Crystal and molecular structure of 2-allyl-2′-hydroxy-5,9-dimethyl-6,7-benzomorphan hydrobromide monohydrate

The structure and absolute configuration of (+)-3-methoxy-N-methylmorphinan (dextromethorphan) hydrobromide monohydrate

“…Strain in the morphinan skeleton may explain why certain angles deviate from normal values but the strain is certainly less pronounced than in the morphine skeleton. This is also evident from the bond angles around the atoms C(11) and C(12) which in morphine, codeine and 7,8-dihydromorphines are heavily distorted [C(11)-C(12)-C(13) _~ 127; C(4)-C(12)-C(13) ~_ 109°], whereas in dextromethorphan and in 6,7-benzomorphanes (Karle, Gilardi, Fratini & Karle, 1969;Fedeli, Giacomello, Cerrini & Vaciago, 1970;Cochran & Abola, 1975), all of which lack the ether bridge, these angles are close to normal trigonal values. The O atom of the methoxy group of dextromethorphan is nearly coplanar with the aromatic ring but deviates towards C(4) so that the C(4)-C(3)-O angle is only 115.5 °.…”

Structural comparisons of meptazinol with opioid analgesics1

“…The initial atomic coordinates for seven of these opiates (ie morphine [14] , 3-O-methyletorphine [15] , azidomorphine [16] , Nallynormetazocine [17] , cyclazocine [18] , naloxone [19] , and nalbuphine [20] ) were obtained from published x-ray crystallographic data and modeled using the CRYSIN tool of SYBYL. The other two opiates, codeine and 6-hydroxylevalorphan, were constructed based on their analogues, the crystal structures of which were available in SYBYL.…”

Structural studies of substituted 6,7-benzomorphan compounds. I. The absolute configuration of (−)-2-cyclopropylmethyl-2'-hydroxy-5-ethyl-9,9-dimethyl-6,7-benzomorphan (gemazocine) hydrobromide

“…This study describes the structure of (-)-gemazocine.HBr (ACF Chemiefarma NV, 1970), which appears to be an antagonist of the narcotic analgesics, while its optical antipode has no activity at all (ACF Chemiefarma NV, private communication). The results can be compared with those for related benzomorphans that have been determined already (Karle, Gilardi, Fratini & Karle, 1969;Fedeli, Giacomello, Cerrini & Vaciago, 1970;Cochran & Abola, 1975) and which have in common the presence of one methyl group at the 9-position, whilst (-)-gemazocine.HBr has two methyl groups at this position. Special attention will be paid to the conformation of the N-C-C-C side chain, one of the most important features in defining the interaction with the opiate narcotic receptor.…”