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Mecamylamine
Systematic (IUPAC) name
(2R)-N,2,3,3-tetramethylbicyclo[2.2.1]heptan-2-amine
Identifiers
CAS number 60-40-2
ATC code C02BB01
PubChem 4032
DrugBank APRD00458
Chemical data
Formula C11H21N 
Mol. mass 167.291 g/mol
SMILES eMolecules & PubChem
Pharmacokinetic data
Protein binding 40%
Therapeutic considerations
Pregnancy cat.  ?
Legal status Prescription only
Routes Oral
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Mecamylamine (Inversine) is a nonselective and noncompetitive antagonist of the nicotinic acetylcholine receptors which was introduced in the 1950s as an antihypertensive agent.[1]

Uses

Mecamylamine has been used as a ganglionic blocker in treating hypertension, but, like most ganglionic blockers, is more often used now as a research tool.

Mecamylamine is also sometimes used as an anti-addictive drug to help people stop smoking tobacco,[2] and is now more widely used for this application than it is for lowering blood pressure. This effect is thought to be due to it blocking α3β4 nicotinic receptors in the brain.

In a recent double-blind, placebo controlled trial in patients with major depression, S-mecamylamine appears to have efficacy as an augmentation therapy. This was the first substantive evidence that compounds where the primary pharmacology is antagonism to neuronal nicotinic receptors will have antidepressant properties.[3][4]

S-(+)-mecamylamine dissociates more slowly from alpha-4 beta-2 and alpha-3 beta-4 receptors than does the R-(-)-enantiomer.[5] The pKa value is 11.2.

A small SAR study was undertaken by Suchocki et al.[6]

References

  1. ^ Bacher I, Wu B, Shytle DR, George TP (November 2009). "Mecamylamine - a nicotinic acetylcholine receptor antagonist with potential for the treatment of neuropsychiatric disorders". Expert Opinion on Pharmacotherapy 10 (16): 2709–21. doi:10.1517/14656560903329102. PMID 19874251. http://informahealthcare.com/doi/abs/10.1517/14656560903329102. 
  2. ^ Shytle RD, Penny E, Silver AA, Goldman J, Sanberg PR (July 2002). "Mecamylamine (Inversine): an old antihypertensive with new research directions". J Hum Hypertens 16 (7): 453–7. doi:10.1038/sj.jhh.1001416. PMID 12080428. http://dx.doi.org/10.1038/sj.jhh.1001416. 
  3. ^ Lippiello PM, Beaver JS, Gatto GJ, et al (2008). "TC-5214 (S-(+)-mecamylamine): a neuronal nicotinic receptor modulator with antidepressant activity". CNS Neurosci Ther 14 (4): 266–77. doi:10.1111/j.1755-5949.2008.00054.x. PMID 19040552. 
  4. ^ Rabenstein RL, Caldarone BJ, Picciotto MR (December 2006). "The nicotinic antagonist mecamylamine has antidepressant-like effects in wild-type but not beta2- or alpha7-nicotinic acetylcholine receptor subunit knockout mice". Psychopharmacology (Berl.) 189 (3): 395–401. doi:10.1007/s00213-006-0568-z. PMID 17016705. 
  5. ^ Papke RL, Sanberg PR, Shytle RD (May 2001). "Analysis of mecamylamine stereoisomers on human nicotinic receptor subtypes". J. Pharmacol. Exp. Ther. 297 (2): 646–56. PMID 11303054. http://jpet.aspetjournals.org/cgi/pmidlookup?view=long&pmid=11303054. 
  6. ^ JMC 1991







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