6-Acetylmorphine: a natural product present in mammalian brain.
Recently, we described three substances in bovine hypothalamus, adrenal, and rat brain recognized by antisera raised against morphine, and we identified one as morphine and another as codeine by GC/MS. We now report the identification of the third immunoreactive (ir) morphinan from bovine brain as 6-acetylmorphine by chemical conversion to morphine, GC/MS, and high-resolution mass measurement. 6-Acetylmorphine has not previously been described as a natural product in plants or animals, but it has long been known as the metabolite in part responsible for the biological properties of heroin. However, we have excluded slaughter-house or laboratory contamination by any morphinan as well as derivation from the morphine in tissues during our procedures. 6-Acetylmorphine is known to be more potent than morphine in vivo chiefly by virtue of its greater penetration into the central nervous system. Should morphinans prove to have physiological functions in animals, the properties of 6-acetylmorphine make it ideal for fulfilling the role of a peripheral-to-central hormone.
Weitz
C J
CJ
Addiction Research Foundation, Palo Alto, CA 94304.
Lowney
L I
LI
Faull
K F
KF
Feistner
G
G
Goldstein
A
A
D000818:Animals; D001923:Brain Chemistry; D002417:Cattle; D002851:Chromatography, High Pressure Liquid; D008401:Gas Chromatography-Mass Spectrometry; D007031:Hypothalamus / Q000032:analysis; D009020:Morphine / Q000032:analysis / Q000378:metabolism; D009022:Morphine Derivatives / Q000032:analysis* / Q000378:metabolism; D051381:Rats
D009022:Morphine Derivatives; D009020:Morphine; C026979:6-O-monoacetylmorphine