Mepyramine

Structural formula
General
Non-proprietary name	Mepyramine
other names	N - (4-methoxybenzyl) - N ′, N ′ -dimethyl- N - (2-pyridinyl) -1,2-ethanediamine ( IUPAC ) ; Pyrilamine; Pyranisamine;
Molecular formula	C 17 H 23 N 3 O
Brief description	Liquid (mepyramine) or colorless to slightly yellowish powder (mepyramine maleate)
External identifiers / databases
EC number	202-102-2
ECHA InfoCard	100.001.912
PubChem	4992
ChemSpider	4818
DrugBank	DB06691
Wikidata	Q3800087
Drug information
ATC code	D04 AA02 ; R06 AC01 ;
Drug class	Antihistamines
properties
Molar mass	255.36 g · mol -1
density	1.014 g cm −3 (25 ° C)
Melting point	98-103 ° C (mepyramine maleate) ; 143-143.5 ° C (mepyramine hydrochloride) ;
boiling point	168-172 ° C (0.06 torr); 210 ° C (166.5 Pa);
pK s value	4; 8.9
solubility	4.818 g l −1 (mepyramine maleate, in water, pH 7.4, 37.5 ° C)
Refractive index	1.5760 - 1.5765 (25 ° C)
safety instructions
	Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
H and P phrases	H: 302-334
	P: 261-342 + 311
Toxicological data	23 mg kg −1 ( LD 50 , mouse , iv ) ; 220 mg kg −1 ( LD 50 , mouse , oral ) ; 950 mg kg −1 ( LD 50 , rat , oral ) ; 25 mg kg −1 ( LD 50 , mouse , iv , hydrochloride) ; 325 mg kg −1 ( LD 50 , mouse , oral , hydrochloride) ; 25 mg kg −1 ( LD 50 , mouse , iv , maleate) ; 220 mg kg −1 ( LD 50 , mouse , oral , maleate) ; 513 mg kg −1 ( LD 50 , rat , oral , maleate) ;
	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

Mepyramine is a chemical compound from the group of ethylenediamine derivatives ( ethylenediamines ). The substance is a drug from the first generation of antihistamines , which were synthesized from the 1940s. Mepyramine is used for allergic reactions such as insect bites or itching . The active ingredient was patented by Rhône-Poulenc in 1950 .

Presentation and extraction

Mepyramine can be obtained in a two-step synthesis. The first step is a reductive coupling of 2-aminopyridine with 4-methoxybenzaldehyde in formic acid . The resulting intermediate product is then reacted with 2-dimethylaminoethyl chloride after deprotonation with sodium amide .

Mode of action

Mepyramine belongs to the ethylene diamine class of active ingredients . In the body, it docks to the histamine H1 receptors and thus prevents the histamine from affecting the cell by means of competitive inhibition . In this way, it relieves itching, hives, and allergic reactions. However, it quickly penetrates the brain and can cause side effects such as drowsiness and drowsiness. Because of this, allergy drugs have been developed which, due to their very specific effects on the H1 receptors, do not get into the brain. The so-called antihistamines of the 2nd generation are the common means nowadays because they are considered to be better tolerated.

Properties and use

Mepyramine is a viscous, moderately water-soluble liquid and is therefore processed as the salt of maleic acid (mepyramine maleate) or hydrochloric acid (mepyramine hydrochloride ) in the manufacture of pharmaceuticals. Mepyramine maleate is a whitish to yellowish crystalline powder with very good solubility in water.

Mepyramine is applied externally as a gel, cream, spray or solution in combination with other active ingredients such as lidocaine . Orally it can be used in cold remedies and menstrual cramps.

Finished medicinal products

Stilex (CH), Parapic (CH)

Individual evidence

↑ ^a ^b ^c data sheet mepyramine / N, N-DIMETHYL-N ′ - (4-METHOXYBENZYL) -N ′ - (2-PYRIDYL) ETHYLENEDIAMINE from Sigma-Aldrich , accessed on December 22, 2015 ( PDF ).
↑ ^a ^b ^c Entry on mepyramine in Pharmawiki , accessed on August 3, 2018.
↑ ^a ^b ^c ^d ^e Entry on Pyrilamine in the DrugBank of the University of Alberta , accessed December 7, 2015.
^ Carl L. Yaws: The Yaws Handbook of Physical Properties for Hydrocarbons and Chemicals: Physical Properties for More Than 54,000 Organic and Inorganic Chemical Compounds, Coverage for C1 to C100 Organics and Ac to Zr Inorganics . Gulf Professional Publishing, 2015, ISBN 978-0-12-801146-1 ( books.google.com ).
↑ ^a ^b ^c ^d ^e ^f Entry on mepyramine. In: Römpp Online . Georg Thieme Verlag, accessed on July 14, 2019.
^ Maria Kuhnert-Brandstätter: Thermomicroscopy in the Analysis of Pharmaceuticals , Pergamon Press 1971, p. 396.
↑ ^a ^b C. P. Huttrer, C. Djerassi: Heterocyclic cardamines with antithistaminic activity. In: Journal of the American Chemical Society. Volume 68, Number 10, October 1946, pp. 1999-2002, PMID 21001124 .
^ NG Lordi, JE Christian: Physical properties and pharmacological activity: antihistaminics. In: Journal of the American Pharmaceutical Association. American Pharmaceutical Association. Volume 45, Number 5, May 1956, pp. 300-305, PMID 13319115 .
^ ^A ^b ^c ^d ^e ^f ^g ^h ⁱ A. Kleemann , J. Engel, B. Kutscher, D. Reichert: Pharmaceutical Substances - Synthesis, Patents, Applications , 4th edition (2001) Thieme-Verlag Stuttgart, ISBN 978-1 -58890-031-9 .
↑ Patent US2502151 : Dimethylaminoalkylamino antihistiminic compounds. Registered on May 15, 1946 , published on March 28, 1950 , applicant: Rhone Poulenc, inventor: Raymond Jacques Horclois. ‌
↑ hausmed.de: Mepyramine .
↑ External identifiers or database links to mepyramine maleate : CAS number: 59-33-6, EC number: 200-422-7, ECHA InfoCard: 100.000.384 , PubChem : 5284451 , ChemSpider : 4447518 , Wikidata : Q27287732 .
↑ External identifiers or database links for mepyramine hydrochloride : CAS number: 6036-95-9, EC number: 227-920-7, ECHA InfoCard: 100.025.382 , PubChem : 80139 , ChemSpider : 72388 , Wikidata : Q27262828 .

[Sigma-1] ta sheet mepyramine / N, N-DIMETHYL-N ′ - (4-METHOXYBENZYL) -N ′ - (2-PYRIDYL) ETHYLENEDIAMINE from Sigma-Aldrich , accessed on December 22, 2015 ( PDF ).

[pharmawiki-2] Entry on mepyramine in Pharmawiki , accessed on August 3, 2018.

[drugbank-3] Entry on Pyrilamine in the DrugBank of the University of Alberta , accessed December 7, 2015.

[4] Carl L. Yaws: The Yaws Handbook of Physical Properties for Hydrocarbons and Chemicals: Physical Properties for More Than 54,000 Organic and Inorganic Chemical Compounds, Coverage for C1 to C100 Organics and Ac to Zr Inorganics . Gulf Professional Publishing, 2015, ISBN 978-0-12-801146-1 ( books.google.com ).

[Roempp-5] ↑ ^a ^b ^c ^d ^e ^f Entry on mepyramine. In: Römpp Online . Georg Thieme Verlag, accessed on July 14, 2019.

[Kuhnert-Brandstätter-6] Maria Kuhnert-Brandstätter: Thermomicroscopy in the Analysis of Pharmaceuticals , Pergamon Press 1971, p. 396.

[Huttrer-7] C. P. Huttrer, C. Djerassi: Heterocyclic cardamines with antithistaminic activity. In: Journal of the American Chemical Society. Volume 68, Number 10, October 1946, pp. 1999-2002, PMID 21001124 .

[8] NG Lordi, JE Christian: Physical properties and pharmacological activity: antihistaminics. In: Journal of the American Pharmaceutical Association. American Pharmaceutical Association. Volume 45, Number 5, May 1956, pp. 300-305, PMID 13319115 .

[Kleemann-9] A ^b ^c ^d ^e ^f ^g ^h ⁱ A. Kleemann , J. Engel, B. Kutscher, D. Reichert: Pharmaceutical Substances - Synthesis, Patents, Applications , 4th edition (2001) Thieme-Verlag Stuttgart, ISBN 978-1 -58890-031-9 .

[10] Patent US2502151 : Dimethylaminoalkylamino antihistiminic compounds. Registered on May 15, 1946 , published on March 28, 1950 , applicant: Rhone Poulenc, inventor: Raymond Jacques Horclois. ‌

[hausmed-11] usmed.de: Mepyramine .

[12] External identifiers or database links to mepyramine maleate : CAS number: 59-33-6, EC number: 200-422-7, ECHA InfoCard: 100.000.384 , PubChem : 5284451 , ChemSpider : 4447518 , Wikidata : Q27287732 .

[13] External identifiers or database links for mepyramine hydrochloride : CAS number: 6036-95-9, EC number: 227-920-7, ECHA InfoCard: 100.025.382 , PubChem : 80139 , ChemSpider : 72388 , Wikidata : Q27262828 .