WARNING: This product is for research use only, not for human or veterinary use.
Hodoodo CAT#: H526848
CAS#: 11041-94-4 (HCl)
Description: Higenamine, also known as norcoclaurine, is a β-adrenoceptor partial agonist potentially for the treatment of coronary heart disease. Higenamine is a chemical compound found in a variety of plants including Nandina domestica (fruit), Aconitum carmichaelii (root), Asarum heterotropioides, Galium divaricatum (stem and vine), Annona squamosa, and Nelumbo nucifera (lotus seeds). Higenamine, also known as norcoclaurine HCl, is legal to use within food supplements in the UK, EU, the USA and Canada.
Hodoodo Cat#: H526848
Name: Higenamine hydrochloride
CAS#: 11041-94-4 (HCl)
Chemical Formula: C16H18ClNO3
Exact Mass: 0.00
Molecular Weight: 307.774
Elemental Analysis: C, 62.44; H, 5.90; Cl, 11.52; N, 4.55; O, 15.59
Related CAS #: 11041-94-4 (HCl) 5843-65-2 (free base),
Synonym: Higenamine HCl; Higenamine hydrochloride; norcoclaurine HCl. (+-)-Demethylcoclaurine hydrochloride.
IUPAC/Chemical Name: 1-[(4-Hydroxyphenyl)methyl]-1,2,3,4-tetrahydroisoquinoline-6,7-diol hydrochloride
InChi Key: SWWQQSDRUYSMAR-UHFFFAOYSA-N
InChi Code: InChI=1S/C16H17NO3.ClH/c18-12-3-1-10(2-4-12)7-14-13-9-16(20)15(19)8-11(13)5-6-17-14;/h1-4,8-9,14,17-20H,5-7H2;1H
SMILES Code: OC1=CC2=C(C(CC3=CC=C(O)C=C3)NCC2)C=C1O.[H]Cl
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: Related CAS# 11041-94-4(Higenamine hydrochloride); 5843-65-2(Higenamine)
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The following data is based on the product molecular weight 307.77 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 |
| Formulation protocol: | |
| In vitro protocol: | |
| In vivo protocol: |
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2: Stajić A, Anđelković M, Dikić N, Rašić J, Vukašinović-Vesić M, Ivanović D, Jančić-Stojanović B. Determination of higenamine in dietary supplements by UHPLC/MS/MS method. J Pharm Biomed Anal. 2017 Aug 15;146:48-52. doi: 10.1016/j.jpba.2017.08.017. [Epub ahead of print] PubMed PMID: 28850863.
3: Okano M, Sato M, Kageyama S. Determination of higenamine and coclaurine levels in human urine after the administration of a throat lozenge containing Nandina domestica fruit. Drug Test Anal. 2017 Aug 12. doi: 10.1002/dta.2258. [Epub ahead of print] PubMed PMID: 28801989.
4: Liang Z, Xu C, Dong L, Fu Y, Wu Q, Zhao J, Ye L, Cai Z, Liu M, Xia B, Tang L, Liu Z. Involvement of UDP-glucuronosyltransferases in higenamine glucuronidation and the gender and species differences in liver. Biomed Pharmacother. 2017 Sep;93:172-179. doi: 10.1016/j.biopha.2017.06.044. PubMed PMID: 28633128.
5: Zhang N, Lian Z, Peng X, Li Z, Zhu H. Applications of Higenamine in pharmacology and medicine. J Ethnopharmacol. 2017 Jan 20;196:242-252. doi: 10.1016/j.jep.2016.12.033. Epub 2016 Dec 19. Review. PubMed PMID: 28007527.
6: Duan W, Chen J, Wu Y, Zhang Y, Xu Y. Protective effect of higenamine ameliorates collagen-induced arthritis through heme oxygenase-1 and PI3K/Akt/Nrf-2 signaling pathways. Exp Ther Med. 2016 Nov;12(5):3107-3112. Epub 2016 Sep 20. PubMed PMID: 27882125; PubMed Central PMCID: PMC5103755.
7: Deldicque L, Francaux M. Potential harmful effects of dietary supplements in sports medicine. Curr Opin Clin Nutr Metab Care. 2016 Nov;19(6):439-445. PubMed PMID: 27552474.
8: Lin MT, Zhang C, Tang SL, Zhao ZZ, Chen HB, Zhang JY. [Metabolites Identification for Alkaloids from Nelumbinis Plumula in Caco-2 Cells by LC/MS/MS]. Zhong Yao Cai. 2015 Dec;38(12):2531-4. Chinese. PubMed PMID: 27352532.
9: Chen S, Jiang H, Cao Y, Wang Y, Hu Z, Zhu Z, Chai Y. Drug target identification using network analysis: Taking active components in Sini decoction as an example. Sci Rep. 2016 Apr 20;6:24245. doi: 10.1038/srep24245. PubMed PMID: 27095146; PubMed Central PMCID: PMC4837341.
10: Wu MP, Zhang YS, Zhou QM, Xiong J, Dong YR, Yan C. Higenamine protects ischemia/reperfusion induced cardiac injury and myocyte apoptosis through activation of β2-AR/PI3K/AKT signaling pathway. Pharmacol Res. 2016 Feb;104:115-23. doi: 10.1016/j.phrs.2015.12.032. Epub 2015 Dec 30. PubMed PMID: 26746354; PubMed Central PMCID: PMC4772856.
11: Ghirga F, Quaglio D, Ghirga P, Berardozzi S, Zappia G, Botta B, Mori M, D'Acquarica I. Occurrence of Enantioselectivity in Nature: The Case of (S)-Norcoclaurine. Chirality. 2016 Mar;28(3):169-80. doi: 10.1002/chir.22566. Epub 2016 Jan 5. Review. PubMed PMID: 26729048.
12: Liu Y, Santillo MF. Cytochrome P450 2D6 and 3A4 enzyme inhibition by amine stimulants in dietary supplements. Drug Test Anal. 2016 Mar-Apr;8(3-4):307-10. doi: 10.1002/dta.1863. Epub 2015 Sep 11. PubMed PMID: 26360628.
13: Jeter J, DeZee KJ, Kennedy L. A Case of Paraspinal Muscle Rhabdomyolysis in a 22-Year-Old Male After Ingesting a Supplement Containing Higenamine. Mil Med. 2015 Jul;180(7):e847-9. doi: 10.7205/MILMED-D-14-00647. PubMed PMID: 26126260.
14: Kato E, Inagaki Y, Kawabata J. Higenamine 4'-O-β-d-glucoside in the lotus plumule induces glucose uptake of L6 cells through β2-adrenergic receptor. Bioorg Med Chem. 2015 Jul 1;23(13):3317-21. doi: 10.1016/j.bmc.2015.04.054. Epub 2015 Apr 25. PubMed PMID: 25943853.
15: Wei H, Wu H, Yu W, Yan X, Zhang X. Shenfu decoction as adjuvant therapy for improving quality of life and hepatic dysfunction in patients with symptomatic chronic heart failure. J Ethnopharmacol. 2015 Jul 1;169:347-55. doi: 10.1016/j.jep.2015.04.016. Epub 2015 May 1. PubMed PMID: 25937255.
16: Liu C, Zhu C, Wang G, Xu R, Zhu Y. Higenamine regulates Nrf2-HO-1-Hmgb1 axis and attenuates intestinal ischemia-reperfusion injury in mice. Inflamm Res. 2015 Jun;64(6):395-403. doi: 10.1007/s00011-015-0817-x. Epub 2015 May 1. PubMed PMID: 25929435.
17: 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.
18: Calvert R, Vohra S, Ferguson M, Wiesenfeld P. A beating heart cell model to predict cardiotoxicity: effects of the dietary supplement ingredients higenamine, phenylethylamine, ephedrine and caffeine. Food Chem Toxicol. 2015 Apr;78:207-13. doi: 10.1016/j.fct.2015.01.022. Epub 2015 Feb 12. PubMed PMID: 25684415.
19: Bloomer RJ, Schriefer JM, Gunnels TA. Clinical safety assessment of oral higenamine supplementation in healthy, young men. Hum Exp Toxicol. 2015 Oct;34(10):935-45. doi: 10.1177/0960327114565490. Epub 2015 Jan 14. PubMed PMID: 25591969.
20: Lee WS, Yun JW, Nagappan A, Lu JN, Kim MJ, Lee JH, Kim DH, Choi YH, Kim HJ, Chang KC, Jung JM. Synthesized tetrahydroisoquinoline alkaloid exerts anticancer effects at least in part by suppressing NF-κB-regulated proteins in A549 human lung cancer cells. Oncol Rep. 2015 Mar;33(3):1141-6. doi: 10.3892/or.2014.3658. Epub 2014 Dec 8. PubMed PMID: 25482101.
