Higenamine hydrochloride - 10mM in DMSO , CAS No.11041-94-4

CAS: 11041-94-4 Cat. No.: H420598 Peso molecular: 307.77 Número EC: 802-566-1

GRADE & PURITY 10mM in DMSO

Synonyms

6,7-ISOQUINOLINEDIOL, 1,2,3,4-TETRAHYDRO-1-((4-HYDROXYPHENYL)METHYL)-, HYDROCHLORIDE, (+/-)- | DTXSID10911673 | 6,7-dihydroxy-1-(4-hydroxybenzyl)-1,2,3,4-tetrahydroisoquinoline hydrochloride | CCG-267555 | DEMETHYLCOCLAURINE HYDROCHLORIDE, (+/-)- | Higena

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

Descripción general

Information

Higenamine (Norcoclaurine, (+-)-Demethylcoclaurine), also known as Norcoclaurine HCl, is a non-selectiveβ2 adrenoceptoragonist which is a chemical compound naturally occurring in a number of plants.

Targets

β2-adrenoceptor ; α1-adrenoceptor

In vitro

Higenamine is a potential β2-adrenoceptor agonist. As a potent cardiotonic and vasodilator, It is also an α1 antagonist and a weak α2 agonist. Higenamine decreases the intracellular dopamine content dose-dependently and shows 55.2% inhibition of dopamine content in PC12 cells at a concentration of 2OM with 24h incubation. The IC50 value of higenamine for inhibiting dopamine biosynthesis in PC12 cells is 18.2 μM. Dopamine content is lowered and reaches minimal level at 12—24h after exposure to higenamine.

In vivo

Higenamine can produce relaxation in tracheal muscle. Higenamine has anti-thrombotic effects in both mouse acute thrombosis model and rat arterio-venous shunt (AV-shunt) models. The oral administration of higenamine (50 or 100 mg/kg) increases the recovery rates from the acute thrombotic challenge in mice and lowers the weight of thrombus formed inside the AV-shunt tube in rats.

Cell Research(from reference)

Cell lines：PC12 cells 

Concentrations：5-20 μM 

Incubation Time：12-48 h 

Specifications

Sinónimos

6, 7-ISOQUINOLINEDIOL, 1, 2, 3, 4-TETRAHYDRO-1-((4-HYDROXYPHENYL)METHYL)-, HYDROCHLORIDE, (+/-)- | DTXSID10911673 | 6, 7-dihydroxy-1-(4-hydroxybenzyl)-1, 2, 3, 4-tetrahydroisoquinoline hydrochloride | CCG-267555 | DEMETHYLCOCLAURINE HYDROCHLORIDE, (+/-)- | Higena

Especificaciones y pureza

10mM in DMSO

Mecanismos bioquímicos y fisiológicos

Higenamine (Norcoclaurine, (+-)-Demethylcoclaurine), also known as Norcoclaurine HCl, is a non-selective β2 adrenoceptor agonist which is a chemical compound naturally occurring in a number of plants.

Condiciones de almacenamiento de almacenamiento

Store at -80°C

Enviado en

Dry ice packs + Cold packs

Este producto requiere envío en cadena de frío. Los servicios terrestres y otros servicios económicos no están disponibles.

Propiedades del producto

• ALogP: 3.031
• Recuento HBD: 4
• Enlace rotable: 2

Nombres e identificadores

• Sonrisas canónicas: C1CNC(C2=CC(=C(C=C21)O)O)CC3=CC=C(C=C3)O.Cl
• IUPAC Name: 1-[(4-hydroxyphenyl)methyl]-1,2,3,4-tetrahydroisoquinoline-6,7-diol;hydrochloride
• InChIKey: SWWQQSDRUYSMAR-UHFFFAOYSA-N
• 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
• Isómeros SMILES: C1CNC(C2=CC(=C(C=C21)O)O)CC3=CC=C(C=C3)O.Cl
• Peso molecular: 307.77
• Reaxy-Rn: 5190862
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=5190862&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Clase Isoquinolines and derivatives
      • Subclass Benzylisoquinolines

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Clase: Isoquinolines and derivatives
• Subclass: Benzylisoquinolines
• Intermediate Tree Nodes: Not available
• Direct Parent: Benzylisoquinolines
• Alternative Parents: Tetrahydroisoquinolines Aralkylamines 1-hydroxy-2-unsubstituted benzenoids Benzene and substituted derivatives Dialkylamines Azacyclic compounds Organopnictogen compounds Organooxygen compounds Hydrochlorides Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Benzylisoquinoline - Tetrahydroisoquinoline - 1-hydroxy-2-unsubstituted benzenoid - Phenol - Aralkylamine - Monocyclic benzene moiety - Benzenoid - Secondary aliphatic amine - Secondary amine - Azacycle - Organopnictogen compound - Organooxygen compound - Organonitrogen compound - Amine - Organic oxygen compound - Hydrocarbon derivative - Organic nitrogen compound - Hydrochloride - Aromatic heteropolycyclic compound
• Descripción: This compound belongs to the class of organic compounds known as benzylisoquinolines. These are organic compounds containing an isoquinoline to which a benzyl group is attached.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Propiedades químicas y físicas

• Sensibilidad: Light and humidity sensitive
• DMSO (mg/ml) Solubilidad máxima: 61
• DMSO (mM) Solubilidad máxima: 198.1999545
• Peso molecular: 307.770 g/mol
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 307.098 Da
• Monoisotopic Mass: 307.098 Da
• Topological Polar Surface Area: 72.700 Ų
• Heavy Atom Count: 21
• Formal Charge: 0
• Complexity: 317.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 1
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 2

XLogP3

Referencias

1. Ying Li, Zhi-Hao Ma, Xiao Liu, Wenting Zhu, Long Chen, Wanyi Xu, Lei Wang, Jingquan Dong, Zi-Bo Dong.  (2025)  Higenamine hydrochloride prevents renal inflammation and fibrosis in diabetic nephropathy by inhibiting the STAT3 signaling pathway.  TOXICOLOGY AND APPLIED PHARMACOLOGY,      [PMID:40701193] [10.1016/j.taap.2025.117483]

2. Li Ying, Wang Lei, Cao Yan, Lu Hujing, Zhou Jiawen, Zhao Panpan, Guan Xinying, Dong Zibo.  (2025)  Higenamine Hydrochloride Attenuates Neuroinflammation in Type I Diabetic Mice by Inhibiting the CRTC2-CREB Signaling Pathway via PAK4.  MOLECULAR NEUROBIOLOGY,      [PMID:40986265] [10.1007/s12035-025-05271-z]

3. Li Ying, Wang Lei, Guan Tianyue, Chen Yaru, Zhu Wenting, Liu Xiao, Li Yusa, Huang Hongyu, Dong Zibo, Zhang Honggang.  (2025)  Higenamine Hydrochloride Ameliorates Diabetic Cardiomyopathy Through RhoA/MEK/ERK Pathway.  INFLAMMATION,      [PMID:41469427] [10.1007/s10753-025-02403-4]