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2D Structure
Also known as: 14357-78-9, Diprenorfin, Revivon, Dea no. 9058, 1f0l5n25zz, Chebi:4650
Molecular Formula
C26H35NO4
Molecular Weight
425.6  g/mol
InChI Key
OIJXLIIMXHRJJH-KNLIIKEYSA-N
FDA UNII
1F0L5N25ZZ

A narcotic antagonist similar in action to NALOXONE. It is used to remobilize animals after ETORPHINE neuroleptanalgesia and is considered a specific antagonist to etorphine.
1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(1S,2S,6R,14R,15R,16R)-5-(cyclopropylmethyl)-16-(2-hydroxypropan-2-yl)-15-methoxy-13-oxa-5-azahexacyclo[13.2.2.12,8.01,6.02,14.012,20]icosa-8(20),9,11-trien-11-ol
2.1.2 InChI
InChI=1S/C26H35NO4/c1-23(2,29)18-13-24-8-9-26(18,30-3)22-25(24)10-11-27(14-15-4-5-15)19(24)12-16-6-7-17(28)21(31-22)20(16)25/h6-7,15,18-19,22,28-29H,4-5,8-14H2,1-3H3/t18-,19-,22-,24-,25+,26-/m1/s1
2.1.3 InChI Key
OIJXLIIMXHRJJH-KNLIIKEYSA-N
2.1.4 Canonical SMILES
CC(C)(C1CC23CCC1(C4C25CCN(C3CC6=C5C(=C(C=C6)O)O4)CC7CC7)OC)O
2.1.5 Isomeric SMILES
CC(C)([C@H]1C[C@@]23CC[C@@]1([C@H]4[C@@]25CCN([C@@H]3CC6=C5C(=C(C=C6)O)O4)CC7CC7)OC)O
2.2 Other Identifiers
2.2.1 UNII
1F0L5N25ZZ
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Diprenorphine Hydrochloride

2. Hydrochloride, Diprenorphine

3. Revivon

2.3.2 Depositor-Supplied Synonyms

1. 14357-78-9

2. Diprenorfin

3. Revivon

4. Dea No. 9058

5. 1f0l5n25zz

6. Chebi:4650

7. Chembl281786

8. M. 5050

9. Diprenorphine (inn)

10. M50-50 Injection

11. M5050

12. Diprenorphine [inn:ban]

13. Diprenorphine [inn]

14. M-5050

15. Diprenorfina [inn-spanish]

16. (1s,2s,6r,14r,15r,16r)-5-(cyclopropylmethyl)-16-(2-hydroxypropan-2-yl)-15-methoxy-13-oxa-5-azahexacyclo[13.2.2.12,8.01,6.02,14.012,20]icosa-8(20),9,11-trien-11-ol

17. Diprenorfina

18. Diprenorphinum

19. 21-cyclopropyl-6,7,8,14-tetrahydro-7alpha-(1-hydroxy-1-methylethyl)-6,14-endo-ethanooripavine

20. Diprenorphinum [inn-latin]

21. Unii-1f0l5n25zz

22. (5?,7?)-17-(cyclopropylmethyl)-4,5-epoxy-18,19-dihydro-3-hydroxy-6-methoxy-?,?-dimethyl-6,14-ethenomorphinan-7-methanol

23. Einecs 238-325-7

24. M 5050 Injection

25. Diprenorphine-hcl

26. Diprenorphine [mi]

27. M50-50

28. Schembl164910

29. Gtpl1617

30. Dtxsid00903941

31. Zinc4102215

32. Bdbm50001714

33. Akos024457358

34. Db01548

35. 6,14-ethenomorphinan-7-methanol, 17-(cyclopropylmethyl)-4,5-epoxy-18,19-dihydro-3-hydroxy-6-methoxy-.alpha.,.alpha.-dimethyl-, (5.alpha.,7.alpha.)-

36. 6,14-ethenomorphinan-7-methanol, 17-(cyclopropylmethyl)-4,5-epoxy-18,19-dihydro-3-hydroxy-6-methoxy-alpha,alpha-dimethyl-, (5alpha,7alpha)-

37. Hy-107742

38. D07863

39. M 5050

40. Q424009

41. Epoxy-18,19-dihydro-3-hydroxy-6-methoxy-alpha,alpha-dimethyl-, (5alpha,7alpha)-

42. (5alpha,7alpha)-17-(cyclopropylmethyl)-4,5-epoxy-18,19-dihydro-3-hydroxy-6-methoxy-alpha,alpha-dimethyl-6,14-ethenomorphinan-7-methanol

43. 17-(cyclopropylmethyl)-4,5-epoxy-18,19-dihydro-3-hydroxy-6-methoxy-?,?-dimethyl-6,14-ethenomorphinan-7-methanol

44. 2-[3-cyclopropylmethyl-11-hydroxy-15-methoxy-(1s,2r,6s,14r,15r,16r)-13-oxa-3-azahexacyclo[13.2.2.12,8.01,6.06,14.07,12]icosa-7,9,11-trien-16-yl]-2-propanol

45. 2-[3-cyclopropylmethyl-11-hydroxy-15-methoxy-(1s,2r,6s,14r,15r,16r)-13-oxa-3-azahexacyclo[13.2.2.12,8.01,6.06,14.07,12]icosa-7,9,11-trien-16-yl]-2-propanol(diprenorphine)

46. 2-[3-cyclopropylmethyl-11-hydroxy-15-methoxy-13-oxa-3-azahexacyclo[13.2.2.12,8.01,6.06,14.07,12]icosa-7(12),8,10-trien-16-yl]-2-propanol

47. 6,14-endo-ethanotetrahydrooripavine, 21-cyclopropyl-7a-(1-hydroxy-1-methylethyl)- (8ci) 1-n-cyclopropylmethyl-6,7,8,14-tetrahydro-6,14-endoethano-7-(2'-hydroxy-2'-propyl)nororipavine

48. 6,14-ethenomorphinan-3-ol, 17-(cyclopropylmethyl)-4,5-epoxy-18,19-dihydro-18-(1-hydroxy-1-methylethyl)-6-methoxy-, (5alpha,6beta,14beta,18r)-

49. 6,14-ethenomorphinan-7-methanol, 17-(cyclopropylmethyl)-4,5-epoxy-18,19-dihydro-3-hydroxy-6-methoxy-alpha,alpha-dimethyl-, (5alpha,7alpha)- (9ci)

2.4 Create Date
2005-06-01
3 Chemical and Physical Properties
Molecular Weight 425.6 g/mol
Molecular Formula C26H35NO4
XLogP33.6
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count5
Rotatable Bond Count4
Exact Mass425.25660860 g/mol
Monoisotopic Mass425.25660860 g/mol
Topological Polar Surface Area62.2 Ų
Heavy Atom Count31
Formal Charge0
Complexity783
Isotope Atom Count0
Defined Atom Stereocenter Count6
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Indication

Diprenorphine is indicated to reverse the effects of powerful opioids including etorphine and carfentanil, often used for tranquilizing large animals. This drug is not approved for use in humans.


5 Pharmacology and Biochemistry
5.1 MeSH Pharmacological Classification

Narcotic Antagonists

Agents inhibiting the effect of narcotics on the central nervous system. (See all compounds classified as Narcotic Antagonists.)


5.2 Mechanism of Action

Diprenorphine binds approximately equally to the three subtypes of opioid receptorsand antagonizes them.