Higenamine

From Infogalactic: the planetary knowledge core
(Redirected from Norcoclaurine)
Jump to: navigation, search
Higenamine
Higenamine.png
Names
IUPAC name
1-[(4-Hydroxyphenyl)methyl]-1,2,3,4-tetrahydroisoquinoline-6,7-diol
Other names
Norcoclaurine; Demethylcoclaurine
Identifiers
5843-65-2 YesY
106032-53-5 (R) N
22672-77-1 (S) N
ChEBI CHEBI:18418 YesY
ChEMBL ChEMBL19344 YesY
ChemSpider 102800 YesY
Jmol 3D model Interactive image
KEGG C06346 YesY
MeSH higenamine
PubChem 114840
  • InChI=1S/C16H17NO3/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 YesY
    Key: WZRCQWQRFZITDX-UHFFFAOYSA-N YesY
  • InChI=1/C16H17NO3/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
    Key: WZRCQWQRFZITDX-UHFFFAOYAH
  • Oc1ccc(cc1)CC3c2c(cc(O)c(O)c2)CCN3
Properties
C16H17NO3
Molar mass 271.32 g·mol−1
Vapor pressure {{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YesYN ?)
Infobox references

Higenamine (norcoclaurine) 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).

Legality

Higenamine, also known as noroclaurine hcl, is legal to use within food supplements in the UK, EU, the USA and Canada. Its main is within food supplements developed for weight management, also known as 'fat burners'. However, products containing (or claiming to contain) pharmacological relevant quantities still require registration as a medicine. The regulatory boundaries for higenamine are unclear as modern formulations have not been clinically evaluated. Traditional formulations with higenamine have been used for thousands of years within Chinese medicine and come from a variety of sources including fruit and orchids. There are no studies comparing the safety of modern formulations (based on synthetic higenamine) with traditional formulations. Nevertheless, it will not be added to the EU 'novel foods' catalogue, which details all food supplements that require a safety assessment certificate before use.[1]

Pharmacology

Since higenamine is present in plants which have a history of use in traditional medicine, the pharmacology of this compound has attracted scientific interest. A variety of effects have been observed in in vitro studies and in animal models, but its effects in humans are unknown.

The results of a 2009 study exposed the compound as a beta-2 adrenergic receptor agonist.[2]

In animal models, higenamine has been demonstrated to be a beta-2 adrenergic receptor agonist.[2][3][4][5][6] Adrenergic receptors, or adrenoceptors, belong to the class of G-protein coupled receptors, and are the most prominent receptors in the adipose membrane, besides also being expressed in skeletal muscle tissue. These adipose-membrane receptors are classified as either alpha- or beta-adrenoceptors. Although these adrenoceptors share the same messenger, cyclic adenosine monophosphate (cAMP), the specific transduction pathway depends on the receptor type (alpha or beta). Higenamine partly exerts its actions by the activation of an enzyme, adenylate cyclase, responsible for boosting the cellular concentrations of the adrenergic second messenger, cAMP.[7]

In a rodent model, it was found that higenamine produced cardiotonic, vascular relaxation, and bronchodilator effects.[8][9] In particular, higenamine, via a beta-adrenoceptor mechanism, induced relaxation in rat corpus cavernosum, leading to improved vasodilation and erectile function.

Related to improved vasodilatory signals, higenamine has been shown in animal models to possess anti-platelet and antithrombotic activity via a cAMP-dependent pathway, suggesting higenamine may contribute to enhanced vasodilation and arterial integrity.[2][7][9][10]

Toxicity

Regarding toxicity, researchers have suggested that the levels of higenamine reported in food consumption (estimated 47.5 mg in a 9-ounce serving of Lotus) would be comparable to the amount used in food supplements.[citation needed] Higenamine is a beta-adrenergic agonist which has effects on the function of trachea and heart muscles.[11][12] During a study of acute toxicity, mice were orally administered the compound at a dose of 2 g per kg of bodyweight. No mice died during the study.[13]

References

  1. ↑ http://ec.europa.eu/food/food/biotechnology/novelfood/novel_food_catalogue_en.htm
  2. ↑ 2.0 2.1 2.2 Lua error in package.lua at line 80: module 'strict' not found.
  3. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  4. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  5. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  6. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  7. ↑ 7.0 7.1 Lua error in package.lua at line 80: module 'strict' not found.
  8. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  9. ↑ 9.0 9.1 Lua error in package.lua at line 80: module 'strict' not found.
  10. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  11. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  12. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  13. ↑ Lua error in package.lua at line 80: module 'strict' not found.
Retrieved from "https://infogalactic.com/w/index.php?title=Higenamine&oldid=5181677"