BCTC

Product NameBCTC
CAS393514-24-4
MFC20H25ClN4O
MW372.89
EINECS
MOL File393514-24-4.mol

Chemical Properties

Melting point	150-152℃
Boiling point	561.6±50.0 °C(Predicted)
Density	1.229±0.06 g/cm3(Predicted)
storage temp.	Sealed in dry,Room Temperature
solubility	DMSO: >10mg/mL
pka	13.95±0.70(Predicted)
form	powder
color	white to beige
Sensitive	Light Sensitive
Stability	Stable for 2 years from date of purchase as supplied. Solutions in DMSO or ethanol may be stord at -20°C for up to 2 months.
InChI	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)
InChIKey	ROGUAPYLUCHQGK-UHFFFAOYSA-N
SMILES	N1(C(NC2=CC=C(C(C)(C)C)C=C2)=O)CCN(C2=NC=CC=C2Cl)CC1

Safety Information

Hazard Codes	Xn
Risk Statements	22
WGK Germany	3
Storage Class	11 - Combustible Solids
Hazard Classifications	Acute Tox. 4 Oral

Usage And Synthesis

Description

BCTC (393514-24-4) is a vanilloid receptor I (TRPV1) blocker, IC50 = 35 nM for capsaicin-induced and 6 nM for acid-induced TRPV1 activation. Displays analgesic activity in rat models of neuropathic pain. BCTC is orally active and cell permeable.

Uses

BCTC is a antagonists of TRPA1 and TRPV1, a non-selective cation channel gated by noxious heat, vanilloids and extracellular protons. BCTC inhibits both capsaicin and proton activation.

Definition

ChEBI: 1-piperazinecarboxamide, 4-(3-chloro-2-pyridinyl)-n-[4-(1,1-dimethylethyl)phenyl]- is a member of piperazines and a member of pyridines.

in vivo

BCTC (1-30 mg/kg; Oral gavage; Single dose) can inhibit inflammatory and neuropathic heat pain and mechanical hyperalgesia in Sprague-Dawley rats by targeting VR1, which has analgesic effect^[2].
BCTC (10-100 mg/kg; Oral gavage, Twice daily for 4 weeks) improves the insulin resistance and systemic glucose and lipid metabolism, and increase insulin secretion in diabetic ob/ob mice^[5].

Animal Model:	Capsaicin-induced Sprague-Dawley rats model^[2]
Dosage:	1 mg/kg, 3 mg/kg, 10 mg/kg, 30 mg/kg
Administration:	Oral gavage (p.o.), Single dose. Before capsaicin (HY-10448) treatment (30 μg; intraplantar injection; Single dose)
Result:	Inhibited capsaicin-mediated thermal hyperalgesia in a dose-dependent manner.

Animal Model:	Freund’s complete adjuvant (FCA) Sprague-Dawley rats model^[2]
Dosage:	1 mg/kg, 3 mg/kg, 10 mg/kg, 30 mg/kg
Administration:	Oral gavage (p.o.), Single dose. After 100 % FAC treatment (50 μL; intraplantar injection; Single dose)
Result:	Significantly reduced FAC-induced inflammation-related thermal pain and mechanical hyperalgesia, and extended the inhibitory effect of mechanical hyperalgesia to 6 h at high doses (10 mg/kg, 30 mg/kg).

Animal Model:	Partial sciatic nerve ligation Sprague-Dawley rats model^[2]
Dosage:	1 mg/kg, 3 mg/kg, 10 mg/kg, 30 mg/kg
Administration:	Oral gavage (p.o.), Single dose. After partial sciatic nerve ligation.
Result:	Reduced post-operative abnormal tactile pain and mechanical hyperalgesia in a dose-dependent manner.

Animal Model:	Particularly strong insulin resistance and hyperinsulinemia ob/ob mice model^[5]
Dosage:	10 mg/kg, 30 mg/kg, 100 mg/kg
Administration:	Oral gavage (p.o.); Twice daily for 4 weeks
Result:	Reduced plasma triglyceride and glucose area under the curve (AUC) level. Decreased calcitonin gene-related peptide (CGRP) levels in a dose-dependent manner.

storage

Room temperature

References

[1] KENNETH J VALENZANO. N-(4-tertiarybutylphenyl)-4-(3-chloropyridin-2-yl)tetrahydropyrazine -1(2H)-carbox-amide (BCTC), a novel, orally effective vanilloid receptor 1 antagonist with analgesic properties: I. in vitro characterization and pharmacokinetic properties.[J]. Journal of Pharmacology and Experimental Therapeutics, 2003, 306 1: 377-386. DOI:10.1124/jpet.102.045674
[2] JAMES D POMONIS. N-(4-Tertiarybutylphenyl)-4-(3-cholorphyridin-2-yl)tetrahydropyrazine -1(2H)-carbox-amide (BCTC), a novel, orally effective vanilloid receptor 1 antagonist with analgesic properties: II. in vivo characterization in rat models of inflammatory and neuropathic pain.[J]. Journal of Pharmacology and Experimental Therapeutics, 2003, 306 1: 387-393. DOI:10.1124/jpet.102.046268

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