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Details

Stereochemistry RACEMIC
Molecular Formula C16H17NO3.ClH
Molecular Weight 307.772
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of HIGENAMINE HYDROCHLORIDE

SMILES

Cl.OC1=CC=C(CC2NCCC3=C2C=C(O)C(O)=C3)C=C1

InChI

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

HIDE SMILES / InChI

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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

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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P07550|||Q53GA6|||Q9UCZ3
Gene ID: 154.0
Gene Symbol: ADRB2
Target Organism: Homo sapiens (Human)
26.0 µM [EC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Higenamine, also called norcoclaurine HCl and Higenamine hydrochloride is used in food supplements for weight loss, known as ‘fat burners’.
PubMed

PubMed

TitleDatePubMed
Molecular characterization of the salutaridinol 7-O-acetyltransferase involved in morphine biosynthesis in opium poppy Papaver somniferum.
2001 Aug 17
Isolation and partial characterization of norcoclaurine synthase, the first committed step in benzylisoquinoline alkaloid biosynthesis, from opium poppy.
2001 Oct
Anti-thrombotic effects of higenamine.
2001 Oct
Purification and characterization of norcoclaurine synthase. The first committed enzyme in benzylisoquinoline alkaloid biosynthesis in plants.
2002 Sep 13
[Experimental study of pharmaceutic stress myocardial perfusion imaging with higenamine].
2005 May
Higenamine reduces apoptotic cell death by induction of heme oxygenase-1 in rat myocardial ischemia-reperfusion injury.
2006 Jul
Effects of higenamine and its 1-naphthyl analogs, YS-49 and YS-51, on platelet TXA2 synthesis and aggregation.
2007
Overexpression of Coptis japonica norcoclaurine 6-O-methyltransferase overcomes the rate-limiting step in Benzylisoquinoline alkaloid biosynthesis in cultured Eschscholzia californica.
2007 Feb
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
Computational systems analysis of dopamine metabolism.
2008 Jun 18
Biochemistry and occurrence of o-demethylation in plant metabolism.
2010
Molecular characterization of O-methyltransferases involved in isoquinoline alkaloid biosynthesis in Coptis japonica.
2010
Norcoclaurine synthase: mechanism of an enantioselective pictet-spengler catalyzing enzyme.
2010 Mar 24
Integration of deep transcriptome and proteome analyses reveals the components of alkaloid metabolism in opium poppy cell cultures.
2010 Nov 18
Patents

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
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 Sat Dec 16 10:30:21 GMT 2023
Edited
by admin
on Sat Dec 16 10:30:21 GMT 2023
Record UNII
PQ432PID6E
Record Status Validated (UNII)
Record Version
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Name Type Language
HIGENAMINE HYDROCHLORIDE
Common Name English
(±)-DEMETHYLCOCLAURINE HYDROCHLORIDE
Common Name English
DEMETHYLCOCLAURINE HYDROCHLORIDE, (±)-
Common Name English
6,7-ISOQUINOLINEDIOL, 1,2,3,4-TETRAHYDRO-1-((4-HYDROXYPHENYL)METHYL)-, HYDROCHLORIDE, (±)-
Systematic Name English
6,7-ISOQUINOLINEDIOL, 1,2,3,4-TETRAHYDRO-1-((4-HYDROXYPHENYL)METHYL)-, HYDROCHLORIDE (1:1)
Systematic Name English
Code System Code Type Description
EPA CompTox
DTXSID10911673
Created by admin on Sat Dec 16 10:30:22 GMT 2023 , Edited by admin on Sat Dec 16 10:30:22 GMT 2023
PRIMARY
PUBCHEM
165901
Created by admin on Sat Dec 16 10:30:22 GMT 2023 , Edited by admin on Sat Dec 16 10:30:22 GMT 2023
PRIMARY
CAS
11041-94-4
Created by admin on Sat Dec 16 10:30:22 GMT 2023 , Edited by admin on Sat Dec 16 10:30:22 GMT 2023
PRIMARY
EVMPD
SUB129643
Created by admin on Sat Dec 16 10:30:22 GMT 2023 , Edited by admin on Sat Dec 16 10:30:22 GMT 2023
PRIMARY
FDA UNII
PQ432PID6E
Created by admin on Sat Dec 16 10:30:22 GMT 2023 , Edited by admin on Sat Dec 16 10:30:22 GMT 2023
PRIMARY
SMS_ID
100000155592
Created by admin on Sat Dec 16 10:30:22 GMT 2023 , Edited by admin on Sat Dec 16 10:30:22 GMT 2023
PRIMARY
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PARENT -> SALT/SOLVATE
ENANTIOMER -> RACEMATE
ENANTIOMER -> RACEMATE
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ACTIVE MOIETY