AM-694

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AM-694
AM-694-2D-skeletal.svg
Systematic (IUPAC) name
1-[(5-fluoropentyl)-1H-indol-3-yl]-(2-iodophenyl)methanone
Clinical data
Legal status Legal
Identifiers
CAS number 335161-03-0 YesY
ATC code ?
PubChem CID 9889172
ChemSpider 8064843 YesY
Chemical data
Formula C20H19FINO 
Mol. mass 435.273 g/mol
 YesY (what is this?)  (verify)

AM-694 (1-(5-fluoropentyl)-3-(2-iodobenzoyl)indole) is a drug that acts as a potent and selective agonist for the cannabinoid receptor CB1. It is used in scientific research for mapping the distribution of CB1 receptors. No public data about AM-694 metabolism is known[citation needed]. AM-694 has already emerged as a designer drug.

Pharmacology[edit]

AM-694 is an agonist for cannabinoid receptors. Affinities are: with a Ki of 0.08nM at CB1 and 18x selectivity over CB2 with a Ki 1.44nM.[1] It is unclear what is responsible for this unusually high CB1 binding affinity, but it makes the 18F radiolabelled derivative of AM-694 useful for mapping the distribution of CB1 receptors in the body.[2]

Pharmacokinetics[edit]

AM-694 metabolism differs only slightly from that of JWH-018. AM-694 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.[3][4]

See also[edit]

References[edit]

  1. ^ WO patent 200128557, Makriyannis A, Deng H, "Cannabimimetic indole derivatives", granted 2001-06-07 
  2. ^ Willis PG, Katoch-Rouse R, Horti AG. Regioselective F-18 radiolabeling of AM694, a CB1 cannabinoid receptor ligand. Journal of Labelled Compounds and Radiopharmaceuticals 2003;46(9):799-804. doi:10.1002/jlcr.720
  3. ^ Millington JE, Pattison FLM. TOXIC FLUORINE COMPOUNDS: XII. ESTERS OF ω-FLUOROALCOHOLS. Canadian Journal of Chemistry. 1956 Nov;34(11):1532-1541.
  4. ^ Pattison FLM, Howell WC, Woolford RG. TOXIC FLUORINE COMPOUNDS: XIII. ω-FLUOROALKYL ETHERS. Canadian Journal of Chemistry. 1957 Feb;35(2):141-148.