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. 2014 Jul 18;11(9):3145–3163. doi: 10.1021/mp500334z

Table 1. Overview of Thermochemical and Structural Investigations of M, C, D and Their HCl Saltsa.

compd anhydrates hydrates
Morphine (M) M-I° M-II M-1H
Kofler and Kofler2830 mp 240 °Cb (dec.c) mp 197 °C existence of a hydrate
Kuhnert-Brandstaetter31 mp 245–255 °C mp 197 °C dehy.d 115–140 °C
CSD Refcode family34 Guguta et al.35,e   MORPHM37,38
MORPIN0136 MORPIN39,f
Codeine (C) C-I°   C-1H
Kofler and Kofler29,30 mp 155 °C   mp 62–68 °C
Kuhnert-Brandstaetter31 mp 156 °C   dehy.d
CSD Refcode family34 ZZZTSE4043   ZZZTZQ (unit cell)40
ZZZTZQ 01(without H)42
Ethylmorphine (D) D-I°   D-1H
Kuhnert-Brandstaetter31 Sluggish melting, softening    
Morphine HCl (MCl) MCl-I° MCl-II MCl-3H
Kofler and Kofler29,30 mp > 300 °C  (dec.c)   trihydrate
Lindpainter32 mp 295–300 °C mp 280–284 °C  
Kuhnert-Brandstaetter31 mp 285–320 °C   dehy.d at 80 °C
CSD Refcode family34 Guguta et al.35,e   MORPHC45
EFASAH44
Codeine HCl (CCl) CCl-I°   CCl-2H
Kuhnert-Brandstaetter31 280–292 °C (dec.c)   partial melting at 165–170 °C
inhom. melting 140–160 °Cg
Kuhnert-Brandstaetter33 290 °C (N2 purge)   mp 140–150 °C (hom.i)
CSD Refcode family34 ZZZRFQ46,h    
Ethylmorphine HCl (DCl) DCl-I   DCl-2H
Kuhnert-Brandstaetter31 170–174 °C   148–155 °C (viscous melt)
Kuhnert-Brandstaetter33     mp 122–125 °C
a

Anhydrate forms are denoted with roman numerals and hydrates according to stoichiometry, e.g., 2H indicates a dihydrate (see also section 1 of the Supporting Information).

b

The same phase exhibits different morphologies.

c

dec: decomposition.

d

dehy: dehydration.

e

Structure solved from PXRD data, not in the Cambridge Structural Database (CSD34).

f

Unit cell parameters reported for anhydrous morphine correspond to those of the monohydrate, as previously noted by Guguta et al.35

g

inhom: inhomogeneous, the authors have corrected the dihdyrate melting point to 140–160 °C.33 In earlier publications, liquefication of the compound was incorrectly described as the melting event of the hydrate31,47

h

No atomic coordinates.

i

hom: homogeneous.