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6-Chloronicotine

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Chemical compound

Pharmaceutical compound

6-Chloronicotine
Identifiers

IUPAC name 2-chloro-5-[(2S)-1-methylpyrrolidin-2-yl]pyridine
CAS Number	112091-17-5^Y
PubChemCID	10631771
ChemSpider	8807133
UNII	YT5WAL3YF3
CompTox Dashboard(EPA)	DTXSID90442718
Chemical and physical data
Formula	C₁₀H₁₃ClN₂
Molar mass	196.68 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CN1CCC[C@H]1C2=CN=C(C=C2)Cl
InChI InChI=1S/C10H13ClN2/c1-13-6-2-3-9(13)8-4-5-10(11)12-7-8/h4-5,7,9H,2-3,6H2,1H3/t9-/m0/s1 Key:SVVOLGNZRGLPIU-VIFPVBQESA-N

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6-Chloronicotine is a drug which acts as anagonist at neuralnicotinic acetylcholine receptors. It substitutes fornicotine in animal studies with around twice the potency, and showsantinociceptive effects.^[1]^[2]^[3]^[4]

^Dukat M, Fiedler W, Dumas D, Damaj I, Martin BR, Rosecrans JA, James JR, Glennon RA (1996). "Pyrrolidine-modified and 6-substituted analogs of nicotine: A structure—affinity investigation".European Journal of Medicinal Chemistry.31 (11):875–888.doi:10.1016/S0223-5234(97)89850-9.
^Damaj MI, Fei-Yin M, Dukat M, Glassco W, Glennon RA, Martin BR (March 1998). "Antinociceptive responses to nicotinic acetylcholine receptor ligands after systemic and intrathecal administration in mice".The Journal of Pharmacology and Experimental Therapeutics.284 (3):1058–65.doi:10.1016/S0022-3565(24)37303-3.PMID 9495867.
^Dukat M, Dowd M, Damaj MI, Martin B, El-Zahabi MA, Glennon RA (1999). "Synthesis, receptor binding and QSAR studies on 6-substituted nicotine derivatives as cholinergic ligands".European Journal of Medicinal Chemistry.34 (1):31–40.doi:10.1016/S0223-5234(99)80038-5.
^Latli B, D'Amour K, Casida JE (June 1999). "Novel and potent 6-chloro-3-pyridinyl ligands for the alpha4beta2 neuronal nicotinic acetylcholine receptor".Journal of Medicinal Chemistry.42 (12):2227–34.doi:10.1021/jm980721x.PMID 10377228.