HC-030031
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MedKoo CAT#: 522647

CAS#: 349085-38-7

Description: HC-030031 is a potent and selective TRPA1 antagonist, attenuates inflammatory- and neuropathy-induced mechanical hypersensitivity. HC-030031 antagonizes AITC- and formalin-evoked calcium influx with IC50 of 6.2 μM and 5.3 μM respectively.


Chemical Structure

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HC-030031
CAS# 349085-38-7

Theoretical Analysis

MedKoo Cat#: 522647
Name: HC-030031
CAS#: 349085-38-7
Chemical Formula: C18H21N5O3
Exact Mass: 355.1644
Molecular Weight: 355.398
Elemental Analysis: C, 60.83; H, 5.96; N, 19.71; O, 13.51

Price and Availability

Size Price Availability Quantity
10.0mg USD 250.0 2 Weeks
50.0mg USD 670.0 2 Weeks
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Synonym: HC-030031; HC 030031; HC030031.

IUPAC/Chemical Name: 2-(1,3-dimethyl-2,6-dioxo-1,2,3,6-tetrahydro-7H-purin-7-yl)-N-(4-isopropylphenyl)acetamide

InChi Key: HEQDZPHDVAOBLN-UHFFFAOYSA-N

InChi Code: InChI=1S/C18H21N5O3/c1-11(2)12-5-7-13(8-6-12)20-14(24)9-23-10-19-16-15(23)17(25)22(4)18(26)21(16)3/h5-8,10-11H,9H2,1-4H3,(H,20,24)

SMILES Code: O=C(NC1=CC=C(C(C)C)C=C1)CN2C=NC(N(C)C(N3C)=O)=C2C3=O

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

Product Data:

Biological target: HC-030031 is a potent and selective TRPA1 inhibitor, which antagonizes AITC- and formalin-evoked calcium influx with IC50s of 6.2±0.2 and 5.3±0.2 μM, respectively.
In vitro activity: Concentrations of HC-030031 from 0.3 to 60 μM were incubated with cells for 10 minutes prior to addition of an EC60 concentration of either cinnamaldehyde or AITC. HC-030031 dose-dependently blocked cinnamaldehyde- and AITC-induced calcium influx with IC50 values of 4.9 and 7.5 μM, respectively (data not shown). Reference: Mol Pain. 2008 Oct 27;4:48. https://pubmed.ncbi.nlm.nih.gov/18954467/
In vivo activity: Next, a possible role for TRPA1 in spinal nerve ligation induced neuropathic pain was investigated using HC-030031. By 6 weeks post surgery, rats with L5/L6 ligation displayed significant mechanical hypersensitivity. This hypersensitivity was significantly reversed by HC-030031 (24 and 41% for 100 and 300 mg/kg, respectively) and pregabalin (56%; RMANOVA, p < 0.003, Figure 3, panel A). Reference: Mol Pain. 2008 Oct 27;4:48. https://pubmed.ncbi.nlm.nih.gov/18954467/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMF 20.0 56.27
DMF:PBS (pH 7.2) (1:1) 0.5 1.41
DMSO 23.51 66.16

Preparing Stock Solutions

The following data is based on the product molecular weight 355.398 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
Formulation protocol: 1. Eid SR, Crown ED, Moore EL, Liang HA, Choong KC, Dima S, Henze DA, Kane SA, Urban MO. HC-030031, a TRPA1 selective antagonist, attenuates inflammatory- and neuropathy-induced mechanical hypersensitivity. Mol Pain. 2008 Oct 27;4:48. doi: 10.1186/1744-8069-4-48. PMID: 18954467; PMCID: PMC2584039.
In vitro protocol: 1. Eid SR, Crown ED, Moore EL, Liang HA, Choong KC, Dima S, Henze DA, Kane SA, Urban MO. HC-030031, a TRPA1 selective antagonist, attenuates inflammatory- and neuropathy-induced mechanical hypersensitivity. Mol Pain. 2008 Oct 27;4:48. doi: 10.1186/1744-8069-4-48. PMID: 18954467; PMCID: PMC2584039.
In vivo protocol: 1. Eid SR, Crown ED, Moore EL, Liang HA, Choong KC, Dima S, Henze DA, Kane SA, Urban MO. HC-030031, a TRPA1 selective antagonist, attenuates inflammatory- and neuropathy-induced mechanical hypersensitivity. Mol Pain. 2008 Oct 27;4:48. doi: 10.1186/1744-8069-4-48. PMID: 18954467; PMCID: PMC2584039.

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1: Sandor Z, Dekany A, Kelemen D, Bencsik T, Papp R, Bartho L. The TRPA1 Activator Allyl Isothiocyanate (AITC) Contracts Human Jejunal Muscle: Pharmacological Analysis. Basic Clin Pharmacol Toxicol. 2016 Mar 1. doi: 10.1111/bcpt.12574. [Epub ahead of print] PubMed PMID: 26928772.

2: Mendes SJ, Sousa FI, Pereira DM, Ferro TA, Pereira IC, Silva BL, Pinheiro AJ, Mouchrek AQ, Monteiro-Neto V, Costa SK, Nascimento JL, Grisotto MA, da Costa R, Fernandes ES. Cinnamaldehyde modulates LPS-induced systemic inflammatory response syndrome through TRPA1-dependent and independent mechanisms. Int Immunopharmacol. 2016 Feb 25;34:60-70. doi: 10.1016/j.intimp.2016.02.012. [Epub ahead of print] PubMed PMID: 26922677.

3: Ribeiro-Filho HV, de Souza Silva CM, de Siqueira RJ, Lahlou S, Dos Santos AA, Magalhães PJ. Biphasic cardiovascular and respiratory effects induced by β-citronellol. Eur J Pharmacol. 2016 Feb 9. pii: S0014-2999(16)30049-8. doi: 10.1016/j.ejphar.2016.02.025. [Epub ahead of print] PubMed PMID: 26872991.

4: Jian T, Yang N, Yang Y, Zhu C, Yuan X, Yu G, Wang C, Wang Z, Shi H, Tang M, He Q, Lan L, Wu G, Tang Z. TRPV1 and PLC Participate in Histamine H4 Receptor-Induced Itch. Neural Plast. 2016;2016:1682972. doi: 10.1155/2016/1682972. Epub 2015 Dec 24. PubMed PMID: 26819760; PubMed Central PMCID: PMC4706928.

5: Yamaguchi K, Ono K, Hitomi S, Ito M, Nodai T, Goto T, Harano N, Watanabe S, Inoue H, Miyano K, Uezono Y, Matoba M, Inenaga K. Distinct TRPV1- and TRPA1-based mechanisms underlying enhancement of oral ulcerative mucositis-induced pain by 5-fluorouracil. Pain. 2016 Jan 22. [Epub ahead of print] PubMed PMID: 26808144.

6: Nakamura T, Miyoshi N, Ishii T, Nishikawa M, Ikushiro S, Watanabe T. Activation of transient receptor potential ankyrin 1 by quercetin and its analogs. Biosci Biotechnol Biochem. 2016 Jan 25:1-6. [Epub ahead of print] PubMed PMID: 26806540.

7: Hamilton NB, Kolodziejczyk K, Kougioumtzidou E, Attwell D. Proton-gated Ca(2+)-permeable TRP channels damage myelin in conditions mimicking ischaemia. Nature. 2016 Jan 28;529(7587):523-7. doi: 10.1038/nature16519. Epub 2016 Jan 13. PubMed PMID: 26760212; PubMed Central PMCID: PMC4733665.

8: Fernandes ES, Russell FA, Alawi KM, Sand C, Liang L, Salamon R, Bodkin JV, Aubdool AA, Arno M, Gentry C, Smillie SJ, Bevan S, Keeble JE, Malcangio M, Brain SD. Environmental cold exposure increases blood flow and affects pain sensitivity in the knee joints of CFA-induced arthritic mice in a TRPA1-dependent manner. Arthritis Res Ther. 2016 Jan 11;18(1):7. doi: 10.1186/s13075-015-0905-x. PubMed PMID: 26754745; PubMed Central PMCID: PMC4718045.

9: Zhu L, Fujita T, Jiang CY, Kumamoto E. Enhancement by citral of glutamatergic spontaneous excitatory transmission in adult rat substantia gelatinosa neurons. Neuroreport. 2016 Feb 10;27(3):166-71. doi: 10.1097/WNR.0000000000000518. PubMed PMID: 26720890.

10: Sun W, Wang Z, Cao J, Cui H, Ma Z. Cold stress increases reactive oxygen species formation via TRPA1 activation in A549 cells. Cell Stress Chaperones. 2015 Dec 3. [Epub ahead of print] PubMed PMID: 26634370.

11: Wang XL, Tian B, Huang Y, Peng XY, Chen LH, Li JC, Liu T. Hydrogen sulfide-induced itch requires activation of Cav3.2 T-type calcium channel in mice. Sci Rep. 2015 Nov 25;5:16768. doi: 10.1038/srep16768. PubMed PMID: 26602811; PubMed Central PMCID: PMC4658482.

12: Jiang CY, Wang C, Xu NX, Fujita T, Murata Y, Kumamoto E. 1,8- and 1,4-cineole enhance spontaneous excitatory transmission by activating different types of TRP channels in the rat spinal substantia gelatinosa. J Neurochem. 2015 Nov 18. doi: 10.1111/jnc.13433. [Epub ahead of print] PubMed PMID: 26578070.

13: Kogure Y, Wang S, Tanaka KI, Hao Y, Yamamoto S, Nishiyama N, Noguchi K, Dai Y. Elevated H(2) O(2) levels in TNBS-induced colitis rats contributes to visceral hyperalgesia through interaction with the TRPA1 cation channel. J Gastroenterol Hepatol. 2015 Nov 17. doi: 10.1111/jgh.13226. [Epub ahead of print] PubMed PMID: 26574143.

14: Klafke JZ, da Silva MA, Rossato MF, de Prá SD, Rigo FK, Walker CI, Bochi GV, Moresco RN, Ferreira J, Trevisan G. Acute and chronic nociceptive phases observed in a rat hind paw ischemia/reperfusion model depend on different mechanisms. Pflugers Arch. 2016 Feb;468(2):229-41. doi: 10.1007/s00424-015-1746-9. Epub 2015 Oct 21. PubMed PMID: 26490459.

15: Xu ZH, Wang C, Fujita T, Jiang CY, Kumamoto E. Action of thymol on spontaneous excitatory transmission in adult rat spinal substantia gelatinosa neurons. Neurosci Lett. 2015 Oct 8;606:94-9. doi: 10.1016/j.neulet.2015.08.042. Epub 2015 Aug 24. PubMed PMID: 26314510.

16: Sinharoy P, Zhang H, Sinha S, Prudner BC, Bratz IN, Damron DS. Propofol restores TRPV1 sensitivity via a TRPA1-, nitric oxide synthase-dependent activation of PKCε. Pharmacol Res Perspect. 2015 Aug;3(4):e00153. doi: 10.1002/prp2.153. Epub 2015 Jun 11. PubMed PMID: 26171233; PubMed Central PMCID: PMC4492729.

17: Bencsik T, Sandor Z, Bartho L. High-Concentration Piperine: Capsaicin-Sensitive and -Insensitive Effects on Isolated Organs. Pharmacology. 2015;96(1-2):86-9. doi: 10.1159/000436976. Epub 2015 Jul 4. PubMed PMID: 26160506.

18: Tani M, Yazawa I, Ikeda K, Kawakami K, Onimaru H. Long-lasting facilitation of respiratory rhythm by treatment with TRPA1 agonist, cinnamaldehyde. J Neurophysiol. 2015 Aug;114(2):989-98. doi: 10.1152/jn.00282.2015. Epub 2015 Jun 24. PubMed PMID: 26108952; PubMed Central PMCID: PMC4725117.

19: 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.

20: Billeter AT, Galbraith N, Walker S, Lawson C, Gardner SA, Sarojini H, Galandiuk S, Polk HC Jr. TRPA1 mediates the effects of hypothermia on the monocyte inflammatory response. Surgery. 2015 Sep;158(3):646-54. doi: 10.1016/j.surg.2015.03.065. Epub 2015 Jun 6. PubMed PMID: 26054320.