876-04-0

Basic information

• Product Name: (R)-Octopamine
• Synonyms: (R)-2-Amino-1-(4-hydroxyphenyl)ethanol;(R)-Octopamine;(R)-α-(Aminomethyl)-p-hydroxybenzyl alcohol;[R,(-)]-α-(Aminomethyl)-4-hydroxybenzyl alcohol;4-[(R)-1-Hydroxy-2-aminoethyl]phenol
• CAS NO: 876-04-0
• Molecular Formula: C₈H₁₁NO₂
• Molecular Weight: 0
• Mol File: 876-04-0.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (R)-Octopamine(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-Octopamine(876-04-0)
• EPA Substance Registry System: (R)-Octopamine(876-04-0)

Safety Data

• Hazardous Substances Data: 876-04-0(Hazardous Substances Data)

Upstream product

• 104-14-3 octopamine 
• 473552-22-6 (R)-(-)-2-azido-1-(4-benzyloxyphenyl)-1-ethanol 
• 123-08-0 4-hydroxy-benzaldehyde 
• 56-40-6 glycine 
• 77943-99-8 (R)-2-(4-hydroxyphenyl)-2-hydroxyacetonitrile 
• 831171-92-7 [2-hydroxy-2-(4-hydroxy-phenyl)-ethyl]-carbamic acid 9H-fluoren-9-ylmethyl ester 
• 851714-32-4 [(R)-2-hydroxy-2-(4-acetoxy-phenyl)-ethyl]-carbamic acid benzyl ester 
• 473552-31-7 (R)-1-(4-benzyloxyphenyl)-2-(p-tolylsulfonyloxy)ethanol 
• 2628-17-3 4-Vinylphenol 

Relevant articles and documents

Ulotaront: A TAAR1 Agonist for the Treatment of Schizophrenia

Ulotaront (SEP-363856) is a trace-amine associated receptor 1 (TAAR1) agonist with 5-HT1A receptor agonist activity in Phase 3 clinical development, with FDA Breakthrough Therapy Designation, for the treatment of schizophrenia. TAAR1 is a G-protein-coupled receptor (GPCR) that is expressed in cortical, limbic, and midbrain monoaminergic regions. It is activated by endogenous trace amines, and is believed to play an important role in modulating dopaminergic, serotonergic, and glutamatergic circuitry. TAAR1 agonism data are reported herein for ulotaront and its analogues in comparison to endogenous TAAR1 agonists. In addition, a human TAAR1 homology model was built around ulotaront to identify key interactions and attempt to better understand the scaffold-specific TAAR1 agonism structure-activity relationships.

Enantioselective Aminohydroxylation of Styrenyl Olefins Catalyzed by an Engineered Hemoprotein

Chiral 1,2-amino alcohols are widely represented in biologically active compounds from neurotransmitters to antivirals. While many synthetic methods have been developed for accessing amino alcohols, the direct aminohydroxylation of alkenes to unprotected, enantioenriched amino alcohols remains a challenge. Using directed evolution, we have engineered a hemoprotein biocatalyst based on a thermostable cytochrome c that directly transforms alkenes to amino alcohols with high enantioselectivity (up to 2500 TTN and 90 % ee) under anaerobic conditions with O-pivaloylhydroxylamine as an aminating reagent. The reaction is proposed to proceed via a reactive iron-nitrogen species generated in the enzyme active site, enabling tuning of the catalyst's activity and selectivity by protein engineering.

Asymmetric transfer hydrogenation of 2-tosyloxy-1-(4-hydroxyphenyl)ethanone derivatives: synthesis of (R)-tembamide, (R)-aegeline, (R)-octopamine, and (R)-denopamine

Catalytic transfer hydrogenation of 2-tosyloxy-1-(4-hydroxyphenyl)ethanone derivatives leads to efficient synthesis of β-adrenergic agonists, (R)-tembamide, (R)-aegeline, (R)-octopamine, and (R)-denopamine.

Synthesis of aromatic 1,2-amino alcohols utilizing a bienzymatic dynamic kinetic asymmetric transformation

The applicability of the recent published bienzymatic protocol for the synthesis of (R)-2-amino-1-phenylethanol was tested using L-threonine aldolase from Pseudomonas putida and L-tyrosine decarboxylase from either Enterococcus faecalis (Efa) or two genes from Enterococcus faecium (Efil, Efi2). In all 21 benzaldehyde derivatives were applied for an initial TLC screening. On a small scale, octopamine and noradrenaline were obtained as (S)-enantiomers using Efil. Three protocols were upscaled yielding enantioenriched (S)-octopamine (yield 99%, ee 81%), (R)-2-amino-1-phenylethanol (yield 61%, ee 62%) and (S)-noradrenaline (yield 76%, ee 79%).

COMPOUNDS AND METHODS FOR TREATMENT OF CANCER AND MODULATION OF PROGRAMMED CELL DEATH FOR MELANOMA AND OTHER CANCER CELLS

Compounds and related methods for synthesis, and the use of compounds and combination therapies for the treatment of cancer and modulation of apoptosis in cells are disclosed. The generation of synthetic combinatorial libraries and the evaluation of library member compounds regarding induction of apoptosis selectively in cancer cells are disclosed. Compounds, methods of making the compounds, and therapeutic methods with application against breast cancer cells, melanoma cancer cells, colon cancer cells, and other cancer cells are described.

Enantiomers of adrenaline-type amino alcohols by Burkholderia cepacia lipase-catalyzed asymmetric acylation

The enantiomers of norphenylephrine and octopamine were prepared using lipase PS-catalyzed enantioselective acylation with butanoic anhydride. Burkholderia cepacia lipase-catalyzed acylation with butanoic anhydride was used for the preparation of pharmaceutically important norphenylephrine and octopamine enantiomers, all in 98% ee. Reactivity of the phenolic OH groups and easy racemization, especially in the case of octopamine, complicated optimization. For norphenylephrine, chemical N-acylation was fast and allowed the subsequent enzymatic benzylic acylation in situ. The preparation of the octopamine enantiomers became possible by using the N-Fmoc protected substrate and by the Candida antarctica lipase B-catalyzed deprotection of the OH groups before the N-deprotection was performed.

Identification from a Combinatorial Library of a Small Molecule that Selectively Induces Apoptosis in Cancer Cells

The selective induction of death in cancer cells is a major challenge in modern medicine. In this communication we describe the synthesis of an 88-membered combinatorial library, and the subsequent evaluation of these compounds for their ability to selectively induce apoptosis in cancerous cells. A compound was identified from the library that induces apoptosis in U-937 and HL-60 cell lines. This compound is a remarkably selective pro-apoptotic agent for these cancer cell lines, as it does not induce significant death in noncancerous white blood cells, even at concentrations as high as 1000 μM. Copyright

Application of optically active 1,2-diol monotosylates for synthesis of β-azido and β-amino alcohols with very high enantiomeric purity. Synthesis of enantiopure (R)-octopamine, (R)-tembamide and (R)-aegeline

A very convenient and highly efficient synthesis of near enantiopure β-azido and β-amino alcohols including biologically active substances such as (R)-octopamine, (R)-tembamide and (R)-aegeline from optically active 1,2-diol monotosylates is reported.

Chiral separation of drug enantiomers by capillary electrophoresis using succinyl-β-cyclodextrin

A capillary electrophoretic method for the enantiomeric separation of 11 drugs was developed using an uncoated fused-silica capillary and succinyl β-cyclodextrin as a chiral additive. The effect of the pH of the background electrolyte on selectivity and resolution was studied in the range pH 3.3-9.3. Best results were obtained in a neutral medium. Generally, the presence of a hydroxy group at the chiral C-atom of the analyte seems to be essential because similar compounds without a hydroxy group at the chiral centre did not show chiral resolution. In addition to the enantioselective inclusion into the chiral cavity, hydrogen bondings and formation of ion pairs between the negatively charged selector and cationic analytes can be assumed as mechanisms.