Demethyl-Coclaurine Chemical Properties

Melting point:

208-210 °C

Boiling point:

522.4±50.0 °C(Predicted)

Density 

1.317±0.06 g/cm3(Predicted)

storage temp. 

Refrigerator

solubility 

DMSO (Slightly), Methanol (Slightly)

form 

Solid

pka

9.72±0.40(Predicted)

color 

White to Off-White

InChI

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

InChIKey

WZRCQWQRFZITDX-UHFFFAOYSA-N

SMILES

C1(CC2=CC=C(O)C=C2)C2=C(C=C(O)C(O)=C2)CCN1

Demethyl-Coclaurine Usage And Synthesis

Chemical Properties

Higenamine (HG), a benzylisoquinoline alkaloid originally isolated from aconite, is widely distributed in nature and is known to be contained in traditional Chinese medicines such as epimedium, spicatum, lotus seed and lotus heart. HG is also used as an ingredient in over-the-counter diet pills and sports supplements in countries such as the U.S. The chemical structure of HG is 1-p-hydroxybenzyl-1,2,3.4-tetrahydroisoquinoline alkaloid with the molecular formula C16H17NO3, which is similar in structure to catechol, and it is an agonist of the β-adrenergic receptor. Currently, HG is manufactured primarily by chemical synthesis, and its chloride salt form is relatively water-soluble and commonly used in the clinic. Nortriptyline hydrochloride is a very stable molecular structure in the form of a dense white powder, which can increase heart rate, cardiac output, myocardial oxygen consumption and coronary blood flow at certain doses, and has recently become a clinically safer drug for cardiac load testing.

Uses

Demethyl-Coclaurine acts through inhibition of middle cerebral artery occlusion (MCAO)-mediated HMGB1 release in vivo. Useful towards ischemic injuries.

Uses

(±)-Norcoclaurine can be used to prevent and treat of Alzheimer’s disease, bind to SARS-CoV-2 S protein:human ACE2 complex, as a bronchodilator to improve lung function in various respiratory diseases, and an antioxidant in lipid-like environments. It can also be used as a racemic salt-acidic compound to produce elevated and sustained ketosis.

Definition

ChEBI: (RS)-norcoclaurine is a norcoclaurine. It is a conjugate base of a (RS)-norcoclaurinium.

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