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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

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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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
Andrea Fiebig et al.
Journal of translational medicine, 21(1), 908-908 (2023-12-13)
Chronic itch (chronic pruritus) is a major therapeutic challenge that remains poorly understood despite the extensive recent analysis of human pruriceptors. It is unclear how the peripheral nervous system differentiates the signaling of non-histaminergic itch and pain. Here we used
Jeffrey R McArthur et al.
British journal of pharmacology, 176(13), 2264-2278 (2019-03-31)
T-type calcium (Cav 3) and transient receptor potential vanilloid-1 (TRPV1) channels play central roles in the control of excitability in the peripheral nervous system and are regarded as potential therapeutic pain targets. Modulators that either activate or inhibit TRPV1-mediated currents
Yuki Nishizawa et al.
Journal of neuroscience research, 96(5), 901-910 (2017-12-29)
T-type Ca2+ channels and TRPA1 are expressed in sensory neurons and both are associated with pain transmission, but their functional interaction is unclear. Here we demonstrate that pharmacological evidence of the functional relation between T-type Ca2+ channels and TRPA1 in
Andrew O Jo et al.
The Journal of physiology, 595(20), 6499-6516 (2017-08-03)
Retinal cells use vanilloid transient receptor potential (TRP) channels to integrate light-evoked signals with ambient mechanical, chemical and temperature information. Localization and function of the polymodal non-selective cation channel TRPV1 (transient receptor potential vanilloid isoform 1) remains elusive. TRPV1 is
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