| DISCOVERED BY | H | C | N | O | |
|---|---|---|---|---|---|
| Wöhler, 1844 | Cotarnine | 12 | 13 | 1 | 3 |
| Formed by oxidizing narcotine; soluble in water. | |||||
| Hesse, 1871 | 1. HYDROCOTARNINE | 12 | 15 | 1 | 3 |
| Crystallizable, alkaline, volatile at 100°. | |||||
| Matthiessen and Wright, 1869 | Apomorphine | 17 | 17 | 1 | 2 |
| From morphine, by hydrochloric acid. Colourless, amorphous, turning green by exposure to air; emetic. | |||||
| Wright, 1871 | Desoxymorphine | 17 | 19 | 1 | 2 |
| Sertürner, 1816 | 2. MORPHINE | 17 | 19 | 1 | 3 |
| Crystallizable, alkaline, levogyre. | |||||
| Pelletier and Thibouméry, 1835 | 3. PSEUDOMORPHINE | 17 | 19 | 1 | 4 |
| Crystallizes with H₂O; does not unite even with acetic acid. | |||||
| Matthiessen and Burnside, 1871 | Apocodeine | 18 | 19 | 1 | 2 |
| From codeine by chloride of zinc; amorphous, emetic. | |||||
| Wright, 1871 | Desoxycodeine | 18 | 21 | 1 | 2 |
| Robiquet, 1832 | 4. CODEINE | 18 | 21 | 1 | 3 |
| Crystallizable, alkaline, soluble in water. | |||||
| Matthiessen and Foster, 1868 | Nornarcotine | 19 | 17 | 1 | 7 |
| Thibouméry, 1835 | 5. THEBAINE | 19 | 21 | 1 | 3 |
| Crystallizable, alkaline, isomeric with buxine. | |||||
| Hesse, 1870 | Thebenine | 19 | 21 | 1 | 3 |
| Hesse, 1870 | Thebaicine | 19 | 21 | 1 | 3 |
| From thebaine or thebenine by hydrochloric acid. | |||||
| Hesse, 1871 | 6. PROTOPINE | 20 | 19 | 1 | 5 |
| Crystallizable, alkaline. | |||||
| Matthiessen and Foster, 1868 | Methylnornarcotine | 20 | 19 | 1 | 7 |
| Hesse, 1871 | Deuteropine | 20 | 21 | 1 | 5 |
| Not yet isolated. | |||||
| Hesse, 1870 | 7. LAUDANINE | 20 | 25 | 1 | 4 |
| An alkaloid which, as well as its salts, forms large crystals; turns orange by hydrochloric acid. | |||||
| Hesse, 1878 | 8. CODAMINE | 20 | 25 | 1 | 4 |
| Crystallizable, alkaline; can be sublimed; becomes green by nitric acid. | |||||
| Merck, 1848 | 9. PAPAVERINE | 21 | 21 | 1 | 4 |
| Crystallizable, also its hydrochlorate; sulphate in sulphuric acid precipitated by water. | |||||
| Hesse, 1865 | 10. RHŒADINE | 21 | 21 | 1 | 6 |
| Crystallizable, not distinctly alkaline; can be sublimed; occurs also in Papaver Rhœas. | |||||
| Hesse, 1865 | Rhœagenine | 21 | 21 | 1 | 6 |
| From rhœadine; Crystallizable, alkaline. | |||||
| Armstrong, 1871 | Dimethylnornarcotine | 21 | 21 | 1 | 7 |
| Hesse, 1870 | 11. MECONIDINE | 21 | 23 | 1 | 4 |
| Amorphous, alkaline, melts at 58°, not stable, the salts also easily altered. | |||||
| T. & H. Smith, 1864 | 12. CRYPTOPINE | 21 | 23 | 1 | 5 |
| Crystallizable, alkaline; salts tend to gelatinize; hydrochlorate crystallizes in tufts. | |||||
| Hesse, 1871 | 13. LAUDANOSINE | 21 | 27 | 1 | 4 |
| Crystallizable, alkaline. | |||||
| Derosne, 1803 | 14. NARCOTINE | 22 | 23 | 1 | 7 |
| Crystallizable, not alkaline; salts not stable. | |||||
| Hesse, 1870 | 15. LANTHOPINE | 23 | 25 | 1 | 4 |
| Microscopic crystals not alkaline, sparingly soluble in hot or cold spirit of wine, ether or benzol. | |||||
| Pelletier, 1832 | 16. NARCEINE | 23 | 29 | 1 | 9 |
| Crystallizable (as a hydrate), readily soluble in boiling water or in alkalis, levogyre. | |||||
| T. & H. Smith, 1868 | 17. GNOSCOPINE | 34 | 36 | 2 | 11 |
| Crystallizable, melts at 233°, soluble in chloroform and bisulphide of carbon, slightly so in benzol, not in ether. The salts have an acid reaction. | |||||
In the year 1826, Dublanc[261] observed in opium a peculiar substance having neither basic nor acid properties which was afterwards (1832) prepared in a state of purity by Couerbe. It has been called Opianyl or (by Couerbe) Meconine. It has the composition C₁₀H₁₀O₄ = C₆H₂·CH₂·O·CO(OCH₃)₂. Meconin forms prisms which fuse under water at 77° C. or per se at 110°, and distil at 155°; it dissolves in about 20 parts of boiling water, from which it may be readily crystallized. Meconin may be formed by heating narcotine with nitric acid.
An analogous substance Meconoiosin C₈H₁₀O₂ = C₆H₂·(OH)₂·(CH₃)₂, has been discovered in 1878 by T. and H. Smith. Meconoiosin is readily soluble in 27 parts of cold water, and melts at 88° C. When heated with slightly diluted sulphuric acid, and when the evaporation has reached a certain point, meconoiosin produces a deep red; with meconin the coloration is a beautiful green.
Proportion of peculiar constituents—The substances described in the foregoing section exist in opium in very variable proportion; and as it is on their presence, but especially that of morphine, that the value of the drug depends, the importance of exact estimation is evident.
Opium whether required for analysis or for pharmaceutical preparations has to be taken exclusively in the dry state. The amount of water it contains is so uncertain that the drug must be reduced to a fixed standard by complete desiccation at 100° C., before any given weight is taken.
Morphine—Guibourt[262] who analysed a large number of samples of opium, and whose skill and care in such research are not disputed, obtained from a sample of French opium produced near Amiens, 22·88 per cent. of morphine crystallized from spirit of wine. This percentage has not to our knowledge been ever exceeded. From another specimen produced in the same district he got 21·23 per cent., from a third 20·67. The lowest percentage from a French opium was 14·96,—in each case reckoned on material previously dried.
Chevallier extracted from opium grown by Aubergier at Clermont in the centre of France, 17·50 per cent. of morphine. Decharmes from a French opium obtained 17·6 per cent., and Biltz from a German opium 20 per cent. Opium produced in Württemberg sent to the Vienna Exhibition of 1873 afforded Hesse 12 to 15 per cent. of morphine; and opium from Silesia 9 to 10 per cent.[263]
A pure American opium collected in the State of Vermont yielded Proctor 15·75 per cent. of morphine and 2 percent of narcotine.[264]
The opium of Asia Minor furnishes very nearly the same proportions of morphine as that of Europe. The maximum recorded by Guibourt is 21·46 per cent. obtained from a Smyrna opium sold in Paris. The mean yield of 8 samples of opium sent by Della Sudda of Constantinople to the Paris Exhibition of 1855 was 14·78 per cent. The mean percentage of morphine afforded by 12 other samples of Turkey opium obtained from various sources was 14·66.
Chevallier[265] states that Smyrna opium, of which several cases were received by Merck of Darmstadt in 1845, afforded 12 to 13 per cent. of pure morphine reckoned upon the drug in its fresh and moist state.