The Preparation of Porphyroxine from Opium

Abstract

Porphyroxine, a minor alkaloid from opium, is isolated by an extraction procedure, passed through Florid and alumina (basic and neutral) columns, and eluted with solvents of varying polarity. Porphyroxine from the chloroform and acetone fractions recrystallised from methanol/chloroform in ribbed plates, darkens at 218" and melts at 234-236" (decomp.) corresponding to CzzHz4NO7, or C,Hz4N07.

UHPLC–MS/MS quantitation of porphyroxine in opium and application of porphyroxine‐acetylated products as signature markers for heroin

“…Porphyroxine has also long been suspected of causing the slight red shade of opium latex that oozes after lancing poppy pods in Afghanistan in comparison to the white latex found in Mexico or Colombia. Academic research eluded porphyroxine alkaloid for a 100 or more years until Genest and Farmilo isolated it from opium and the structure was later elucidated using nuclear magnetic resonance spectroscopy (NMR) . Albeit a minor alkaloid, the phenolic ‐OH group of this tetracyclic compound makes it more susceptible to extraction along with morphine from opium and as a result, gets acetylated to neutral amides in the final heroin product, including compounds B , C , and N , O 8 ‐diacetylporphyroxine (DAP, 2–423 ) (Figure ).…”

“…Academic research eluded porphyroxine alkaloid for a 100 or more years until Genest and Farmilo isolated it from opium and the structure was later elucidated using nuclear magnetic resonance spectroscopy (NMR). 10,11 Albeit a minor alkaloid, the phenolic -OH group of this tetracyclic compound makes it more susceptible to extraction along with morphine from opium and as a result, gets acetylated to neutral amides in the final heroin product, including compounds B, C, and N, O 8 -diacetylporphyroxine (DAP, 2-423) (Figure 1). In the four decades of heroin profiling, the HSP results have always demonstrated higher amounts of B and C in SWA's crude heroin samples than any other types of heroin.…”

Characterization and origin of the ‘B’ and ‘C’ compounds in the acid/neutral forensic signatures of heroin – products from the acylation of porphyroxine and subsequent hydrolysis

“…Porphyroxine (1), sometimes referred to as Papaverrubine-D, is a rhoeadine alkaloid found at trace levels in the opium poppy, Papaver somniferum. It was first described and crudely isolated over 170 years ago by Merck, [11] and first isolated in a pure state by Genest and Farmilo; [12] its structure was elucidated in the 1960s via nuclear magnetic resonance spectroscopy (NMR). [13] Since the mid-1800s, rhoeadines and papaverrubines have been associated with opium characterization using strong acids, and porphyroxine has been employed forensically since the 1950s as an identification marker for raw opium.…”