Chemistry:6-Chloronicotine

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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 [Es; Es]).[5]

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

See also

References

  1. ↑ 1.0 1.1 "Pyrrolidine-modified and 6-substituted analogs of nicotine: A structure—affinity investigation.". European Journal of Medicinal Chemistry 31 (11): 875–888. 1996. doi:10.1016/S0223-5234(97)89850-9. 
  2. ↑ "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. March 1998. doi:10.1016/S0022-3565(24)37303-3. PMID 9495867. 
  3. ↑ "Synthesis, receptor binding and QSAR studies on 6-substituted nicotine derivatives as cholinergic ligands.". European Journal of Medicinal Chemistry 34 (1): 31–40. 1999. doi:10.1016/S0223-5234(99)80038-5. 
  4. ↑ "Novel and potent 6-chloro-3-pyridinyl ligands for the alpha4beta2 neuronal nicotinic acetylcholine receptor". Journal of Medicinal Chemistry 42 (12): 2227–34. June 1999. doi:10.1021/jm980721x. PMID 10377228. 
  5. ↑ "A Five-Step Synthesis of ( S )-Macrostomine from ( S )-Nicotine". Organic Letters 12 (20): 4513–4515. 15 October 2010. doi:10.1021/ol101887b. https://pubs.acs.org/doi/10.1021/ol101887b. 
  6. ↑ "Synthesis of ( S )-Brevicolline". Synfacts 2006 (12): 1198–1198. December 2006. doi:10.1055/s-2006-955590. http://www.thieme-connect.de/DOI/DOI?10.1055/s-2006-955590. 
  7. ↑ "Six-Step Synthesis of ( S )-Brevicolline from ( S )-Nicotine". Organic Letters 8 (16): 3549–3552. 1 August 2006. doi:10.1021/ol061334h. https://pubs.acs.org/doi/10.1021/ol061334h. 



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