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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

Quality Level

100

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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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
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
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
Mauricio Guzmán et al.
Mucosal immunology, 11(5), 1441-1453 (2018-06-06)
Immunological interdependence between the two eyes has been reported for the cornea and the retina but not for the ocular mucosal surface. Intriguingly, patients frequently report ocular surface-related symptoms in the other eye after unilateral ocular surgery. Here we show
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
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