Details
Stereochemistry | RACEMIC |
Molecular Formula | C16H17NO3 |
Molecular Weight | 271.3111 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
OC1=CC=C(CC2NCCC3=C2C=C(O)C(O)=C3)C=C1
InChI
InChIKey=WZRCQWQRFZITDX-UHFFFAOYSA-N
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
Molecular Formula | C16H17NO3 |
Molecular Weight | 271.3111 |
Charge | 0 |
Count |
|
Stereochemistry | RACEMIC |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Optical Activity | ( + / - ) |
Higenamine HCl (norcoclaurine) is a plant-based alkaloid widely used as nutritional supplement in food and beverage industries. It exists in variety of plants including Tinospora crispa, Nandina domestica, Gnetum Parvifolium C.Y. Cheng, sarum Heterotropoides, Nelumbo nucifera. It was initially isolated from Aconitum and identified as the active cardiotonic component of this medicinal plant used as local and traditional medicines in many Asian regions for the treatment of various diseases such as collapse, syncope, painful joints, oedema, bronchial asthma etc. Various pharmacological properties and potentially multi-spectral medical applications of higenamine have been reviled in many in vitro and in vivo studies conducted in animals and humans. Pharmacological properties of higenamine include positive inotropic and chronotropic effect, activating slow channel effect, vascular and tracheal relaxation effect, anti-thrombotic, anti-apoptotic and anti-oxidative effect, anti-inflammatory and immunomodulatory effect. Studies on higenamine showed potential therapeutic effects for diseases like heart failure, disseminated intravascular coagulation (DIC), shock, arthritis, asthma, ischemia/reperfusion injuries and erectile dysfunction. Higenamine has been tested as a candidate of pharmacologic stress agent in the detection of coronary artery diseases (CADs) in human clinical studies in China. In animal models, higenamine has been demonstrated to be a β2 adrenoreceptor agonist. It partly exerts its actions by the activation of adenylate cyclase, responsible for boosting the cellular concentrations of the adrenergic second messenger, cAMP. Via a beta-adrenoceptor mechanism higenamine, induced relaxation in rat corpus cavernosum, leading to improved vasodilation and erectile function. Related to improved vasodilatory signals, higenamine has been shown to possess antiplatelet and antithrombotic activity via a cAMP-dependent pathway, suggesting it may contribute to enhanced vasodilation and arterial integrity. Anti-apoptotic and cardiac protective effects of higenamine were shown to be mediated by the β2-AR/PI3K/AKT cascade. Higenamine is marketed as a dietary supplement for weight loss and sport performance, and is added to many fat burning supplements. Along with many other β2 agonists, higenamine is prohibited by World Anti-Doping Agency for use in sports.
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/22183510
Curator's Comment: Known to be CNS penetrant in mouse; rats. Human data not available. Administration of higenamine (i.p) significantly reduced brain infarct size, mortality rate, MPO activity and tissue expression of HMGB1 in MCAO rats.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: P07550|||Q53GA6|||Q9UCZ3 Gene ID: 154.0 Gene Symbol: ADRB2 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/18817623 |
26.0 µM [EC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Unknown Approved UseHigenamine, also called norcoclaurine HCl and Higenamine hydrochloride is used in food supplements for weight loss, known as ‘fat burners’. |
PubMed
Title | Date | PubMed |
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Molecular characterization of the salutaridinol 7-O-acetyltransferase involved in morphine biosynthesis in opium poppy Papaver somniferum. | 2001 Aug 17 |
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Antithrombotic effects of YS-49 and YS-51--1-naphthylmethyl analogs of higenamine. | 2001 Nov 15 |
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Isolation and partial characterization of norcoclaurine synthase, the first committed step in benzylisoquinoline alkaloid biosynthesis, from opium poppy. | 2001 Oct |
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Anti-thrombotic effects of higenamine. | 2001 Oct |
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The effects of higenamine on LPS-induced experimental disseminated intravascular coagulation (DIC) in rats. | 2002 Apr |
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[Effects of higeramine on hemodynamics and its tolerability and safety, an experimental study]. | 2002 Mar |
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Purification and characterization of norcoclaurine synthase. The first committed enzyme in benzylisoquinoline alkaloid biosynthesis in plants. | 2002 Sep 13 |
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[The influence on hemodynamics of myocardial ischemic dogs and blood pressure of animals with shenfu injection]. | 2003 Mar |
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[Effects of higenamine on the cardio-circulatory system]. | 2003 Oct |
|
Analysis of benzylisoquinoline-type alkaloids by electrospray tandem mass spectrometry and atmospheric pressure photoionization. | 2005 |
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Anti-HIV benzylisoquinoline alkaloids and flavonoids from the leaves of Nelumbo nucifera, and structure-activity correlations with related alkaloids. | 2005 Jan 17 |
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Protective effect of Shenfu injection on myocardial mitochondria injured by ischemia-reperfusion in rabbits. | 2005 Mar 20 |
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[Experimental study of pharmaceutic stress myocardial perfusion imaging with higenamine]. | 2005 May |
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Enantiomers of higenamine inhibit LPS-induced iNOS in a macrophage cell line and improve the survival of mice with experimental endotoxemia. | 2006 Feb |
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Higenamine reduces apoptotic cell death by induction of heme oxygenase-1 in rat myocardial ischemia-reperfusion injury. | 2006 Jul |
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Effects of higenamine and its 1-naphthyl analogs, YS-49 and YS-51, on platelet TXA2 synthesis and aggregation. | 2007 |
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[Characterization of polyphenoloxidase from the latex of greater celandine (Chelidonium majus L.)]. | 2007 Apr |
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Overexpression of Coptis japonica norcoclaurine 6-O-methyltransferase overcomes the rate-limiting step in Benzylisoquinoline alkaloid biosynthesis in cultured Eschscholzia californica. | 2007 Feb |
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Functional analysis of norcoclaurine synthase in Coptis japonica. | 2007 Mar 2 |
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Enantioselective synthesis of (R)-(+)- and (S)-(-)-higenamine and their analogues with effects on platelet aggregation and experimental animal model of disseminated intravascular coagulation. | 2008 Jul 15 |
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Computational systems analysis of dopamine metabolism. | 2008 Jun 18 |
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Identification of higenamine in Radix Aconiti Lateralis Preparata as a beta2-adrenergic receptor agonist1. | 2008 Oct |
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Structural basis of enzymatic (S)-norcoclaurine biosynthesis. | 2009 Jan 9 |
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Functional characterization of a novel benzylisoquinoline O-methyltransferase suggests its involvement in papaverine biosynthesis in opium poppy (Papaver somniferum L). | 2009 Oct |
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Beta2-adrenoceptor-mediated tracheal relaxation induced by higenamine from Nandina domestica Thunberg. | 2009 Oct |
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Biochemistry and occurrence of o-demethylation in plant metabolism. | 2010 |
|
Molecular characterization of O-methyltransferases involved in isoquinoline alkaloid biosynthesis in Coptis japonica. | 2010 |
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Norcoclaurine synthase: mechanism of an enantioselective pictet-spengler catalyzing enzyme. | 2010 Mar 24 |
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Integration of deep transcriptome and proteome analyses reveals the components of alkaloid metabolism in opium poppy cell cultures. | 2010 Nov 18 |
Patents
Sample Use Guides
Higenamine is usually dosed between 20-40 mg. However, some preworkout supplements go as high as 75 mg. Currently there is no evidence to support the optimal dose. Intravenous administration of 22.5 μg/kg higenamine was reported to be well-tolerated in healthy volunteers.
Route of Administration:
Other
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/11138724
Effects of higenamine on Na+, K+ and Cl- transport were studied on stripped guinea pig distal colonic mucosa in vitro using Ussing chambers. Addition of 10(-5) M higenamine induced a biphasic change in short circuit current (Isc): a transient increase followed by a long-lasting decrease that was accompanied by an increase in transepithelial conductance (Gt). The initial transient increase was not observed at the lower concentration of higenamine (10(-8)-10(-6) M).
Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 07:09:27 UTC 2023
by
admin
on
Sat Dec 16 07:09:27 UTC 2023
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Record UNII |
TBV5O16GAP
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Record Status |
Validated (UNII)
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Record Version |
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DSLD |
2067 (Number of products:121)
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TBV5O16GAP
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HIGENAMINE
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Related Record | Type | Details | ||
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ENANTIOMER -> RACEMATE | |||
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SALT/SOLVATE -> PARENT | |||
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ENANTIOMER -> RACEMATE |
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ACTIVE MOIETY |