86:
508:
25:
365:
686:
Neilan CL, Husbands SM, Breeden S, Ko MC, Aceto MD, Lewis JW, et al. (September 2004). "Characterization of the complex morphinan derivative BU72 as a high efficacy, long-lasting mu-opioid receptor agonist".
407:
InChI=InChI=1S/C28H32N2O2/c1-25-17-26-11-12-28(25,32-3)24(29-23(25)18-7-5-4-6-8-18)27(26)13-14-30(2)22(26)15-19-9-10-20(31)16-21(19)27/h4-12,16,22-24,29,31H,13-15,17H2,1-3H3/t22-,23-,24+,25+,26-,27+,28+/m1/s1
43:
1080:
Husbands, S. M., Lewis, J. W. (December 1995). "Morphinan cyclic imines and pyrrolidines containing a constrained phenyl group: High affinity opioid agonists".
1123:
379:
994:
Zou R, Wang X, Li S, Chan HS, Vogel H, Yuan S (2022). "The role of metal ions in G protein-coupled receptor signalling and drug discovery".
1113:
399:
61:
101:
1118:
235:
830:"Computational insights into the G-protein-biased activation and inactivation mechanisms of the μ opioid receptor"
879:
Sena DM, Cong X, Giorgetti A (March 2021). "Ligand based conformational space studies of the μ-opioid receptor".
204:
454:
493:
446:
264:
953:
Huang W, Manglik A, Venkatakrishnan AJ, Laeremans T, Feinberg EN, Sanborn AL, et al. (August 2020).
582:
Huang W, Manglik A, Venkatakrishnan AJ, Laeremans T, Feinberg EN, Sanborn AL, et al. (August 2015).
195:
784:
595:
442:
150:
935:
904:
504:, since the compound binds reversibly, and preventing bond formation has no effect on affinity.
285:
1062:
1011:
976:
896:
861:
810:
753:
704:
668:
621:
477:
275:
724:"Opioid Antagonists from the Orvinol Series as Potential Reversal Agents for Opioid Overdose"
480:
of the active μ-opioid receptor, and is now widely used to model the activation process. The
224:
1089:
1052:
1042:
1003:
966:
927:
888:
851:
841:
800:
792:
743:
735:
722:
Disney A, Olson KM, Shafer AM, Moore SC, Anand JP, Traynor JR, et al. (November 2022).
696:
658:
648:
611:
603:
308:
159:
244:
922:
Munro TA (April 2020). "Revised (β-phenyl) stereochemistry of ultrapotent μ opioid BU72".
771:
Sounier R, Mas C, Steyaert J, Laeremans T, Manglik A, Huang W, et al. (August 2015).
481:
1031:"Reanalysis of a μ opioid receptor crystal structure reveals a covalent adduct with BU72"
1057:
1030:
788:
663:
640:
599:
856:
829:
805:
772:
748:
723:
616:
583:
639:
Zhao J, Elgeti M, O'Brien ES, Sár CP, Ei
Daibani A, Heng J, et al. (April 2024).
184:
1107:
1093:
939:
908:
552:
537:
497:
485:
85:
892:
739:
700:
450:
1047:
653:
971:
954:
931:
341:
215:
1015:
641:"Ligand efficacy modulates conformational dynamics of the µ-opioid receptor"
557:
507:
465:
1066:
980:
900:
865:
814:
773:"Propagation of conformational changes during μ-opioid receptor activation"
757:
708:
672:
625:
955:"Author Correction: Structural insights into μ-opioid receptor activation"
846:
796:
607:
547:
501:
458:
438:
170:
1007:
516:
426:
255:
77:
542:
532:
506:
461:
364:
355:
291:
828:
Cheng JX, Cheng T, Li WH, Liu GX, Zhu WL, Tang Y (January 2018).
496:. In the crystal structure, BU72 appears to bond to the receptor
137:)-3a-methoxy-3,14-dimethyl-2-phenyl-2,3,3a,6,7,11c-hexahydro-1
18:
457:, giving a stronger maximal effect than the standard full
881:
Biochimica et
Biophysica Acta (BBA) - General Subjects
584:"Structural insights into µ-opioid receptor activation"
39:
141:-6,11b-(epiminoethano)-3,5a-methanonaphthoindol-10-ol
353:
340:
307:
302:
274:
254:
234:
214:
203:
194:
169:
149:
92:
34:
may be too technical for most readers to understand
468:, with a slow onset and long duration of action.
464:. In animal studies, it was found to be a potent
387:CO12C=C34C1(C)(N235CCN(C)4Cc6ccc(O)cc56)c7ccccc7
183:
158:
445:with exceptionally high binding affinity and
8:
1082:Bioorganic & Medicinal Chemistry Letters
577:
575:
573:
76:
223:
84:
1056:
1046:
970:
855:
845:
804:
747:
662:
652:
615:
243:
62:Learn how and when to remove this message
46:, without removing the technical details.
569:
404:
384:
106:
75:
996:WIREs Computational Molecular Science
284:
263:
44:make it understandable to non-experts
7:
484:has recently been revised, with the
290:
1124:Heterocyclic compounds with 6 rings
511:BU72 original proposed structure ((
476:BU72 was used to produce the first
174:
429:used in pharmacological research.
14:
689:European Journal of Pharmacology
325:
319:
23:
412:Key:RGJHUVJQGAAZLK-GKTFKBBASA-N
500:, but this seems not to occur
331:
313:
1:
453:. It also has extremely high
1094:10.1016/0960-894X(95)00522-1
893:10.1016/j.bbagen.2020.129838
740:10.1021/acschemneuro.2c00464
701:10.1016/j.ejphar.2004.07.097
1114:Mu-opioid receptor agonists
1140:
1048:10.1186/s12915-023-01689-w
834:Acta Pharmacologica Sinica
654:10.1038/s41586-024-07295-2
303:Chemical and physical data
1029:Munro TA (October 2023).
972:10.1038/s41586-020-2542-z
932:10.1101/2020.04.01.020883
728:ACS Chemical Neuroscience
395:
375:
97:
83:
425:is an extremely potent
520:
1119:Nitrogen heterocycles
510:
16:Opioid analgesic drug
847:10.1038/aps.2017.158
797:10.1038/nature14680
789:2015Natur.524..375S
608:10.1038/nature14886
600:2015Natur.524..315H
80:
521:
1088:(24): 2969–2974.
1008:10.1002/wcms.1565
783:(7565): 375–378.
734:(21): 3108–3117.
594:(7565): 315–321.
478:crystal structure
443:μ-opioid receptor
420:
419:
366:Interactive image
72:
71:
64:
1131:
1098:
1097:
1077:
1071:
1070:
1060:
1050:
1026:
1020:
1019:
991:
985:
984:
974:
950:
944:
943:
919:
913:
912:
876:
870:
869:
859:
849:
825:
819:
818:
808:
768:
762:
761:
751:
719:
713:
712:
695:(1–2): 107–116.
683:
677:
676:
666:
656:
636:
630:
629:
619:
579:
449:, comparable to
368:
348:
333:
327:
321:
315:
294:
288:
267:
247:
227:
207:
187:
177:
176:
162:
88:
81:
79:
67:
60:
56:
53:
47:
27:
26:
19:
1139:
1138:
1134:
1133:
1132:
1130:
1129:
1128:
1104:
1103:
1102:
1101:
1079:
1078:
1074:
1028:
1027:
1023:
993:
992:
988:
952:
951:
947:
921:
920:
916:
878:
877:
873:
827:
826:
822:
770:
769:
765:
721:
720:
716:
685:
684:
680:
638:
637:
633:
581:
580:
571:
566:
529:
482:stereochemistry
474:
435:
416:
413:
408:
403:
402:
391:
388:
383:
382:
371:
346:
336:
330:
324:
318:
298:
270:
250:
230:
210:
190:
173:
165:
145:
142:
105:
104:
68:
57:
51:
48:
40:help improve it
37:
28:
24:
17:
12:
11:
5:
1137:
1135:
1127:
1126:
1121:
1116:
1106:
1105:
1100:
1099:
1072:
1021:
986:
945:
914:
871:
840:(1): 154–164.
820:
763:
714:
678:
631:
568:
567:
565:
562:
561:
560:
555:
550:
545:
540:
535:
528:
525:
473:
470:
434:
431:
418:
417:
415:
414:
411:
409:
406:
398:
397:
396:
393:
392:
390:
389:
386:
378:
377:
376:
373:
372:
370:
369:
361:
359:
351:
350:
344:
338:
337:
334:
328:
322:
316:
311:
305:
304:
300:
299:
297:
296:
280:
278:
272:
271:
269:
268:
260:
258:
252:
251:
249:
248:
240:
238:
232:
231:
229:
228:
220:
218:
212:
211:
209:
208:
200:
198:
192:
191:
189:
188:
180:
178:
167:
166:
164:
163:
155:
153:
147:
146:
144:
143:
108:
100:
99:
98:
95:
94:
90:
89:
70:
69:
31:
29:
22:
15:
13:
10:
9:
6:
4:
3:
2:
1136:
1125:
1122:
1120:
1117:
1115:
1112:
1111:
1109:
1095:
1091:
1087:
1083:
1076:
1073:
1068:
1064:
1059:
1054:
1049:
1044:
1040:
1036:
1032:
1025:
1022:
1017:
1013:
1009:
1005:
1001:
997:
990:
987:
982:
978:
973:
968:
965:(7820): E16.
964:
960:
956:
949:
946:
941:
937:
933:
929:
925:
918:
915:
910:
906:
902:
898:
894:
890:
887:(3): 129838.
886:
882:
875:
872:
867:
863:
858:
853:
848:
843:
839:
835:
831:
824:
821:
816:
812:
807:
802:
798:
794:
790:
786:
782:
778:
774:
767:
764:
759:
755:
750:
745:
741:
737:
733:
729:
725:
718:
715:
710:
706:
702:
698:
694:
690:
682:
679:
674:
670:
665:
660:
655:
650:
646:
642:
635:
632:
627:
623:
618:
613:
609:
605:
601:
597:
593:
589:
585:
578:
576:
574:
570:
563:
559:
556:
554:
553:M320 (opioid)
551:
549:
546:
544:
541:
539:
538:Buprenorphine
536:
534:
531:
530:
526:
524:
518:
514:
509:
505:
503:
499:
495:
494:configuration
491:
487:
483:
479:
471:
469:
467:
463:
460:
456:
452:
448:
444:
440:
432:
430:
428:
424:
410:
405:
401:
394:
385:
381:
374:
367:
363:
362:
360:
357:
352:
345:
343:
339:
312:
310:
306:
301:
293:
292:RCSB PDB
287:
282:
281:
279:
277:
273:
266:
265:ChEMBL4649916
262:
261:
259:
257:
253:
246:
242:
241:
239:
237:
233:
226:
222:
221:
219:
217:
213:
206:
202:
201:
199:
197:
193:
186:
182:
181:
179:
172:
168:
161:
157:
156:
154:
152:
148:
140:
136:
132:
128:
124:
120:
116:
112:
107:
103:
96:
91:
87:
82:
74:
66:
63:
55:
45:
41:
35:
32:This article
30:
21:
20:
1085:
1081:
1075:
1038:
1034:
1024:
999:
995:
989:
962:
958:
948:
923:
917:
884:
880:
874:
837:
833:
823:
780:
776:
766:
731:
727:
717:
692:
688:
681:
644:
634:
591:
587:
522:
512:
489:
486:phenyl group
475:
436:
433:Pharmacology
422:
421:
138:
134:
130:
126:
122:
118:
114:
110:
73:
58:
49:
33:
1035:BMC Biology
523:Synthesis:
451:carfentanil
437:BU72 is an
349: g·mol
160:173265-76-4
93:Identifiers
1108:Categories
1041:(1): 213.
564:References
498:covalently
354:3D model (
342:Molar mass
276:PDB ligand
245:KVN8RP2FQX
216:ChemSpider
196:IUPHAR/BPS
151:CAS Number
102:IUPAC name
52:March 2021
1016:1759-0876
940:215551137
909:229721515
558:TH-030418
515:)-phenyl
472:Chemistry
466:analgesic
185:137348291
1067:37817141
1058:10566028
981:32724208
901:33373630
866:29188799
815:26245377
758:36223082
709:15363957
673:38600384
664:11078757
626:26245379
527:See also
488:in the (
455:efficacy
441:for the
924:bioRxiv
857:5758664
806:4820006
785:Bibcode
749:9634796
617:4639397
596:Bibcode
548:BU08028
502:in vivo
459:agonist
447:potency
439:agonist
347:428.576
309:Formula
225:9662011
171:PubChem
38:Please
1065:
1055:
1014:
979:
959:Nature
938:
907:
899:
864:
854:
813:
803:
777:Nature
756:
746:
707:
671:
661:
645:Nature
624:
614:
588:Nature
517:epimer
427:opioid
380:SMILES
256:ChEMBL
1002:(2).
936:S2CID
905:S2CID
543:BU-48
533:7-PET
462:DAMGO
400:InChI
356:JSmol
283:VF1 (
1063:PMID
1012:ISSN
977:PMID
897:PMID
885:1865
862:PMID
811:PMID
754:PMID
705:PMID
669:PMID
622:PMID
423:BU72
286:PDBe
236:UNII
205:9363
133:,11c
129:,11b
78:BU72
1090:doi
1053:PMC
1043:doi
1004:doi
967:doi
963:584
928:doi
889:doi
852:PMC
842:doi
801:PMC
793:doi
781:524
744:PMC
736:doi
697:doi
693:499
659:PMC
649:doi
612:PMC
604:doi
592:524
175:CID
121:,5a
117:,3a
42:to
1110::
1084:.
1061:.
1051:.
1039:21
1037:.
1033:.
1010:.
1000:12
998:.
975:.
961:.
957:.
934:.
926:.
903:.
895:.
883:.
860:.
850:.
838:39
836:.
832:.
809:.
799:.
791:.
779:.
775:.
752:.
742:.
732:13
730:.
726:.
703:.
691:.
667:.
657:.
647:.
643:.
620:.
610:.
602:.
590:.
586:.
572:^
492:)
323:32
317:28
289:,
125:,6
113:,3
109:(2
1096:.
1092::
1086:5
1069:.
1045::
1018:.
1006::
983:.
969::
942:.
930::
911:.
891::
868:.
844::
817:.
795::
787::
760:.
738::
711:.
699::
675:.
651::
628:.
606::
598::
519:)
513:S
490:R
358:)
335:2
332:O
329:2
326:N
320:H
314:C
295:)
139:H
135:S
131:R
127:R
123:R
119:R
115:S
111:R
65:)
59:(
54:)
50:(
36:.
Text is available under the Creative Commons Attribution-ShareAlike License. Additional terms may apply.
