Vesamicol

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 591419

CAS#: 22232-64-0

Description: Vesamicol is an experimental drug, acting presynaptically by inhibiting acetylcholine uptake into synaptic vesicles and reducing its release. Vesamicol may have applications for the treatment of adenocarcinoma in situ of the lung.


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Vesamicol is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 591419
Name: Vesamicol
CAS#: 22232-64-0
Chemical Formula: C17H25NO
Exact Mass: 259.1936
Molecular Weight: 259.39
Elemental Analysis: C, 78.72; H, 9.71; N, 5.40; O, 6.17


Synonym: Vesamicol; AH 5183; AH-5183; AH5183

IUPAC/Chemical Name: Cyclohexanol, 2-(4-phenyl-1-piperidinyl)-

InChi Key: YSSBJODGIYRAMI-UHFFFAOYSA-N

InChi Code: 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

SMILES Code: OC1C(N2CCC(C3=CC=CC=C3)CC2)CCCC1


Technical Data

Appearance:
Solid powder

Purity:
>98% (or refer to the Certificate of Analysis)

Shipping Condition:
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition:
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility:
Soluble in DMSO

Shelf Life:
>2 years if stored properly

Drug Formulation:
This drug may be formulated in DMSO

Stock Solution Storage:
0 - 4 C for short term (days to weeks), or -20 C for long term (months).

Harmonized System Code:
293490


References

1: Ogawa K, Masuda R, Mizuno Y, Makino A, Kozaka T, Kitamura Y, Kiyono Y, Shiba K, Odani A. Development of a novel radiobromine-labeled sigma-1 receptor imaging probe. Nucl Med Biol. 2018 Apr 6;61:28-35. doi: 10.1016/j.nucmedbio.2018.03.005. [Epub ahead of print] PubMed PMID: 29704822.

2: Lindemann M, Deuther-Conrad W, Moldovan R, Sekhar KVGC, Brust P, Wenzel B. Do spiroindolines have the potential to replace vesamicol as lead compound for the development of radioligands targeting the vesicular acetylcholine transporter? Bioorg Med Chem. 2017 Oct 1;25(19):5107-5113. doi: 10.1016/j.bmc.2017.03.028. Epub 2017 Mar 18. PubMed PMID: 28347632.

3: Sharma A, Agarwal J, Peddinti RK. Direct access to the optically active VAChT inhibitor vesamicol and its analogues via the asymmetric aminolysis of meso-epoxides with secondary aliphatic amines. Org Biomol Chem. 2017 Feb 22;15(8):1913-1920. doi: 10.1039/c6ob02479c. PubMed PMID: 28169381.

4: Gaydukov AE, Bogacheva PO, Balezina OP. Calcitonin gene-related peptide increases acetylcholine quantal size in neuromuscular junctions of mice. Neurosci Lett. 2016 Aug 15;628:17-23. doi: 10.1016/j.neulet.2016.06.014. Epub 2016 Jun 7. PubMed PMID: 27288020.

5: Jin H, Zhang X, Yue X, Liu H, Li J, Yang H, Flores H, Su Y, Parsons SM, Perlmutter JS, Tu Z. Kinetics modeling and occupancy studies of a novel C-11 PET tracer for VAChT in nonhuman primates. Nucl Med Biol. 2016 Feb;43(2):131-9. doi: 10.1016/j.nucmedbio.2015.11.003. Epub 2015 Nov 7. PubMed PMID: 26872437; PubMed Central PMCID: PMC4753027.

6: Kitamura Y, Kozaka T, Miwa D, Uno I, Azim MA, Ogawa K, Taki J, Kinuya S, Shiba K. Synthesis and evaluation of a new vesamicol analog o-[(11)C]methyl-trans-decalinvesamicol as a PET ligand for the vesicular acetylcholine transporter. Ann Nucl Med. 2016 Feb;30(2):122-9. doi: 10.1007/s12149-015-1039-6. Epub 2015 Nov 25. PubMed PMID: 26608176.

7: Shen B, James ML, Andrews L, Lau C, Chen S, Palner M, Miao Z, Arksey NC, Shuhendler AJ, Scatliffe S, Kaneshige K, Parsons SM, McCurdy CR, Salehi A, Gambhir SS, Chin FT. Further validation to support clinical translation of [(18)F]FTC-146 for imaging sigma-1 receptors. EJNMMI Res. 2015 Dec;5(1):49. doi: 10.1186/s13550-015-0122-2. Epub 2015 Sep 17. PubMed PMID: 26384292; PubMed Central PMCID: PMC4573970.

8: Nassenstein C, Wiegand S, Lips KS, Li G, Klein J, Kummer W. Cholinergic activation of the murine trachealis muscle via non-vesicular acetylcholine release involving low-affinity choline transporters. Int Immunopharmacol. 2015 Nov;29(1):173-80. doi: 10.1016/j.intimp.2015.08.007. Epub 2015 Aug 13. PubMed PMID: 26278668.

9: Tu Z, Zhang X, Jin H, Yue X, Padakanti PK, Yu L, Liu H, Flores HP, Kaneshige K, Parsons SM, Perlmutter JS. Synthesis and biological characterization of a promising F-18 PET tracer for vesicular acetylcholine transporter. Bioorg Med Chem. 2015 Aug 1;23(15):4699-709. doi: 10.1016/j.bmc.2015.05.058. Epub 2015 Jun 5. PubMed PMID: 26138195; PubMed Central PMCID: PMC4524497.

10: Barthel C, Sorger D, Deuther-Conrad W, Scheunemann M, Schweiger S, Jäckel P, Roghani A, Steinbach J, Schüürmann G, Sabri O, Brust P, Wenzel B. New systematically modified vesamicol analogs and their affinity and selectivity for the vesicular acetylcholine transporter - A critical examination of the lead structure. Eur J Med Chem. 2015 Jul 15;100:50-67. doi: 10.1016/j.ejmech.2015.05.033. Epub 2015 May 22. PubMed PMID: 26071858.

11: Zou Q, Leung SW, Vanhoutte PM. Transient Receptor Potential Channel Opening Releases Endogenous Acetylcholine, which Contributes to Endothelium-Dependent Relaxation Induced by Mild Hypothermia in Spontaneously Hypertensive Rat but Not Wistar-Kyoto Rat Arteries. J Pharmacol Exp Ther. 2015 Aug;354(2):121-30. doi: 10.1124/jpet.115.223693. Epub 2015 Jun 9. PubMed PMID: 26060231.

12: Bergman S, Estrada S, Hall H, Rahman R, Blomgren A, Larhed M, Svedberg M, Thibblin A, Wångsell F, Antoni G. Synthesis and labeling of a piperazine-based library of ¹¹C-labeled ligands for imaging of the vesicular acetylcholine transporter. J Labelled Comp Radiopharm. 2014 Jun 30;57(8):525-32. doi: 10.1002/jlcr.3208. Epub 2014 Jul 3. PubMed PMID: 24991704.

13: Azim MA, Kozaka T, Uno I, Miwa D, Kitamura Y, Ogawa K, Makino A, Kiyono Y, Shiba K. The potential of o-bromo-trans-decalinvesamicol as a new PET ligand for vesicular acetylcholine transporter imaging. Synapse. 2014 Oct;68(10):445-53. doi: 10.1002/syn.21756. Epub 2014 Jul 4. PubMed PMID: 24953217.

14: Bader S, Klein J, Diener M. Choline acetyltransferase and organic cation transporters are responsible for synthesis and propionate-induced release of acetylcholine in colon epithelium. Eur J Pharmacol. 2014 Jun 15;733:23-33. doi: 10.1016/j.ejphar.2014.03.036. Epub 2014 Mar 31. PubMed PMID: 24698650.

15: Nishiyama S, Ohba H, Kobashi T, Nakamasu Y, Nakao H, Ogata T, Kitashoji T, Tsukada H. Development of novel PET probe [¹¹C](R,R)HAPT and its stereoisomer [¹¹C](S,S)HAPT for vesicular acetylcholine transporter imaging: a PET study in conscious monkey. Synapse. 2014 Jul;68(7):283-92. doi: 10.1002/syn.21743. Epub 2014 Apr 12. PubMed PMID: 24687885.

16: Petrou M, Frey KA, Kilbourn MR, Scott PJ, Raffel DM, Bohnen NI, Müller ML, Albin RL, Koeppe RA. In vivo imaging of human cholinergic nerve terminals with (-)-5-(18)F-fluoroethoxybenzovesamicol: biodistribution, dosimetry, and tracer kinetic analyses. J Nucl Med. 2014 Mar;55(3):396-404. doi: 10.2967/jnumed.113.124792. Epub 2014 Jan 30. PubMed PMID: 24481024.

17: Kilbourn MR. PET radioligands for the vesicular transporters for monoamines and acetylcholine. J Labelled Comp Radiopharm. 2013 Mar-Apr;56(3-4):167-71. doi: 10.1002/jlcr.2998. Review. PubMed PMID: 24285322.

18: Rodrigues HA, Fonseca Mde C, Camargo WL, Lima PM, Martinelli PM, Naves LA, Prado VF, Prado MA, Guatimosim C. Reduced expression of the vesicular acetylcholine transporter and neurotransmitter content affects synaptic vesicle distribution and shape in mouse neuromuscular junction. PLoS One. 2013 Nov 8;8(11):e78342. doi: 10.1371/journal.pone.0078342. eCollection 2013. PubMed PMID: 24260111; PubMed Central PMCID: PMC3832638.

19: Kozaka T, Uno I, Kitamura Y, Miwa D, Anwar-Ul Azim M, Ogawa K, Shiba K. Regional brain imaging of vesicular acetylcholine transporter using o-[125 I]iodo-trans-decalinvesamicol as a new potential imaging probe. Synapse. 2014 Mar;68(3):107-13. doi: 10.1002/syn.21720. Epub 2013 Nov 15. PubMed PMID: 24174343.

20: Ogawa K, Kanbara H, Kiyono Y, Kitamura Y, Kiwada T, Kozaka T, Kitamura M, Mori T, Shiba K, Odani A. Development and evaluation of a radiobromine-labeled sigma ligand for tumor imaging. Nucl Med Biol. 2013 May;40(4):445-50. doi: 10.1016/j.nucmedbio.2013.02.008. Epub 2013 Mar 23. PubMed PMID: 23528561.