3422-42-2

Usage

Uses

Used in Pharmaceutical Industry:
(-)-Coclaurine Hydrochloride is used as a pharmaceutical compound for its ability to modulate dopamine receptors. This property makes it a potential candidate for the development of drugs targeting dopamine-related conditions, such as Parkinson's disease or other neurological disorders involving dopamine dysregulation.
Used in Research Applications:
In the field of neuroscience and pharmacology, (-)-Coclaurine Hydrochloride is used as a research tool to study the effects of dopamine receptor modulation. Its selective blocking of postsynaptic dopamine receptors can provide valuable insights into the mechanisms of dopamine signaling and contribute to the development of novel therapeutic strategies.
Used in Drug Development:
(-)-Coclaurine Hydrochloride's interaction with dopamine receptors suggests its potential use in the development of new drugs for the treatment of various conditions related to dopamine dysregulation. It can be utilized as a starting point for the synthesis of more potent and selective dopamine receptor modulators, which could lead to improved treatment options for patients.

Upstream product

• 38474-17-8 (-)-OO'-dibenzylcoclaurine 
• 38474-19-0 7,12-O,O'-dibenzylcoclaurine 
• 74-88-4 methyl iodide 
• 132257-14-8 (+)-OO'-dibenzylcoclaurine hydrochloride 

Downstream Products

• 3423-07-2 (S)-N-methylcoclaurine 
• 5096-70-8 (-)-(R)-(N)-methylcoclaurine 

Relevant academic research and scientific papers

Organocatalytic Enantioselective Pictet-Spengler Approach to Biologically Relevant 1-Benzyl-1,2,3,4-Tetrahydroisoquinoline Alkaloids

(Figure Presented) A general procedure for the synthesis of 1-benzyl-1,2,3,4-tetrahydroisoquinolines was developed, based on organocatalytic, regio- and enantioselective Pictet-Spengler reactions (86-92% ee) of N-(o-nitrophenylsulfenyl)-2-arylethylamines with arylacetaldehydes. The presence of the o-nitrophenylsulfenyl group, together with the MOM-protection in the catechol part of the tetrahydroisoquinoline ring system, appeared to be a productive combination. To demonstrate the versatility of this approach, 10 biologically and pharmaceutically relevant alkaloids were prepared using (R)-TRIP as the chiral catalyst: (R)-norcoclaurine, (R)-coclaurine, (R)-norreticuline, (R)-reticuline, (R)-trimemetoquinol, (R)-armepavine, (R)-norprotosinomenine, (R)-protosinomenine, (R)-laudanosine, and (R)-5-methoxylaudanosine.

THE STRUCTURE, ABSOLUTE CONFIGURATION AND BIOSYNTHESIS OF NORTILIACORININE A

The incorporation of (+/-)-norcoclaurine, (+/-)-coclaurine, (+/-)-N-methylcoclaurine and dehydro-N-methylcoclaurine into nortiliacorinine A in Tilicora racemosa colebr has been studied and specific utilisation of the (+/-)-coclaurine demonstrated.The evidence supports oxidative dimerization of two coclaurine units to give nortiliacorinine A.Experiments with (+/-)-N-methylcoclaurine and (+/-)-N-methylcoclaurine established that only one N-methylcoclaurine unit is specifically utilised to constitute that the H atom at the asymmetric centre in the 1-benzylisoquinoline precursor is retained in the bioconversion into nortiliacorine A.Double labelling experiment with (+/-)-N-methylcoclaurine showed that O-Me function of the precursor is lost in the bioconversion into nortiliacorine A.Parallel feedings of (+)-(S)-, and (-)-(R)-N-methyl-coclaurines and (-)-(S)-, and (+)-(R)-coclaurines revealed that the stereo-specificity is maintained in the biosynthesis of nortiliacorinine A from 1-benzylisoquinoline precursors and established S,S'-configuration at the two asymmetric centres in nortiliacorinine A.

Absolute Configuration and Biosynthesis of Tiliacorine and Tiliacorinine

The incorporation of (+/-)-coclaurine, (+/-)-norcoclaurine, (+/-)-N-methylcoclaurine, and didehydro-N-methylcoclaurinium iodide into tiliacorinine and tiliacorine in Tiliacora racemosa Colebr. has been studied, and specific utilization of the (+/-)-N-meth