D1CTI()NAI!V l)F 'I'lIK ACTIVK l'KINCIl'l,KS OF I'l.ANTS. 



Colour tests : 



Cloncentrated Isulphuvic acid, no coloration ; vapours of bBiizoic 



acid on warmiuw. 

 Concentrated hyumcM.j: ic acid, decomposes with formation of 



Ecgonine. 

 Per-iodic acid, minute fragment of alkaloid dissolved in A to 1 cc. 



concentrated sulphuric acid, then sodium periodate or per-iodic 



acid in small quantity (two or three times as much as alkaloid), 



jiroduces on gentle warming, Inigiit green changing to blue and 



violet, with evolution of violet, fumes (Vitali). 

 NoTK : Atropine, Thebaine, (Jlielidonine, and Corydaline give 



colour changes under these circumstances, but not same sequence. 



Reaction is really due to benzoic acid. 



(hi) DEXTRO-COCAINE A., UijH.iNO.,. Formed artificially from benzoyl- 

 chloriile aud dextro-methylecgonine (Einhorn and Marquardt). Oily 

 substance becoming crystalline ; M.P. 4;'>°. 



Soluble in alcohol (less so than ordinary Cocaine), in ether, benzene, 

 and petroleum spirit. 



Ui^sembles ordinary Cocaine (Laivo-cooaine) in chemical properties 

 and physiological action, but its anaesthetic effect is more transient. 



(li) ETHYL-COCAINE A., C,sH.,,NOj (Homo-cocaine, Cocethyline, lien- 

 zoyl-ethyleogonine). Prepared by ethylationof Benzoyl-ecgonine. Crys. 

 glassy prisms ; M.P. l()8°-10y°. 



Soluble HI alcohol aud ether ; not iu water. 



Weaker physiological action than Cocaine. 



(2) BENZOYL-ECGONINE A., C„;H,,,NOj . [CsH„N(C0On)()-C-H|iO]. 

 Occurs naturally, and produced by decomposition of Cocaine, which may 

 be reformed from it by methylation. Benzoyl-ecgoniiie is also prepared 

 by synthesis from benzoic anhydride and Ecgonine. Crystallizes with 

 4H.>0 in transparent prisms — M.P. variable (87-140°) — or in long needles 

 from chloroform. The hydrate in alcohol has tevo-rotatory power of 

 — 44"6''. Scarcely anaesthetic ; reaction neutral. 



Soluble in alcohol, wood spirit, hot acetone, hot water (with difficulty 

 colli), an I liot chloroform (crys. needles on cooling) ; scarcely in ether. 

 Reactions : 



Alkaline hydrates ) ^.^^^j^^_ 



Ammonia ) 



Gold chloride, pp. yellow crys., sol. hot alcohol, slightly in water. 



{■A) ECGONINE A., C^HuNO:, (C„H,;,X(0H)C00H ; Methyl-tetra- 

 hydro-pyriditie-/3-oxypropioiiic acidl. Occurs in the amorphous bases 

 obtained after separation of Cocaine, and producible (together with 

 Benzoyl-ecgonine and (Cocaine benzoate) from Cocaine by mere heating of 

 the aqueous solution to 80° (Hesse). Rhombic crystals with 1 molecule 

 H.,0 ; M.P. HW. or when anhydrous '211;'/ ; reaction neutral : taste slightly 

 bitter and siveet. 



Soluble very readily in water, with difficulty in absolute alcohol or 

 chlornfonii. and insoluble in ether or carbon bisulphide (Mussi). 



Reactions : 



Alkaline hydrates / ,. , 

 . ■ • dissolve. 



Ammonia \ 



[No pp. platinum chloride, the double salt being very soluble.] 

 Cold chloride to concentrated solution, yellow amorphous pp. 

 [No pp. o per cent, chromic acid solution.] 

 Phospho-molybdic acid, pp. yellow. 



lodo-potassic iodide, reddish-brown, becoming crystalline, micro- 

 scopic tufts, rhombic plates or prisms (Vitali), 1 in oOO for 

 crystals. 

 Treated with phosphoric pentachloride. anhydro-ecgonine is formed : 

 see (36). 



(3a) Dt'XTHO-ECGONINE A., C,,H,5N0.,; from preceding alkaloid by 

 heating with potash ; M.P. 257°; dextro rotatory. 



(■Ml) ANHYDRO-ECGONINE A.. C<,H,jN0,; from Ecgonine by heating 



with phosphorus pentachloride, or from Cocaine by heating to 140' with 



a solution of hydrochloric acid gas in glacial acetic acid ; crys. M.P. •Si:>'. 



Soluble in water and alcohol, but nul in ether, chloroform, benzene, or 



petroleum spirit. 



(4) CINNAMYL-ECGONINE A„ C,aH.,,NO,. May be prepared from 

 Ecgonine and Cinnamic anhydride, and derivable from Cinnamyl-cocaiiie 

 [see (a)], which occurs naturally. 



(;")) CINNAMYL-COCAINE A., C„H„:,NOj ; the methyl ether (ester) of the 

 preceding, or Cinnamyl-methyl-ecgonine. Occurs naturally (Giesel 

 obtained .') per cent., together with 15 per cent, of other bases besides 

 Coc.une, from a Java Coca) ; producible also by methylatioa of (4). 

 Crystalline ; M.V. UV. 



Soluble in ether and alcohol, but not in water. 



Odour of bitter almonds on treatment with potassium permanganate in 

 the cold. 



