AM-1235

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AM-1235
AM-1235 structure.png
Systematic (IUPAC) name
1-[(5-fluoropentyl)-6-nitro-1H-indol-3-yl]-(naphthalen-1-yl)methanone
Clinical data
Legal status
Identifiers
CAS Number 335161-27-8 YesY
ChemSpider 26633899
UNII 2HV9AH611M YesY
Chemical data
Formula C24H21FN2O3
Molecular mass 404.433 g/mol
  • c24ccccc2cccc4C(=O)c(c3)c1ccc([N](=O)=O)cc1n3CCCCCF
  • InChI=1S/C24H21FN2O3/c25-13-4-1-5-14-26-16-22(20-12-11-18(27(29)30)15-23(20)26)24(28)21-10-6-8-17-7-2-3-9-19(17)21/h2-3,6-12,15-16H,1,4-5,13-14H2
  • Key:LNGVQORPSNNMSZ-UHFFFAOYSA-N
  (verify)

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.

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

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Main article: Pharmacokinetic data of JWH-018 are generally applicable to AM-1235.

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. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  3. ↑ WO patent 200128557, Makriyannis A, Deng H, "Cannabimimetic indole derivatives", granted 2001-06-07 
  4. ↑ Millington JE, Pattison FLM. TOXIC FLUORINE COMPOUNDS: XII. ESTERS OF ω-FLUOROALCOHOLS. Canadian Journal of Chemistry. 1956 Nov;34(11):1532-1541.
  5. ↑ Pattison FLM, Howell WC, Woolford RG. TOXIC FLUORINE COMPOUNDS: XIII. ω-FLUOROALKYL ETHERS. Canadian Journal of Chemistry. 1957 Feb;35(2):141-148.
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