Structure via PubChem · Public domain (PubChem)
higenamine
Sign in to saveAlso known as (+-)-1,2,3,4-Tetrahydro-1-((4-hydroxyphenyl)methyl)-6,7-isoquinolinediol, (+-)-O-Demethylcoclaurine, (+-)-Norcoclaurine, (+-)-Demethylcoclaurine
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).
Chemical data
- Formula
- C16H17NO3
- Molecular weight
- 271.31 g/mol
- IUPAC name
- 1-[(4-hydroxyphenyl)methyl]-1,2,3,4-tetrahydroisoquinoline-6,7-diol
- SMILES
- C1CNC(C2=CC(=C(C=C21)O)O)CC3=CC=C(C=C3)O
- InChIKey
- WZRCQWQRFZITDX-UHFFFAOYSA-N
- XLogP
- 2.2
- Polar surface area
- 72.7 Ų
- H-bond donors
- 4
- H-bond acceptors
- 4
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Phase 1
- Molecule type
- Small molecule
via ChEMBL · EBI
Research
217 papers- Higenamine in Plants as a Source of Unintentional Doping.Plants (Basel, Switzerland) · 2022
- Role of Higenamine in Heart Diseases: A Mini-Review.Frontiers in pharmacology · 2021
- β(2) -Adrenoceptor agonist activity of higenamine.Drug testing and analysis · 2021
- Applications of Higenamine in pharmacology and medicine.Journal of ethnopharmacology · 2017
- Higenamine as a Potential Pharmacologic Stress Agent in the Detection of Coronary Artery Disease.Chinese medical sciences journal = Chung-kuo i hsueh k'o hsueh tsa chih · 2022
via PubMed
Wikidata facts
- Subclass of
- isoquinoline alkaloid
- Mass
- 271.120843
Show 4 more facts
- chemical formula
- C₁₆H₁₇NO₃
- canonical SMILES
- C1CNC(C2=CC(=C(C=C21)O)O)CC3=CC=C(C=C3)O
- found in taxon
- Nelumbo nucifera
- Commons category
- Higenamine
Sources (2)
via Wikidata · CC0
~6 min read
Encyclopedic overview
6 sectionsContents
- Legality
- Pharmacology
- Toxicity
- Biosynthesis
- See also
- 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).
Higenamine is found as an ingredient in sports and weight loss dietary supplements sold in the US. The US Food and Drug Administration has received reports of adverse effects from higenamine-containing supplements since 2014, but higenamine's health risks remain poorly understood.
Excerpted from Wikipedia’s “higenamine” article, available under the CC BY-SA 4.0 licence.