6-Chloronicotine

6-Chloronicotine
Identifiers
  • 2-chloro-5-[(2S)-1-methylpyrrolidin-2-yl]pyridine
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC10H13ClN2
Molar mass196.68 g·mol−1
3D model (JSmol)
  • CN1CCC[C@H]1C2=CN=C(C=C2)Cl
  • 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

6-Chloronicotine is a drug which acts as an agonist at nicotinic acetylcholine receptors. It substitutes for nicotine in animal studies with around twice the potency, and shows antinociceptive effects.[1][2][3][4]

Pharmacology

The antinociceptive effects of 6-chloronicotine are reported to be some 15.4 times the relative potency of nicotine in the tail flick test.[1] 6-Bromonicotine was 14.4 times nicotine in this same test.

Application

6-Chloronicotine is used in the synthesis of macrostomine (c.f. Arenina).[5]

Another application is in the synthesis of brevicolline, a naturally occuring harmala alkaloid present in Carex brevicollis.[6][7]

See also

References

  1. 1 2 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.
  2. ↑ 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.
  3. ↑ 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.
  4. ↑ 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.
  5. ↑ Enamorado, M. F., Ondachi, P. W., Comins, D. L. (15 October 2010). "A Five-Step Synthesis of ( S )-Macrostomine from ( S )-Nicotine". Organic Letters. 12 (20): 4513–4515. doi:10.1021/ol101887b.
  6. ↑ Wagner, F., Comins, D. (December 2006). "Synthesis of ( S )-Brevicolline". Synfacts. 2006 (12): 1198–1198. doi:10.1055/s-2006-955590.
  7. ↑ Wagner, F. F., Comins, D. L. (1 August 2006). "Six-Step Synthesis of ( S )-Brevicolline from ( S )-Nicotine". Organic Letters. 8 (16): 3549–3552. doi:10.1021/ol061334h.
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