloids and their derivatives for antibacterial and antifungal activities. Gaoxiong Yi Xue Ke Xue Za Zhi. 1989 Mar;5(3):132-45. PubMed PMID: 2733073.