N.ALPHA.-METHYLHISTAMINE DIHYDROCHLORIDE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C6H11N3.2ClH
Molecular Weight	198.094
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure of N.ALPHA.-METHYLHISTAMINE DIHYDROCHLORIDE

Structure Search

SMILES

Cl.Cl.CNCCC1=CN=CN1

InChI

InChIKey=AYUQICXJAMPXPF-UHFFFAOYSA-N

InChI=1S/C6H11N3.2ClH/c1-7-3-2-6-4-8-5-9-6;;/h4-5,7H,2-3H2,1H3,(H,8,9);2*1H

HIDE SMILES / InChI

Molecular Formula	C6H11N3
Molecular Weight	125.1716
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	ClH
Molecular Weight	36.461
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/24534036

alpha-N-methyl-histamine is a metabolite of histamine that plays an important role in several (patho) physiological processes. alpha-N-methyl-histamine is being a potent agonist of histamine H3 receptor can be used as an effective therapeutic alternative in migraine patients.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Histamine H3 receptor 46 Target ID: Q9QYN8 Gene ID: 85268.0 Gene Symbol: Hrh3 Target Organism: Rattus norvegicus (Rat) Sources: https://www.ncbi.nlm.nih.gov/pubmed/2161226	Agonist 2752		0.4 nM [Kd]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Migraine 107 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24534036	Preventing		Not Provided 511	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
What a Difference a Methyl Group Makes: The Selectivity of Monoamine Oxidase B Towards Histamine and N-Methylhistamine.	2017-02-24	28052533
N alpha methyl histamine versus propranolol in migraine prophylaxis.	2014-03	24534036
Review of commonly used clinical pathology parameters for general gastrointestinal disease with emphasis on small animals.	2014-01	24129757
Systematic analysis of histamine and N-methylhistamine concentrations in organs from two common laboratory mouse strains: C57Bl/6 and Balb/c.	2011-12	21912978
Characterization and tissue distribution of H3 histamine receptors in guinea pigs by N alpha-methylhistamine.	1990-05-16	2161226

Patents

Sample Use Guides

In Vivo Use Guide

in migraine prophylaxis: 1 to 3 ug twice a week

Route of Administration: Other

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Mon Mar 31 21:05:58 GMT 2025` Edited by `admin` on `Mon Mar 31 21:05:58 GMT 2025`
Record UNII	S6S98U0517
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

1H-IMIDAZOLE-4-ETHANAMINE, N-METHYL-, DIHYDROCHLORIDE

Preferred Name

English

N.ALPHA.-METHYLHISTAMINE DIHYDROCHLORIDE

Systematic Name

English

NAMH DIHYDROCHLORIDE

Common Name

English

N-METHYL-1H-IMIDAZOLE-4-ETHANAMINE DIHYDROCHLORIDE

Systematic Name

English

IMIDAZOLE, 4-(2-(METHYLAMINO)ETHYL)-, DIHYDROCHLORIDE

Common Name

English

IMIDAZOLE, 4(OR 5)-(2-METHYLAMINOETHYL)-, DIHYDROCHLORIDE

Common Name

English

1H-IMIDAZOLE-5-ETHANAMINE, N-METHYL-, HYDROCHLORIDE (1:2)

Systematic Name

English

N-METHYLHISTAMINE DIHYDROCHLORIDE

Systematic Name

English

Code System Code Type Description

CAS

16503-22-3