Aminopyridines

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Aminopyridines
Surname 2-aminopyridine 3-aminopyridine 4-aminopyridine
other names α-aminopyridine
o -aminopyridine
2-pyridylamine
 
  		β-aminopyridine
m -aminopyridine
3-pyridylamine
 
  		γ-aminopyridine
p aminopyridine
4-pyridylamine
fampridine ( INN )
dalfampridine (USAN)
Structural formula Structure of 2-aminopyridine Structure of 3-aminopyridine Structure of 4-aminopyridine
CAS number 504-29-0 462-08-8 504-24-5
PubChem 10439 10009 1727
Molecular formula C 5 H 6 N 2
Molar mass 94.12 g mol −1
Physical state firmly
Brief description colorless to yellowish, flammable crystals with an unpleasant odor
Melting point 55-58 ° C 60-63 ° C 158 ° C
boiling point 209-211 ° C 250-252 ° C 274 ° C
pK s value
(of the conjugate
acid BH + ) 		6.71 6.03 9.114
density 1.26 g cm −3
solubility soluble in water and alcohol
GHS
labeling
06 - Toxic or very toxic 09 - Dangerous for the environment
danger
06 - Toxic or very toxic
danger
06 - Toxic or very toxic 09 - Dangerous for the environment
danger
H and P phrases 301-311-331-411 301-312-315-319-335 300-311-315-319-335-411
no EUH phrases no EUH phrases no EUH phrases
273-280-302 + 352
304 + 340-309 + 310 		270-280-305 + 351 + 338
309-310 		270-273-280-301 + 310
302 + 352-305 + 351 + 338

In chemistry, the aminopyridines form a group of organic compounds that belong to the heterocycles (more precisely: heteroaromatics ). They consist of a pyridine ring which is substituted with an amino group  (-NH 2 ). Due to the different arrangement, there are three constitutional isomers with the empirical formula C 5 H 6 N 2 .

properties

The aminopyridines are colorless to yellowish solids with a pyridine-like odor. They are soluble in water and alcohol. The 4-aminopyridine , which has the highest symmetry, has the highest melting point.

use

4-aminopyridine is used in the manufacture of 4-halopyridines and drugs. It itself serves as a bird poison and in medicine as a reversible potassium channel blocker (e.g. in multiple sclerosis ).

4-aminopyridine was approved by the United States Medicines Agency in 2010 under the non-proprietary name (USAN) Dalfampridine for the supportive treatment of multiple sclerosis . However, a corresponding application for the European Union was provisionally rejected due to an inadequate risk-benefit ratio . A decision by the Swiss authorities is still pending.

Related links

Individual evidence

  1. ↑ a b c Entry on 2-aminopyridine in the GESTIS substance database of the IFA , accessed on August 12, 2012(JavaScript required) .
  2. ↑ a b c Entry on 3-aminopyridine in the GESTIS substance database of the IFA , accessed on August 12, 2012(JavaScript required) .
  3. ↑ a b c d Entry on 4-aminopyridine in the GESTIS substance database of the IFA , accessed on August 12, 2012(JavaScript required) .
  4. ↑ a b c CRC Handbook of Tables for Organic Compound Identification , Third Edition, 1984, ISBN 0-8493-0303-6 .
  5. ↑ US Environmental Protection Agency (September 27, 2007): Reregistration Eligibility Decision for 4-aminopyridine. EPA 738-R-07-013. (PDF; 917 kB) Accessed February 2, 2011.
  6. ↑ Goodman AD, Brown TR, Krupp LB, Schapiro RT, Schwid SR, Cohen R, Marinucci LN, Blight AR: "Sustained-release oral fampridine in multiple sclerosis: a randomized, double-blind, controlled trial", in: The Lancet , 2009 , 373 , pp. 732-738; PMID 19249634 .
  7. ↑ US Food and Drug Administration. FDA Approves Ampyra to Improve Walking in Adults with Multiple Sclerosis (FDA News Release January 22, 2010). Retrieved January 26, 2010.
  8. ↑ European Medicines Agency (January 20, 2011): Refusal of the marketing authorization for Fampyra (fampridine). (PDF; 51 kB) Accessed January 30, 2011.