3-Pyrrolidin-2-yl-pyridine

ID: ALA1132

Chembl Id: CHEMBL1132

Cas Number: 5746-86-1

PubChem CID: 412

Product Number: S48559

Max Phase: Phase

Molecular Formula: C9H12N2

Molecular Weight: 148.21

Molecule Type: Small molecule

Associated Items:

Names and Identifiers

Synonyms: 1'-demethylnicotine | 3-(2-pyrrolidinyl)-(s)-pyridine | Nicotine related compound f | Nornicotine | 3-(pyrrolidin-2-yl)pyridine|5746-86-1|nornicotine|3-(2-Pyrrolidinyl)pyridine|(R,S)-Nornicotine|3-pyrrolidin-2-ylpyridine|(+/-)-Nornicotine|3-pyrrolidin-2-yl-pyridine|(+-)-Nornicotine|2-(3-Pyridyl)pyrrolidine|3-(2-Pyrrolidyl)pyridine|(+-)-1'-Demethylnicotine|DL-NORNICOTINE|(+-)-3-(2-Pyrrolidinyl)pyridine|MFCD00016913|CHEMBL1132|3-[(2RS)-Pyrrolidin-2-yl]pyridine ((RS)-Nornicotine)|(S)-3-Pyrrolidin-2Show More

Canonical SMILES:  c1cncc(C2CCCN2)c1

Standard InChI:  InChI=1S/C9H12N2/c1-3-8(7-10-5-1)9-4-2-6-11-9/h1,3,5,7,9,11H,2,4,6H2

Standard InChI Key:  MYKUKUCHPMASKF-UHFFFAOYSA-N

Alternative Forms

  1. Parent:

Associated Targets(Human)

CHRNB2 Tclin Neuronal acetylcholine receptor; alpha4/beta2 (3972 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CHRNA7 Tchem Neuronal acetylcholine receptor protein alpha-7 subunit (3524 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
EHMT2 Tchem Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 (93046 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

chrnd Acetylcholine receptor protein delta chain (49 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Chrna3 Neuronal acetylcholine receptor (756 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CHRNA1 Acetylcholine receptor (120 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Rattus norvegicus (775804 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Chrna4 Neuronal acetylcholine receptor; alpha4/beta2 (3557 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
nAChRalpha5 Nicotinic acetylcholine receptor alpha 5 subunit (134 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Ache Acetylcholinesterase (135 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Musca domestica (713 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Candida albicans (78123 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Cryptococcus neoformans (21258 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Escherichia coli (133304 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Klebsiella pneumoniae (43867 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Pseudomonas aeruginosa (123386 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Acinetobacter baumannii (41033 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Staphylococcus aureus (210822 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Chrna3 Neuronal acetylcholine receptor; alpha3/beta4 (1368 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Chrna7 Neuronal acetylcholine receptor protein alpha-7 subunit (3047 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: YesOral: NoChemical Probe: NoParenteral: No
Molecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: No
Chirality: YesAvailability: NoProdrug: No

Drug Indications

MESH IDMESH Heading EFO IDsEFO TermsMax Phase for IndicationReferences

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Calculated Properties

Molecular Weight: 148.21Molecular Weight (Monoisotopic): 148.1000AlogP: 1.51#Rotatable Bonds: 1
Polar Surface Area: 24.92Molecular Species: BASEHBA: 2HBD: 1
#RO5 Violations: HBA (Lipinski): 2HBD (Lipinski): 1#RO5 Violations (Lipinski):
CX Acidic pKa: CX Basic pKa: 9.92CX LogP: 0.78CX LogD: -1.67
Aromatic Rings: 1Heavy Atoms: 11QED Weighted: 0.65Np Likeness Score: -0.09

References

1. Schmitt JD, Sharples CG, Caldwell WS..  (1999)  Molecular recognition in nicotinic acetylcholine receptors: the importance of pi-cation interactions.,  42  (16): [PMID:10447950] [10.1021/jm990093z]
2. Kanne DB, Abood LG..  (1988)  Synthesis and biological characterization of pyridohomotropanes. Structure-activity relationships of conformationally restricted nicotinoids.,  31  (3): [PMID:3346870] [10.1021/jm00398a004]
3. Ferretti G, Dukat M, Giannella M, Piergentili A, Pigini M, Quaglia W, Damaj MI, Martin BR, Glennon RA..  (2003)  Binding of nicotine and homoazanicotine analogues at neuronal nicotinic acetylcholinergic (nACh) receptors.,  13  (4): [PMID:12639569] [10.1016/s0960-894x(02)01031-4]
4. Kanne DB, Tomizawa M, Durkin KA, Casida JE..  (2005)  6'-Methylpyrido[3,4-b]norhomotropane: synthesis and outstanding potency in relation to the alpha4beta2 nicotinic receptor pharmacophore model.,  15  (4): [PMID:15686879] [10.1016/j.bmcl.2004.12.069]
5. Dukat M, Ramunno A, Banzi R, Damaj MI, Martin B, Glennon RA..  (2005)  3-(2-Aminoethyl)pyridine analogs as alpha4beta2 nicotinic cholinergic receptor ligands.,  15  (19): [PMID:16039854] [10.1016/j.bmcl.2005.06.053]
6. PubChem BioAssay data set, 
7. TOMIZAWA M, YAMAMOTO I.  (1992)  Binding of Nicotinoids and the Related Compounds to the Insect Nicotinic Acetyicholine Receptor,  17  (4): [10.1584/jpestics.17.4_231]
8. TOMIZAWA M, YAMAMOTO I.  (1992)  Binding of Nicotinoids and the Related Compounds to the Insect Nicotinic Acetyicholine Receptor,  17  (4): [10.1584/jpestics.17.4_231]
9. Unpublished dataset, 
10. Johannes Zuegg, Alysha Elliott, Maite Amado, Emma Cowie, Ali Hinton, Geraldine Kaeslin, Angela Kavanagh, Anne Kunert, Gabriell Lowe, Soumya Ramu, Janet Reid, Robin Trauer, Mathilde Desselle, Ruth Neale, Karl Hansford, Mark Blascovich, Matthew Cooper. CO-ADD screening of NIH (USA) - Clinical Collection,  [10.6019/CHEMBL4513141]
11. Lin SX,Curtis MA,Sperry J.  (2020)  Pyridine alkaloids with activity in the central nervous system.,  28  (24): [PMID:33120080] [10.1016/j.bmc.2020.115820]