Benzquinamide hydrochloride | CAS# 113-69-9 (HCl) | Anti-Emetic

MedKoo Cat#: 317315 | Name: Benzquinamide hydrochloride

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Benzquinamide hydrochloride is an antiemetic compound with antihistaminic, mild anticholinergic, and sedative properties. The mechanism of action is not known, but presumably benzquinamide works via antagonism of muscarinic acetycholine receptors and histamine H1 receptors.

Chemical Structure

Benzquinamide hydrochloride

CAS#113-69-9 (HCl)

Theoretical Analysis

MedKoo Cat#: 317315

Name: Benzquinamide hydrochloride

CAS#: 113-69-9 (HCl)

Chemical Formula: C22H33ClN2O5

Exact Mass: 0.0000

Molecular Weight: 440.96

Elemental Analysis: C, 59.92; H, 7.54; Cl, 8.04; N, 6.35; O, 18.14

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Related CAS #

63-12-7 (free base) 113-69-9 (HCl)

Synonym

Benzquinamide hydrochloride; Benzquinamide HCl; P-2647 hydrochloride; P-2647 HCl; P 2647 HCl; P2647 HCl; Benzquinamida;

IUPAC/Chemical Name

3-(diethylcarbamoyl)-9,10-dimethoxy-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinolin-2-yl acetate hydrochloride

InChi Key

JSZILQVIPPROJI-UHFFFAOYSA-N

InChi Code

InChI=1S/C22H32N2O5/c1-6-23(7-2)22(26)17-13-24-9-8-15-10-20(27-4)21(28-5)11-16(15)18(24)12-19(17)29-14(3)25/h10-11,17-19H,6-9,12-13H2,1-5H3

SMILES Code

[H]Cl.CC(OC1C(C(N(CC)CC)=O)CN2CCC3=CC(OC)=C(OC)C=C3C2C1)=O

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO, not in water

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 440.96 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

1: Gregori-Puigjané E, Setola V, Hert J, Crews BA, Irwin JJ, Lounkine E, Marnett L, Roth BL, Shoichet BK. Identifying mechanism-of-action targets for drugs and probes. Proc Natl Acad Sci U S A. 2012 Jul 10;109(28):11178-83. doi: 10.1073/pnas.1204524109. Epub 2012 Jun 18. PubMed PMID: 22711801; PubMed Central PMCID: PMC3396511. 2: Mazzanti R, Croop JM, Gatmaitan Z, Budding M, Steiglitz K, Arceci R, Arias IM. Benzquinamide inhibits P-glycoprotein mediated drug efflux and potentiates anticancer agent cytotoxicity in multidrug resistant cells. Oncol Res. 1992;4(8-9):359-65. PubMed PMID: 1362504. 3: Maurer H, Pfleger K. Identification and differentiation of alkylamine antihistamines and their metabolites in urine by computerized gas chromatography-mass spectrometry. J Chromatogr. 1988 Aug 19;430(1):31-41. PubMed PMID: 2905706. 4: Laszlo J. Nausea and vomiting as major complications of cancer chemotherapy. Drugs. 1983 Feb;25 Suppl 1:1-7. PubMed PMID: 6840017. 5: Nietsch P. [Dose-response relationship of intravenous administration of benzquinamide hydrochloride for suppression of cytostatic-induced emesis]. Arzneimittelforschung. 1983;33(12):1694-5. German. PubMed PMID: 6689400. 6: Niemegeers CJ. Antiemetic specificity of dopamine antagonists. Psychopharmacology (Berl). 1982;78(3):210-3. PubMed PMID: 6130555. 7: Neidhart JA, Gagen M, Young D, Wilson HE. Specific antiemetics for specific cancer chemotherapeutic agents: haloperidol versus benzquinamide. Cancer. 1981 Mar 15;47(6):1439-43. PubMed PMID: 7013968. 8: Coruzzi G, Scarpignato C, Zappia L, Bertaccini G. [Effect of benzquinamide on gastrointestinal motility]. Farmaco Prat. 1980 Sep;35(9):466-72. Italian. PubMed PMID: 6893823. 9: Smith DJ, Rushin JM, Urquilla PR, Rhee CW, Yoon HJ, Simpson FA, Srichomkuan T, Lee HS, Knapp RB. Cardiovascular effects of benzquinamide. Anesth Analg. 1979 May-Jun;58(3):189-94. PubMed PMID: 582237. 10: Hobbs DC, Connolly AG. Pharmacokinetics of benzquinamide in man. J Pharmacokinet Biopharm. 1978 Dec;6(6):477-85. PubMed PMID: 581593. 11: Amin MM, Ban TA, Lehmann HE. A standard-controlled clinical study with benzquinamide in the treatment of chronic schizophrenic patients. Psychopharmacol Bull. 1977 Jul;13(3):20-1. PubMed PMID: 329325. 12: Chapin JW, Wingard DW. Physostigmine reversal of benzquinamide-induced delirium. Anesthesiology. 1977 May;46(5):364-5. PubMed PMID: 576777. 13: Moertel CG, Schutt AJ, Hahn RG, O'Fallon JR. Oral benzquinamide in the treatment of nausea and vomiting. Clin Pharmacol Ther. 1975 Nov;18(5 Pt 1):554-7. PubMed PMID: 1102233. 14: Rose TE, Averbuch SD. Letter: Acute dystonic reaction due to benzquinamide. Ann Intern Med. 1975 Aug;83(2):231-2. PubMed PMID: 1173745. 15: Leander JD. Rate-dependent Effects of drugs. II. effects of some major tranquilizers on multiple fixed-ratio, fixed-interval schedule performance. J Pharmacol Exp Ther. 1975 May;193(2):689-700. PubMed PMID: 238028. 16: Kingston RS, Heurich AE, Thomas JS, Steen SN. Cardiovascular effects of benzquinamide in man. Acta Anaesthesiol Scand. 1975;19(3):187-92. PubMed PMID: 241192. 17: Mull TD, Smith TC. Comparison of the ventilatory effects of two antiemetics, benzquinamide and prochlorperazine. Anesthesiology. 1974 Jun;40(6):581-7. PubMed PMID: 4406574. 18: Kleibel F, Immich H. [Antiemetic effect of benzquinamide in generalized radiation reaction]. Ther Ggw. 1973 May;112(5):820 passim. German. PubMed PMID: 4740156. 19: Steen SN, Yates M. The effects of benzquinamide and prochlorperazine, separately and combined, on the human respiratory center. Anesthesiology. 1972 May;36(5):519-20. PubMed PMID: 5067296. 20: Lutz H, Immich H. Antiemetic effect of benzquinamide in postoperative vomiting. Curr Ther Res Clin Exp. 1972 Apr;14(4):178-84. PubMed PMID: 4623597.

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