MedKoo Biosciences, Inc.
Tel:   +1-919-636-5577    Fax:   +1-919-980-4831    Email:   sales@medkoo.com
Search
Login Register
Search
MedKoo Cat#: 596433 | Name: Reticuline

Description:

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

Reticuline is discontinued. Reticuline is an opium alkaloid; dopamine receptor blocker.

Chemical Structure

Reticuline
Reticuline
CAS#485-19-8

Theoretical Analysis

MedKoo Cat#: 596433

Name: Reticuline

CAS#: 485-19-8

Chemical Formula: C19H23NO4

Exact Mass: 329.1627

Molecular Weight: 329.39

Elemental Analysis: C, 69.28; H, 7.04; N, 4.25; O, 19.43

Price and Availability

This product was removed for the commercial reasons.
Related CAS #
No Data
Synonym
Reticuline; EINECS 207-611-3; d-Reticuline; S-(+)-Reticuline;
IUPAC/Chemical Name
(S)-1-(3-hydroxy-4-methoxybenzyl)-6-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-7-ol
InChi Key
BHLYRWXGMIUIHG-HNNXBMFYSA-N
InChi Code
InChI=1S/C19H23NO4/c1-20-7-6-13-10-19(24-3)17(22)11-14(13)15(20)8-12-4-5-18(23-2)16(21)9-12/h4-5,9-11,15,21-22H,6-8H2,1-3H3/t15-/m0/s1
SMILES Code
OC1=CC2=C(C=C1OC)CCN(C)[C@H]2CC3=CC=C(OC)C(O)=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
>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 329.39 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: Matsumura E, Nakagawa A, Tomabechi Y, Ikushiro S, Sakaki T, Katayama T, Yamamoto K, Kumagai H, Sato F, Minami H. Microbial production of novel sulphated alkaloids for drug discovery. Sci Rep. 2018 May 22;8(1):7980. doi: 10.1038/s41598-018-26306-7. PubMed PMID: 29789647; PubMed Central PMCID: PMC5964154. 2: Lipp A, Ferenc D, Gütz C, Geffe M, Vierengel N, Schollmeyer D, Schäfer HJ, Waldvogel SR, Opatz T. A Regio- and Diastereoselective Anodic Aryl-Aryl-Coupling in the Biomimetic Total Synthesis of (-)-Thebaine. Angew Chem Int Ed Engl. 2018 May 22. doi: 10.1002/anie.201803887. [Epub ahead of print] PubMed PMID: 29786941. 3: Toplak M, Wiedemann G, Ulićević J, Daniel B, Hoernstein SNW, Kothe J, Niederhauser J, Reski R, Winkler A, Macheroux P. The single berberine bridge enzyme homolog of Physcomitrella patens is a cellobiose oxidase. FEBS J. 2018 Apr 6. doi: 10.1111/febs.14458. [Epub ahead of print] PubMed PMID: 29633551. 4: Averesch NJH, Krömer JO. Metabolic Engineering of the Shikimate Pathway for Production of Aromatics and Derived Compounds-Present and Future Strain Construction Strategies. Front Bioeng Biotechnol. 2018 Mar 26;6:32. doi: 10.3389/fbioe.2018.00032. eCollection 2018. PubMed PMID: 29632862; PubMed Central PMCID: PMC5879953. 5: Aljaafri WAR, McNeece BT, Lawaju BR, Sharma K, Niruala PM, Pant SR, Long DH, Lawrence KS, Lawrence GW, Klink VP. A harpin elicitor induces the expression of a coiled-coil nucleotide binding leucine rich repeat (CC-NB-LRR) defense signaling gene and others functioning during defense to parasitic nematodes. Plant Physiol Biochem. 2017 Dec;121:161-175. doi: 10.1016/j.plaphy.2017.10.004. Epub 2017 Oct 13. PubMed PMID: 29107936. 6: Riley-Saldaña CA, Cruz-Ortega MDR, Martínez Vázquez M, De-la-Cruz-Chacón I, Castro-Moreno M, González-Esquinca AR. Acetogenins and alkaloids during the initial development of Annona muricata L. (Annonaceae). Z Naturforsch C. 2017 Oct 26;72(11-12):497-506. doi: 10.1515/znc-2017-0060. PubMed PMID: 28937967. 7: Purwanto R, Hori K, Yamada Y, Sato F. Unraveling Additional O-Methylation Steps in Benzylisoquinoline Alkaloid Biosynthesis in California Poppy (Eschscholzia californica). Plant Cell Physiol. 2017 Sep 1;58(9):1528-1540. doi: 10.1093/pcp/pcx093. PubMed PMID: 28922749. 8: Pinto NCC, Silva JB, Menegati LM, Guedes MCMR, Marques LB, Silva TPD, Melo RCN, Souza-Fagundes EM, Salvador MJ, Scio E, Fabri RL. Cytotoxicity and bacterial membrane destabilization induced by Annona squamosa L. extracts. An Acad Bras Cienc. 2017;89(3 Suppl):2053-2073. doi: 10.1590/0001-3765201720150702. Epub 2017 Aug 14. PubMed PMID: 28813096. 9: Gómez Villalobos MJ, Vidrio S, Giles López R, Flores Gómez G, Chagoya de Sánchez V. A novel Golgi-Cox staining method for detecting and characterizing roles of the hepatic stellate cells in liver injury. Pathophysiology. 2017 Dec;24(4):267-274. doi: 10.1016/j.pathophys.2017.06.003. Epub 2017 Jun 30. PubMed PMID: 28712861. 10: Yang X, Gao X, Cao Y, Guo Q, Li S, Zhu Z, Zhao Y, Tu P, Chai X. Anti-Inflammatory Effects of Boldine and Reticuline Isolated from Litsea cubeba through JAK2/STAT3 and NF-κB Signaling Pathways. Planta Med. 2018 Jan;84(1):20-25. doi: 10.1055/s-0043-113447. Epub 2017 Jun 26. PubMed PMID: 28651290. 11: Bakiri A, Hubert J, Reynaud R, Lanthony S, Harakat D, Renault JH, Nuzillard JM. Computer-Aided (13)C NMR Chemical Profiling of Crude Natural Extracts without Fractionation. J Nat Prod. 2017 May 26;80(5):1387-1396. doi: 10.1021/acs.jnatprod.6b01063. Epub 2017 Apr 17. PubMed PMID: 28414230. 12: Prades JM, Peoc'h M, Petcu C, Karkas A, Dumollard JM, Gavid M. The anterior commissure of the human larynx revisited. Surg Radiol Anat. 2017 Aug;39(8):871-876. doi: 10.1007/s00276-017-1814-2. Epub 2017 Apr 12. PubMed PMID: 28405749. 13: Klink VP, Sharma K, Pant SR, McNeece B, Niraula P, Lawrence GW. Components of the SNARE-containing regulon are co-regulated in root cells undergoing defense. Plant Signal Behav. 2017 Feb;12(2):e1274481. doi: 10.1080/15592324.2016.1274481. PubMed PMID: 28010187; PubMed Central PMCID: PMC5351740. 14: Matsumura E, Nakagawa A, Tomabechi Y, Koyanagi T, Kumagai H, Yamamoto K, Katayama T, Sato F, Minami H. Laboratory-scale production of (S)-reticuline, an important intermediate of benzylisoquinoline alkaloids, using a bacterial-based method. Biosci Biotechnol Biochem. 2017 Feb;81(2):396-402. doi: 10.1080/09168451.2016.1243985. Epub 2016 Oct 14. PubMed PMID: 27740901. 15: Morris JS, Facchini PJ. Isolation and Characterization of Reticuline N-Methyltransferase Involved in Biosynthesis of the Aporphine Alkaloid Magnoflorine in Opium Poppy. J Biol Chem. 2016 Nov 4;291(45):23416-23427. Epub 2016 Sep 15. PubMed PMID: 27634038; PubMed Central PMCID: PMC5095398. 16: Torres MA, Hoffarth E, Eugenio L, Savtchouk J, Chen X, Morris JS, Facchini PJ, Ng KK. Structural and Functional Studies of Pavine N-Methyltransferase from Thalictrum flavum Reveal Novel Insights into Substrate Recognition and Catalytic Mechanism. J Biol Chem. 2016 Nov 4;291(45):23403-23415. Epub 2016 Aug 29. PubMed PMID: 27573242; PubMed Central PMCID: PMC5095397. 17: Rottscholl R, Haegele M, Jainsch B, Xu H, Respondek G, Höllerhage M, Rösler TW, Bony E, Le Ven J, Guérineau V, Schmitz-Afonso I, Champy P, Oertel WH, Yamada ES, Höglinger GU. Chronic consumption of Annona muricata juice triggers and aggravates cerebral tau phosphorylation in wild-type and MAPT transgenic mice. J Neurochem. 2016 Nov;139(4):624-639. doi: 10.1111/jnc.13835. Epub 2016 Sep 16. PubMed PMID: 27569447. 18: Saidi N, Morita H, Litaudon M, Nafiah MA, Awang K, Mustanir. New Phenyl Propanoids from Cryptocarya bracteolata. Nat Prod Commun. 2016 Jun;11(6):815-6. PubMed PMID: 27534124. 19: Thakur P, Chawla R, Goel R, Narula A, Arora R, Sharma RK. Augmenting the potency of third-line antibiotics with Berberis aristata: In vitro synergistic activity against carbapenem-resistant Escherichia coli. J Glob Antimicrob Resist. 2016 Sep;6:10-16. doi: 10.1016/j.jgar.2016.01.015. Epub 2016 Mar 29. PubMed PMID: 27530832. 20: Wan Othman WNN, Liew SY, Khaw KY, Murugaiyah V, Litaudon M, Awang K. Cholinesterase inhibitory activity of isoquinoline alkaloids from three Cryptocarya species (Lauraceae). Bioorg Med Chem. 2016 Sep 15;24(18):4464-4469. doi: 10.1016/j.bmc.2016.07.043. Epub 2016 Jul 21. PubMed PMID: 27492195.