99746-73-3

Basic information

• Product Name: (S)-2,3,6,7-Tetrahydro-1H-pyrazino[2,1-a]isoquinolin-4(11bH)-one
• Synonyms: (S)-2,3,6,7-Tetrahydro-1H-pyrazino[2,1-a]isoquinolin-4(11bH)-one;L-Praziquanamine
• CAS NO: 99746-73-3
• Molecular Formula: C₁₂H₁₄N₂O
• Molecular Weight: 202.25236
• Mol File: 99746-73-3.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• Solubility: Chloroform; Dichloromethane; Methanol
• CAS DataBase Reference: (S)-2,3,6,7-Tetrahydro-1H-pyrazino[2,1-a]isoquinolin-4(11bH)-one(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-2,3,6,7-Tetrahydro-1H-pyrazino[2,1-a]isoquinolin-4(11bH)-one(99746-73-3)
• EPA Substance Registry System: (S)-2,3,6,7-Tetrahydro-1H-pyrazino[2,1-a]isoquinolin-4(11bH)-one(99746-73-3)

Safety Data

• Hazardous Substances Data: 99746-73-3(Hazardous Substances Data)

Usage

Uses

L-Praziquanamine is an intermediate in the synthesis of Unlabeled (S)-Praziquante-d11 (P702105), used in the synthetic preparation of perphenylcarbamated β-cyclodextrin based chiral stationary phases via thiol-ene click chemistry for HPLC enantioseparations. (S)-Praziquantel is also the inactive enantiomer of praziquantel regarding activity against juvenile S. mansoni infestations in mice.

Upstream product

• 99700-59-1 C₂₂H₂₁F₃N₂O₃ 
• 210223-97-5 2-[(2,2-dimethoxyethyl)amino]-N-(2-phenylethyl)acetamide hydrochloride 
• 64-04-0 phenethylamine 
• 13156-95-1 2-chloro-N-phenethylacetamide 
• 1622136-46-2 (S)-praziquanamine-hemi-dibenzoyl-D-tataric acid salt 
• 61196-37-0 2,3,6,7-tetrahydro-1H-pyrazino[2,1-a]isoquinolin-4(11bH)-one 
• 55268-74-1 2-cyclohexanecarbonyl-1,2,3,6,7,11b-hexahydro-pyrazino[2,1-a]isoquinolin-4-one 
• 1558003-70-5 (S)-(+)-2-((S)-2-(6-methoxynaphthalen-2-yl)propanoyl)-1,2,3,6,7,11b-hexahydro-4H-pyrazino[2,1-a]isoquinolin-4-one 

Downstream Products

• 57452-32-1 (+)-2-(4-oxocyclohexylcarbonyl)-1,2,3,6,7,11b-hexahydro-4H-pyrazino<2,1-a>isoquinolin-4-one 
• 57452-97-8 (+)-Praziquantel 
• 135526-78-2 (-)-Praziquantel 
• 55375-92-3 (R)-(-)-1,2,3,6,7,11b-hexahydro-4H-pyrazino[2,1-a]isoquinolin-4-one 
• 61196-37-0 2,3,6,7-tetrahydro-1H-pyrazino[2,1-a]isoquinolin-4(11bH)-one 
• 134924-70-2 (+)-2-(4-cis-hydroxycyclohexylcarbonyl)-1,2,3,6,7,11b-hexahydro-4H-pyrazino<2,1-a>isoquinolin-4-one 
• 134924-72-4 (+)-2-(4-trans-hydroxycyclohexylcarbonyl)-1,2,3,6,7,11b-hexahydro-4H-pyrazino<2,1-a>isoquinolin-4-one 
• 99780-88-8 (-)-1,3,4,6,7,11b-Hexahydro-2H-pyrazino<2,1-a>isochinolin 
• 99780-87-7 (+)-1,3,4,6,7,11b-Hexahydro-2H-pyrazino<2,1-a>isochinolin 

Relevant articles and documents

One-pot palladium-catalyzed racemization of (S)-praziquanamine: A key intermediate for the anthelmintic agent (R)-praziquantel

An one-pot palladium-catalyzed procedure for racemization of (S)-praziquanamine, which is the undesired enantiomer and produced during the resolution step for preparing the anthelmintic drug (R)-praziquantel, has been developed through dehydrogenation of

Development of chiral praziquantel analogues as potential drug candidates with activity to juvenile Schistosoma japonicum

A series of chiral praziquantel analogues were synthesized and evaluated against Schistosoma japonicum both in vitro and in vivo. All compounds exhibited low to considerable good activity in vivo. Remarkably, worm reduction rate of R-3 was 60.0% at a sing

A straightforward and efficient synthesis of praziquantel enantiomers and their 4′-hydroxy derivatives

A new method for the synthesis of praziquantel enantiomers via resolution of praziquanamine with (S)-(+)-naproxen was developed. The four 4′-hydroxy derivatives were obtained through each single praziquanamine enantiomer, coupling with cis- and trans-4-(benzyloxy)cyclohexanecarboxylic acids and subsequent hydrogenolysis for the deprotection of the 4′-OH cyclohexane residue. Additionally, the in vitro cysticidal activity of the compounds was tested, finding that (R)-(-)-praziquantel is the eutomer.