Quinisocaine

Structural formula
General
Non-proprietary name	Quinisocaine
other names	3-butyl-1- (2-dimethylamino-ethoxy) isoquinoline ( IUPAC ) ; Quinisocainum ( Latin ) ; Dimethisoquine ( USAN ) ; Quinisocaine;
Molecular formula	C 17 H 24 N 2 O (quinisocaine) ; C 17 H 24 N 2 O HCl (quinisocaine monohydrochloride) ;
External identifiers / databases
EC number	201-700-0
ECHA InfoCard	100.001.546
PubChem	6857
ChemSpider	6596
Wikidata	Q1478199
Drug information
ATC code	D04 AB05
Drug class	Local anesthetics
properties
Molar mass	272,39 g · mol -1 (quinisocaine)
Melting point	146 ° C (quinisocaine) ; 144–148 ° C (quinisocaine monohydrochloride) ;
boiling point	155–157 ° C (4 h Pa )
Refractive index	1.5486 (20 ° C)
safety instructions
	Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS hazard labeling ; no classification available
Toxicological data	8 mg kg −1 ( LD 50 , mouse , iv )
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

Quinisocaine ( INN ), also Dimethisoquine ( USAN ), is a local anesthetic that is used in dermatology for topical application for burning and itching (pruritus) with ano-rectal symptom complex. Quinisocaine was patented by Smith, Kline & French in 1952 .

Manufacturing

The molecule has an isoquinoline core. The starting point of the multi-stage chemical synthesis is α- n -butylphenethylamine.

effect

Research into the mechanism of action of this molecule suggests that it interacts lipophilically with a membrane protein of nerve cells. The mechanism is based on an inhibition of the nicotinic acetylcholine receptor .

Trade names

Haenal ^® acute cream from Strathmann GmbH & Co. KG , Germany
Isochinol ^® ointment from Vifor SA , ( Villars-sur-Glâne ), Switzerland

Individual evidence

↑ ^a ^b Entry on quinisocaine in the ChemIDplus database of the United States National Library of Medicine (NLM)
↑ ^a ^b ^c Entry on quinisocaine. In: Römpp Online . Georg Thieme Verlag, accessed on October 1, 2014.
↑ David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Physical Constants of Organic Compounds, pp. 3-186.
↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
↑ Ashutosh Kar: Medicinal Chemistry . Anshan Ltd, 2006, ISBN 978-1-904798-76-7 ( full text in Google Book Search).
^ Gentry CL, Lukas RJ: Local anesthetics noncompetitively inhibit function of four distinct nicotinic acetylcholine receptor subtypes . In: Journal of Pharmacology and Experimental Therapeutics . 299, No. 3, December 2001, pp. 1038-1048. PMID 11714893 .

[ChemIDplus-1] Entry on quinisocaine in the ChemIDplus database of the United States National Library of Medicine (NLM)

[RÖMPP_Online-2] Entry on quinisocaine. In: Römpp Online . Georg Thieme Verlag, accessed on October 1, 2014.

[CRC90_3_186-3] David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Physical Constants of Organic Compounds, pp. 3-186.

[NV-4] This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.

[5] Ashutosh Kar: Medicinal Chemistry . Anshan Ltd, 2006, ISBN 978-1-904798-76-7 ( full text in Google Book Search).

[pmid11714893-6] Gentry CL, Lukas RJ: Local anesthetics noncompetitively inhibit function of four distinct nicotinic acetylcholine receptor subtypes . In: Journal of Pharmacology and Experimental Therapeutics . 299, No. 3, December 2001, pp. 1038-1048. PMID 11714893 .