Chlorcyclizine free base

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

MedKoo CAT#: 330149

CAS#: 82-93-9 (free base)

Description: Chlorcyclizine is a first-generation antihistamine of the phenylpiperazine class marketed in the United States and certain other countries. It is used primarily to treat allergy symptoms such as rhinitis, urticaria, and pruritus, and may also be used as an antiemetic. In addition to its antihistamine effects, chlorcyclizine also has some anticholinergic, antiserotonergic, and local anesthetic properties. It also has been studied as a potential treatment for hepatitis C.

Chemical Structure

Chlorcyclizine free base

CAS# 82-93-9 (free base)

Instruction

Theoretical Analysis

MedKoo Cat#: 330149
Name: Chlorcyclizine free base
CAS#: 82-93-9 (free base)
Chemical Formula: C18H21ClN2
Exact Mass: 300.14
Molecular Weight: 300.830
Elemental Analysis: C, 71.87; H, 7.04; Cl, 11.78; N, 9.31

Price and Availability

Size	Price	Availability	Quantity
5mg	USD 275
10mg	USD 650
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Related CAS #: 1620-21-9 (HCl) 82-93-9 (free base)

Synonym: Di-Paralene, Mantadil, Pruresidine, Trihistan, Chlorcyclizine; Chlorcyclizine; Chlorcyclizine free base

IUPAC/Chemical Name: 1-((4-chlorophenyl)(phenyl)methyl)-4-methylpiperazine

InChi Key: WFNAKBGANONZEQ-UHFFFAOYSA-N

InChi Code: InChI=1S/C18H21ClN2/c1-20-11-13-21(14-12-20)18(15-5-3-2-4-6-15)16-7-9-17(19)10-8-16/h2-10,18H,11-14H2,1H3

SMILES Code: CN1CCN(C(C2=CC=C(Cl)C=C2)C3=CC=CC=C3)CC1

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

Shelf Life: >3 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: 2934.99.03.00

More Info:

Instruction:

View handling instruction

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 300.83 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

Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: He S, Xiao J, Dulcey AE, Lin B, Rolt A, Hu Z, Hu X, Wang AQ, Xu X, Southall N, Ferrer M, Zheng W, Liang TJ, Marugan JJ. Discovery, Optimization, and Characterization of Novel Chlorcyclizine Derivatives for the Treatment of Hepatitis C Virus Infection. J Med Chem. 2015 Nov 24. [Epub ahead of print] PubMed PMID: 26599718.

2: He S, Lin B, Chu V, Hu Z, Hu X, Xiao J, Wang AQ, Schweitzer CJ, Li Q, Imamura M, Hiraga N, Southall N, Ferrer M, Zheng W, Chayama K, Marugan JJ, Liang TJ. Repurposing of the antihistamine chlorcyclizine and related compounds for treatment of hepatitis C virus infection. Sci Transl Med. 2015 Apr 8;7(282):282ra49. doi: 10.1126/scitranslmed.3010286. PubMed PMID: 25855495.

3: Enright BP, Gu YZ, Snyder RD, Dugyala RR, Obert LA, Treinen KA, McIntyre BS, Veneziale RW. Effects of the histamine H1 antagonist chlorcyclizine on rat fetal palate development. Birth Defects Res B Dev Reprod Toxicol. 2010 Dec;89(6):474-84. doi: 10.1002/bdrb.20261. PubMed PMID: 21058326.

4: Kvisselgaard N. Chlorpromazine and chlorcyclizine in the prevention of postoperative nausea and vomiting. Acta Anaesth. Scandinav. 1958, 2, 153-162. Acta Anaesthesiol Scand. 2007 Sep;51(8):979-88; discussion 989-90. PubMed PMID: 17697290.

5: Dastidar SG, Ganguly K, Mahapatra SK, Dutta NK, Mazumdar K, Chakrabarty AN, Motohashi N. Pronounced inhibitory effect of chlorcyclizine (CCZ) in experimental hepatocarcinoma. In Vivo. 2006 Jan-Feb;20(1):97-102. PubMed PMID: 16433035.

6: Kandimalla KK, Donovan MD. Carrier mediated transport of chlorpheniramine and chlorcyclizine across bovine olfactory mucosa: implications on nose-to-brain transport. J Pharm Sci. 2005 Mar;94(3):613-24. PubMed PMID: 15666293.

7: Ho Y, Wu H, Wu S, Chen S, Kou H. Quantitative enantiomeric analysis of chlorcyclizine, hydroxyzine, and meclizine by capillary electrophoresis. Anal Bioanal Chem. 2003 Jul;376(6):859-63. Epub 2003 Jun 26. PubMed PMID: 12830360.

8: Brinkley LL, Morris-Wiman J. Effects of chlorcyclizine-induced glycosaminoglycan alterations on patterns of hyaluronate distribution during morphogenesis of the mouse secondary palate. Development. 1987 Aug;100(4):637-40. PubMed PMID: 2894970.

9: Brinkley LL, Morris-Wiman J. The effects of chlorcyclizine-induced glycosaminoglycan alterations on palatal mesenchyme-basal lamina relationships in the mouse. Am J Anat. 1986 Jul;176(3):379-89. PubMed PMID: 2874737.

10: Heyns CF. Failure of chlorcyclizine to induce cryptorchism in the pig fetus. S Afr Med J. 1985 Aug 17;68(4):212-3. PubMed PMID: 2863877.

11: Ashton MJ, Ashford A, Loveless AH, Riddell D, Salmon J, Stevenson GV. Heterocyclic analogues of chlorcyclizine with potent hypolipidemic activity. J Med Chem. 1984 Oct;27(10):1245-53. PubMed PMID: 6148419.

12: Reasor MJ, Heyneman CA, Walker ER. Chlorcyclizine--induced pulmonary phospholipidosis in rats. Res Commun Chem Pathol Pharmacol. 1982 Nov;38(2):235-46. PubMed PMID: 6131507.

13: Kacew S. Alterations in newborn and adult rat lung morphology and phospholipid levels after chlorcyclizine or chlorphentermine treatment. Toxicol Appl Pharmacol. 1982 Aug;65(1):100-8. PubMed PMID: 6128805.

14: Brinkley LL, Vickerman MM. The effects of chlorcyclizine-induced alterations of glycosaminoglycans on mouse palatal shelf elevation in vivo and in vitro. J Embryol Exp Morphol. 1982 Jun;69:193-213. PubMed PMID: 6126516.

15: Joshi VV, Balsara JJ, Jadhav JH, Chandorkar AG. Effect of L-histidine and chlorcyclizine on apomorphine-induced climbing behaviour and methamphetamine stereotypy in mice. Eur J Pharmacol. 1981 Feb 19;69(4):499-502. PubMed PMID: 6113966.

16: Wilk AL, King CT, Pratt RM. Chlorcyclizine induction of cleft palate in the rat: degradation of palatal glycosaminoglycans. Teratology. 1978 Oct;18(2):199-209. PubMed PMID: 31013.

17: Wilk AL, King CT, Pratt RM Jr. Enhancement of chlorcyclizine teratogenicity in the rat by coadministration of calcium chelating agents. Teratology. 1978 Oct;18(2):193-8. PubMed PMID: 31012.

18: Barnhart JW. The effect of chlorcyclizine on cholesterol metabolism in mice. Toxicol Appl Pharmacol. 1974 Feb;27(2):449-55. PubMed PMID: 4153110.

19: Kuntzman R, Jacobson M, Tsai I, Burns JJ, Burchall J, Koch A. Certain aspects of drug binding to nonplasma proteins as illustrated by studies with cyclizine, chlorcyclizine, and polymyxin B. Ann N Y Acad Sci. 1973 Nov 26;226:131-47. PubMed PMID: 4148961.

20: Waddell WJ. The distribution of chlorcyclizine-14C in pregnant mice. Drug Metab Dispos. 1973 May-Jun;1(3):598-601. PubMed PMID: 4149455.

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