[Histamine analogues with nicotine-like action. 11th communication: Structure-activity relationships among histamine analogues (author's transl)].
Structure-activity relationships between histamine and nicrotine are described. If alkyl groups are substituted on the primary amino group of the side chain in histamine the histamine-like action decreases stepwise. While N,N-diethylhistamine (I) clearly shows histamine-like activity, 4-(2-pyrrolidinoethyl)-imidazole (II), an analogue having a pyrrolidine ring in place of the diethylamino group, possesses, on the other hand, distinct nicotine-like properties. The ganglionic stimulation was investigated on the isolated ileum of the guinea-pig, as well as on the blood pressure of the narcotized rat. The nicotine-like effects remained as the imidazole ring was replaced with a pyridine or benzene ring. These results make it plausible to assume that the effect of nicotine-like acting substances is due to an angular conformation, corresponding to nicotine.
D000818:Animals; D001794:Blood Pressure / Q000187:drug effects; D006168:Guinea Pigs; D006632:Histamine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D066298:In Vitro Techniques; D008968:Molecular Conformation; D009119:Muscle Contraction / Q000187:drug effects; D009538:Nicotine / Q000494:pharmacology*; D051381:Rats; D013329:Structure-Activity Relationship
D009538:Nicotine; D006632:Histamine
Nikotinartig wirksame Histaminanalog. 11. Mitt.: Struktur-Wirkungs-Beziehung bei Histaminanaloga.