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MedKoo Cat#: 551033 | Name: AMTB HCl
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Description:

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

AMTB is a novel TRPM8 channel blocker and is effective for pain and urinary diseases. For rats, AMTB (10 mg/kg) significantly attenuated reflex responses to noxious urinary bladder distension (UBD) to 5.42 and 56.51% of the maximal visceromotor reflex (VMR) response and pressor response, respectively. The ID50 value on VMR response was 2.42 +/- 0.46 mg/kg. AMTB can act on the bladder afferent pathway to attenuate the bladder micturition reflex and nociceptive reflex responses in the rat.

Chemical Structure

AMTB HCl
AMTB HCl
CAS#926023-82-7 (HCl)

Theoretical Analysis

MedKoo Cat#: 551033

Name: AMTB HCl

CAS#: 926023-82-7 (HCl)

Chemical Formula: C23H27ClN2O2S

Exact Mass: 430.1482

Molecular Weight: 430.99

Elemental Analysis: C, 64.10; H, 6.31; Cl, 8.23; N, 6.50; O, 7.42; S, 7.44

Price and Availability

Size Price Availability Quantity
25mg USD 250.00 2 Weeks
50mg USD 450.00 2 Weeks
100mg USD 750.00 2 Weeks
200mg USD 1,350.00 2 Weeks
500mg USD 2,650.00 2 Weeks
1g USD 3,850.00 2 Weeks
2g USD 6,250.00 2 Weeks
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Related CAS #
926068-88-4 (free base) 926023-82-7 (HCl)
Synonym
AMTB; AMTB hydrochloride; AMTB HCl;
IUPAC/Chemical Name
N-(3-Aminopropyl)-2-{[(3-methylphenyl) methyl]oxy}-N-(2-thienylmethyl)benzamide hydrochloride
InChi Key
UDXGBANGPYONOK-UHFFFAOYSA-N
InChi Code
InChI=1S/C23H26N2O2S.ClH/c1-18-7-4-8-19(15-18)17-27-22-11-3-2-10-21(22)23(26)25(13-6-12-24)16-20-9-5-14-28-20;/h2-5,7-11,14-15H,6,12-13,16-17,24H2,1H3;1H
SMILES Code
O=C(N(CCCN)CC1=CC=CS1)C2=CC=CC=C2OCC3=CC=CC(C)=C3.[H]Cl
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).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 430.99 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: Liu Y, Leng A, Li L, Yang B, Shen S, Chen H, Zhu E, Xu Q, Ma X, Shi P, Liu Y, Liu T, Li L, Li K, Zhang D, Xiao J. AMTB, a TRPM8 antagonist, suppresses growth and metastasis of osteosarcoma through repressing the TGFβ signaling pathway. Cell Death Dis. 2022 Mar 31;13(3):288. doi: 10.1038/s41419-022-04744-6. PMID: 35361751; PMCID: PMC8971393. 2: Das HK. Azotobacters as biofertilizer. Adv Appl Microbiol. 2019;108:1-43. doi: 10.1016/bs.aambs.2019.07.001. Epub 2019 Aug 28. PMID: 31495403. 3: Li XD, Lupo D, Zheng L, Winkler F. Structural and functional insights into the AmtB/Mep/Rh protein family. Transfus Clin Biol. 2006 Mar-Apr;13(1-2):65-9. doi: 10.1016/j.tracli.2006.02.014. Epub 2006 Mar 24. PMID: 16564194. 4: Khademi S, Stroud RM. The Amt/MEP/Rh family: structure of AmtB and the mechanism of ammonia gas conduction. Physiology (Bethesda). 2006 Dec;21:419-29. doi: 10.1152/physiol.00051.2005. PMID: 17119155. 5: Yakunin AF, Hallenbeck PC. AmtB is necessary for NH(4)(+)-induced nitrogenase switch-off and ADP-ribosylation in Rhodobacter capsulatus. J Bacteriol. 2002 Aug;184(15):4081-8. doi: 10.1128/JB.184.15.4081-4088.2002. PMID: 12107124; PMCID: PMC135213. 6: Mirandela GD, Tamburrino G, Hoskisson PA, Zachariae U, Javelle A. The lipid environment determines the activity of the Escherichia coli ammonium transporter AmtB. FASEB J. 2019 Feb;33(2):1989-1999. doi: 10.1096/fj.201800782R. Epub 2018 Sep 13. PMID: 30211659; PMCID: PMC6338640. 7: Blauwkamp TA, Ninfa AJ. Antagonism of PII signalling by the AmtB protein of Escherichia coli. Mol Microbiol. 2003 May;48(4):1017-28. doi: 10.1046/j.1365-2958.2003.03479.x. PMID: 12753193. 8: Paz-Yepes J, Herrero A, Flores E. The NtcA-regulated amtB gene is necessary for full methylammonium uptake activity in the cyanobacterium Synechococcus elongatus. J Bacteriol. 2007 Nov;189(21):7791-8. doi: 10.1128/JB.00404-07. Epub 2007 Aug 17. PMID: 17704220; PMCID: PMC2168756. 9: Moure VR, Siöberg CLB, Valdameri G, Nji E, Oliveira MAS, Gerdhardt ECM, Pedrosa FO, Mitchell DA, Seefeldt LC, Huergo LF, Högbom M, Nordlund S, Souza EM. The ammonium transporter AmtB and the PII signal transduction protein GlnZ are required to inhibit DraG in Azospirillum brasilense. FEBS J. 2019 Mar;286(6):1214-1229. doi: 10.1111/febs.14745. Epub 2019 Feb 12. PMID: 30633437. 10: Kume H, Tsukimoto M. TRPM8 channel inhibitor AMTB suppresses murine T-cell activation induced by T-cell receptor stimulation, concanavalin A, or external antigen re-stimulation. Biochem Biophys Res Commun. 2019 Feb 19;509(4):918-924. doi: 10.1016/j.bbrc.2019.01.004. Epub 2019 Jan 11. PMID: 30642628. 11: Boogerd FC, Ma H, Bruggeman FJ, van Heeswijk WC, García-Contreras R, Molenaar D, Krab K, Westerhoff HV. AmtB-mediated NH3 transport in prokaryotes must be active and as a consequence regulation of transport by GlnK is mandatory to limit futile cycling of NH4(+)/NH3. FEBS Lett. 2011 Jan 3;585(1):23-8. doi: 10.1016/j.febslet.2010.11.055. Epub 2010 Dec 8. PMID: 21134373. 12: Bousquet J, Agache I, Blain H, Jutel M, Ventura MT, Worm M, Del Giacco S, Benetos A, Bilo BM, Czarlewski W, Abdul Latiff AH, Al-Ahmad M, Angier E, Annesi- Maesano I, Atanaskovic-Markovic M, Bachert C, Barbaud A, Bedbrook A, Bennoor KS, Berghea EC, Bindslev-Jensen C, Bonini S, Bosnic-Anticevich S, Brockow K, Brussino L, Camargos P, Canonica GW, Cardona V, Carreiro-Martins P, Carriazo A, Casale T, Caubet JC, Cecchi L, Cherubini A, Christoff G, Chu DK, Cruz AA, Dokic D, El-Gamal Y, Ebisawa M, Eberlein B, Farrell J, Fernandez-Rivas M, Fokkens WJ, Fonseca JA, Gao Y, Gavazzi G, Gawlik R, Gelincik A, Gemicioğlu B, Gotua M, Guérin O, Haahtela T, Hoffmann-Sommergruber K, Hoffmann HJ, Hofmann M, Hrubisko M, Illario M, Irani C, Ispayeva Z, Ivancevich JC, Julge K, Kaidashev I, Khaitov M, Knol E, Kraxner H, Kuna P, Kvedariene V, Lauerma A, Le LTT, Le Moing V, Levin M, Louis R, Lourenco O, Mahler V, Martin FC, Matucci A, Milenkovic B, Miot S, Montella E, Morais-Almeida M, Mortz CG, Mullol J, Namazova-Baranova L, Neffen H, Nekam K, Niedoszytko M, Odemyr M, O'Hehir RE, Okamoto Y, Ollert M, Palomares O, Papadopoulos NG, Panzner P, Passalacqua G, Patella V, Petrovic M, Pfaar O, Pham- Thi N, Plavec D, Popov TA, Recto MT, Regateiro FS, Reynes J, Roller-Winsberger RE, Rolland Y, Romano A, Rondon C, Rottem M, Rouadi PW, Salles N, Samolinski B, Santos AF, S Sarquis F, Sastre J, M G A Schols J, Scichilone N, Sediva A, Shamji MH, Sheikh A, Skypala I, Smolinska S, Sokolowska M, Sousa-Pinto B, Sova M, Stelmach R, Sturm G, Suppli Ulrik C, Todo-Bom AM, Toppila-Salmi S, Tsiligianni I, Torres M, Untersmayr E, Urrutia Pereira M, Valiulis A, Vitte J, Vultaggio A, Wallace D, Walusiak-Skorupa J, Wang DY, Waserman S, Yorgancioglu A, Yusuf OM, Zernotti M, Zidarn M, Chivato T, Akdis CA, Zuberbier T, Klimek L. Management of anaphylaxis due to COVID-19 vaccines in the elderly. Allergy. 2021 Oct;76(10):2952-2964. doi: 10.1111/all.14838. PMID: 33811358; PMCID: PMC8251336. 13: Li Z, Liu X, Wang J, Wang Y, Zheng G, Lu Y, Zhao G, Wang J. Insight into the Molecular Mechanism of the Transcriptional Regulation of amtB Operon in Streptomyces coelicolor. Front Microbiol. 2018 Feb 20;9:264. doi: 10.3389/fmicb.2018.00264. PMID: 29515546; PMCID: PMC5826061. 14: Yapa KTDS, Deuis J, Peters AA, Kenny PA, Roberts-Thomson SJ, Vetter I, Monteith GR. Assessment of the TRPM8 inhibitor AMTB in breast cancer cells and its identification as an inhibitor of voltage gated sodium channels. Life Sci. 2018 Apr 1;198:128-135. doi: 10.1016/j.lfs.2018.02.030. Epub 2018 Feb 26. PMID: 29496495. 15: Wingreen NS. Ammonia Transport. EcoSal Plus. 2004 Dec;1(1). doi: 10.1128/ecosalplus.3.3.2.1. PMID: 26443371. 16: Baday S, Wang S, Lamoureux G, Bernèche S. Different hydration patterns in the pores of AmtB and RhCG could determine their transport mechanisms. Biochemistry. 2013 Oct 8;52(40):7091-8. doi: 10.1021/bi400015f. Epub 2013 Sep 24. PMID: 24021113. 17: Durand A, Merrick M. In vitro analysis of the Escherichia coli AmtB-GlnK complex reveals a stoichiometric interaction and sensitivity to ATP and 2-oxoglutarate. J Biol Chem. 2006 Oct 6;281(40):29558-67. doi: 10.1074/jbc.M602477200. Epub 2006 Jul 24. PMID: 16864585. 18: Javelle A, Thomas G, Marini AM, Krämer R, Merrick M. In vivo functional characterization of the Escherichia coli ammonium channel AmtB: evidence for metabolic coupling of AmtB to glutamine synthetase. Biochem J. 2005 Aug 15;390(Pt 1):215-22. doi: 10.1042/BJ20042094. PMID: 15876187; PMCID: PMC1184577. 19: Lashinger ES, Steiginga MS, Hieble JP, Leon LA, Gardner SD, Nagilla R, Davenport EA, Hoffman BE, Laping NJ, Su X. AMTB, a TRPM8 channel blocker: evidence in rats for activity in overactive bladder and painful bladder syndrome. Am J Physiol Renal Physiol. 2008 Sep;295(3):F803-10. doi: 10.1152/ajprenal.90269.2008. Epub 2008 Jun 18. PMID: 18562636. 20: Fong RN, Kim KS, Yoshihara C, Inwood WB, Kustu S. The W148L substitution in the Escherichia coli ammonium channel AmtB increases flux and indicates that the substrate is an ion. Proc Natl Acad Sci U S A. 2007 Nov 20;104(47):18706-11. doi: 10.1073/pnas.0709267104. Epub 2007 Nov 12. PMID: 17998534; PMCID: PMC2141841.