FSL0945

Structure

• InChI=1S/C17H25NO/c19-17-9-5-4-8-16(17)18-12-10-15(11-13-18)14-6-2-1-3-7-14/h1-3,6-7,15-17,19H,4-5,8-13H2/t16-,17-/m1/s1
• InChIKey=YSSBJODGIYRAMI-IAGOWNOFSA-N

Synonyms

• (+/-)-Vesamicol hydrochloride
• 120447-62-3

Origin

Chemically synthesized

Biological activities

Inhibition of acetylcholine transport

Therapeutic

Molecular beacon for a cholinergic marker

Target

Vesicular acetylcholine transporter (VAChT)

Assay information

Vesamicol binds tightly (Ki: 41 nM) to VAChT and inhibits transport of acetylcholine noncompetitively
(+/-)-Vesamicol inhibits in vitro acetylcholine storage (IC₅₀: 40 nM), and shows acute toxicity in mice (LD₅₀: 16 μmol/kg)
(-)-Vesamicol is more biologically active than (+)-vesamicol

References

• Rogers GA, Parsons SM, Anderson DC, Nilsson LM, Bahr BA, Kornreich WD, Kaufman R, Jacobs RS, Kirtman B
  Synthesis, in vitro acetylcholine-storage-blocking activities, and biological properties of derivatives and analogues of trans-2-(4-phenylpiperidino)cyclohexanol (vesamicol).
  J Med Chem, 32(6): 1217-1230 (1989)  2724295
• Bahr BA, Parsons SM
  Acetylcholine transport and drug inhibition kinetics in Torpedo synaptic vesicles.
  J Neurochem, 46(4): 1214-1218 (1986)  3950625
• Marshall IG
  A comparison between the blocking actions of 2-(4-phenylpiperidino) cyclohexanol (AH 5183) and its N-methyl quaternary analogue (AH 5954).
  Br J Pharmacol, 40(1): 68-77 (1970)  4395087
• Marshall IG
  Studies on the blocking action of 2-(4-phenyl piperidino) cyclohexanol (AH5183).
  Br J Pharmacol, 38(3): 503-516 (1970)  4392539
• Brittain RT, Levy GP, Tyers MB
  The neuromuscular blocking action of 2-(4-phenylpiperidino) cyclohexanol (AH 5183).
  Eur J Pharmacol, 8(1): 93-99 (1969)  4243404
• Brittain RT, Levy GP, Tyers MB
  Observations on the neuromuscular blocking action of 2-(4-phenylpiperidino)-cyclohexanol (AH 5183).
  Br J Pharmacol, 36(1): 173P-174P (1969)  5768089