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SML0355

Sigma-Aldrich

BCTC

≥98% (HPLC)

Synonym(s):

4-(3-Chloro-2-pyridinyl)-N-[4-(1,1-dimethylethyl)phenyl]-1-piperazinecarboxamide

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About This Item

Empirical Formula (Hill Notation):
C20H25ClN4O
CAS Number:
393514-24-4
Molecular Weight:
372.89
MDL number:
MFCD08690556
UNSPSC Code:
12352200
PubChem Substance ID:
329825357
NACRES:
NA.77

Assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: >10 mg/mL

storage temp.

room temp

SMILES string

CC(C)(C)c1ccc(NC(=O)N2CCN(CC2)c3ncccc3Cl)cc1

InChI

1S/C20H25ClN4O/c1-20(2,3)15-6-8-16(9-7-15)23-19(26)25-13-11-24(12-14-25)18-17(21)5-4-10-22-18/h4-10H,11-14H2,1-3H3,(H,23,26)

InChI key

ROGUAPYLUCHQGK-UHFFFAOYSA-N

Application

BCTC or (4-Tertbutylphenyl)-4-(3-chloropyridin-2-Yl) tetrahydropyrazine-1(2H)-carbox-amide has been used as transient receptor potential melastatin 8 (TRPM8) antagonist to study its effects on proliferation and cell viability.

Biochem/physiol Actions

BCTC is a potent antagonist of the vanilloid receptor TRPV1. BCTC blocks capsaicin-induced contractions in a variety of smooth muscle tissues, including guinea pig ileum, bladder and trachea with no effects on capsaicin-sensitive, sensory neuron-mediated positive inotropy. The compound penetrates the CNS and has strong analgesic properties.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302

Precautionary Statements

P264 - P270 - P301 + P312 - P501

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Mayu Oshida et al.
Bioscience, biotechnology, and biochemistry, 81(5), 987-994 (2017-01-18)
Transient receptor potential vanilloid 1 (TRPV1) was identified as a receptor of capsaicin, which is a pungent ingredient in hot red peppers. Due to its relevance for nociception, a physiological and pharmacological study of TRPV1 has also been developed. Therefore
Mirjam J Eberhardt et al.
Scientific reports, 7(1), 12775-12775 (2017-10-08)
The irritant receptor TRPA1 was suggested to mediate analgesic, antipyretic but also pro-inflammatory effects of the non-opioid analgesic acetaminophen, presumably due to channel activation by the reactive metabolites parabenzoquinone (pBQ) and N-acetyl-parabenzoquinonimine (NAPQI). Here we explored the effects of these
Sulma I Mohammed et al.
Molecular oncology, 13(6), 1400-1418 (2019-04-27)
The leading cause of breast cancer-associated death is metastasis. In 80% of solid tumors, metastasis via the lymphatic system precedes metastasis via the vascular system. However, the molecular properties of tumor cells as they exit the primary tumor into the
Haipei Liu et al.
Inflammation, 41(4), 1266-1275 (2018-04-10)
Bronchial asthma is a chronic inflammatory airway disease that can be aggravated by cold air. However, its mechanism remains largely unknown. As a thermo-sensing cation channel, transient receptor potential melastatin 8 (TRPM8) can be activated by cold stimuli (8-22 °C) and
Miriam M Düll et al.
Pain, 160(11), 2497-2507 (2019-06-21)
The endogenous metabolite methylglyoxal (MG) accumulates in diabetic patients with neuropathic pain. Methylglyoxal could be a mediator of diabetes-induced neuropathic pain through TRPA1 activation and sensitization of the voltage-gated sodium channel subtype 1.8. In this study, we tested the algogenic
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