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Chemistry

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Also known as: Diamorphine hydrochloride, Diacetylmorphine hydrochloride, 1502-95-0, Diacetylmorphine hcl, Heroine hydrochloride, (-)-heroin hydrochloride
Molecular Formula
C21H24ClNO5
Molecular Weight
405.9  g/mol
InChI Key
FZJYQGFGNHGSFX-PVQKIFDLSA-N
FDA UNII
8H672SHT8E

Diamorphine Hydrochloride
A narcotic analgesic that may be habit-forming. It is a controlled substance (opium derivative) listed in the U.S. Code of Federal Regulations, Title 21 Parts 329.1, 1308.11 (1987). Sale is forbidden in the United States by Federal statute. (Merck Index, 11th ed)
1 2D Structure

Diamorphine Hydrochloride

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
[(4R,4aR,7S,7aR,12bS)-9-acetyloxy-3-methyl-2,4,4a,7,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7-yl] acetate;hydrochloride
2.1.2 InChI
InChI=1S/C21H23NO5.ClH/c1-11(23)25-16-6-4-13-10-15-14-5-7-17(26-12(2)24)20-21(14,8-9-22(15)3)18(13)19(16)27-20;/h4-7,14-15,17,20H,8-10H2,1-3H3;1H/t14-,15+,17-,20-,21-;/m0./s1
2.1.3 InChI Key
FZJYQGFGNHGSFX-PVQKIFDLSA-N
2.1.4 Canonical SMILES
CC(=O)OC1C=CC2C3CC4=C5C2(C1OC5=C(C=C4)OC(=O)C)CCN3C.Cl
2.1.5 Isomeric SMILES
CC(=O)O[C@H]1C=C[C@H]2[C@H]3CC4=C5[C@]2([C@H]1OC5=C(C=C4)OC(=O)C)CCN3C.Cl
2.2 Other Identifiers
2.2.1 UNII
8H672SHT8E
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Diacetylmorphine

2. Diacetylmorphine Hydrochloride

3. Diagesil

4. Diamorf

5. Diamorphine

6. Heroin

7. Hydrochloride, Diacetylmorphine

8. Hydrochloride, Heroin

9. Min I Jet Morphine Sulphate

10. Min-i-jet Morphine Sulphate

2.3.2 Depositor-Supplied Synonyms

1. Diamorphine Hydrochloride

2. Diacetylmorphine Hydrochloride

3. 1502-95-0

4. Diacetylmorphine Hcl

5. Heroine Hydrochloride

6. (-)-heroin Hydrochloride

7. Heroin Hydrochloride Solution

8. O,o'-diacetylmorphine Hydrochloride

9. Nsc-302357

10. 8h672sht8e

11. Diacetylmorphine Hydrochloride Ci

12. Morphine, Diacetate (ester), Hydrochloride

13. Morphinan-3,6-diol, 7,8-didehydro-4,5-epoxy-17-methyl-, Diacetate

14. Morphinan-3,6alpha-diol, 7,8-didehydro-4,5alpha-epoxy-17-methyl-,

15. Morphinan-3,6-alpha-diol, 7,8-didehydro-4,5-alpha-epoxy-17-methyl-, Diacetate (ester), Hydrochloride

16. Einecs 216-124-5

17. Nsc 302357

18. Unii-8h672sht8e

19. Diamorphine (tn)

20. Heroin, Hydrochloride

21. Diamorphine, Hydrochloride

22. Ncgc00247702-01

23. Dsstox_cid_28835

24. Dsstox_rid_83104

25. Dsstox_gsid_48909

26. Schembl116481

27. Chembl2106627

28. Dtxsid2048909

29. Diamorphine Hydrochloride Anhydrous

30. Baa50295

31. Tox21_112854

32. Diacetylmorphine Hydrochloride [usp]

33. Nsc302357

34. Diamorphine Hydrochloride [mart.]

35. Diamorphine Hydrochloride [who-dd]

36. Morphinan-3,6-diol, 7,8-didehydro-4,5-epoxy-17-methyl- (5alpha,6alpha)-, Diacetate (ester), Hydrochloride

37. Morphinan-3,6-diol, 7,8-didehydro-4,5-epoxy-17-methyl- (5alpha,6alpha)-,diacetate (ester), Hydrochloride

38. Morphinan-3,6alpha-diol, 7,8-didehydro-4,5alpha-epoxy-17-methyl-, Diacetate (ester), Hydrochloride

39. Cas-1502-95-0

40. D07810

41. Diacetylmorphine Hydrochloride Ci [usp-rs]

42. Q27270475

43. Morphinan-3, 7,8-didehydro-4,5.alpha.-epoxy-17-methyl-, Diacetate (ester) Hydrochloride

44. Morphinan-3, 7,8-didehydro-4,5.alpha.-epoxy-17-methyl-, Diacetate (ester), Hydrochloride

45. Wln: T B6566 B6/co 4abbc R Bx Ho Pn Du Ght&&ttj Fov1 Jov1 P1 &gh

46. (5.alpha.,6.alpha.)-7,8-didehydro-4,5-epoxy-17-methylmorphinan-3,6-diol Diacetate (ester) Hydrochloride

47. [(4r,4ar,7s,7ar,12bs)-9-acetyloxy-3-methyl-2,4,4a,7,7a,13-hexahydro-1h-4,12-methanobenzofuro[3,2-e]isoquinolin-7-yl] Acetate;hydrochloride

48. Heroin Hydrochloride Solution, 100 Mug/ml In Methanol, Analytical Standard, For Drug Analysis

49. Morphinan-3, 7,8-didehydro-4,5-epoxy-17-methyl- (5.alpha.,6.alpha.)-, Diacetate (ester), Hydrochloride

50. Morphinan-3, 7,8-didehydro-4,5-epoxy-17-methyl- (5.alpha.,6.alpha.)-,diacetate (ester), Hydrochloride

51. Morphinan-3, 7,8-didehydro-4,5-epoxy-17-methyl-, Diacetate (ester), Hydrochloride, (5.alpha.,6.alpha.)-

2.3.3 Other Synonyms

1. Heroin

2. Acetomorphine

3. Diamorphine

4. Acetomorfine

5. Diacetylmorfin

6. Aspron

7. Heroien

8. Morphacetin

2.4 Create Date
2006-10-25
3 Chemical and Physical Properties
Molecular Weight 405.9 g/mol
Molecular Formula C21H24ClNO5
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count6
Rotatable Bond Count4
Exact Mass405.1343006 g/mol
Monoisotopic Mass405.1343006 g/mol
Topological Polar Surface Area65.1 Ų
Heavy Atom Count28
Formal Charge0
Complexity692
Isotope Atom Count0
Defined Atom Stereocenter Count5
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count2
4 Drug and Medication Information
4.1 Drug Indication

Dependence to intravenous heroin use


5 Pharmacology and Biochemistry
5.1 MeSH Pharmacological Classification

Analgesics, Opioid

Compounds with activity like OPIATE ALKALOIDS, acting at OPIOID RECEPTORS. Properties include induction of ANALGESIA or NARCOSIS. (See all compounds classified as Analgesics, Opioid.)


Narcotics

Agents that induce NARCOSIS. Narcotics include agents that cause somnolence or induced sleep (STUPOR); natural or synthetic derivatives of OPIUM or MORPHINE or any substance that has such effects. They are potent inducers of ANALGESIA and OPIOID-RELATED DISORDERS. (See all compounds classified as Narcotics.)


API SUPPLIERS

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USDMF

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Evans Medical Ltd

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Evans Medical Ltd

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GDUFA

DMF Review : N/A

Rev. Date :

Pay. Date :

DMF Number : 6161

Submission : 1985-11-04

Status : Inactive

Type : II

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Europe

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DiaMo Narcotics GmbH

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Diamorphine hydrochloride anhydricum

Brand Name : Diaphin IR

Dosage Form : Tabl

Dosage Strength : 200mg

Packaging :

Approval Date :

Application Number :

Regulatory Info :

Registration Country : Switzerland

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DiaMo Narcotics GmbH

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Diamorphine hydrochloride anhydricum

Brand Name : Diaphin SR

Dosage Form : Ret Filmtabl

Dosage Strength : 200mg

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Approval Date :

Application Number :

Regulatory Info :

Registration Country : Switzerland

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DiaMo Narcotics GmbH

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Diamorphini hydrochloridum monohydricum

Brand Name : Diaphin

Dosage Form : Dry Sub

Dosage Strength : 5g

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Regulatory Info :

Registration Country : Switzerland

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Canada

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DIAMORPHINE HYDROCHLORIDE

Brand Name : DIACETYLMORPHINE HYDROCHLORIDE

Dosage Form : POWDER FOR SOLUTION

Dosage Strength : 200MG/VIAL

Packaging :

Approval Date :

Application Number : 2524996

Regulatory Info : Narcotic (CDSA I)

Registration Country : Canada

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DIAMORPHINE HYDROCHLORIDE

Brand Name : DIACETYLMORPHINE HYDROCHLORIDE

Dosage Form : POWDER FOR SOLUTION

Dosage Strength : 5000MG/VIAL

Packaging :

Approval Date :

Application Number : 2525003

Regulatory Info : Narcotic (CDSA I)

Registration Country : Canada

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