Higenamine

Base Information

• Chemical Name: Higenamine
• CAS No.: 5843-65-2
• Deprecated CAS: 17072-47-8
• Molecular Formula: C16H17NO3
• Molecular Weight: 271.316
• UNII: TBV5O16GAP
• DSSTox Substance ID: DTXSID70973974
• Wikipedia: Higenamine
• Wikidata: Q5754240
• Metabolomics Workbench ID: 125618
• ChEMBL ID: CHEMBL19344
• Mol file: 5843-65-2.mol

Synonyms:1(S)-norcoclaurine;1-(p-hydroxybenzyl)-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline;higenamine;higenamine hydrobromide, (+-)-isomer;higenamine hydrochloride, (S)-isomer;higenamine oxalate (1:1), (+-)-isomer;higenamine, tartrate (1:1), R-(R*,R*)-(+-)-isomer;norcoclaurine;O-demethylcoclaurine

Chemical Property of Higenamine

Chemical Property:

• Vapor Pressure: 1.56E-11mmHg at 25°C
• Melting Point: 208-210 °C
• Refractive Index: 1.666
• Boiling Point: 522.4 °C at 760 mmHg
• PKA: 9.72±0.40(Predicted)
• Flash Point: 209.6 °C
• PSA: 72.72000
• Density: 1.317 g/cm³
• LogP: 2.56170
• Storage Temp.: Refrigerator
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 271.12084340
• Heavy Atom Count: 20
• Complexity: 317

Purity/Quality:

97% ^*data from raw suppliers

Higenamine >98%,StandardReferencesGrade ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CNC(C2=CC(=C(C=C21)O)O)CC3=CC=C(C=C3)O
• Recent ClinicalTrials: Pharmacokinetics and Pharmacodynamics of Higenamine in Chinese Healthy Subjects
• General Description: Demethyl-Coclaurine (also known as Higenamine or Norcoclaurine) is a tetrahydroisoquinoline alkaloid derived from the condensation of dopamine with 4-hydroxyphenylacetaldehyde. It serves as a key intermediate in the biosynthesis of benzylisoquinoline alkaloids (BIAs), which exhibit diverse pharmacological activities. The compound can be synthesized through biomimetic methods involving hypochlorite-mediated decarboxylation of amino acids followed by Pictet-Spengler condensation, yielding either racemic or enantioselective forms depending on reaction conditions. Its structural features make it a valuable precursor for the production of bioactive alkaloids.

Technology Process of Higenamine

There total 29 articles about Higenamine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

dopamine (51-61-6) + 4-hydroxyphenylacetaldehyde (7339-87-9) → (1S)-1-(4-hydroxybenzyl)-1,2,3,4-tetrahydroisoquinoline-6,7-diol (5843-65-2,17072-47-8,106032-53-5,22672-77-1)

Guidance literature:

With CjNCS₂; In acetonitrile; at 37 ℃; for 3h; pH=7.4; Enzymatic reaction;

DOI:10.1002/adsc.201200641

Reference yield: 69.0%

4-hydroxyphenylacetaldehyde (7339-87-9) + dopamine hydrochloride (62-31-7) → higenamine (5843-65-2)

Guidance literature:

In aq. phosphate buffer; water; at 37 ℃; for 1.25h;

DOI:10.1016/j.tetlet.2014.07.043

Reference yield: 44.0%

dopamine (51-61-6) + tyrosamine (51-67-2) → higenamine (5843-65-2)

Guidance literature:

tyrosamine; With pyridoxal 5'-phosphate; transaminase from chromobacterium violaceum; sodium pyruvate; sodium L-ascorbate; In aq. phosphate buffer; acetonitrile; at 37 ℃; for 6h; pH=7.5; Inert atmosphere; Enzymatic reaction;

dopamine; In aq. phosphate buffer; acetonitrile; at 60 ℃; for 18h; Inert atmosphere;

DOI:10.1002/anie.201902761

upstream raw materials:

p-hydroxyphenethyl alcohol

4-hydroxyphenylacetaldehyde

dopamine hydrochloride

dopamine

Downstream raw materials:

1,2,3,4-tetrahydro-1-[(4-hydroxyphenyl)methyl]-2-methyl-6,7-Isoquinolinediol

C₂₁H₂₅NO₅

(2S)-1-(6,7-dihydroxy-1-(4-hydroxybenzyl)-3,4-dihydroisoquinolin-2(1H)-yl)-3,3,3-trifluoro-2-methoxy-2-phenylpropan-1-one

(1R)-1-(4-hydroxybenzyl)-1,2,3,4-tetrahydroisoquinoline-6,7-diol

Refernces

Facile one-pot synthesis of tetrahydroisoquinolines from amino acids via hypochlorite-mediated decarboxylation and Pictet-Spengler condensation

10.1016/j.tetlet.2014.07.043

The study presents an optimized biomimetic method for the conversion of various α-amino acids to aldehydes using sodium hypochlorite (NaOCl), which serves as an oxidizing agent for the decarboxylation of amino acids. The aldehyde products can then be transformed into tetrahydroisoquinolines, either racemic or (S)-enantiomer forms, through the Pictet–Spengler reaction with dopamine. The study utilizes a phosphate buffer to maximize regioselectivity for the racemic products and a maleic acid buffer for the enantioselective enzymatic synthesis of (S)-enantiomer products using norcoclaurine synthase. The purpose of these chemicals is to facilitate the synthesis of tetrahydroisoquinolines, which are found in numerous natural products and synthetic compounds with pharmacological activity, including benzoisoquinoline alkaloids. The study aims to synthesize novel BIAs with potential pharmacological utility by employing precursor-directed biosynthesis, avoiding the need for chromatography and ensuring the preparations are free of toxic chemical species.