MedKoo Cat#: 522646 | Name: AP-18

Description:

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

AP-18 is a channel blocker which reversibly inhibits TRPA1 (IC50 = 3.1 and 4.5 µM, human and mouse, respectively). AP-18 inhibited cholinergic twitch responses evoked by electrical field stimulation of cholinergic nerves as well as contractions in response to acetylcholine and histamine in the guinea pig small intestine. AP-18 (30 µmol/l) blocked spontaneous contractions of longitudinal strips of human jejunum.

Chemical Structure

AP-18
AP-18
CAS#55224-94-7

Theoretical Analysis

MedKoo Cat#: 522646

Name: AP-18

CAS#: 55224-94-7

Chemical Formula: C11H12ClNO

Exact Mass: 209.0607

Molecular Weight: 209.67

Elemental Analysis: C, 63.01; H, 5.77; Cl, 16.91; N, 6.68; O, 7.63

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
AP-18; AP 18; AP18.
IUPAC/Chemical Name
(2E,3E)-4-(4-chlorophenyl)-3-methylbut-3-en-2-one oxime
InChi Key
MHTJEUOFLVQMCL-NJHPPEEMSA-N
InChi Code
InChI=1S/C11H12ClNO/c1-8(9(2)13-14)7-10-3-5-11(12)6-4-10/h3-7,14H,1-2H3/b8-7+,13-9+
SMILES Code
ClC1=CC=C(/C=C(C)/C(C)=N/O)C=C1
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, not in water
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).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 209.67 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Kunkler PE, Zhang L, Pellman JJ, Oxford GS, Hurley JH. Sensitization of the trigeminovascular system following environmental irritant exposure. Cephalalgia. 2015 Nov;35(13):1192-201. doi: 10.1177/0333102415574845. Epub 2015 Feb 27. PubMed PMID: 25724913. 2: Bartho L, Sándor Z, Kelemen D, Papp R, Benko R. Smooth muscle-depressant activity of AP-18, a putative TRPA1 antagonist in the guinea pig intestine. Pharmacology. 2014;94(3-4):131-4. doi: 10.1159/000366023. Epub 2014 Sep 18. PubMed PMID: 25247599. 3: Cheah EY, Burcham PC, Mann TS, Henry PJ. Acrolein relaxes mouse isolated tracheal smooth muscle via a TRPA1-dependent mechanism. Biochem Pharmacol. 2014 May 1;89(1):148-56. doi: 10.1016/j.bcp.2014.02.009. Epub 2014 Feb 19. PubMed PMID: 24561178. 4: Morales-Ramírez P, Vallarino-Kelly T, Cruz-Vallejo V. Kinetics of micronucleus induction and cytotoxicity caused by distinct antineoplastics and alkylating agents in vivo. Toxicol Lett. 2014 Jan 30;224(3):319-25. doi: 10.1016/j.toxlet.2013.11.012. Epub 2013 Nov 21. Review. PubMed PMID: 24269717. 5: Biringerova Z, Gavliakova S, Brozmanova M, Tatar M, Hanuskova E, Poliacek I, Plevkova J. The effects of nasal irritant induced responses on breathing and cough in anaesthetized and conscious animal models. Respir Physiol Neurobiol. 2013 Dec 1;189(3):588-93. doi: 10.1016/j.resp.2013.08.003. Epub 2013 Aug 30. PubMed PMID: 23994043. 6: Maione S, Costa B, Piscitelli F, Morera E, De Chiaro M, Comelli F, Boccella S, Guida F, Verde R, Ortar G, Di Marzo V. Piperazinyl carbamate fatty acid amide hydrolase inhibitors and transient receptor potential channel modulators as "dual-target" analgesics. Pharmacol Res. 2013 Oct;76:98-105. doi: 10.1016/j.phrs.2013.07.003. Epub 2013 Aug 2. PubMed PMID: 23911581. 7: Valan AM, Asha KR, Duraipandiyan V, Ignacimuthu S, Agastian P. Characterization and phylogenetic analysis of novel polyene type antimicrobial metabolite producing actinomycetes from marine sediments: Bay of Bengal, India. Asian Pac J Trop Biomed. 2012 Oct;2(10):803-10. doi: 10.1016/S2221-1691(12)60233-0. PubMed PMID: 23569851; PubMed Central PMCID: PMC3609223. 8: Kimura Y, Mikami Y, Osumi K, Tsugane M, Oka J, Kimura H. Polysulfides are possible H2S-derived signaling molecules in rat brain. FASEB J. 2013 Jun;27(6):2451-7. doi: 10.1096/fj.12-226415. Epub 2013 Feb 14. PubMed PMID: 23413359. 9: Andersson DA, Gentry C, Bevan S. TRPA1 has a key role in the somatic pro-nociceptive actions of hydrogen sulfide. PLoS One. 2012;7(10):e46917. doi: 10.1371/journal.pone.0046917. Epub 2012 Oct 11. PubMed PMID: 23071662; PubMed Central PMCID: PMC3469557. 10: Hernández-Arias AN, Rodríguez-Méndez BG, López-Callejas R, Alcántara-Díaz D, Valencia-Alvarado R, Mercado-Cabrera A, Peña-Eguiluz R, Muñoz-Castro AE, Barocio SR, de la Piedad-Beneitez A. Inactivation of Escherichia coli in water by pulsed dielectric barrier discharge in coaxial reactor. J Water Health. 2012 Sep;10(3):371-9. doi: 10.2166/wh.2012.132. PubMed PMID: 22960481. 11: Taylor AK, Cao W, Vora KP, De La Cruz J, Shieh WJ, Zaki SR, Katz JM, Sambhara S, Gangappa S. Protein energy malnutrition decreases immunity and increases susceptibility to influenza infection in mice. J Infect Dis. 2013 Feb 1;207(3):501-10. doi: 10.1093/infdis/jis527. Epub 2012 Sep 4. PubMed PMID: 22949306. 12: Cao DS, Zhong L, Hsieh TH, Abooj M, Bishnoi M, Hughes L, Premkumar LS. Expression of transient receptor potential ankyrin 1 (TRPA1) and its role in insulin release from rat pancreatic beta cells. PLoS One. 2012;7(5):e38005. doi: 10.1371/journal.pone.0038005. Epub 2012 May 31. PubMed PMID: 22701540; PubMed Central PMCID: PMC3365106. 13: Brozmanova M, Mazurova L, Ru F, Tatar M, Kollarik M. Comparison of TRPA1-versus TRPV1-mediated cough in guinea pigs. Eur J Pharmacol. 2012 Aug 15;689(1-3):211-8. doi: 10.1016/j.ejphar.2012.05.048. Epub 2012 Jun 7. PubMed PMID: 22683866; PubMed Central PMCID: PMC4667741. 14: Kubasov IV, Dobretsov M. Two types of extracellular action potentials recorded with narrow-tipped pipettes in skeletal muscle of frog, Rana temporaria. J Physiol. 2012 Jun 15;590(12):2937-44. doi: 10.1113/jphysiol.2012.230813. Epub 2012 Apr 23. PubMed PMID: 22526885; PubMed Central PMCID: PMC3448157. 15: Saluja P, Yelchuri RK, Sohal SK, Bhagat G, Paramjit, Prasad GS. Torulaspora indica a novel yeast species isolated from coal mine soils. Antonie Van Leeuwenhoek. 2012 May;101(4):733-42. doi: 10.1007/s10482-011-9687-6. Epub 2011 Dec 27. PubMed PMID: 22200779. 16: Rodríguez-Reyes R, Morales-Ramírez P. The in vivo induction of sister chromatid exchange by the demethylating agent 5-aza-2'-deoxycytidine. Mutagenesis. 2011 Jul;26(4):551-4. doi: 10.1093/mutage/ger015. Epub 2011 Mar 30. PubMed PMID: 21454325. 17: Fernandes ES, Russell FA, Spina D, McDougall JJ, Graepel R, Gentry C, Staniland AA, Mountford DM, Keeble JE, Malcangio M, Bevan S, Brain SD. A distinct role for transient receptor potential ankyrin 1, in addition to transient receptor potential vanilloid 1, in tumor necrosis factor α-induced inflammatory hyperalgesia and Freund's complete adjuvant-induced monarthritis. Arthritis Rheum. 2011 Mar;63(3):819-29. doi: 10.1002/art.30150. PubMed PMID: 21360511. 18: Heitkemper T, Hofmann T, Phan NQ, Ständer S. Aquagenic pruritus: associated diseases and clinical pruritus characteristics. J Dtsch Dermatol Ges. 2010 Oct;8(10):797-804. doi: 10.1111/j.1610-0387.2010.07463.x. Epub 2010 Jun 8. English, German. PubMed PMID: 20546386. 19: Chen C, Takahashi K, Yoshida A, Takizawa Y, Lee Y, Nakui M, Doi H, Takebayashi Y, Fukumoto M, Yamada T, Katagiri H, Oka Y, Satoh J. Characterization of a novel murine preadipocyte line, AP-18, isolated from subcutaneous tissue: analysis of adipocyte-related gene expressions. Cell Biol Int. 2010 Feb 22;34(3):293-9. doi: 10.1042/CBI20090063. PubMed PMID: 19947910. 20: Hu H, Tian J, Zhu Y, Wang C, Xiao R, Herz JM, Wood JD, Zhu MX. Activation of TRPA1 channels by fenamate nonsteroidal anti-inflammatory drugs. Pflugers Arch. 2010 Mar;459(4):579-92. doi: 10.1007/s00424-009-0749-9. Epub 2009 Nov 4. PubMed PMID: 19888597; PubMed Central PMCID: PMC2828537.