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Cat. No.: HY-N2037B

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(S)-Higenamine

(Synonyms: (S)-Norcoclaurine)

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(S)-Higenamine ((S)-Norcoclaurine), a S-enantiomer of Higenamine, is the entry compound in benzylisoquinoline alkaloid biosynthesis. (S)-Higenamine is produced by the condensation of dopamine and 4-hydroxyphenylacetaldehyde (4-HPAA) by norcoclaurine synthase (NCS).

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CAS No.: 22672-77-1
Formule: C₁₆H₁₇NO₃
Masse moléculaire:271.31

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Data Sheet (267 KB)

(S)-Higenamine Chemical Structure

CAS No.: 22672-77-1

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Cellular Effect

Cell Line	Type	Value	Description	References
Platelet	IC₅₀	1.6 μM Compound: 1S, (S)-(-)-higenamine	Inhibition of epinephrine-induced platelet aggregation in rat blood Inhibition of epinephrine-induced platelet aggregation in rat blood	[PMID: 18556200]
Platelet	IC₅₀	25 μM Compound: 1S, (S)-(-)-higenamine	Inhibition of U46619-induced platelet aggregation in rat blood Inhibition of U46619-induced platelet aggregation in rat blood	[PMID: 18556200]
Platelet	IC₅₀	450 μM Compound: 1S, (S)-(-)-higenamine	Inhibition of collagen-induced platelet aggregation in rat blood Inhibition of collagen-induced platelet aggregation in rat blood	[PMID: 18556200]
Platelet	IC₅₀	9.1 μM Compound: 1S, (S)-(-)-higenamine	Inhibition of NaAA-induced platelet aggregation in rat blood Inhibition of NaAA-induced platelet aggregation in rat blood	[PMID: 18556200]
Platelet	IC₅₀	>1000 μM Compound: 1S, (S)-(-)-higenamine	Inhibition of ADP-induced platelet aggregation in rat blood Inhibition of ADP-induced platelet aggregation in rat blood	[PMID: 18556200]

In Vitro

The biosynthetic pathway leading to benzylisoquinoline alkaloids originates from the enzyme-catalyzed condensation of dopamine and 4-hydrophenylacetaldehyde to yield (S)-norcoclaurine. Both substrates are secondary metabolites derived from the decarboxylation/hydroxylation/deamination of tyrosine^[1].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

Chemical Information

CAS No. 22672-77-1
Masse moléculaire 271.31
Formule C₁₆H₁₇NO₃
SMILES

OC1=CC2=C([C@H](CC3=CC=C(O)C=C3)NCC2)C=C1O
Synonyms

(S)-Norcoclaurine
Structure Classification
- Alkaloids
- Isoquinoline Alkaloids
- Phenols
- Polyphenols
Initial Source
- Endogenous metabolite
Livraison

Room temperature in continental US; may vary elsewhere.
Stockage

Please store the product under the recommended conditions in the Certificate of Analysis.

Publications (1)

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Int J Biol Macromol

Genome-wide identification of O-methyltransferase genes in Stephania yunnanensis and their roles in benzylisoquinoline alkaloid biosynthesis. [Abstract]

2026 Apr:356:151603. PMID: 41876022

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Pureté: 99.98%

Assay: 99.98%

ee.: 99.98%

Fiche technique (267 KB)
COA (2659 KB)
Elemental Analysis Report (2659 KB)
HNMR (2659 KB)
CNMR (2659 KB)
RP-HPLC (2659 KB)
NP-HPLC (2659 KB)
MS (2659 KB)
LCMS (2659 KB)
IR (2659 KB)
GC (2659 KB)
OR (2659 KB)
SDS-PAGE (2659 KB)
SEC-HPLC (2659 KB)
Other Report (2659 KB)
Instruction de manipulation (2659 KB)

Références

[1]. Minami H, et al. Functional analysis of norcoclaurine synthase in Coptis japonica. J Biol Chem. 2007;282(9):6274‐6282. [Content Brief]

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Keywords

(S)-Higenamine

1 Cited Publications

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(S)-Higenamine

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(S)-Higenamine Related Classifications

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