Mepyramine: Difference between revisions
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{{Drugbox | {{Drugbox | ||
| IUPAC_name = | | Verifiedfields = changed | ||
| verifiedrevid = 408591350 | |||
| IUPAC_name = ''N''-(4-methoxybenzyl)-''N<nowiki>'</nowiki>'',''N<nowiki>'</nowiki>''-dimethyl-''N''-pyridin-2-ylethane-1,2-diamine | |||
| image = Mepyramine.png | | image = Mepyramine.png | ||
<!--Clinical data--> | |||
| tradename = | |||
| Drugs.com = {{drugs.com|international|mepyramine}} | |||
| MedlinePlus = a606008 | |||
| pregnancy_category = | |||
| legal_status = | |||
| routes_of_administration = | |||
<!--Pharmacokinetic data--> | |||
| bioavailability = | |||
| protein_bound = | |||
| metabolism = | |||
| elimination_half-life = | |||
| excretion = | |||
<!--Identifiers--> | |||
| CASNo_Ref = {{cascite|correct|CAS}} | |||
| CAS_number_Ref = {{cascite|correct|??}} | |||
| CAS_number = 91-84-9 | | CAS_number = 91-84-9 | ||
| ATC_prefix | | CAS_supplemental = <br/>{{CAS|59-33-6}} (maleate) | ||
| ATC_suffix | | ATC_prefix = R06 | ||
| ATC_supplemental | | ATC_suffix = AC01 | ||
| PubChem | | ATC_supplemental = {{ATC|D04|AA02}} | ||
| DrugBank | | PubChem = 4992 | ||
| C=17 | H=23 | N=3 | O=1 | | IUPHAR_ligand = 1220 | ||
| DrugBank_Ref = {{drugbankcite|changed|drugbank}} | |||
| DrugBank = DB06691 | |||
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | |||
| ChemSpiderID = 4818 | |||
| UNII_Ref = {{fdacite|correct|FDA}} | |||
| UNII = HPE317O9TL | |||
| KEGG_Ref = {{keggcite|correct|kegg}} | |||
| KEGG = D08183 | |||
| ChEBI_Ref = {{ebicite|changed|EBI}} | |||
| ChEBI = 6762 | |||
| ChEMBL_Ref = {{ebicite|correct|EBI}} | |||
| ChEMBL = 511 | |||
<!--Chemical data--> | |||
| C=17 | H=23 | N=3 | O=1 | |||
| molecular_weight = 285.38 g/mol | | molecular_weight = 285.38 g/mol | ||
| | | smiles = O(c1ccc(cc1)CN(c2ncccc2)CCN(C)C)C | ||
| | | InChI = 1/C17H23N3O/c1-19(2)12-13-20(17-6-4-5-11-18-17)14-15-7-9-16(21-3)10-8-15/h4-11H,12-14H2,1-3H3 | ||
| | | InChIKey = YECBIJXISLIIDS-UHFFFAOYAS | ||
| | | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | ||
| | | StdInChI = 1S/C17H23N3O/c1-19(2)12-13-20(17-6-4-5-11-18-17)14-15-7-9-16(21-3)10-8-15/h4-11H,12-14H2,1-3H3 | ||
| | | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | ||
| StdInChIKey = YECBIJXISLIIDS-UHFFFAOYSA-N | |||
| synonyms = <small>''N''-[2-(dimethylamino)ethyl]-''N''-[(4-methoxyphenyl)methyl]pyridin-2-amine</small> | |||
| | |||
| | |||
}} | }} | ||
'''Mepyramine''' | __Notoc__ | ||
{{SI}} | |||
It is used in over-the-counter combination products | {{CMG}} | ||
==Overview== | |||
'''Mepyramine''', also known as '''pyrilamine''', is a [[Antihistamine#H1-receptor antagonists|first generation antihistamine]], targeting the [[Histamine H1 receptor|H<sub>1</sub> receptor]].<ref>{{cite journal | last1 = Parsons | first1 = Mike E. | last2 = Ganellin |first2 = C. Robin | title = Histamine and its receptors | journal = British Journal of Pharmacology | volume = 147 | pages = S127–S135 |date=January 2006 | pmid = 16402096 | doi = 10.1038/sj.bjp.0706440 | pmc = 1760721 | issue = S1}}</ref> However, it rapidly permeates the brain often causing [[drowsiness]]. It also has [[anticholinergic]] properties. It is used in over-the-counter combination products to treat the common cold and menstrual symptoms.<ref>[http://midol.com/menstrual_complete_caps.html#q1 Active Ingredients for Midol Complete]</ref> It is also the active ingredient of the topical antihistamine creams ''Anthisan'' and ''Neoantergan'', sold for the treatment of insect bites, stings, and nettle rash. | |||
==Synthesis== | |||
[[File:Pyrilamine synthesis.png |thumb|center|700px|Pyrilamine synthesis:<ref>R.J. Horclois, {{US Patent|2502151}} (1950).</ref><ref>{{Cite doi|10.1021/ja01214a037}}</ref><ref>D. Bovet, R. Horclois, F. Walthert, C.R. Soc. Biol., 138, 99 (1944).</ref>]] | |||
< | |||
< | |||
==See also== | |||
*[[Chloropyramine]] (chloro instead of methoxy) | |||
== References == | |||
{{Reflist|2}} | |||
{{Antipruritics}} | {{Antipruritics}} | ||
{{Antihistamines}} | {{Antihistamines}} | ||
{{Cholinergics}} | |||
{{Hallucinogens}} | |||
{{Histaminergics}} | |||
[[Category: | [[Category:Drug]] | ||
[[Category:Amines]] | |||
[[Category:Aromatic amines]] | |||
[[Category:H1 receptor antagonists]] | |||
[[Category:Phenol ethers]] | |||
[[Category:Pyridines]] | [[Category:Pyridines]] | ||
{{ | {{respiratory-system-drug-stub}} | ||
{{ | {{dermatologic-drug-stub}} |
Latest revision as of 12:46, 9 April 2015
Clinical data | |
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Synonyms | N-[2-(dimethylamino)ethyl]-N-[(4-methoxyphenyl)methyl]pyridin-2-amine |
AHFS/Drugs.com | International Drug Names |
MedlinePlus | a606008 |
ATC code | |
Identifiers | |
| |
CAS Number | |
PubChem CID | |
IUPHAR/BPS | |
DrugBank | |
ChemSpider | |
UNII | |
KEGG | |
ChEBI | |
ChEMBL | |
E number | {{#property:P628}} |
ECHA InfoCard | {{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value). |
Chemical and physical data | |
Formula | C17H23N3O |
Molar mass | 285.38 g/mol |
3D model (JSmol) | |
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(what is this?) (verify) |
WikiDoc Resources for Mepyramine |
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Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]
Overview
Mepyramine, also known as pyrilamine, is a first generation antihistamine, targeting the H1 receptor.[1] However, it rapidly permeates the brain often causing drowsiness. It also has anticholinergic properties. It is used in over-the-counter combination products to treat the common cold and menstrual symptoms.[2] It is also the active ingredient of the topical antihistamine creams Anthisan and Neoantergan, sold for the treatment of insect bites, stings, and nettle rash.
Synthesis
See also
- Chloropyramine (chloro instead of methoxy)
References
- ↑ Parsons, Mike E.; Ganellin, C. Robin (January 2006). "Histamine and its receptors". British Journal of Pharmacology. 147 (S1): S127–S135. doi:10.1038/sj.bjp.0706440. PMC 1760721. PMID 16402096.
- ↑ Active Ingredients for Midol Complete
- ↑ R.J. Horclois, Template:US Patent (1950).
- ↑ Template:Cite doi
- ↑ D. Bovet, R. Horclois, F. Walthert, C.R. Soc. Biol., 138, 99 (1944).
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Template:Dermatologic-drug-stub
- Pages with script errors
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- Drug
- Amines
- Aromatic amines
- H1 receptor antagonists
- Phenol ethers
- Pyridines