230617-65-9

Basic information

• Product Name: 5-(1-AZETIDINYLMETHYL)-2-CHLORO-PYRIDINE
• Synonyms: 5-(1-AZETIDINYLMETHYL)-2-CHLORO-PYRIDINE
• CAS NO: 230617-65-9
• Molecular Formula: C9H11ClN2
• Molecular Weight: 182.653
• Mol File: 230617-65-9.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 5-(1-AZETIDINYLMETHYL)-2-CHLORO-PYRIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-(1-AZETIDINYLMETHYL)-2-CHLORO-PYRIDINE(230617-65-9)
• EPA Substance Registry System: 5-(1-AZETIDINYLMETHYL)-2-CHLORO-PYRIDINE(230617-65-9)

Safety Data

• Hazardous Substances Data: 230617-65-9(Hazardous Substances Data)

Upstream product

• 70258-18-3 2-chloro-5-(chloromethyl)pyridine 
• 78797-58-7 azetidine hydrochloride 
• 230617-75-1 1-<(6-chloro-3-pyridinyl)methyl>-2-chloropropylamine 

Relevant articles and documents

PYRIDYLOXYMETHYL AND BENZISOXAZOLE AZABICYCLIC DERIVATIVES

An aminomethylpyridyloxymethyl/benzisoxazole substituted azabicyclic compound according to formula (I) a pharmaceutical composition comprising same, and a method of treating one or more CNS or other disorders, including concurrent treatment of disorders such as chizophrenia and depression. Or the (R) or (S) enantiomer thereof, or the cis or trans isomer thereof, or a pharmaceutically acceptable salt, solvate or prodrug thereof, or of any of the foregoing, wherein m is 0 or 1, Z is wherein R7 is hydrogen or (C1-C3)alkoxy; R8 is hydrogen, hydroxy, or (C1-C3)alkoxy; and R9 is (C1-C3)alkoxy; X is oxygen or NR, wherein R is hydrogen or (C1-C6)alkyl; Y is methylene, wherein n is 0, 1 or 2; or oxygen, nitrogen or sulfur, wherein n is 2, 3 or 4; R1 and R2 are each independently hydrogen, halogen, or a (C1-C6)alkyl, (C1-C6)alkoxy or a (C1-C6)alkoxy(C1-C6)alkyl group, any one of which groups may be unsbustituted or substituted with one or more halogens.

Novel and potent 6-chloro-3-pyridinyl ligands for the α4β2 neuronal nicotinic acetylcholine receptor

1-[(6-Chloro-3-pyridinyl)methyl]-2-imidazolidine (1), the N-desnitro metabolite of the major insecticide imidacloprid, is known to have similar potency to that of (-)-nicotine as an inhibitor of [3H](-)-nicotine binding at the rat recombinant α4β2 neuronal nicotinic acetylcholine receptor (nAChR); IC50 values in the present study are 3.8 nM for (-)-nicotine, 6.0 nM for 1, and 155 nM for imidacloprid. Synthesis of new analogues of 1, modified only in the heterocyclic moiety (five-, six-, or seven-membered rings with NH, S, O, and CH2 substituents), gave compounds varying from 4- fold higher potency (2-iminothiazole analogue 10) to > 6000-fold less active than (-)-nicotine. Other potent N-[(6-chloro-3-pyridinyl)methyl] compounds are those in which the heterocyclic imine is replaced with pyrrolidine (19) (IC50 9 nM) or trimethylammonium (22) (IC50 18 nM). A novel conversion of (-)-nicotine to its 6-chloro analogue increased the potency 2-fold. These 6- chloro-3-pyridinyl compounds are of interest as novel nAChR probes and potential metabolites of candidate insecticides.