AM-1235

AM-1235

AM-1235
Systematic (IUPAC) name
1-[(5-fluoropentyl)-6-nitro-1H-indol-3-yl]-(naphthalen-1-yl)methanone
Clinical data
Legal status
?
Identifiers
CAS number  YesY
ATC code ?
ChemSpider
Chemical data
Formula C24H21FN2O3 
Mol. mass 404.433 g/mol
 YesY   

AM-1235 (1-(5-fluoropentyl)-3-(naphthalen-1-oyl)-6-nitroindole) is a drug that acts as a potent and reasonably selective agonist for the cannabinoid receptor CB1.

Contents

  • Pharmacology 1
    • Pharmacodynamics 1.1
    • Pharmacokinetics 1.2
  • See also 2
  • References 3

Pharmacology

Pharmacodynamics

AM-1235 is a cannabinoid receptor agonist with Ki of 1.5nM at CB1 compared to 20.4nM at CB2.[1] While the 6-nitro substitution on the indole ring reduces affinity for both CB1 and CB2 relative to the unsubstituted parent compound AM-2201, CB2 affinity is reduced much more, resulting in a CB1 selectivity of around 13x.[2] This is in contrast to other related compounds such as AM-1221 where a 6-nitro substitution instead confers significant selectivity for CB2.[3]

Pharmacokinetics

AM-1235 metabolism differs only slightly from that of JWH-018. AM-1235 N-dealkylation produces fluoropentane instead of pentane (or plain alkanes in general). It has been speculated that the fluoropentane might function as an alkylating agent or is further metabolized into toxic fluoroacetic acid. This is not true since fluoroalkanes do not act as alkylating agents under normal conditions and uneven fluoroalkane chains metabolize into substantially less toxic fluoropropanoic acid.[4][5]

See also

References

  1. ^ US patent 7241799, Makriyannis A, Deng H, "Cannabimimetic indole derivatives", granted 2007-07-10 
  2. ^ Deng, Hongfeng (2000). Design and synthesis of selective cannabinoid receptor ligands: Aminoalkylindole and other heterocyclic analogs (PhD. Dissertation). University of Connecticut. 
  3. ^ WO patent 200128557, Makriyannis A, Deng H, "Cannabimimetic indole derivatives", granted 2001-06-07 
  4. ^ . 1956 Nov;34(11):1532-1541.Canadian Journal of ChemistryMillington JE, Pattison FLM. TOXIC FLUORINE COMPOUNDS: XII. ESTERS OF ω-FLUOROALCOHOLS.
  5. ^ . 1957 Feb;35(2):141-148.Canadian Journal of ChemistryPattison FLM, Howell WC, Woolford RG. TOXIC FLUORINE COMPOUNDS: XIII. ω-FLUOROALKYL ETHERS.