α-Methylhistamine

α-Methylhistamine
Names
	IUPAC name 1-(3H-Imidazol-4-yl)propan-2-amine
	Systematic IUPAC name 1-(1H-Imidazol-4-yl)propan-2-amine
Identifiers
CAS Number	6986-90-9 ; 75614-87-8 (R) ; 75614-93-6 (S) ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:295965 ;
ChEMBL	ChEMBL116655 ;
ChemSpider	3489 ;
IUPHAR/BPS	1239;
MeSH	Alpha-methylhistamine
PubChem CID	3615; 156615 (R); 6603865 (S);
CompTox Dashboard (EPA)	DTXSID80990132 ;
	InChI InChI=1S/C6H11N3/c1-5(7)2-6-3-8-4-9-6/h3-5H,2,7H2,1H3,(H,8,9) Key: XNQIOISZPFVUFG-UHFFFAOYSA-N ; InChI=1/C6H11N3/c1-5(7)2-6-3-8-4-9-6/h3-5H,2,7H2,1H3,(H,8,9) Key: XNQIOISZPFVUFG-UHFFFAOYAW;
	SMILES CC(N)CC1=CNC=N1;
Properties
Chemical formula	C6H11N3
Molar mass	125.175 g·mol−1
log P	−0.346
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

α-Methylhistamine is a synthetic derivative and a selective histamine H₃ receptor agonist. It decreases blood pressure and heart rate in guinea pigs.^[2] The drug also has sedative and hypnotic effects in animals.^[3]^[4]^[5]^[6]

References

^ "Chemical Entities of Biological Interest (ChEBI)".
^ McLeod, RL; Gertner, SB; Hey, JA (1993). "Production by R-alpha-methylhistamine of a histamine H3 receptor-mediated decrease in basal vascular resistance in guinea-pigs". Br J Pharmacol. 110 (2): 553–558. doi:10.1111/j.1476-5381.1993.tb13846.x. PMC 2175947. PMID 7902173.
^ Thakkar MM (February 2011). "Histamine in the regulation of wakefulness". Sleep Med Rev. 15 (1): 65–74. doi:10.1016/j.smrv.2010.06.004. PMC 3016451. PMID 20851648.
^ Billiard M (June 2008). "Narcolepsy: current treatment options and future approaches". Neuropsychiatr Dis Treat. 4 (3): 557–566. doi:10.2147/ndt.s12160232 (inactive 6 October 2025). PMC 2526380. PMID 18830438. it was shown, as early as 1990, that oral administration of alpha-methylhistamine, a H3 receptor agonist, signifi cantly increased deep slow wave sleep, while that of thiopiramide, a H3 receptor antagonist, enhanced wakefulness in a marked and dose-dependent manner (Lin et al 1990).{{cite journal}}: CS1 maint: DOI inactive as of October 2025 (link)
^ Lin JS, Sakai K, Vanni-Mercier G, Arrang JM, Garbarg M, Schwartz JC, Jouvet M (July 1990). "Involvement of histaminergic neurons in arousal mechanisms demonstrated with H3-receptor ligands in the cat". Brain Res. 523 (2): 325–330. doi:10.1016/0006-8993(90)91508-e. PMID 2169324.
^ Monti JM, Jantos H, Boussard M, Altier H, Orellana C, Olivera S (December 1991). "Effects of selective activation or blockade of the histamine H3 receptor on sleep and wakefulness". Eur J Pharmacol. 205 (3): 283–287. doi:10.1016/0014-2999(91)90911-9. PMID 1667912.

[1] "Chemical Entities of Biological Interest (ChEBI)".

[2] McLeod, RL; Gertner, SB; Hey, JA (1993). "Production by R-alpha-methylhistamine of a histamine H3 receptor-mediated decrease in basal vascular resistance in guinea-pigs". Br J Pharmacol. 110 (2): 553–558. doi:10.1111/j.1476-5381.1993.tb13846.x. PMC 2175947. PMID 7902173.

[Thakkar2011-3] Thakkar MM (February 2011). "Histamine in the regulation of wakefulness". Sleep Med Rev. 15 (1): 65–74. doi:10.1016/j.smrv.2010.06.004. PMC 3016451. PMID 20851648.

[Billiard2008-4] Billiard M (June 2008). "Narcolepsy: current treatment options and future approaches". Neuropsychiatr Dis Treat. 4 (3): 557–566. doi:10.2147/ndt.s12160232 (inactive 6 October 2025). PMC 2526380. PMID 18830438. it was shown, as early as 1990, that oral administration of alpha-methylhistamine, a H3 receptor agonist, signifi cantly increased deep slow wave sleep, while that of thiopiramide, a H3 receptor antagonist, enhanced wakefulness in a marked and dose-dependent manner (Lin et al 1990).{{cite journal}}: CS1 maint: DOI inactive as of October 2025 (link)

[LinSakaiVanni-Mercier1990-5] Lin JS, Sakai K, Vanni-Mercier G, Arrang JM, Garbarg M, Schwartz JC, Jouvet M (July 1990). "Involvement of histaminergic neurons in arousal mechanisms demonstrated with H3-receptor ligands in the cat". Brain Res. 523 (2): 325–330. doi:10.1016/0006-8993(90)91508-e. PMID 2169324.

[MontiJantosBoussard1991-6] Monti JM, Jantos H, Boussard M, Altier H, Orellana C, Olivera S (December 1991). "Effects of selective activation or blockade of the histamine H3 receptor on sleep and wakefulness". Eur J Pharmacol. 205 (3): 283–287. doi:10.1016/0014-2999(91)90911-9. PMID 1667912.

[1]

[2]

[3]

[4]

[5]

[6]

See also

References