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 Kofler28−30 | 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 | ZZZTSE40−43 | 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 |
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).
The same phase exhibits different morphologies.
dec: decomposition.
dehy: dehydration.
Structure solved from PXRD data, not in the Cambridge Structural Database (CSD34).
Unit cell parameters reported for anhydrous morphine correspond to those of the monohydrate, as previously noted by Guguta et al.35
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
No atomic coordinates.
hom: homogeneous.