Tembetarine iodide

• CAT Number: I037107
• CAS Number: 77794-96-8
• Molecular Formula: C20H26INO4
• Molecular Weight: 471.34
• Purity: 98%
• Synonyms: (S)-tembetarine; Tembetarine; Tembetarine iodide; (+)-Tembetarine iodide; N-Methylreticulinium iodide; d-Tembetarine iodide
• Solubility: Soluble in DMSO
• Appearance: Solid powder
• Storage: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
• IUPAC Name: Isoquinolinium, 1,2,3,4-tetrahydro-7-hydroxy-1-((3-hydroxy-4-methoxyphenyl)methyl)-6-methoxy-2,2-dimethyl-, (S)-, iodide
• InChI: InChI=1S/C20H25NO4.HI/c1-21(2)8-7-14-11-20(25-4)18(23)12-15(14)16(21)9-13-5-6-19(24-3)17(22)10-13;/h5-6,10-12,16H,7-9H2,1-4H3,(H-,22,23);1H/t16-;/m0./s1
• InChIKey: YHESZQUPLJBSNE-NTISSMGPSA-N
• SMILES: C[N+]1(C)[C@@H](CC2=CC=C(OC)C(O)=C2)C3=C(C=C(OC)C(O)=C3)CC1.[I-]

Tembetarine (Cat.No:I037107) is a tembetarine obtained by methylation of the tertiary amino function of (R)-reticuline. It has a role as a plant metabolite. It is a benzylisoquinoline alkaloid and a tembetarine. It derives from a (S)-reticuline. It is an enantiomer of a (R)-tembetarine.

Reference

1: Isolation and Characterization of Reticuline N-Methyltransferase Involved in Biosynthesis of the Aporphine Alkaloid Magnoflorine in Opium Poppy Jeremy S. Morris, Peter J. Facchini J Biol Chem. 2016 Nov 4; 291(45): 23416–23427. Published online 2016 Sep 15. doi: 10.1074/jbc.M116.750893 PMCID: PMC5095398
2: Studies on the Alkaloids of the Bark of Magnolia officinalis: Isolation and On-line Analysis by HPLC-ESI-MSn Renyi Yan, Weihao Wang, Jian Guo, Hongliang Liu, Jianyong Zhang, Bin Yang Molecules. 2013 Jul; 18(7): 7739 7750. Published online 2013 Jul 3. doi: 10.3390/molecules18077739 PMCID: PMC6270518
3: Study on the Material Basis of Houpo Wenzhong Decoction by HPLC Fingerprint, UHPLC-ESI-LTQ-Orbitrap-MS, and Network Pharmacology Juyuan Luo, Gongsen Chen, Donghan Liu, Yan Wang, Qi Qi, Haiyan Hu, Pengyue Li, Jie Bai, Shouying Du, Yang Lu, Yuming Wang, Cun Liu Molecules. 2019 Jul; 24(14): 2561. Published online 2019 Jul 14. doi: 10.3390/molecules24142561 PMCID: PMC6681077
4: Rapid Characterization and Identification of Non-Diterpenoid Constituents in Tinospora sinensis by HPLC-LTQ-Orbitrap MSn Qi-Shu Jiao, Lu-Lu Xu, Jia-Yu Zhang, Zi-Jian Wang, Yan-Yan Jiang, Bin Liu Molecules. 2018 Feb; 23(2): 274. Published online 2018 Jan 28. doi: 10.3390/molecules23020274 PMCID: PMC6017642
5: Novel findings to the biosynthetic pathway of magnoflorine and taspine through transcriptomic and metabolomic analysis of Croton draco (Euphorbiaceae) Anahí Canedo-Téxon, Feliza Ramón-Farias, Juan Luis Monribot-Villanueva, Emanuel Villafán, Alexandro Alonso-Sánchez, Claudia Anahí Pérez-Torres, Guillermo Ángeles, José Antonio Guerrero-Analco, Enrique Ibarra-Laclette BMC Plant Biol. 2019; 19: 560. Published online 2019 Dec 18. doi: 10.1186/s12870-019-2195-y PMCID: PMC6921603
6: Antibacterial activities of Fagara macrophylla, Canarium schweinfurthii, Myrianthus arboreus, Dischistocalyx grandifolius and Tragia benthamii against multi-drug resistant Gram-negative bacteria Jackson A. Seukep, Bonaventure Ngadjui, Victor Kuete Springerplus. 2015; 4: 567. Published online 2015 Oct 1. doi: 10.1186/s40064-015-1375-y PMCID: PMC4627964
7: Comparison of Anticancer Activity and HPLC-DAD Determination of Selected Isoquinoline Alkaloids from Thalictrum foetidum, Berberis sp. and Chelidonium majus Extracts Anna Petruczynik, Tomasz Tuzimski, Tomasz Plech, Justyna Misiurek, Karolina Szalast, Grażyna Szymczak Molecules. 2019 Oct; 24(19): 3417. Published online 2019 Sep 20. doi: 10.3390/molecules24193417 PMCID: PMC6803846
8: Ethnomedicinal Investigation of Medicinal Plants of Chakrata Region (Uttarakhand) Used in the Traditional Medicine for Diabetes by Jaunsari Tribe Ankit Kumar, Sonali Aswal, Ashutosh Chauhan, Ruchi Badoni Semwal, Abhimanyu Kumar, Deepak Kumar Semwal Nat Prod Bioprospect. 2019 Jun; 9(3): 175–200. Published online 2019 Apr 9. doi: 10.1007/s13659-019-0202-5 PMCID: PMC6538708
9: Phellodendri Cortex: A Phytochemical, Pharmacological, and Pharmacokinetic Review Yue Sun, George Binh Lenon, Angela Wei Hong Yang Evid Based Complement Alternat Med. 2019; 2019: 7621929. Published online 2019 Apr 1. doi: 10.1155/2019/7621929 PMCID: PMC6463642
10: Medicinal plants commonly used against cancer in traditional medicine formulae in Sri Lanka Anchala I. Kuruppu, Priyani Paranagama, Charitha L. Goonasekara Saudi Pharm J. 2019 May; 27(4): 565–573. Published online 2019 Feb 7. doi: 10.1016/j.jsps.2019.02.004 PMCID: PMC6488922