(±)-Verapamil hydrochloride

SKU: V0007

Category: API's & Intermediates

Synonyms: Manidon; 152-11-4
CAS-Number: C₂₇H₃₈N₂O₄ · HCl
Molecular Formula: 491.06
Molecular Weight

Product Data
Handling
Safety Information
Details

Specifications

Purity: ≥99% (Titration)
Identity: 1H-NMR
Appearance: White powder

Properties

Other: pKa: 8.92, pKb: 8.97
Melting Point: 142 °C (dec.)(lit.)
Solvents: methanol (50 mg/ml), ethanol, water

Handling Advice: Protect from light and moisture.
Use / Stability: Stable for at least 2 years after receipt when stored at +4°C.
Long Term Storage: +4°C
Short Term Storage: +4°C
Shipping: AMBIENT

Transportation: Packing Group III
RIDADR: UN2811 6.1
Signal word: Danger
GHS Symbol: GHS06
Precautionary statements: P261, P264, P270, P271, P280, P301 + P310, P302 + P352, P304 + P340, P312, P322, P330, P361, P363, P403 + P233, P405, P501
Hazard statements: H301, H311, H331

Description: Verapamil hydrochloride is an α-adrenergic receptor (α-AR) antagonist and calcium channel protein inhibitor that blocks the L-type Ca2+ channels in smooth and cardiac muscle cells. Verapamil is an antiarrhythmic agent and vasodilator known to reduce the renal clearance of digoxin and induce apoptosis in primary and metastatic colon adenocarcinoma human cell lines in vitro. It has been observed that verapamil can induce currents by itself, presumably by acting on the potassium and chloride leakage. Verapamil has also been used as an inhibitor of drug efflux pump proteins such as Mdr (P-glycoprotein). Verapamil is a substrate of CYP3A4 and CYP2C6. It is also used in fluorescent cell sorting for DNA content, as it blocks efflux of a variety of DNA-binding fluorophores such as Hoechst 33342. Recent research has shown verapamil to be an effective treatment for diabetes in animal models. Verapamil helps treat diabetes by limiting TXNIP expression.
InChi: InChI=1S/C27H38N2O4.ClH/c1-20(2)27(19-28,22-10-12-24(31-5)26(18-22)33-7)14-8-15-29(3)16-13-21-9-11-23(30-4)25(17-21)32-6
References: (1) A. Fleckenstein:Annu. Rev. Pharmacol. Toxicol. 17, 149 (1977) , (2) I.B. Shchepotin, et al.: Anticancer Res. 14, 1027 (1994) , (3) B.B. Lonsberry, et al.: Pharmacol. 49, 23 (1994) , (4) W.T. Bellamy: Annu. Rev. Pharmacol. Toxicol. 36, 161 (1996) , (5) T. Kantola, et al.: Clin. Pharmacol. Ther. 64, 177 (1998) , (6) M. Verschraagen, et al.: Pharmacol. Res. 40, 301 (1999) , (7) G. Xu, et al.: Diabetes. 61, 848 (2012)
InChi Key: DOQPXTMNIUCOSY-UHFFFAOYSA-N
Smiles: CN(CCC1=CC(OC)=C(OC)C=C1)CCCC(C(C)C)(C#N)C2=CC(OC)=C(OC)C=C2.Cl

Verapamil hydrochloride is an α-adrenergic receptor (α-AR) antagonist and calcium channel protein inhibitor that blocks the L-type Ca2+ channels in smooth and cardiac muscle cells. Verapamil is an antiarrhythmic agent and vasodilator known to reduce the renal clearance of digoxin and induce apoptosis in primary and metastatic colon adenocarcinoma human cell lines in vitro. It has been observed that verapamil can induce currents by itself, presumably by acting on the potassium and chloride leakage. Verapamil has also been used as an inhibitor of drug efflux pump proteins such as Mdr (P-glycoprotein). Verapamil is a substrate of CYP3A4 and CYP2C6. It is also used in fluorescent cell sorting for DNA content, as it blocks efflux of a variety of DNA-binding fluorophores such as Hoechst 33342. Recent research has shown verapamil to be an effective treatment for diabetes in animal models. Verapamil helps treat diabetes by limiting TXNIP expression.

SKU: V0007 Category: API's & Intermediates

Additional information

Additional information

Synonyms	Manidon
Purity	≥99% (Titration)
Appearance	White powder
CAS-Number	152-11-4
Molecular Formula	C27H38N2O4 · HCl
Molecular Weight	491.06
Identity	1H-NMR
Solvents	methanol (50 mg/ml), ethanol, water
Melting Point	142 °C (dec.)(lit.)
Other	pKa: 8.92, pKb: 8.97
Smiles	CN(CCC1=CC(OC)=C(OC)C=C1)CCCC(C(C)C)(C#N)C2=CC(OC)=C(OC)C=C2.Cl
InChi Key	DOQPXTMNIUCOSY-UHFFFAOYSA-N
Shipping	AMBIENT
Short Term Storage	+4°C
Long Term Storage	+4°C
Handling Advice	Protect from light and moisture.
Use / Stability	Stable for at least 2 years after receipt when stored at +4°C.
Hazard statements	H301, H311, H331
Precautionary statements	P261, P264, P270, P271, P280, P301 + P310, P302 + P352, P304 + P340, P312, P322, P330, P361, P363, P403 + P233, P405, P501
GHS Symbol	GHS06
Signal word	Danger
RIDADR	UN2811 6.1
Transportation	Packing Group III
References	(1) A. Fleckenstein:Annu. Rev. Pharmacol. Toxicol. 17, 149 (1977), (2) I.B. Shchepotin, et al.: Anticancer Res. 14, 1027 (1994), (3) B.B. Lonsberry, et al.: Pharmacol. 49, 23 (1994), (4) W.T. Bellamy: Annu. Rev. Pharmacol. Toxicol. 36, 161 (1996), (5) T. Kantola, et al.: Clin. Pharmacol. Ther. 64, 177 (1998), (6) M. Verschraagen, et al.: Pharmacol. Res. 40, 301 (1999), (7) G. Xu, et al.: Diabetes. 61, 848 (2012)
InChi	InChI=1S/C27H38N2O4.ClH/c1-20(2)27(19-28,22-10-12-24(31-5)26(18-22)33-7)14-8-15-29(3)16-13-21-9-11-23(30-4)25(17-21)32-6
Quantity	100 mg, 1 g, 5 g, Bulk